[DB] 1-(1-'[H,C]'-1-nitroprop-1-en-2-yl)-2,3,4,5,6-penta'GH'benzene

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Date

65 substances in Reaxys

2018-08-17 22h:00m:49s (UTC)

GH GH

NO 2

1. Query

L GH

GH

[H,C]

GH

Search as: As drawn, Ignore stereo, No salts, No mixtures, No isotopes, No charges, No radicals, No additional rings ))

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Reaxys ID 2413678 View in Reaxys

1/65 CAS Registry Number: 5670-65-5; 15241-24-4; 15795-70-7 Chemical Name: 1-nitro-2-phenylpropene; α-methyl-α-nitrostyrene; (E/ Z)-1-nitro-2-phenylprop-1-ene; (1-methyl-2-nitrovinyl)benzene; (1-nitroprop-1-en-2-yl)benzene; (E/Z)-1-nitro-2-phenylpropene; 1-nitro-2phenylprop-1-ene Linear Structure Formula: C9H9NO2 Molecular Formula: C9H9NO2 Molecular Weight: 163.176 Type of Substance: isocyclic InChI Key: KFNFMBKUWFTFAE-UHFFFAOYSA-N Note:

O N O

Substance Label (24) Label References 5m

Feng, Bin; Chen, Jia-Rong; Yang, Yun-Fang; Lu, Bin; Xiao, Wen-Jing; Chemistry - A European Journal; vol. 24; nb.

7; (2018); p. 1714 - 1719, View in Reaxys

S-5

Li, Jing; Lear, Martin J.; Hayashi, Yujiro; Chemical Communications; vol. 54; nb. 49; (2018); p. 6360 - 6363, View in Reaxys

1a

Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5, View in Reaxys

2s

Wei, Qi; Hou, Wenduan; Liao, Na; Peng, Yungui; Advanced Synthesis and Catalysis; vol. 359; nb. 14; (2017); p.

2364 - 2368, View in Reaxys

2a'

Lu, Ning; Bai, Fuquan; Fang, Yanhong; Wei, Zhonglin; Cao, Jungang; Liang, Dapeng; Lin, Yingjie; Duan, Haifeng; Advanced Synthesis and Catalysis; vol. 359; nb. 23; (2017); p. 4111 - 4116, View in Reaxys

1

Howlader, Prodip; Das, Paramita; Zangrando, Ennio; Mukherjee, Partha Sarathi; Journal of the American Chemical Society; vol. 138; nb. 5; (2016); p. 1668 - 1676, View in Reaxys; Foli, Giacomo; D'Elia, Cecilia Sasso; Fochi, Mariafrancesca; Bernardi, Luca; RSC Advances; vol. 6; nb. 71; (2016); p. 66490 - 66494, View in Reaxys

2a

Choudhary, Manoj K.; Rao Ganga, Venkata Subba; Menapara, Tusharkumar; Kureshy, Rukhsana I.; Khan, Noor-Ul H.; Abdi, Sayed H. R.; Suresh, Eringathodi; RSC Advances; vol. 6; nb. 106; (2016); p. 104148 - 104153, View in Reaxys

2

Howlader, Prodip; Mukherjee, Partha Sarathi; Chemical Science; vol. 7; nb. 9; (2016); p. 5893 - 5899, View in Reaxys

1w

Kiyokawa, Kensuke; Nagata, Takaya; Hayakawa, Junpei; Minakata, Satoshi; Chemistry - A European Journal; vol.

21; nb. 3; (2015); p. 1280 - 1285, View in Reaxys

1d

Reß, Tina; Hummel, Werner; Hanlon, Steven P.; Iding, Hans; Gröger, Harald; ChemCatChem; vol. 7; nb. 8; (2015); p. 1302 - 1311, View in Reaxys

2l

Chen, Jiean; Meng, Sixuan; Wang, Leming; Tang, Hongmei; Huang, Yong; Chemical Science; vol. 6; nb. 7; (2015); p. 4184 - 4189, View in Reaxys

6

Anderson, James C.; Koovits, Paul J.; Chemical Science; vol. 4; nb. 7; (2013); p. 2897 - 2901,5, View in Reaxys

19a

Durchschein, Katharina; Wallner, Silvia; MacHeroux, Peter; Schwab, Wilfried; Winkler, Thorsten; Kreis, Wolfgang; Faber, Kurt; European Journal of Organic Chemistry; nb. 26; (2012); p. 4963 - 4968, View in Reaxys

e

Patent; Sumitomo Chemical Company, Limited; Carreira, Erick M.; EP2311846; (2011); (A1) English, View in Reaxys

Table1, entry9, product

Ramgopal; Ramesh; Chakradhar; Reddy, N. Maasi; Rajanna; Tetrahedron Letters; vol. 48; nb. 23; (2007); p. 4043 4045, View in Reaxys

5l

Jang, Yeong-Jiunn; Lin, Wen-Wei; Shih, Yuh-Kuo; Liu, Ju-Tsung; Hwang, Ming-Hsing; Yao, Ching-Fa; Tetrahedron; vol. 59; nb. 27; (2003); p. 4979 - 4992, View in Reaxys

3k

Bandgar; Kasture; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 40; nb. 12; (2001); p. 1239 - 1241, View in Reaxys

t.,pr.,sr.no.10

Bandgar; Uppalla; Synthetic Communications; vol. 30; nb. 12; (2000); p. 2071 - 2075, View in Reaxys

10

Abbenante, Giovanni; Hughes, Robert; Prager, Rolf H.; Australian Journal of Chemistry; vol. 47; nb. 8; (1994); p.

1441 - 1452, View in Reaxys

entry 3

Ranu; Chakraborty; Tetrahedron; vol. 48; nb. 25; (1992); p. 5317 - 5322, View in Reaxys

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IIb

Yandovskii, V. N.; Ryabinkin, I. I.; Tselinskii, I. V.; Journal of Organic Chemistry USSR (English Translation); vol.

16; nb. 10; (1980); p. 1773 - 1775; Zhurnal Organicheskoi Khimii; vol. 16; nb. 10; (1980); p. 2084 - 2086, View in Reaxys

19

Bordwell et al.; Journal of Organic Chemistry; vol. 43; (1978); p. 3107,3108, View in Reaxys

I

Vasil'eva,O.S. et al.; Zhurnal Organicheskoi Khimii; vol. 14; nb. 7; (1978); p. 1420 - 1422,1326 - 1327, View in Reaxys

II

Bluhm; Weinstein; Journal of the American Chemical Society; vol. 87; (1965); p. 5511, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.678

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

Boiling Point (3) Boiling Point [°C]

Pressure (Boiling Point) [Torr]

References

125

5

Tuaillon; Perrot; Helvetica Chimica Acta; vol. 61; (1978); p. 558,563, View in Reaxys

85 - 90

1-2

Vasil'eva,O.S. et al.; Zhurnal Organicheskoi Khimii; vol. 14; nb. 7; (1978); p. 1420 - 1422,1326 1327, View in Reaxys

90 - 100

0.5 - 0.8

Kaufman; Miller; Journal of Organic Chemistry; vol. 34; (1969); p. 1495, View in Reaxys

Refractive Index (1) Refractive Index Wavelength (ReTemperature (Refractive Index) [nm] fractive Index) [°C] 1.578

589

20

References Vasil'eva,O.S. et al.; Zhurnal Organicheskoi Khimii; vol. 14; nb. 7; (1978); p. 1420 - 1422,1326 - 1327, View in Reaxys

Electrochemical Behaviour (1) Description (Elec- References trochemical Behaviour) Electrochemical properties

Berndt,A.; Angewandte Chemie; vol. 79; (1967); p. 240 - 241, View in Reaxys

Further Information (1) Description (FurReferences ther Information) Further information Bluhm; Weinstein; Journal of the American Chemical Society; vol. 87; (1965); p. 5511, View in Reaxys Solubility (MCS) (1) 1 of 1

Comment (Solubility (MCS))

insoluble in water

Howlader, Prodip; Mukherjee, Partha Sarathi; Chemical Science; vol. 7; nb. 9; (2016); p. 5893 - 5899, View in Reaxys NMR Spectroscopy (5) 1 of 5

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Taniguchi, Tsuyoshi; Fujii, Tatsuya; Ishibashi, Hiroyuki; Journal of Organic Chemistry; vol. 75; nb. 23; (2010); p. 8126 8132, View in Reaxys

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2 of 5

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Taniguchi, Tsuyoshi; Fujii, Tatsuya; Ishibashi, Hiroyuki; Journal of Organic Chemistry; vol. 75; nb. 23; (2010); p. 8126 8132, View in Reaxys 3 of 5

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Temperature (NMR Spectroscopy) [°C]

17.54

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Wang, Xiao; Chen, Yong-Fei; Niu, Liang-Feng; Xu, Peng-Fei; Organic Letters; vol. 11; nb. 15; (2009); p. 3310 - 3313, View in Reaxys 4 of 5

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 360 scopy) [MHz] Hall, Melanie; Stueckler, Clemens; Ehammer, Heidemarie; Pointner, Eva; Oberdorfer, Gustav; Gruber, Karl; Hauer, Bernard; Stuermer, Rainer; Kroutil, Wolfgang; Macheroux, Peter; Faber, Kurt; Advanced Synthesis and Catalysis; vol.

350; nb. 3; (2008); p. 411 - 418, View in Reaxys 5 of 5

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Penczek,S. et al.; Journal of the American Chemical Society; vol. 90; nb. 8; (1968); p. 2174 - 2175, View in Reaxys IR Spectroscopy (4) 1 of 4

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

1520 - 1340 cm**(-1)

Abbenante, Giovanni; Hughes, Robert; Prager, Rolf H.; Australian Journal of Chemistry; vol. 47; nb. 8; (1994); p. 1441 1452, View in Reaxys 2 of 4

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CCl4

Comment (IR Spectroscopy)

1620 - 1340 cm**(-1)

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Yandovskii, V. N.; Ryabinkin, I. I.; Tselinskii, I. V.; Journal of Organic Chemistry USSR (English Translation); vol. 16; nb.

10; (1980); p. 1773 - 1775; Zhurnal Organicheskoi Khimii; vol. 16; nb. 10; (1980); p. 2084 - 2086, View in Reaxys 3 of 4

Description (IR Spectroscopy)

IR

Tuaillon; Perrot; Helvetica Chimica Acta; vol. 61; (1978); p. 558,563, View in Reaxys 4 of 4

Description (IR Spectroscopy)

Bands

Vasil'eva,O.S. et al.; Zhurnal Organicheskoi Khimii; vol. 14; nb. 7; (1978); p. 1420 - 1422,1326 - 1327, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry) HRMS (High resolution mass spectrometry); FAB (Fast atom bombardment); Spectrum

Taniguchi, Tsuyoshi; Fujii, Tatsuya; Ishibashi, Hiroyuki; Journal of Organic Chemistry; vol. 75; nb. 23; (2010); p.

8126 - 8132, View in Reaxys

spectrum; chemical ionization (CI)

Abbenante, Giovanni; Hughes, Robert; Prager, Rolf H.; Australian Journal of Chemistry; vol. 47; nb. 8; (1994); p.

1441 - 1452, View in Reaxys

UV/VIS Spectroscopy (1) 1 of 1

Description (UV/VIS Spectroscopy)

UV/VIS

Bordwell et al.; Journal of Organic Chemistry; vol. 43; (1978); p. 3107,3108, View in Reaxys

Reaxys ID 2413679 View in Reaxys

2/65 CAS Registry Number: 5670-65-5 Chemical Name: (Z)-(1-nitroprop-1-en-2-yl)benzene; (Z)-2-phenyl-1-nitroprop-1-ene; (Z)-1-nitro-2-phenylpropene; 1-nitro-2-phenyl-1-propene Linear Structure Formula: C9H9NO2 Molecular Formula: C9H9NO2 Molecular Weight: 163.176 Type of Substance: isocyclic InChI Key: KFNFMBKUWFTFAE-FPLPWBNLSA-N Note:

N O

O

Substance Label (12) Label References 1a

Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5, View in Reaxys

1n

Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb.

26; (2016); p. 4812 - 4815, View in Reaxys

(Z)-5a

Gao, Jian-Rong; Wu, Hao; Xiang, Bin; Yu, Wu-Bin; Han, Liang; Jia, Yi-Xia; Journal of the American Chemical Society; vol. 135; nb. 8; (2013); p. 2983 - 2986, View in Reaxys

(Z)-4m

Maity, Soham; Manna, Srimanta; Rana, Sujoy; Naveen, Togati; Mallick, Arijit; Maiti, Debabrata; Journal of the American Chemical Society; vol. 135; nb. 9; (2013); p. 3355 - 3358, View in Reaxys

(Z)-10a

Mansell, David J.; Toogood, Helen S.; Waller, John; Hughes, John M.X.; Levy, Colin W.; Gardiner, John M.; Scrutton, Nigel S.; ACS Catalysis; vol. 3; nb. 3; (2013); p. 370 - 379, View in Reaxys

19a

Durchschein, Katharina; Wallner, Silvia; MacHeroux, Peter; Schwab, Wilfried; Winkler, Thorsten; Kreis, Wolfgang; Faber, Kurt; European Journal of Organic Chemistry; nb. 26; (2012); p. 4963 - 4968, View in Reaxys

Z-product, entry 8

Campos, Pedro J.; Garcia, Barbara; Rodriguez, Miguel A.; Tetrahedron Letters; vol. 41; nb. 6; (2000); p. 979 - 982, View in Reaxys

4d

Barco, Achille; Benetti, Simonetta; De Risi, Carmela; Morelli, Carlo F.; Pollini, Gian P.; Zanirato, Vinicio; Tetrahedron; vol. 52; nb. 27; (1996); p. 9275 - 9288, View in Reaxys

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(Z)-10

Abbenante, Giovanni; Hughes, Robert; Prager, Rolf H.; Australian Journal of Chemistry; vol. 47; nb. 8; (1994); p.

1441 - 1452, View in Reaxys

2b

Felluga, F.; Nitti, P.; Pitacco, G.; Valentin, E.; Tetrahedron Letters; vol. 29; nb. 33; (1988); p. 4165 - 4168, View in Reaxys

11b

Miller et al.; Journal of Organic Chemistry; vol. 41; (1976); p. 2112,2118, View in Reaxys

2, cis

Sousa et al.; Journal of Organic Chemistry; vol. 34; (1969); p. 3320,3323, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.678

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

Refractive Index (1) Refractive Index Wavelength (ReTemperature (Refractive Index) [nm] fractive Index) [°C] 1.569

589

Chromatographic Data (1) Chromatographic Location data GC (Gas chromatography)

20

References Miller et al.; Journal of Organic Chemistry; vol. 41; (1976); p. 2112,2118, View in Reaxys

References

supporting informa- Durchschein, Katharina; Wallner, Silvia; MacHeroux, Peter; Schwab, Wilfried; Winkler, tion Thorsten; Kreis, Wolfgang; Faber, Kurt; European Journal of Organic Chemistry; nb. 26; (2012); p. 4963 - 4968, View in Reaxys

Crystal Property Description (1) Colour & Other References Properties yellow

Toogood, Helen S.; Fryszkowska, Anna; Hare, Victoria; Fisher, Karl; Roujeinikova, Anna; Leys, David; Gardiner, John M.; Stephens, Gill M.; Scrutton, Nigel S.; Advanced Synthesis and Catalysis; vol. 350; nb. 17; (2008); p.

2789 - 2803, View in Reaxys

NMR Spectroscopy (7) 1 of 7

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 300 scopy) [MHz] Location

supporting information

Toogood, Helen S.; Fryszkowska, Anna; Hare, Victoria; Fisher, Karl; Roujeinikova, Anna; Leys, David; Gardiner, John M.; Stephens, Gill M.; Scrutton, Nigel S.; Advanced Synthesis and Catalysis; vol. 350; nb. 17; (2008); p. 2789 - 2803, View in Reaxys 2 of 7

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 75 scopy) [MHz]

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Location

supporting information

Toogood, Helen S.; Fryszkowska, Anna; Hare, Victoria; Fisher, Karl; Roujeinikova, Anna; Leys, David; Gardiner, John M.; Stephens, Gill M.; Scrutton, Nigel S.; Advanced Synthesis and Catalysis; vol. 350; nb. 17; (2008); p. 2789 - 2803, View in Reaxys 3 of 7

Description (NMR Spectroscopy)

DEPT (Distorsionless Enhancement by Polarisation Transfer); Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 75 scopy) [MHz] Location

supporting information

Toogood, Helen S.; Fryszkowska, Anna; Hare, Victoria; Fisher, Karl; Roujeinikova, Anna; Leys, David; Gardiner, John M.; Stephens, Gill M.; Scrutton, Nigel S.; Advanced Synthesis and Catalysis; vol. 350; nb. 17; (2008); p. 2789 - 2803, View in Reaxys 4 of 7

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Greenop, Michael W.; Thomas, C. Barry; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 8; (1995); p. 1595 - 1600, View in Reaxys; Barco, Achille; Benetti, Simonetta; De Risi, Carmela; Morelli, Carlo F.; Pollini, Gian P.; Zanirato, Vinicio; Tetrahedron; vol. 52; nb. 27; (1996); p. 9275 - 9288, View in Reaxys 5 of 7

Description (NMR Spectroscopy)

Spin-spin coupling constants

Solvents (NMR Spectroscopy)

CDCl3

Comment (NMR Spectroscopy)

1H-1H

Greenop, Michael W.; Thomas, C. Barry; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 8; (1995); p. 1595 - 1600, View in Reaxys; Barco, Achille; Benetti, Simonetta; De Risi, Carmela; Morelli, Carlo F.; Pollini, Gian P.; Zanirato, Vinicio; Tetrahedron; vol. 52; nb. 27; (1996); p. 9275 - 9288, View in Reaxys 6 of 7

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CCl4

Abbenante, Giovanni; Hughes, Robert; Prager, Rolf H.; Australian Journal of Chemistry; vol. 47; nb. 8; (1994); p. 1441 1452, View in Reaxys 7 of 7

Description (NMR Spectroscopy)

NMR

Sousa et al.; Journal of Organic Chemistry; vol. 34; (1969); p. 3320,3323, View in Reaxys; Miller et al.; Journal of Organic Chemistry; vol. 41; (1976); p. 2112,2118, View in Reaxys IR Spectroscopy (3) 1 of 3

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

neat liquid

Toogood, Helen S.; Fryszkowska, Anna; Hare, Victoria; Fisher, Karl; Roujeinikova, Anna; Leys, David; Gardiner, John M.; Stephens, Gill M.; Scrutton, Nigel S.; Advanced Synthesis and Catalysis; vol. 350; nb. 17; (2008); p. 2789 - 2803, View in Reaxys

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2 of 3

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

1500 - 1330 cm**(-1)

Barco, Achille; Benetti, Simonetta; De Risi, Carmela; Morelli, Carlo F.; Pollini, Gian P.; Zanirato, Vinicio; Tetrahedron; vol. 52; nb. 27; (1996); p. 9275 - 9288, View in Reaxys 3 of 3

Description (IR Spectroscopy)

IR

Sousa et al.; Journal of Organic Chemistry; vol. 34; (1969); p. 3320,3323, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry) EI (Electron impact); Spectrum

Toogood, Helen S.; Fryszkowska, Anna; Hare, Victoria; Fisher, Karl; Roujeinikova, Anna; Leys, David; Gardiner, John M.; Stephens, Gill M.; Scrutton, Nigel S.; Advanced Synthesis and Catalysis; vol. 350; nb. 17; (2008); p.

2789 - 2803, View in Reaxys

HRMS (High resolution mass spectrometry); CI (Chemical ionization); Spectrum

Toogood, Helen S.; Fryszkowska, Anna; Hare, Victoria; Fisher, Karl; Roujeinikova, Anna; Leys, David; Gardiner, John M.; Stephens, Gill M.; Scrutton, Nigel S.; Advanced Synthesis and Catalysis; vol. 350; nb. 17; (2008); p.

2789 - 2803, View in Reaxys

UV/VIS Spectroscopy (2) 1 of 2

Absorption Maxima (UV/ VIS) [nm]

208

Toogood, Helen S.; Fryszkowska, Anna; Hare, Victoria; Fisher, Karl; Roujeinikova, Anna; Leys, David; Gardiner, John M.; Stephens, Gill M.; Scrutton, Nigel S.; Advanced Synthesis and Catalysis; vol. 350; nb. 17; (2008); p. 2789 - 2803, View in Reaxys 2 of 2

Description (UV/VIS Spectroscopy)

Absorption maxima

Sousa et al.; Journal of Organic Chemistry; vol. 34; (1969); p. 3320,3323, View in Reaxys

Reaxys ID 2413680 View in Reaxys

3/65 CAS Registry Number: 5670-65-5; 15795-70-7; 15241-24-4 Chemical Name: (E)-1-nitro-2-phenyl-1-propene; trans-α-methyl-α-nitrostyrene; (E)-α-methyl-α-nitrostyrene; α-methyl-α-nitrostyrene; (E)-(1-nitroprop-1-en-2-yl)benzene; [(E)-1-methyl-2-nitrovinyl]benzene; (E)-1-nitro-2-phenylprop-1-ene Linear Structure Formula: C9H9NO2 Molecular Formula: C9H9NO2 Molecular Weight: 163.176 Type of Substance: isocyclic InChI Key: KFNFMBKUWFTFAE-BQYQJAHWSA-N Note:

O N O

Substance Label (21) Label References 1a

Wu, Jing; Mampreian, Dawn M.; Hoveyda, Amir H.; Journal of the American Chemical Society; vol. 127; nb. 13; (2005); p. 4584 - 4585, View in Reaxys; Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p. 8976 - 8977, View in Reaxys; Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys; Zhao, Qingyang; Li, Shengkun; Huang, Kexuan; Wang, Rui; Zhang, Xumu; Organic Letters; vol.

15; nb. 15; (2013); p. 4014 - 4017, View in Reaxys; Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys; Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p. 3875 - 3879, View in Reaxys; Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys; Xu, Weici; Arieno, Marcus; Löw, Henrik; Huang, Kaifang; Xie, Xiulan; Cruchter, Thomas; Ma, Qiao; Xi, Jianwei; Huang, Biao; Wiest, Olaf; Gong,

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Lei; Meggers, Eric; Journal of the American Chemical Society; vol. 138; nb. 28; (2016); p. 8774 - 8780, View in Reaxys; Bernardi, Luca; Fochi, Mariafrancesca; Molecules; vol. 21; nb. 8; (2016); Art.No: 1000, View in Reaxys; Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5, View in Reaxys; Lei, Xue; Zheng, Lei; Zhang, Chuanxin; Shi, Xiaodong; Chen, Yunfeng; Journal of Organic Chemistry; vol. 83; nb. 4; (2018); p. 1772 1778, View in Reaxys 2

Trost, Barry M.; Bringley, Dustin A.; O'Keefe, B. Michael; Organic Letters; vol. 15; nb. 22; (2013); p. 5630 - 5633, View in Reaxys; Yuan, Jia-Ni; Liu, Hui-Xia; Tian, Qin-Qin; Ji, Nan; Shen, Kuo; He, Wei; Synthesis (Germany); vol. 50; nb. 13; (2018); p. 2577 - 2586, View in Reaxys

13a

Pei, Xiao-Qiong; Xu, Meng-Yu; Wu, Zhong-Liu; Journal of Molecular Catalysis B: Enzymatic; vol. 123; (2016); p. 91 - 99, View in Reaxys

4a

Zhao, An; Jiang, Qing; Jia, Jing; Xu, Bin; Liu, Yufeng; Zhang, Mingzhong; Liu, Qiang; Luo, Weiping; Guo, Cancheng; Tetrahedron Letters; vol. 57; nb. 1; (2016); p. 80 - 84, View in Reaxys

(E)-1a

Bertolotti, Mattia; Brenna, Elisabetta; Crotti, Michele; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Santangelo, Sara; ChemCatChem; vol. 8; nb. 3; (2016); p. 577 - 583, View in Reaxys

2a

Wu, Hao; Sheng, Wei-Jian; Chen, Bin; Liu, Ren-Rong; Gao, Jian-Rong; Jia, Yi-Xia; Synlett; vol. 26; nb. 20; (2015); p. 2817 - 2820; Art.No: ST-2015-S0581-C, View in Reaxys

1m

Wu, Na; Wahl, Benoit; Woodward, Simon; Lewis, William; Chemistry - A European Journal; vol. 20; nb. 25; (2014); p. 7718 - 7724, View in Reaxys

(E)-5a

Gao, Jian-Rong; Wu, Hao; Xiang, Bin; Yu, Wu-Bin; Han, Liang; Jia, Yi-Xia; Journal of the American Chemical Society; vol. 135; nb. 8; (2013); p. 2983 - 2986, View in Reaxys

(E)-4m

Maity, Soham; Manna, Srimanta; Rana, Sujoy; Naveen, Togati; Mallick, Arijit; Maiti, Debabrata; Journal of the American Chemical Society; vol. 135; nb. 9; (2013); p. 3355 - 3358, View in Reaxys

a13

Xu, Changzhu; Du, Jianguo; Ma, Lichao; Li, Guowei; Tao, Minli; Zhang, Wenqin; Tetrahedron; vol. 69; nb. 23; (2013); p. 4749 - 4757, View in Reaxys

4q

Naveen, Togati; Maity, Soham; Sharma, Upendra; Maiti, Debabrata; Journal of Organic Chemistry; vol. 78; nb. 12; (2013); p. 5949 - 5954, View in Reaxys

(E)-10a

Mansell, David J.; Toogood, Helen S.; Waller, John; Hughes, John M.X.; Levy, Colin W.; Gardiner, John M.; Scrutton, Nigel S.; ACS Catalysis; vol. 3; nb. 3; (2013); p. 370 - 379, View in Reaxys

2b

Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; nb. 39; (2013); p.

6713 - 6716, View in Reaxys

19a

Durchschein, Katharina; Wallner, Silvia; MacHeroux, Peter; Schwab, Wilfried; Winkler, Thorsten; Kreis, Wolfgang; Faber, Kurt; European Journal of Organic Chemistry; nb. 26; (2012); p. 4963 - 4968, View in Reaxys

1

Czekelius, Constantin; Carreira, Erick M.; Angewandte Chemie - International Edition; vol. 42; nb. 39; (2003); p.

4793 - 4795, View in Reaxys; Czekelius, Constantin; Carreira, Erick M.; Organic Process Research and Development; vol. 11; nb. 3; (2007); p. 633 - 636, View in Reaxys

5a

Zagozda, Marcin; Plenkiewicz, Jan; Tetrahedron Asymmetry; vol. 18; nb. 12; (2007); p. 1457 - 1464, View in Reaxys

7a

Hall, Melanie; Stueckler, Clemens; Kroutil, Wolfgang; Macheroux, Peter; Faber, Kurt; Angewandte Chemie - International Edition; vol. 46; nb. 21; (2007); p. 3934 - 3937, View in Reaxys

1f

Shen, Kao-Hsien; Liu, Ju-Tsung; Wu, Yih-Ru; Yao, Ching-Fa; Synthetic Communications; vol. 37; nb. 20; (2007); p.

3677 - 3687, View in Reaxys

1b

Sun, Xiaohua; Sengupta, Sujata; Petersen; Wang, Hong; Lewis, James P.; Shi, Xiaodong; Organic Letters; vol. 9; nb. 22; (2007); p. 4495 - 4498, View in Reaxys

E-product, entry 8

Campos, Pedro J.; Garcia, Barbara; Rodriguez, Miguel A.; Tetrahedron Letters; vol. 41; nb. 6; (2000); p. 979 - 982, View in Reaxys

1l

Chu, Cheng-Ming; Liu, Ju-Tsung; Lin, Wen-Wei; Yao, Ching-Fa; Journal of the Chemical Society - Perkin Transactions 1; nb. 1; (1999); p. 47 - 52, View in Reaxys

Patent-Specific Data (3) References Patent; Yuanjiang Hualong Catalysis Technology Co., Ltd.; Guo Cancheng; Cao Zhongzhong; Guo Xin; (25 pag.); CN106995373; (2017); (A) Chinese, View in Reaxys Patent; Yuanjiang Hualong Catalysis Technology Co., Ltd.; Guo Cancheng; Cao Zhongzhong; Guo Xin; (25 pag.); CN107032939; (2017); (A) Chinese, View in Reaxys

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Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; CARREIRA, Erick, M.; WO2004/103951; (2004); (A1) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

2.678

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

Melting Point (2) 1 of 2

Melting Point [°C]

54 - 56

Location

supporting information

Xu, Changzhu; Du, Jianguo; Ma, Lichao; Li, Guowei; Tao, Minli; Zhang, Wenqin; Tetrahedron; vol. 69; nb. 23; (2013); p.

4749 - 4757, View in Reaxys 2 of 2

Melting Point [°C]

15 - 20

Miller et al.; Journal of Organic Chemistry; vol. 41; (1976); p. 2112,2118, View in Reaxys Refractive Index (1) Refractive Index Wavelength (ReTemperature (Refractive Index) [nm] fractive Index) [°C] 1.6014

589

Chromatographic Data (2) Chromatographic Location data

20

References Miller et al.; Journal of Organic Chemistry; vol. 41; (1976); p. 2112,2118, View in Reaxys

References

GC (Gas chromatography)

supporting informa- Durchschein, Katharina; Wallner, Silvia; MacHeroux, Peter; Schwab, Wilfried; Winkler, tion Thorsten; Kreis, Wolfgang; Faber, Kurt; European Journal of Organic Chemistry; nb. 26; (2012); p. 4963 - 4968, View in Reaxys; Pei, Xiao-Qiong; Xu, Meng-Yu; Wu, Zhong-Liu; Journal of Molecular Catalysis B: Enzymatic; vol. 123; (2016); p. 91 - 99, View in Reaxys

TLC (Thin layer chromatography)

supporting informa- Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; tion nb. 39; (2013); p. 6713 - 6716, View in Reaxys

Crystal Property Description (5) Colour & Other Location Properties yellow

References Naveen, Togati; Maity, Soham; Sharma, Upendra; Maiti, Debabrata; Journal of Organic Chemistry; vol. 78; nb. 12; (2013); p. 5949 - 5954, View in Reaxys; Lei, Xue; Zheng, Lei; Zhang, Chuanxin; Shi, Xiaodong; Chen, Yunfeng; Journal of Organic Chemistry; vol. 83; nb. 4; (2018); p. 1772 - 1778, View in Reaxys

yellow

Paragraph 0128

Patent; Yuanjiang Hualong Catalysis Technology Co., Ltd.; Guo Cancheng; Cao Zhongzhong; Guo Xin; (25 pag.); CN106995373; (2017); (A) Chinese, View in Reaxys

yellow

Paragraph 0129

Patent; Yuanjiang Hualong Catalysis Technology Co., Ltd.; Guo Cancheng; Cao Zhongzhong; Guo Xin; (25 pag.); CN107032939; (2017); (A) Chinese, View in Reaxys

yellow

supporting informa- Maity, Soham; Manna, Srimanta; Rana, Sujoy; Naveen, Togati; Mallick, Arijit; Maiti, Debation brata; Journal of the American Chemical Society; vol. 135; nb. 9; (2013); p. 3355 - 3358, View in Reaxys; Xu, Changzhu; Du, Jianguo; Ma, Lichao; Li, Guowei; Tao, Minli; Zhang, Wenqin; Tetrahedron; vol. 69; nb. 23; (2013); p. 4749 - 4757, View in Reaxys; Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; nb. 39; (2013); p.

6713 - 6716, View in Reaxys; Trost, Barry M.; Bringley, Dustin A.; O'Keefe, B. Michael; Organic Letters; vol. 15; nb. 22; (2013); p. 5630 - 5633, View in Reaxys; Zhao, An; Jiang, Qing; Jia, Jing; Xu, Bin; Liu, Yufeng; Zhang, Mingzhong; Liu, Qiang; Luo, Weiping; Guo, Cancheng; Tetrahedron Letters; vol. 57; nb. 1; (2016); p. 80 - 84, View in Reaxys; Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p. 3875 - 3879, View in Reaxys; Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 4815, View in Reaxys

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yellow

Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys

NMR Spectroscopy (33) 1 of 33

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys; Maity, Soham; Manna, Srimanta; Rana, Sujoy; Naveen, Togati; Mallick, Arijit; Maiti, Debabrata; Journal of the American Chemical Society; vol. 135; nb. 9; (2013); p. 3355 - 3358, View in Reaxys; Xu, Changzhu; Du, Jianguo; Ma, Lichao; Li, Guowei; Tao, Minli; Zhang, Wenqin; Tetrahedron; vol. 69; nb. 23; (2013); p. 4749 - 4757, View in Reaxys; Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys; Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; nb. 39; (2013); p. 6713 - 6716, View in Reaxys; Zhao, An; Jiang, Qing; Jia, Jing; Xu, Bin; Liu, Yufeng; Zhang, Mingzhong; Liu, Qiang; Luo, Weiping; Guo, Cancheng; Tetrahedron Letters; vol. 57; nb. 1; (2016); p. 80 - 84, View in Reaxys; Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p. 3875 - 3879, View in Reaxys; Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys; Yuan, Jia-Ni; Liu, Hui-Xia; Tian, Qin-Qin; Ji, Nan; Shen, Kuo; He, Wei; Synthesis (Germany); vol. 50; nb.

13; (2018); p. 2577 - 2586, View in Reaxys 2 of 33

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 500 scopy) [MHz] Location

supporting information

Lei, Xue; Zheng, Lei; Zhang, Chuanxin; Shi, Xiaodong; Chen, Yunfeng; Journal of Organic Chemistry; vol. 83; nb. 4; (2018); p. 1772 - 1778, View in Reaxys 3 of 33

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 125 scopy) [MHz] Location

supporting information

Lei, Xue; Zheng, Lei; Zhang, Chuanxin; Shi, Xiaodong; Chen, Yunfeng; Journal of Organic Chemistry; vol. 83; nb. 4; (2018); p. 1772 - 1778, View in Reaxys 4 of 33

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz]

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Location

Paragraph 0128

Patent; Yuanjiang Hualong Catalysis Technology Co., Ltd.; Guo Cancheng; Cao Zhongzhong; Guo Xin; (25 pag.); CN106995373; (2017); (A) Chinese, View in Reaxys 5 of 33

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 101 scopy) [MHz] Location

Paragraph 0128

Patent; Yuanjiang Hualong Catalysis Technology Co., Ltd.; Guo Cancheng; Cao Zhongzhong; Guo Xin; (25 pag.); CN106995373; (2017); (A) Chinese, View in Reaxys 6 of 33

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

Paragraph 0043; 0129

Patent; Yuanjiang Hualong Catalysis Technology Co., Ltd.; Guo Cancheng; Cao Zhongzhong; Guo Xin; (25 pag.); CN107032939; (2017); (A) Chinese, View in Reaxys 7 of 33

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 101 scopy) [MHz] Location

Paragraph 0044; 0129

Patent; Yuanjiang Hualong Catalysis Technology Co., Ltd.; Guo Cancheng; Cao Zhongzhong; Guo Xin; (25 pag.); CN107032939; (2017); (A) Chinese, View in Reaxys 8 of 33

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Naveen, Togati; Maity, Soham; Sharma, Upendra; Maiti, Debabrata; Journal of Organic Chemistry; vol. 78; nb. 12; (2013); p. 5949 - 5954, View in Reaxys; Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys; Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; nb. 39; (2013); p. 6713 - 6716, View in Reaxys; Zhao, An; Jiang, Qing; Jia, Jing; Xu, Bin; Liu, Yufeng; Zhang, Mingzhong; Liu, Qiang; Luo, Weiping; Guo, Cancheng; Tetrahedron Letters; vol.

57; nb. 1; (2016); p. 80 - 84, View in Reaxys; Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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9 of 33

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 101 scopy) [MHz] Location

supporting information

Maity, Soham; Manna, Srimanta; Rana, Sujoy; Naveen, Togati; Mallick, Arijit; Maiti, Debabrata; Journal of the American Chemical Society; vol. 135; nb. 9; (2013); p. 3355 - 3358, View in Reaxys 10 of 33

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Coupling Nuclei

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Naveen, Togati; Maity, Soham; Sharma, Upendra; Maiti, Debabrata; Journal of Organic Chemistry; vol. 78; nb. 12; (2013); p. 5949 - 5954, View in Reaxys 11 of 33

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Coupling Nuclei

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 500 scopy) [MHz] Location

supporting information

Trost, Barry M.; Bringley, Dustin A.; O'Keefe, B. Michael; Organic Letters; vol. 15; nb. 22; (2013); p. 5630 - 5633, View in Reaxys 12 of 33

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Schneider, Jakob F.; Lauber, Markus B.; Muhr, Vanessa; Kratzer, Domenic; Paradies, Jan; Organic and Biomolecular Chemistry; vol. 9; nb. 11; (2011); p. 4323 - 4327, View in Reaxys; Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys 13 of 33

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

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2018-08-17 22:03:33

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 250 scopy) [MHz] Location

supporting information

Schneider, Jakob F.; Falk, Florian C.; Froehlich, Roland; Paradies, Jan; European Journal of Organic Chemistry; nb. 12; (2010); p. 2265 - 2269, View in Reaxys; Schneider, Jakob F.; Lauber, Markus B.; Muhr, Vanessa; Kratzer, Domenic; Paradies, Jan; Organic and Biomolecular Chemistry; vol. 9; nb. 11; (2011); p. 4323 - 4327, View in Reaxys 14 of 33

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 400 scopy) [MHz] Wu, Jing; Mampreian, Dawn M.; Hoveyda, Amir H.; Journal of the American Chemical Society; vol. 127; nb. 13; (2005); p.

4584 - 4585, View in Reaxys; Zagozda, Marcin; Plenkiewicz, Jan; Tetrahedron Asymmetry; vol. 18; nb. 12; (2007); p. 1457 1464, View in Reaxys; Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys 15 of 33

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 100 scopy) [MHz] Zagozda, Marcin; Plenkiewicz, Jan; Tetrahedron Asymmetry; vol. 18; nb. 12; (2007); p. 1457 - 1464, View in Reaxys; Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p.

4295 - 4298, View in Reaxys 16 of 33

Description (NMR Spectroscopy)

Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 100 scopy) [MHz] Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys 17 of 33

Description (NMR Spectroscopy)

Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 400 scopy) [MHz] Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys 18 of 33

Description (NMR Spectroscopy)

Chemical shifts

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 360 scopy) [MHz] Location

supporting information

Hall, Melanie; Stueckler, Clemens; Hauer, Bernhard; Stuermer, Rainer; Friedrich, Thomas; Breuer, Michael; Kroutil, Wolfgang; Faber, Kurt; European Journal of Organic Chemistry; nb. 9; (2008); p. 1511 - 1516, View in Reaxys 19 of 33

Description (NMR Spectroscopy)

HMBC (Heteronuclear Multiple Bond Coherence)

Nucleus (NMR Spectroscopy)

1H; 13C

Location

supporting information

Hall, Melanie; Stueckler, Clemens; Hauer, Bernhard; Stuermer, Rainer; Friedrich, Thomas; Breuer, Michael; Kroutil, Wolfgang; Faber, Kurt; European Journal of Organic Chemistry; nb. 9; (2008); p. 1511 - 1516, View in Reaxys 20 of 33

Description (NMR Spectroscopy)

Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Temperature (NMR Spectroscopy) [°C]

26.84

Frequency (NMR Spectro- 300.13 scopy) [MHz] Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p.

8976 - 8977, View in Reaxys 21 of 33

Description (NMR Spectroscopy)

Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Temperature (NMR Spectroscopy) [°C]

26.84

Frequency (NMR Spectro- 75.4677 scopy) [MHz] Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p.

8976 - 8977, View in Reaxys 22 of 33

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Temperature (NMR Spectroscopy) [°C]

26.84

Frequency (NMR Spectro- 300 scopy) [MHz] Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p.

8976 - 8977, View in Reaxys

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23 of 33

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Temperature (NMR Spectroscopy) [°C]

26.84

Frequency (NMR Spectro- 75 scopy) [MHz] Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p.

8976 - 8977, View in Reaxys 24 of 33

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 360 scopy) [MHz] Hall, Melanie; Stueckler, Clemens; Kroutil, Wolfgang; Macheroux, Peter; Faber, Kurt; Angewandte Chemie - International Edition; vol. 46; nb. 21; (2007); p. 3934 - 3937, View in Reaxys 25 of 33

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Temperature (NMR Spectroscopy) [°C]

25

Frequency (NMR Spectro- 300 scopy) [MHz] Czekelius, Constantin; Carreira, Erick M.; Organic Process Research and Development; vol. 11; nb. 3; (2007); p. 633 - 636, View in Reaxys 26 of 33

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Temperature (NMR Spectroscopy) [°C]

25

Frequency (NMR Spectro- 75 scopy) [MHz] Czekelius, Constantin; Carreira, Erick M.; Organic Process Research and Development; vol. 11; nb. 3; (2007); p. 633 - 636, View in Reaxys 27 of 33

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

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Temperature (NMR Spectroscopy) [°C]

25

Frequency (NMR Spectro- 300 scopy) [MHz] Czekelius, Constantin; Carreira, Erick M.; Organic Letters; vol. 6; nb. 24; (2004); p. 4575 - 4577, View in Reaxys 28 of 33

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Temperature (NMR Spectroscopy) [°C]

25

Frequency (NMR Spectro- 75 scopy) [MHz] Czekelius, Constantin; Carreira, Erick M.; Organic Letters; vol. 6; nb. 24; (2004); p. 4575 - 4577, View in Reaxys 29 of 33

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Greenop, Michael W.; Thomas, C. Barry; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 8; (1995); p. 1595 - 1600, View in Reaxys; Berg, Ulf; Butts, Craig P.; Eberson, Lennart; Hartshorn, Michael P.; Persson, Ola; Acta Chemica Scandinavica; vol. 52; nb. 6; (1998); p. 761 - 769, View in Reaxys 30 of 33

Description (NMR Spectroscopy)

Spin-spin coupling constants

Solvents (NMR Spectroscopy)

CDCl3

Comment (NMR Spectroscopy)

1H-1H

Greenop, Michael W.; Thomas, C. Barry; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 8; (1995); p. 1595 - 1600, View in Reaxys; Berg, Ulf; Butts, Craig P.; Eberson, Lennart; Hartshorn, Michael P.; Persson, Ola; Acta Chemica Scandinavica; vol. 52; nb. 6; (1998); p. 761 - 769, View in Reaxys 31 of 33

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CCl4

Ohta, Hiromichi; Kobayashi, Naoki; Ozaki, Kazuhiko; Journal of Organic Chemistry; vol. 54; nb. 8; (1989); p. 1802 - 1804, View in Reaxys; Abbenante, Giovanni; Hughes, Robert; Prager, Rolf H.; Australian Journal of Chemistry; vol. 47; nb. 8; (1994); p. 1441 - 1452, View in Reaxys 32 of 33

Description (NMR Spectroscopy)

Spin-spin coupling constants

Solvents (NMR Spectroscopy)

CCl4

Comment (NMR Spectroscopy)

1H-1H

Abbenante, Giovanni; Hughes, Robert; Prager, Rolf H.; Australian Journal of Chemistry; vol. 47; nb. 8; (1994); p. 1441 1452, View in Reaxys 33 of 33

Description (NMR Spectroscopy)

NMR

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Sousa et al.; Journal of Organic Chemistry; vol. 34; (1969); p. 3320,3323, View in Reaxys; Miller et al.; Journal of Organic Chemistry; vol. 41; (1976); p. 2112,2118, View in Reaxys IR Spectroscopy (6) 1 of 6

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat liquid

Location

supporting information

Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; nb. 39; (2013); p. 6713 6716, View in Reaxys 2 of 6

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat liquid

Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys 3 of 6

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

film

Czekelius, Constantin; Carreira, Erick M.; Organic Process Research and Development; vol. 11; nb. 3; (2007); p. 633 - 636, View in Reaxys 4 of 6

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

film

Czekelius, Constantin; Carreira, Erick M.; Organic Letters; vol. 6; nb. 24; (2004); p. 4575 - 4577, View in Reaxys 5 of 6

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

3100 - 600 cm**(-1)

Ohta, Hiromichi; Kobayashi, Naoki; Ozaki, Kazuhiko; Journal of Organic Chemistry; vol. 54; nb. 8; (1989); p. 1802 - 1804, View in Reaxys 6 of 6

Description (IR Spectroscopy)

IR

Sousa et al.; Journal of Organic Chemistry; vol. 34; (1969); p. 3320,3323, View in Reaxys Mass Spectrometry (8) Description (Mass Location Spectrometry)

References

gas chromatograParagraph 0128 phy mass spectrometry (GCMS); spectrum

Patent; Yuanjiang Hualong Catalysis Technology Co., Ltd.; Guo Cancheng; Cao Zhongzhong; Guo Xin; (25 pag.); CN106995373; (2017); (A) Chinese, View in Reaxys

gas chromatograParagraph 0129 phy mass spectrometry (GCMS); spectrum

Patent; Yuanjiang Hualong Catalysis Technology Co., Ltd.; Guo Cancheng; Cao Zhongzhong; Guo Xin; (25 pag.); CN107032939; (2017); (A) Chinese, View in Reaxys

spectrum

supporting informa- Zhao, An; Jiang, Qing; Jia, Jing; Xu, Bin; Liu, Yufeng; Zhang, Mingzhong; Liu, Qiang; tion Luo, Weiping; Guo, Cancheng; Tetrahedron Letters; vol. 57; nb. 1; (2016); p. 80 - 84, View in Reaxys

gas chromatograsupporting informa- Maity, Soham; Manna, Srimanta; Rana, Sujoy; Naveen, Togati; Mallick, Arijit; Maiti, Debaphy mass spectrom- tion brata; Journal of the American Chemical Society; vol. 135; nb. 9; (2013); p. 3355 - 3358, etry (GCMS); specView in Reaxys trum gas chromatography mass spectrom-

Naveen, Togati; Maity, Soham; Sharma, Upendra; Maiti, Debabrata; Journal of Organic Chemistry; vol. 78; nb. 12; (2013); p. 5949 - 5954, View in Reaxys

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etry (GCMS); spectrum electron impact (EI); spectrum

supporting informa- Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; tion nb. 39; (2013); p. 6713 - 6716, View in Reaxys

spectrum; electron impact (EI)

Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p. 8976 - 8977, View in Reaxys; Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p.

4295 - 4298, View in Reaxys

spectrum

Ohta, Hiromichi; Kobayashi, Naoki; Ozaki, Kazuhiko; Journal of Organic Chemistry; vol. 54; nb. 8; (1989); p. 1802 - 1804, View in Reaxys

UV/VIS Spectroscopy (2) 1 of 2

Absorption Maxima (UV/ VIS) [nm]

306

Toogood, Helen S.; Fryszkowska, Anna; Hare, Victoria; Fisher, Karl; Roujeinikova, Anna; Leys, David; Gardiner, John M.; Stephens, Gill M.; Scrutton, Nigel S.; Advanced Synthesis and Catalysis; vol. 350; nb. 17; (2008); p. 2789 - 2803, View in Reaxys 2 of 2

Description (UV/VIS Spectroscopy)

Absorption maxima

Sousa et al.; Journal of Organic Chemistry; vol. 34; (1969); p. 3320,3323, View in Reaxys

Reaxys ID 2363534 View in Reaxys

4/65 CAS Registry Number: 66618-75-5 Chemical Name: α,α-Dimethyl-α-nitrostyrol Linear Structure Formula: C10H11NO2 Molecular Formula: C10H11NO2 Molecular Weight: 177.203 Type of Substance: isocyclic InChI Key: SMLHUHINFZJSHO-UHFFFAOYSA-N Note:

O N O

Druglikeness (1) 1 of 1

LogP

2.918

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

Boiling Point (1) Boiling Point [°C] 103 - 106

Pressure (Boiling Point) [Torr]

References

4

Tuaillon; Perrot; Helvetica Chimica Acta; vol. 61; (1978); p. 558,563, View in Reaxys

IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

IR

Tuaillon; Perrot; Helvetica Chimica Acta; vol. 61; (1978); p. 558,563, View in Reaxys

Reaxys ID 2521190 View in Reaxys

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CAS Registry Number: 90922-14-8 Chemical Name: 1-Nitro-2-p-tolyl-propen-(1) Linear Structure Formula: C10H11NO2 Molecular Formula: C10H11NO2 Molecular Weight: 177.203 Type of Substance: isocyclic InChI Key: URWVMIBYTLBWKH-UHFFFAOYSA-N Note:

O N O

Substance Label (1) Label References 2d

Wu, Hao; Sheng, Wei-Jian; Chen, Bin; Liu, Ren-Rong; Gao, Jian-Rong; Jia, Yi-Xia; Synlett; vol. 26; nb. 20; (2015); p. 2817 - 2820; Art.No: ST-2015-S0581-C, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.115

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

Boiling Point (1) Boiling Point [°C] 115 - 120

Pressure (Boiling Point) [Torr]

References

2

Ogloblin,K.A. et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 34; (1964); p. 170 - 181,168 - 178, View in Reaxys

Refractive Index (1) Refractive Index Wavelength (ReTemperature (Refractive Index) [nm] fractive Index) [°C] 1.5695

589

20

References Ogloblin,K.A. et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 34; (1964); p. 170 - 181,168 - 178, View in Reaxys

Density (1) 1 of 1

Density [g·cm-3]

1.0961

Reference Temperature [°C]

4

Measurement Temperature 20 [°C] Ogloblin,K.A. et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 34; (1964); p. 170 - 181,168 - 178, View in Reaxys

Reaxys ID 6502151 View in Reaxys

6/65 CAS Registry Number: 91923-49-8 Chemical Name: (Z)-(3-nitrobut-2-en-2-yl)benzene; (Z)-2-nitro-3phenylbut-2-ene; (Z)-3-phenyl-2-nitro-2-butene Linear Structure Formula: C10H11NO2 Molecular Formula: C10H11NO2 Molecular Weight: 177.203 Type of Substance: isocyclic InChI Key: SMLHUHINFZJSHO-HJWRWDBZSA-N Note:

N O

O

Substance Label (3) Label References 1

Kawai, Yasushi; Inaba, Yoshikazu; Hayashi, Motoko; Tokitoh, Norihiro; Tetrahedron Letters; vol. 42; nb. 19; (2001); p. 3367 - 3368, View in Reaxys

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3a

Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318, View in Reaxys

24

Grant, Richard D.; Pinhey, John T.; Australian Journal of Chemistry; vol. 37; nb. 6; (1984); p. 1231 - 1244, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.918

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

Boiling Point (1) Boiling Point [°C] 114

Pressure (Boiling Point) [Torr]

References

20

Grant, Richard D.; Pinhey, John T.; Australian Journal of Chemistry; vol. 37; nb. 6; (1984); p.

1231 - 1244, View in Reaxys

NMR Spectroscopy (5) 1 of 5

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Brenna, Elisabetta; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Serra, Stefano; Advanced Synthesis and Catalysis; vol. 354; nb. 1; (2012); p. 105 - 112, View in Reaxys 2 of 5

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Brenna, Elisabetta; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Serra, Stefano; Advanced Synthesis and Catalysis; vol. 354; nb. 1; (2012); p. 105 - 112, View in Reaxys 3 of 5

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Grant, Richard D.; Pinhey, John T.; Australian Journal of Chemistry; vol. 37; nb. 6; (1984); p. 1231 - 1244, View in Reaxys; Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318, View in Reaxys 4 of 5

Nucleus (NMR Spectroscopy)

1H

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Coupling Nuclei

1H

Solvents (NMR Spectroscopy)

CDCl3

Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318, View in Reaxys 5 of 5

Description (NMR Spectroscopy)

Spin-spin coupling constants

Solvents (NMR Spectroscopy)

CDCl3

Comment (NMR Spectroscopy)

1H-1H

Grant, Richard D.; Pinhey, John T.; Australian Journal of Chemistry; vol. 37; nb. 6; (1984); p. 1231 - 1244, View in Reaxys IR Spectroscopy (2) 1 of 2

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318, View in Reaxys 2 of 2

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

1515 - 705 cm**(-1)

Grant, Richard D.; Pinhey, John T.; Australian Journal of Chemistry; vol. 37; nb. 6; (1984); p. 1231 - 1244, View in Reaxys Mass Spectrometry (2) Description (Mass Location Spectrometry) GCMS (Gas chromatography mass spectrometry); EI (Electron impact); Spectrum

References

supporting informa- Brenna, Elisabetta; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Serra, Stefation no; Advanced Synthesis and Catalysis; vol. 354; nb. 1; (2012); p. 105 - 112, View in Reaxys

spectrum

Grant, Richard D.; Pinhey, John T.; Australian Journal of Chemistry; vol. 37; nb. 6; (1984); p.

1231 - 1244, View in Reaxys

UV/VIS Spectroscopy (1) 1 of 1

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ VIS) [nm]

215; 269

Ext./Abs. Coefficient [l·mol-1cm-1]

8420; 3520

Grant, Richard D.; Pinhey, John T.; Australian Journal of Chemistry; vol. 37; nb. 6; (1984); p. 1231 - 1244, View in Reaxys

Reaxys ID 8830731 View in Reaxys

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Chemical Name: (E)-(3-nitrobut-2-en-2-yl)benzene; (E)-3-phenyl-2nitro-2-butene Linear Structure Formula: C10H11NO2 Molecular Formula: C10H11NO2 Molecular Weight: 177.203 Type of Substance: isocyclic InChI Key: SMLHUHINFZJSHO-CMDGGOBGSA-N Note:

O N O

Substance Label (1) Label References 3b

Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.918

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

NMR Spectroscopy (4) 1 of 4

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Brenna, Elisabetta; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Serra, Stefano; Advanced Synthesis and Catalysis; vol. 354; nb. 1; (2012); p. 105 - 112, View in Reaxys 2 of 4

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Brenna, Elisabetta; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Serra, Stefano; Advanced Synthesis and Catalysis; vol. 354; nb. 1; (2012); p. 105 - 112, View in Reaxys 3 of 4

Nucleus (NMR Spectroscopy)

1H

Coupling Nuclei

1H

Solvents (NMR Spectroscopy)

CDCl3

Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318, View in Reaxys 4 of 4

Description (NMR Spectroscopy)

Chemical shifts

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Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) GCMS (Gas chromatography mass spectrometry); EI (Electron impact); Spectrum

References

supporting informa- Brenna, Elisabetta; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Serra, Stefation no; Advanced Synthesis and Catalysis; vol. 354; nb. 1; (2012); p. 105 - 112, View in Reaxys

Reaxys ID 11138717 View in Reaxys

8/65 CAS Registry Number: 947383-46-2 Chemical Name: (E)-1-methyl-4-(1-nitroprop-1-en-2-yl)benzene; (E)-2-(4-methylphenyl)-1-nitro-1-propene; (E)-1-nitro-2-(4-methylphenyl)propene Linear Structure Formula: C10H11NO2 Molecular Formula: C10H11NO2 Molecular Weight: 177.203 InChI Key: URWVMIBYTLBWKH-VQHVLOKHSA-N Note:

O N O

Substance Label (10) Label References 1e

Xu, Weici; Arieno, Marcus; Löw, Henrik; Huang, Kaifang; Xie, Xiulan; Cruchter, Thomas; Ma, Qiao; Xi, Jianwei; Huang, Biao; Wiest, Olaf; Gong, Lei; Meggers, Eric; Journal of the American Chemical Society; vol. 138; nb.

28; (2016); p. 8774 - 8780, View in Reaxys; Lei, Xue; Zheng, Lei; Zhang, Chuanxin; Shi, Xiaodong; Chen, Yunfeng; Journal of Organic Chemistry; vol. 83; nb. 4; (2018); p. 1772 - 1778, View in Reaxys

1i

Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5, View in Reaxys

2q

Yang, Zan; Li, Jiao; Hua, Jie; Yang, Tao; Yi, Jianmin; Zhou, Congshan; Synlett; vol. 28; nb. 9; (2017); p. 1079 1082; Art.No: ST-2016-W0789-L, View in Reaxys

4c

Manna, Srimanta; Antonchick, Andrey P.; Chemistry - A European Journal; vol. 23; nb. 32; (2017); p. 7825 - 7829, View in Reaxys

1b

Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb.

26; (2016); p. 4812 - 4815, View in Reaxys

1f

Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb.

18; (2015); p. 3875 - 3879, View in Reaxys

1l

Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol.

19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys

2c

Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; nb. 39; (2013); p.

6713 - 6716, View in Reaxys

1d

Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p. 8976 - 8977, View in Reaxys

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5c

Zagozda, Marcin; Plenkiewicz, Jan; Tetrahedron Asymmetry; vol. 18; nb. 12; (2007); p. 1457 - 1464, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.115

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

Chromatographic Data (1) Chromatographic Location data TLC (Thin layer chromatography)

supporting informa- Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; tion nb. 39; (2013); p. 6713 - 6716, View in Reaxys

Crystal Property Description (2) Colour & Other Location Properties yellow yellow

References

References Lei, Xue; Zheng, Lei; Zhang, Chuanxin; Shi, Xiaodong; Chen, Yunfeng; Journal of Organic Chemistry; vol. 83; nb. 4; (2018); p. 1772 - 1778, View in Reaxys

supporting informa- Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; tion nb. 39; (2013); p. 6713 - 6716, View in Reaxys; Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p. 3875 3879, View in Reaxys; Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys; Yang, Zan; Li, Jiao; Hua, Jie; Yang, Tao; Yi, Jianmin; Zhou, Congshan; Synlett; vol. 28; nb.

9; (2017); p. 1079 - 1082; Art.No: ST-2016-W0789-L, View in Reaxys

NMR Spectroscopy (11) 1 of 11

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys; Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys; Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; nb. 39; (2013); p. 6713 - 6716, View in Reaxys; Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol.

357; nb. 18; (2015); p. 3875 - 3879, View in Reaxys; Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys; Yang, Zan; Li, Jiao; Hua, Jie; Yang, Tao; Yi, Jianmin; Zhou, Congshan; Synlett; vol. 28; nb. 9; (2017); p. 1079 - 1082; Art.No: ST-2016-W0789-L, View in Reaxys; Lei, Xue; Zheng, Lei; Zhang, Chuanxin; Shi, Xiaodong; Chen, Yunfeng; Journal of Organic Chemistry; vol. 83; nb. 4; (2018); p. 1772 - 1778, View in Reaxys 2 of 11

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

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Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys; Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys; Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; nb. 39; (2013); p. 6713 - 6716, View in Reaxys; Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys; Yang, Zan; Li, Jiao; Hua, Jie; Yang, Tao; Yi, Jianmin; Zhou, Congshan; Synlett; vol. 28; nb. 9; (2017); p. 1079 - 1082; Art.No: ST-2016-W0789-L, View in Reaxys; Lei, Xue; Zheng, Lei; Zhang, Chuanxin; Shi, Xiaodong; Chen, Yunfeng; Journal of Organic Chemistry; vol. 83; nb. 4; (2018); p. 1772 - 1778, View in Reaxys 3 of 11

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 500 scopy) [MHz] Location

supporting information

Manna, Srimanta; Antonchick, Andrey P.; Chemistry - A European Journal; vol. 23; nb. 32; (2017); p. 7825 - 7829, View in Reaxys 4 of 11

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 250 scopy) [MHz] Location

supporting information

Schneider, Jakob F.; Lauber, Markus B.; Muhr, Vanessa; Kratzer, Domenic; Paradies, Jan; Organic and Biomolecular Chemistry; vol. 9; nb. 11; (2011); p. 4323 - 4327, View in Reaxys 5 of 11

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 63 scopy) [MHz] Location

supporting information

Schneider, Jakob F.; Lauber, Markus B.; Muhr, Vanessa; Kratzer, Domenic; Paradies, Jan; Organic and Biomolecular Chemistry; vol. 9; nb. 11; (2011); p. 4323 - 4327, View in Reaxys 6 of 11

Description (NMR Spectroscopy)

Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Temperature (NMR Spectroscopy) [°C]

26.84

Frequency (NMR Spectro- 75.4677 scopy) [MHz] Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p.

8976 - 8977, View in Reaxys

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7 of 11

Description (NMR Spectroscopy)

Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Temperature (NMR Spectroscopy) [°C]

26.84

Frequency (NMR Spectro- 300.13 scopy) [MHz] Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p.

8976 - 8977, View in Reaxys 8 of 11

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Temperature (NMR Spectroscopy) [°C]

26.84

Frequency (NMR Spectro- 75 scopy) [MHz] Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p.

8976 - 8977, View in Reaxys 9 of 11

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Temperature (NMR Spectroscopy) [°C]

26.84

Frequency (NMR Spectro- 300 scopy) [MHz] Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p.

8976 - 8977, View in Reaxys 10 of 11

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 400 scopy) [MHz] Zagozda, Marcin; Plenkiewicz, Jan; Tetrahedron Asymmetry; vol. 18; nb. 12; (2007); p. 1457 - 1464, View in Reaxys 11 of 11

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 100 scopy) [MHz]

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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Zagozda, Marcin; Plenkiewicz, Jan; Tetrahedron Asymmetry; vol. 18; nb. 12; (2007); p. 1457 - 1464, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat liquid

Location

supporting information

Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; nb. 39; (2013); p. 6713 6716, View in Reaxys Mass Spectrometry (2) Description (Mass Location Spectrometry)

References

high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); time-offlight mass spectra (TOFMS); spectrum

supporting informa- Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; tion nb. 39; (2013); p. 6713 - 6716, View in Reaxys

spectrum; electron impact (EI)

Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p. 8976 - 8977, View in Reaxys

Reaxys ID 22818473 View in Reaxys

9/65 CAS Registry Number: 1402166-80-6 Chemical Name: (E)-1-methyl-2-(1-nitroprop-1-en-2-yl)benzene Linear Structure Formula: C10H11NO2 Molecular Formula: C10H11NO2 Molecular Weight: 177.203 InChI Key: ADOKEWZOTKPCEX-VQHVLOKHSA-N Note:

O N O

Substance Label (1) Label References 1k

Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb.

18; (2015); p. 3875 - 3879, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.115

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

Crystal Property Description (1) Colour & Other Location Properties yellow

References

supporting informa- Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and tion Catalysis; vol. 357; nb. 18; (2015); p. 3875 - 3879, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys; Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p. 3875 - 3879, View in Reaxys 2 of 2

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys

Reaxys ID 28862758 View in Reaxys

10/65 O

Linear Structure Formula: C10H11NO2 Molecular Formula: C10H11NO2 Molecular Weight: 177.203 InChI Key: UYTSNSJVBSRZKN-UHFFFAOYSA-N Note:

N O

Substance Label (1) Label References 2c

Wu, Hao; Sheng, Wei-Jian; Chen, Bin; Liu, Ren-Rong; Gao, Jian-Rong; Jia, Yi-Xia; Synlett; vol. 26; nb. 20; (2015); p. 2817 - 2820; Art.No: ST-2015-S0581-C, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.115

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

Reaxys ID 30915347 View in Reaxys

11/65 O

Chemical Name: (E)-1-methyl-3-(1-nitroprop-1-en-2-yl)benzene Linear Structure Formula: C10H11NO2 Molecular Formula: C10H11NO2 Molecular Weight: 177.203 InChI Key: UYTSNSJVBSRZKN-VQHVLOKHSA-N Note:

N O

Substance Label (1)

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Label

References

1h

Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.115

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

Crystal Property Description (1) Colour & Other Location Properties yellow

References

supporting informa- Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; tion (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 500 scopy) [MHz] Location

supporting information

Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew.

Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5, View in Reaxys 2 of 2

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 125 scopy) [MHz] Location

supporting information

Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew.

Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5, View in Reaxys

Reaxys ID 11138720 View in Reaxys

12/65 CAS Registry Number: 947383-48-4 Chemical Name: (E)-1-fluoro-4-(1-nitroprop-1-en-2-yl)benzene; (E)-2-(4'-fluoro-phenyl)-1-nitro-propene; (E)-2-(4-fluorophenyl)-1-nitro-1-propene; (E)-2-(4-fluorophenyl)-1-nitropropene Linear Structure Formula: C9H8FNO2 Molecular Formula: C9H8FNO2 Molecular Weight: 181.166 InChI Key: RLYORAKGBASPCU-VOTSOKGWSA-N Note:

O N O

F

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Substance Label (6) Label References 1d

Lei, Xue; Zheng, Lei; Zhang, Chuanxin; Shi, Xiaodong; Chen, Yunfeng; Journal of Organic Chemistry; vol. 83; nb.

4; (2018); p. 1772 - 1778, View in Reaxys

(E)-1e

Bertolotti, Mattia; Brenna, Elisabetta; Crotti, Michele; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Santangelo, Sara; ChemCatChem; vol. 8; nb. 3; (2016); p. 577 - 583, View in Reaxys

1e

Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb.

26; (2016); p. 4812 - 4815, View in Reaxys

1b

Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb.

11; (2008); p. 4295 - 4298, View in Reaxys; Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p. 3875 - 3879, View in Reaxys

1i

Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol.

19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys

1f

Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p. 8976 - 8977, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.839

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

Crystal Property Description (3) Colour & Other Location Properties yellow yellow

References Lei, Xue; Zheng, Lei; Zhang, Chuanxin; Shi, Xiaodong; Chen, Yunfeng; Journal of Organic Chemistry; vol. 83; nb. 4; (2018); p. 1772 - 1778, View in Reaxys

supporting informa- Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and tion Catalysis; vol. 357; nb. 18; (2015); p. 3875 - 3879, View in Reaxys; Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys

yellow

Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys

NMR Spectroscopy (14) 1 of 14

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 500 scopy) [MHz] Location

supporting information

Lei, Xue; Zheng, Lei; Zhang, Chuanxin; Shi, Xiaodong; Chen, Yunfeng; Journal of Organic Chemistry; vol. 83; nb. 4; (2018); p. 1772 - 1778, View in Reaxys 2 of 14

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

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Frequency (NMR Spectro- 125 scopy) [MHz] Location

supporting information

Lei, Xue; Zheng, Lei; Zhang, Chuanxin; Shi, Xiaodong; Chen, Yunfeng; Journal of Organic Chemistry; vol. 83; nb. 4; (2018); p. 1772 - 1778, View in Reaxys 3 of 14

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys; Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys; Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p.

3875 - 3879, View in Reaxys; Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys 4 of 14

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Coupling Nuclei

19F

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb.

33; (2013); p. 10840 - 10844, View in Reaxys; Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys 5 of 14

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Schneider, Jakob F.; Lauber, Markus B.; Muhr, Vanessa; Kratzer, Domenic; Paradies, Jan; Organic and Biomolecular Chemistry; vol. 9; nb. 11; (2011); p. 4323 - 4327, View in Reaxys; Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys 6 of 14

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

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Frequency (NMR Spectro- 250 scopy) [MHz] Location

supporting information

Schneider, Jakob F.; Lauber, Markus B.; Muhr, Vanessa; Kratzer, Domenic; Paradies, Jan; Organic and Biomolecular Chemistry; vol. 9; nb. 11; (2011); p. 4323 - 4327, View in Reaxys 7 of 14

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 400 scopy) [MHz] Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys 8 of 14

Description (NMR Spectroscopy)

Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 400 scopy) [MHz] Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys 9 of 14

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 100 scopy) [MHz] Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys 10 of 14

Description (NMR Spectroscopy)

Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 100 scopy) [MHz] Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys 11 of 14

Description (NMR Spectroscopy)

Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Temperature (NMR Spectroscopy) [°C]

29.84

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Frequency (NMR Spectro- 100.613 scopy) [MHz] Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p.

8976 - 8977, View in Reaxys 12 of 14

Description (NMR Spectroscopy)

Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Temperature (NMR Spectroscopy) [°C]

29.84

Frequency (NMR Spectro- 400.13 scopy) [MHz] Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p.

8976 - 8977, View in Reaxys 13 of 14

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Temperature (NMR Spectroscopy) [°C]

29.84

Frequency (NMR Spectro- 400 scopy) [MHz] Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p.

8976 - 8977, View in Reaxys 14 of 14

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Temperature (NMR Spectroscopy) [°C]

29.84

Frequency (NMR Spectro- 100 scopy) [MHz] Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p.

8976 - 8977, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat liquid

Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum; electron impact (EI)

Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p. 8976 - 8977, View in Reaxys; Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys

UV/VIS Spectroscopy (1)

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1 of 1

Absorption Maxima (UV/ VIS) [nm]

312

Toogood, Helen S.; Fryszkowska, Anna; Hare, Victoria; Fisher, Karl; Roujeinikova, Anna; Leys, David; Gardiner, John M.; Stephens, Gill M.; Scrutton, Nigel S.; Advanced Synthesis and Catalysis; vol. 350; nb. 17; (2008); p. 2789 - 2803, View in Reaxys

Reaxys ID 19761860 View in Reaxys

13/65 O

Linear Structure Formula: C9H8FNO2 Molecular Formula: C9H8FNO2 Molecular Weight: 181.166 InChI Key: RLYORAKGBASPCU-UHFFFAOYSA-N Note:

N O

F

Substance Label (1) Label References 2c

Choudhary, Manoj K.; Rao Ganga, Venkata Subba; Menapara, Tusharkumar; Kureshy, Rukhsana I.; Khan, Noor-Ul H.; Abdi, Sayed H. R.; Suresh, Eringathodi; RSC Advances; vol. 6; nb. 106; (2016); p. 104148 - 104153, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.839

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

Reaxys ID 21214379 View in Reaxys

14/65 O

Linear Structure Formula: C9H8FNO2 Molecular Formula: C9H8FNO2 Molecular Weight: 181.166 InChI Key: OEJPIBJTMNJHLB-UHFFFAOYSA-N Note:

N F

O

Druglikeness (1) 1 of 1

LogP

2.839

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

NMR Spectroscopy (2) 1 of 2

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

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Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Uraguchi, Daisuke; Oyaizu, Keigo; Ooi, Takashi; Chemistry - A European Journal; vol. 18; nb. 27; (2012); p. 8306 - 8309, View in Reaxys 2 of 2

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 101 scopy) [MHz] Location

supporting information

Uraguchi, Daisuke; Oyaizu, Keigo; Ooi, Takashi; Chemistry - A European Journal; vol. 18; nb. 27; (2012); p. 8306 - 8309, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Location

supporting information

Comment (IR Spectroscopy)

neat (no solvent)

Uraguchi, Daisuke; Oyaizu, Keigo; Ooi, Takashi; Chemistry - A European Journal; vol. 18; nb. 27; (2012); p. 8306 - 8309, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) HRMS (High resolution mass spectrometry); ESI (Electrospray ionisation); Spectrum

References

supporting informa- Uraguchi, Daisuke; Oyaizu, Keigo; Ooi, Takashi; Chemistry - A European Journal; vol. 18; nb. tion 27; (2012); p. 8306 - 8309, View in Reaxys

Reaxys ID 22818467 View in Reaxys

15/65 CAS Registry Number: 1402166-81-7 Chemical Name: (E)-1-fluoro-3-(1-nitroprop-1-en-2-yl)benzene Linear Structure Formula: C9H8FNO2 Molecular Formula: C9H8FNO2 Molecular Weight: 181.166 InChI Key: VOKBIRZROHZDAP-VOTSOKGWSA-N Note:

O F

N O

Substance Label (1) Label References 1d

Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol.

19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.839

H Bond Donors

0

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H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

NMR Spectroscopy (3) 1 of 3

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys; Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys 2 of 3

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Coupling Nuclei

19F

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb.

33; (2013); p. 10840 - 10844, View in Reaxys 3 of 3

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys

Reaxys ID 23875298 View in Reaxys

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

16/65

37/100

2018-08-17 22:03:33

O

CAS Registry Number: 1279693-17-2 Chemical Name: (E)-1-fluoro-2-(1-nitroprop-1-en-2-yl)benzene Linear Structure Formula: C9H8FNO2 Molecular Formula: C9H8FNO2 Molecular Weight: 181.166 InChI Key: OEJPIBJTMNJHLB-VOTSOKGWSA-N Note:

N F

O

Substance Label (2) Label References 1j

Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb.

18; (2015); p. 3875 - 3879, View in Reaxys

1p

Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol.

19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.839

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

Crystal Property Description (1) Colour & Other Location Properties yellow

References

supporting informa- Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and tion Catalysis; vol. 357; nb. 18; (2015); p. 3875 - 3879, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb.

33; (2013); p. 10840 - 10844, View in Reaxys; Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p. 3875 - 3879, View in Reaxys 2 of 2

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Coupling Nuclei

19F

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb.

33; (2013); p. 10840 - 10844, View in Reaxys

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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Reaxys ID 11138718 View in Reaxys

17/65 O

CAS Registry Number: 947383-47-3 Chemical Name: (E)-4-(1-nitroprop-1-en-2-yl)benzonitrile; (E)-2-(4cyanophenyl)-1-nitro-1-propene Linear Structure Formula: C10H8N2O2 Molecular Formula: C10H8N2O2 Molecular Weight: 188.186 InChI Key: VLTFYWXLCRPRRQ-BQYQJAHWSA-N Note:

N O

N

Substance Label (2) Label References 1g

Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb.

26; (2016); p. 4812 - 4815, View in Reaxys

1e

Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p. 8976 - 8977, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.401

H Bond Donors

0

H Bond Acceptors

1

Rotatable Bonds

2

TPSA

69.61

Lipinski Number

4

Veber Number

2

Melting Point (1) 1 of 1

Melting Point [°C]

54 - 56

Location

supporting information

Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys Crystal Property Description (1) Colour & Other Location Properties yellow

References

supporting informa- Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Comtion munications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys

NMR Spectroscopy (7) 1 of 7

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Schneider, Jakob F.; Lauber, Markus B.; Muhr, Vanessa; Kratzer, Domenic; Paradies, Jan; Organic and Biomolecular Chemistry; vol. 9; nb. 11; (2011); p. 4323 - 4327, View in Reaxys; Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, ShouFei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys 2 of 7

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

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Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys 3 of 7

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 250 scopy) [MHz] Location

supporting information

Schneider, Jakob F.; Lauber, Markus B.; Muhr, Vanessa; Kratzer, Domenic; Paradies, Jan; Organic and Biomolecular Chemistry; vol. 9; nb. 11; (2011); p. 4323 - 4327, View in Reaxys 4 of 7

Description (NMR Spectroscopy)

Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Temperature (NMR Spectroscopy) [°C]

26.84

Frequency (NMR Spectro- 300.13 scopy) [MHz] Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p.

8976 - 8977, View in Reaxys 5 of 7

Description (NMR Spectroscopy)

Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Temperature (NMR Spectroscopy) [°C]

26.84

Frequency (NMR Spectro- 75.4677 scopy) [MHz] Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p.

8976 - 8977, View in Reaxys 6 of 7

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Temperature (NMR Spectroscopy) [°C]

26.84

Frequency (NMR Spectro- 300 scopy) [MHz] Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p.

8976 - 8977, View in Reaxys

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7 of 7

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Temperature (NMR Spectroscopy) [°C]

26.84

Frequency (NMR Spectro- 75 scopy) [MHz] Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p.

8976 - 8977, View in Reaxys Mass Spectrometry (2) Description (Mass Location Spectrometry) high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

References

supporting informa- Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Comtion munications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys

spectrum; electron impact (EI)

Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p. 8976 - 8977, View in Reaxys

Reaxys ID 19317763 View in Reaxys

18/65 CAS Registry Number: 1141388-24-0 Linear Structure Formula: C10H8N2O2 Molecular Formula: C10H8N2O2 Molecular Weight: 188.186 InChI Key: VLTFYWXLCRPRRQ-UHFFFAOYSA-N Note:

N O

O

N

Druglikeness (1) 1 of 1

LogP

2.401

H Bond Donors

0

H Bond Acceptors

1

Rotatable Bonds

2

TPSA

69.61

Lipinski Number

4

Veber Number

2

Reaxys ID 22818475 View in Reaxys

19/65 CAS Registry Number: 1402166-88-4 Chemical Name: (E)-1-ethyl-4-(1-nitroprop-1-en-2-yl)benzene Linear Structure Formula: C11H13NO2 Molecular Formula: C11H13NO2 Molecular Weight: 191.23 InChI Key: GVRHONFBASHPTD-CMDGGOBGSA-N Note:

O N O

Substance Label (1) Label References

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

41/100

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1m

Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol.

19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.579

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

3

TPSA

45.82

Lipinski Number

4

Veber Number

2

NMR Spectroscopy (3) 1 of 3

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys; Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys 2 of 3

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys; Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys 3 of 3

Description (NMR Spectroscopy)

COSY (Correlation Spectroscopy); Spectrum

Nucleus (NMR Spectroscopy)

1H; 1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys

Reaxys ID 7528724 View in Reaxys

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

20/65

42/100

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Chemical Name: 2-(4-methoxyphenyl)-1-nitro-1-propene Linear Structure Formula: C10H11NO3 Molecular Formula: C10H11NO3 Molecular Weight: 193.202 Type of Substance: isocyclic InChI Key: MTXXEBUHPMRMGA-FPLPWBNLSA-N Note:

N O

O

O

Druglikeness (1) 1 of 1

LogP

2.593

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

3

TPSA

55.05

Lipinski Number

4

Veber Number

2

NMR Spectroscopy (2) 1 of 2

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Barco, Achille; Benetti, Simonetta; De Risi, Carmela; Morelli, Carlo F.; Pollini, Gian P.; Zanirato, Vinicio; Tetrahedron; vol. 52; nb. 27; (1996); p. 9275 - 9288, View in Reaxys 2 of 2

Description (NMR Spectroscopy)

Spin-spin coupling constants

Solvents (NMR Spectroscopy)

CDCl3

Comment (NMR Spectroscopy)

1H-1H

Barco, Achille; Benetti, Simonetta; De Risi, Carmela; Morelli, Carlo F.; Pollini, Gian P.; Zanirato, Vinicio; Tetrahedron; vol. 52; nb. 27; (1996); p. 9275 - 9288, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

1500 - 1330 cm**(-1)

Barco, Achille; Benetti, Simonetta; De Risi, Carmela; Morelli, Carlo F.; Pollini, Gian P.; Zanirato, Vinicio; Tetrahedron; vol. 52; nb. 27; (1996); p. 9275 - 9288, View in Reaxys

Reaxys ID 9617849 View in Reaxys

21/65 CAS Registry Number: 615552-91-5 Chemical Name: (E)-1-methoxy-4-(1-nitroprop-1-en-2-yl)benzene; (E)-2-(4-methoxyphenyl)-1-nitro-1-propene; (E)-2-(4-methoxy-phenyl)-1-nitro-propene; (E)-1-nitro-2-(4-methoxyphenyl)propene; (E)-2-(4-methoxyphenyl)-1-nitropropene Linear Structure Formula: C10H11NO3 Molecular Formula: C10H11NO3 Molecular Weight: 193.202 Type of Substance: isocyclic InChI Key: MTXXEBUHPMRMGA-BQYQJAHWSA-N

O N O

O

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Note: Substance Label (9) Label References 1b

Lei, Xue; Zheng, Lei; Zhang, Chuanxin; Shi, Xiaodong; Chen, Yunfeng; Journal of Organic Chemistry; vol. 83; nb.

4; (2018); p. 1772 - 1778, View in Reaxys

1f

Xu, Weici; Arieno, Marcus; Löw, Henrik; Huang, Kaifang; Xie, Xiulan; Cruchter, Thomas; Ma, Qiao; Xi, Jianwei; Huang, Biao; Wiest, Olaf; Gong, Lei; Meggers, Eric; Journal of the American Chemical Society; vol. 138; nb.

28; (2016); p. 8774 - 8780, View in Reaxys; Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5, View in Reaxys

2r

Yang, Zan; Li, Jiao; Hua, Jie; Yang, Tao; Yi, Jianmin; Zhou, Congshan; Synlett; vol. 28; nb. 9; (2017); p. 1079 1082; Art.No: ST-2016-W0789-L, View in Reaxys

(E)-1l

Bertolotti, Mattia; Brenna, Elisabetta; Crotti, Michele; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Santangelo, Sara; ChemCatChem; vol. 8; nb. 3; (2016); p. 577 - 583, View in Reaxys

1c

Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb.

26; (2016); p. 4812 - 4815, View in Reaxys

1e

Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb.

11; (2008); p. 4295 - 4298, View in Reaxys; Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p. 3875 - 3879, View in Reaxys

2d

Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; nb. 39; (2013); p.

6713 - 6716, View in Reaxys

5d

Zagozda, Marcin; Plenkiewicz, Jan; Tetrahedron Asymmetry; vol. 18; nb. 12; (2007); p. 1457 - 1464, View in Reaxys

Table 1, entry 3

Czekelius, Constantin; Carreira, Erick M.; Angewandte Chemie - International Edition; vol. 42; nb. 39; (2003); p.

4793 - 4795, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.593

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

3

TPSA

55.05

Lipinski Number

4

Veber Number

2

Melting Point (1) 1 of 1

Melting Point [°C]

31 - 32

Czekelius, Constantin; Carreira, Erick M.; Organic Letters; vol. 6; nb. 24; (2004); p. 4575 - 4577, View in Reaxys Chromatographic Data (1) Chromatographic Location data TLC (Thin layer chromatography)

supporting informa- Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; tion nb. 39; (2013); p. 6713 - 6716, View in Reaxys

Crystal Property Description (3) Colour & Other Location Properties yellow yellow

References

References Lei, Xue; Zheng, Lei; Zhang, Chuanxin; Shi, Xiaodong; Chen, Yunfeng; Journal of Organic Chemistry; vol. 83; nb. 4; (2018); p. 1772 - 1778, View in Reaxys

supporting informa- Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; tion nb. 39; (2013); p. 6713 - 6716, View in Reaxys; Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p. 3875 3879, View in Reaxys; Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys; Yang, Zan; Li, Jiao; Hua, Jie; Yang, Tao; Yi, Jianmin; Zhou, Congshan; Synlett; vol. 28; nb.

9; (2017); p. 1079 - 1082; Art.No: ST-2016-W0789-L, View in Reaxys

yellow

Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys

NMR Spectroscopy (13)

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1 of 13

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys; Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; nb. 39; (2013); p. 6713 - 6716, View in Reaxys; Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p. 3875 - 3879, View in Reaxys; Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys; Yang, Zan; Li, Jiao; Hua, Jie; Yang, Tao; Yi, Jianmin; Zhou, Congshan; Synlett; vol. 28; nb. 9; (2017); p. 1079 - 1082; Art.No: ST-2016-W0789-L, View in Reaxys; Lei, Xue; Zheng, Lei; Zhang, Chuanxin; Shi, Xiaodong; Chen, Yunfeng; Journal of Organic Chemistry; vol. 83; nb. 4; (2018); p. 1772 - 1778, View in Reaxys 2 of 13

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; nb. 39; (2013); p. 6713 6716, View in Reaxys; Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys; Yang, Zan; Li, Jiao; Hua, Jie; Yang, Tao; Yi, Jianmin; Zhou, Congshan; Synlett; vol. 28; nb. 9; (2017); p. 1079 - 1082; Art.No: ST-2016-W0789-L, View in Reaxys; Lei, Xue; Zheng, Lei; Zhang, Chuanxin; Shi, Xiaodong; Chen, Yunfeng; Journal of Organic Chemistry; vol. 83; nb. 4; (2018); p. 1772 - 1778, View in Reaxys 3 of 13

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Schneider, Jakob F.; Lauber, Markus B.; Muhr, Vanessa; Kratzer, Domenic; Paradies, Jan; Organic and Biomolecular Chemistry; vol. 9; nb. 11; (2011); p. 4323 - 4327, View in Reaxys; Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys 4 of 13

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 250 scopy) [MHz] Location

supporting information

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

45/100

2018-08-17 22:03:33

Schneider, Jakob F.; Lauber, Markus B.; Muhr, Vanessa; Kratzer, Domenic; Paradies, Jan; Organic and Biomolecular Chemistry; vol. 9; nb. 11; (2011); p. 4323 - 4327, View in Reaxys 5 of 13

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Brenna, Elisabetta; Fronza, Giovanni; Fuganti, Claudio; Gatti, Francesco G.; European Journal of Organic Chemistry; nb.

26; (2010); p. 5077 - 5084, View in Reaxys 6 of 13

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100.6 scopy) [MHz] Location

supporting information

Brenna, Elisabetta; Fronza, Giovanni; Fuganti, Claudio; Gatti, Francesco G.; European Journal of Organic Chemistry; nb.

26; (2010); p. 5077 - 5084, View in Reaxys 7 of 13

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 400 scopy) [MHz] Zagozda, Marcin; Plenkiewicz, Jan; Tetrahedron Asymmetry; vol. 18; nb. 12; (2007); p. 1457 - 1464, View in Reaxys; Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p.

4295 - 4298, View in Reaxys 8 of 13

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 100 scopy) [MHz] Zagozda, Marcin; Plenkiewicz, Jan; Tetrahedron Asymmetry; vol. 18; nb. 12; (2007); p. 1457 - 1464, View in Reaxys; Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p.

4295 - 4298, View in Reaxys 9 of 13

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

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Temperature (NMR Spectroscopy) [°C]

25

Frequency (NMR Spectro- 300 scopy) [MHz] Czekelius, Constantin; Carreira, Erick M.; Organic Process Research and Development; vol. 11; nb. 3; (2007); p. 633 - 636, View in Reaxys 10 of 13

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Temperature (NMR Spectroscopy) [°C]

25

Frequency (NMR Spectro- 75 scopy) [MHz] Czekelius, Constantin; Carreira, Erick M.; Organic Process Research and Development; vol. 11; nb. 3; (2007); p. 633 - 636, View in Reaxys 11 of 13

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Temperature (NMR Spectroscopy) [°C]

25

Frequency (NMR Spectro- 300 scopy) [MHz] Czekelius, Constantin; Carreira, Erick M.; Organic Letters; vol. 6; nb. 24; (2004); p. 4575 - 4577, View in Reaxys 12 of 13

Nucleus (NMR Spectroscopy)

1H

Coupling Nuclei

1H

Solvents (NMR Spectroscopy)

CDCl3

Temperature (NMR Spectroscopy) [°C]

25

Frequency (NMR Spectro- 300 scopy) [MHz] Czekelius, Constantin; Carreira, Erick M.; Organic Letters; vol. 6; nb. 24; (2004); p. 4575 - 4577, View in Reaxys 13 of 13

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Temperature (NMR Spectroscopy) [°C]

25

Frequency (NMR Spectro- 75 scopy) [MHz] Czekelius, Constantin; Carreira, Erick M.; Organic Letters; vol. 6; nb. 24; (2004); p. 4575 - 4577, View in Reaxys IR Spectroscopy (3)

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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1 of 3

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat liquid

Location

supporting information

Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; nb. 39; (2013); p. 6713 6716, View in Reaxys 2 of 3

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat liquid

Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys 3 of 3

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

film

Czekelius, Constantin; Carreira, Erick M.; Organic Letters; vol. 6; nb. 24; (2004); p. 4575 - 4577, View in Reaxys Mass Spectrometry (2) Description (Mass Location Spectrometry) high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); time-offlight mass spectra (TOFMS); spectrum

References

supporting informa- Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; tion nb. 39; (2013); p. 6713 - 6716, View in Reaxys

spectrum; electron impact (EI)

Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys

Reaxys ID 18552729 View in Reaxys

22/65 CAS Registry Number: 1029124-38-6 Chemical Name: (E)-2-(2-methoxy-phenyl)-1-nitro-propene; (E)-2-(2-methoxyphenyl)-1-nitropropene Linear Structure Formula: C10H11NO3 Molecular Formula: C10H11NO3 Molecular Weight: 193.202 InChI Key: CUMNBOGVEFJGQB-BQYQJAHWSA-N Note:

O N O

O

Substance Label (4) Label References 1d

Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5, View in Reaxys

(E)-1j

Bertolotti, Mattia; Brenna, Elisabetta; Crotti, Michele; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Santangelo, Sara; ChemCatChem; vol. 8; nb. 3; (2016); p. 577 - 583, View in Reaxys

1r

Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol.

19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys

1f

Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb.

11; (2008); p. 4295 - 4298, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.593

H Bond Donors

0

H Bond Acceptors

0

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

48/100

2018-08-17 22:03:33

Rotatable Bonds

3

TPSA

55.05

Lipinski Number

4

Veber Number

2

Crystal Property Description (1) Colour & Other References Properties yellow

Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb.

11; (2008); p. 4295 - 4298, View in Reaxys

NMR Spectroscopy (6) 1 of 6

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Brenna, Elisabetta; Fronza, Giovanni; Fuganti, Claudio; Gatti, Francesco G.; European Journal of Organic Chemistry; nb.

26; (2010); p. 5077 - 5084, View in Reaxys 2 of 6

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100.6 scopy) [MHz] Location

supporting information

Brenna, Elisabetta; Fronza, Giovanni; Fuganti, Claudio; Gatti, Francesco G.; European Journal of Organic Chemistry; nb.

26; (2010); p. 5077 - 5084, View in Reaxys 3 of 6

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 400 scopy) [MHz] Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys 4 of 6

Description (NMR Spectroscopy)

Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 400 scopy) [MHz] Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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5 of 6

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 100 scopy) [MHz] Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys 6 of 6

Description (NMR Spectroscopy)

Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 100 scopy) [MHz] Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat liquid

Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum; electron impact (EI)

Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb.

11; (2008); p. 4295 - 4298, View in Reaxys

Reaxys ID 18552733 View in Reaxys

23/65 CAS Registry Number: 1029124-39-7 Chemical Name: (E)-1-methoxy-3-(1-nitroprop-1-en-2-yl)benzene; (E)-2-(3-methoxyphenyl)-1-nitropropene Linear Structure Formula: C10H11NO3 Molecular Formula: C10H11NO3 Molecular Weight: 193.202 InChI Key: CJOTWMDGBWCLRZ-BQYQJAHWSA-N Note:

O O

N O

Substance Label (4) Label References 1e

Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5, View in Reaxys

1i

Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb.

18; (2015); p. 3875 - 3879, View in Reaxys; Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, QiLin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys

(E)-1k

Bertolotti, Mattia; Brenna, Elisabetta; Crotti, Michele; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Santangelo, Sara; ChemCatChem; vol. 8; nb. 3; (2016); p. 577 - 583, View in Reaxys

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

50/100

2018-08-17 22:03:33

1g

Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb.

11; (2008); p. 4295 - 4298, View in Reaxys; Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.593

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

3

TPSA

55.05

Lipinski Number

4

Veber Number

2

Melting Point (1) 1 of 1

Melting Point [°C]

48 - 50

Location

supporting information

Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys Crystal Property Description (2) Colour & Other Location Properties yellow

References

supporting informa- Trost, Barry M.; Bringley, Dustin A.; O'Keefe, B. Michael; Organic Letters; vol. 15; nb. 22; tion (2013); p. 5630 - 5633, View in Reaxys; Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p. 3875 - 3879, View in Reaxys; Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys

yellow

Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys

NMR Spectroscopy (7) 1 of 7

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys; Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys; Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p.

3875 - 3879, View in Reaxys; Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys 2 of 7

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys; Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu,

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

51/100

2018-08-17 22:03:33

Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys; Yu, YanBo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p.

4812 - 4815, View in Reaxys 3 of 7

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Coupling Nuclei

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Trost, Barry M.; Bringley, Dustin A.; O'Keefe, B. Michael; Organic Letters; vol. 15; nb. 22; (2013); p. 5630 - 5633, View in Reaxys 4 of 7

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 400 scopy) [MHz] Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys 5 of 7

Description (NMR Spectroscopy)

Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 400 scopy) [MHz] Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys 6 of 7

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 100 scopy) [MHz] Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys 7 of 7

Description (NMR Spectroscopy)

Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 100 scopy) [MHz]

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Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat liquid

Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum; electron impact (EI)

Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb.

11; (2008); p. 4295 - 4298, View in Reaxys

Reaxys ID 18879057 View in Reaxys

24/65 O

CAS Registry Number: 181058-95-7 Linear Structure Formula: C10H11NO3 Molecular Formula: C10H11NO3 Molecular Weight: 193.202 InChI Key: MTXXEBUHPMRMGA-UHFFFAOYSA-N Note:

N O

O

Substance Label (1) Label References 2e

Wu, Hao; Sheng, Wei-Jian; Chen, Bin; Liu, Ren-Rong; Gao, Jian-Rong; Jia, Yi-Xia; Synlett; vol. 26; nb. 20; (2015); p. 2817 - 2820; Art.No: ST-2015-S0581-C, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.593

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

3

TPSA

55.05

Lipinski Number

4

Veber Number

2

Reaxys ID 4989271 View in Reaxys

25/65 CAS Registry Number: 119880-56-7; 109757-70-2 Chemical Name: (E)-1-chloro-4-(1-nitroprop-1-en-2-yl)benzene; (E)-2-(4-chlorophenyl)-1-nitro-1-propene; (E)-2-(4'-chlorophenyl)-1nitropropene; (E)-1-nitro-2-(4-chlorophenyl)propene; (E)-2-(4-chlorophenyl)-1-nitropropene; 2-(4'-chlorophenyl)-1-nitropropene Linear Structure Formula: C9H8ClNO2 Molecular Formula: C9H8ClNO2 Molecular Weight: 197.621 Type of Substance: isocyclic InChI Key: TZMYDRHHJHGISG-VOTSOKGWSA-N Note:

O N O

Cl

Substance Label (10) Label References

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

53/100

2018-08-17 22:03:33

1m

Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5, View in Reaxys

1g

Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p. 8976 - 8977, View in Reaxys; Xu, Weici; Arieno, Marcus; Löw, Henrik; Huang, Kaifang; Xie, Xiulan; Cruchter, Thomas; Ma, Qiao; Xi, Jianwei; Huang, Biao; Wiest, Olaf; Gong, Lei; Meggers, Eric; Journal of the American Chemical Society; vol. 138; nb. 28; (2016); p. 8774 - 8780, View in Reaxys

(E)-1h

Bertolotti, Mattia; Brenna, Elisabetta; Crotti, Michele; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Santangelo, Sara; ChemCatChem; vol. 8; nb. 3; (2016); p. 577 - 583, View in Reaxys

1d

Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb.

26; (2016); p. 4812 - 4815, View in Reaxys

1c

Ohta, Hiromichi; Kobayashi, Naoki; Ozaki, Kazuhiko; Journal of Organic Chemistry; vol. 54; nb. 8; (1989); p. 1802 - 1804, View in Reaxys; Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p. 3875 - 3879, View in Reaxys

1j

Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol.

19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys

(E)-1c

Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb.

11; (2008); p. 4295 - 4298, View in Reaxys

5b

Zagozda, Marcin; Plenkiewicz, Jan; Tetrahedron Asymmetry; vol. 18; nb. 12; (2007); p. 1457 - 1464, View in Reaxys

1b

Ohta, Hiromichi; Ozaki, Kazuhiko; Tsuchihashi, Gen-ichi; Chemistry Letters; (1987); p. 191 - 192, View in Reaxys; Wu, Jing; Mampreian, Dawn M.; Hoveyda, Amir H.; Journal of the American Chemical Society; vol. 127; nb. 13; (2005); p. 4584 - 4585, View in Reaxys

Table 1, entry 2

Czekelius, Constantin; Carreira, Erick M.; Angewandte Chemie - International Edition; vol. 42; nb. 39; (2003); p.

4793 - 4795, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.3

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

Crystal Property Description (2) Colour & Other Location Properties yellow

References

supporting informa- Trost, Barry M.; Bringley, Dustin A.; O'Keefe, B. Michael; Organic Letters; vol. 15; nb. 22; tion (2013); p. 5630 - 5633, View in Reaxys; Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p. 3875 - 3879, View in Reaxys; Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys

yellow

Wu, Jing; Mampreian, Dawn M.; Hoveyda, Amir H.; Journal of the American Chemical Society; vol. 127; nb. 13; (2005); p. 4584 - 4585, View in Reaxys; Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p.

4295 - 4298, View in Reaxys

NMR Spectroscopy (21) 1 of 21

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys; Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys; Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p.

3875 - 3879, View in Reaxys; Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys 2 of 21

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys 3 of 21

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb.

33; (2013); p. 10840 - 10844, View in Reaxys 4 of 21

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Coupling Nuclei

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Trost, Barry M.; Bringley, Dustin A.; O'Keefe, B. Michael; Organic Letters; vol. 15; nb. 22; (2013); p. 5630 - 5633, View in Reaxys 5 of 21

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Schneider, Jakob F.; Lauber, Markus B.; Muhr, Vanessa; Kratzer, Domenic; Paradies, Jan; Organic and Biomolecular Chemistry; vol. 9; nb. 11; (2011); p. 4323 - 4327, View in Reaxys; Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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6 of 21

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 250 scopy) [MHz] Location

supporting information

Schneider, Jakob F.; Lauber, Markus B.; Muhr, Vanessa; Kratzer, Domenic; Paradies, Jan; Organic and Biomolecular Chemistry; vol. 9; nb. 11; (2011); p. 4323 - 4327, View in Reaxys 7 of 21

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 400 scopy) [MHz] Wu, Jing; Mampreian, Dawn M.; Hoveyda, Amir H.; Journal of the American Chemical Society; vol. 127; nb. 13; (2005); p.

4584 - 4585, View in Reaxys; Zagozda, Marcin; Plenkiewicz, Jan; Tetrahedron Asymmetry; vol. 18; nb. 12; (2007); p. 1457 1464, View in Reaxys; Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys 8 of 21

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 100 scopy) [MHz] Wu, Jing; Mampreian, Dawn M.; Hoveyda, Amir H.; Journal of the American Chemical Society; vol. 127; nb. 13; (2005); p.

4584 - 4585, View in Reaxys; Zagozda, Marcin; Plenkiewicz, Jan; Tetrahedron Asymmetry; vol. 18; nb. 12; (2007); p. 1457 1464, View in Reaxys; Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys 9 of 21

Description (NMR Spectroscopy)

2D-NMR

Nucleus (NMR Spectroscopy)

1H; 13C

Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys 10 of 21

Description (NMR Spectroscopy)

Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 100 scopy) [MHz] Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys 11 of 21

Description (NMR Spectroscopy)

Spectrum

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Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 400 scopy) [MHz] Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys 12 of 21

Description (NMR Spectroscopy)

Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Temperature (NMR Spectroscopy) [°C]

29.84

Frequency (NMR Spectro- 400.13 scopy) [MHz] Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p.

8976 - 8977, View in Reaxys 13 of 21

Description (NMR Spectroscopy)

Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Temperature (NMR Spectroscopy) [°C]

29.84

Frequency (NMR Spectro- 100.613 scopy) [MHz] Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p.

8976 - 8977, View in Reaxys 14 of 21

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Temperature (NMR Spectroscopy) [°C]

29.84

Frequency (NMR Spectro- 100 scopy) [MHz] Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p.

8976 - 8977, View in Reaxys 15 of 21

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Temperature (NMR Spectroscopy) [°C]

29.84

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Frequency (NMR Spectro- 400 scopy) [MHz] Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p.

8976 - 8977, View in Reaxys 16 of 21

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Temperature (NMR Spectroscopy) [°C]

25

Frequency (NMR Spectro- 300 scopy) [MHz] Czekelius, Constantin; Carreira, Erick M.; Organic Process Research and Development; vol. 11; nb. 3; (2007); p. 633 - 636, View in Reaxys 17 of 21

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

dimethylsulfoxide-d6

Temperature (NMR Spectroscopy) [°C]

25

Frequency (NMR Spectro- 75 scopy) [MHz] Czekelius, Constantin; Carreira, Erick M.; Organic Process Research and Development; vol. 11; nb. 3; (2007); p. 633 - 636, View in Reaxys 18 of 21

Nucleus (NMR Spectroscopy)

1H

Coupling Nuclei

1H

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 400 scopy) [MHz] Wu, Jing; Mampreian, Dawn M.; Hoveyda, Amir H.; Journal of the American Chemical Society; vol. 127; nb. 13; (2005); p.

4584 - 4585, View in Reaxys 19 of 21

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Temperature (NMR Spectroscopy) [°C]

25

Frequency (NMR Spectro- 300 scopy) [MHz] Czekelius, Constantin; Carreira, Erick M.; Organic Letters; vol. 6; nb. 24; (2004); p. 4575 - 4577, View in Reaxys 20 of 21

Nucleus (NMR Spectroscopy)

1H

Coupling Nuclei

1H

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Solvents (NMR Spectroscopy)

CDCl3

Temperature (NMR Spectroscopy) [°C]

25

Frequency (NMR Spectro- 300 scopy) [MHz] Czekelius, Constantin; Carreira, Erick M.; Organic Letters; vol. 6; nb. 24; (2004); p. 4575 - 4577, View in Reaxys 21 of 21

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

dimethylsulfoxide-d6

Temperature (NMR Spectroscopy) [°C]

25

Frequency (NMR Spectro- 75 scopy) [MHz] Czekelius, Constantin; Carreira, Erick M.; Organic Letters; vol. 6; nb. 24; (2004); p. 4575 - 4577, View in Reaxys IR Spectroscopy (3) 1 of 3

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat liquid

Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys 2 of 3

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

film

Czekelius, Constantin; Carreira, Erick M.; Organic Process Research and Development; vol. 11; nb. 3; (2007); p. 633 - 636, View in Reaxys 3 of 3

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

film

Czekelius, Constantin; Carreira, Erick M.; Organic Letters; vol. 6; nb. 24; (2004); p. 4575 - 4577, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum; electron impact (EI)

Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p. 8976 - 8977, View in Reaxys; Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys

UV/VIS Spectroscopy (1) 1 of 1

Absorption Maxima (UV/ VIS) [nm]

310

Toogood, Helen S.; Fryszkowska, Anna; Hare, Victoria; Fisher, Karl; Roujeinikova, Anna; Leys, David; Gardiner, John M.; Stephens, Gill M.; Scrutton, Nigel S.; Advanced Synthesis and Catalysis; vol. 350; nb. 17; (2008); p. 2789 - 2803, View in Reaxys

Reaxys ID 11138721 View in Reaxys

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CAS Registry Number: 947383-49-5 Chemical Name: (E)-1-chloro-3-(1-nitroprop-1-en-2-yl)benzene; (E)-2-(3-chlorophenyl)-1-nitro-1-propene Linear Structure Formula: C9H8ClNO2 Molecular Formula: C9H8ClNO2 Molecular Weight: 197.621 InChI Key: QAAPSWCQZSSQAU-VOTSOKGWSA-N Note:

O Cl

N O

Substance Label (7) Label References 1l

Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5, View in Reaxys

(E)-1g

Bertolotti, Mattia; Brenna, Elisabetta; Crotti, Michele; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Santangelo, Sara; ChemCatChem; vol. 8; nb. 3; (2016); p. 577 - 583, View in Reaxys

1j

Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb.

26; (2016); p. 4812 - 4815, View in Reaxys

6

Gini, Andrea; Bamberger, Julia; Luis-Barrera, Javier; Zurro, Mercedes; Mas-Ballesté, Rubén; Alemán, José; Mancheño, Olga García; Advanced Synthesis and Catalysis; vol. 358; nb. 24; (2016); p. 4049 - 4056, View in Reaxys

1h

Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p. 8976 - 8977, View in Reaxys; Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p. 3875 - 3879, View in Reaxys

Ib-NO2

Patent; LEK PHARMACEUTICALS D.D.; STAVBER, Gaj; GAZIC SMILOVIC, Ivana; CLUZEAU, Jerome; RICHTER, Frank; WO2014/202765; (2014); (A1) English, View in Reaxys

1e

Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol.

19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.3

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

Melting Point (1) 1 of 1

Melting Point [°C]

62 - 64

Location

supporting information

Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys Crystal Property Description (2) Colour & Other Location Properties

References

yellow

supporting informa- Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and tion Catalysis; vol. 357; nb. 18; (2015); p. 3875 - 3879, View in Reaxys; Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys; Gini, Andrea; Bamberger, Julia; Luis-Barrera, Javier; Zurro, Mercedes; Mas-Ballesté, Rubén; Alemán, José; Mancheño, Olga García; Advanced Synthesis and Catalysis; vol. 358; nb. 24; (2016); p. 4049 - 4056, View in Reaxys

yellow

Page/Page column 42

Patent; LEK PHARMACEUTICALS D.D.; STAVBER, Gaj; GAZIC SMILOVIC, Ivana; CLUZEAU, Jerome; RICHTER, Frank; WO2014/202765; (2014); (A1) English, View in Reaxys

NMR Spectroscopy (10) 1 of 10

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

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Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys; Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys; Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p.

3875 - 3879, View in Reaxys; Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys 2 of 10

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys; Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys; Yu, YanBo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p.

4812 - 4815, View in Reaxys 3 of 10

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 300 scopy) [MHz] Location

supporting information

Gini, Andrea; Bamberger, Julia; Luis-Barrera, Javier; Zurro, Mercedes; Mas-Ballesté, Rubén; Alemán, José; Mancheño, Olga García; Advanced Synthesis and Catalysis; vol. 358; nb. 24; (2016); p. 4049 - 4056, View in Reaxys 4 of 10

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 75 scopy) [MHz] Location

supporting information

Gini, Andrea; Bamberger, Julia; Luis-Barrera, Javier; Zurro, Mercedes; Mas-Ballesté, Rubén; Alemán, José; Mancheño, Olga García; Advanced Synthesis and Catalysis; vol. 358; nb. 24; (2016); p. 4049 - 4056, View in Reaxys 5 of 10

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

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Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 500 scopy) [MHz] Original Text (NMR Spec- 1H NMR (500 MHz, ODd3, ppm) 6 7.45-7.30 (m, 4ArH), 7.24 (m, 1 H), 2.65 (m, 3H); troscopy) Location

Page/Page column 42

Patent; LEK PHARMACEUTICALS D.D.; STAVBER, Gaj; GAZIC SMILOVIC, Ivana; CLUZEAU, Jerome; RICHTER, Frank; WO2014/202765; (2014); (A1) English, View in Reaxys 6 of 10

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 125 scopy) [MHz] Original Text (NMR Spec- 130 NMR (125 MHz, ODd3, ppm) 6 148.2, 140.1, 136.9, 135.5, 130.4, 126.4, 125.0,18.5. troscopy) Location

Page/Page column 42

Patent; LEK PHARMACEUTICALS D.D.; STAVBER, Gaj; GAZIC SMILOVIC, Ivana; CLUZEAU, Jerome; RICHTER, Frank; WO2014/202765; (2014); (A1) English, View in Reaxys 7 of 10

Description (NMR Spectroscopy)

Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Temperature (NMR Spectroscopy) [°C]

29.84

Frequency (NMR Spectro- 100.613 scopy) [MHz] Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p.

8976 - 8977, View in Reaxys 8 of 10

Description (NMR Spectroscopy)

Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Temperature (NMR Spectroscopy) [°C]

29.84

Frequency (NMR Spectro- 400.13 scopy) [MHz] Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p.

8976 - 8977, View in Reaxys 9 of 10

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

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Temperature (NMR Spectroscopy) [°C]

29.84

Frequency (NMR Spectro- 400 scopy) [MHz] Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p.

8976 - 8977, View in Reaxys 10 of 10

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Temperature (NMR Spectroscopy) [°C]

29.84

Frequency (NMR Spectro- 100 scopy) [MHz] Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p.

8976 - 8977, View in Reaxys Mass Spectrometry (2) Description (Mass Location Spectrometry)

References

electron impact supporting informa- Gini, Andrea; Bamberger, Julia; Luis-Barrera, Javier; Zurro, Mercedes; Mas-Ballesté, Ru(EI); time-of-flight tion bén; Alemán, José; Mancheño, Olga García; Advanced Synthesis and Catalysis; vol. 358; nb. mass spectra 24; (2016); p. 4049 - 4056, View in Reaxys (TOFMS); high resolution mass spectrometry (HRMS); spectrum spectrum; electron impact (EI)

Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p. 8976 - 8977, View in Reaxys

Reaxys ID 18552736 View in Reaxys

27/65 O

CAS Registry Number: 119880-56-7 Chemical Name: 2-(4-chlorophenyl)-1-nitropropene Linear Structure Formula: C9H8ClNO2 Molecular Formula: C9H8ClNO2 Molecular Weight: 197.621 InChI Key: TZMYDRHHJHGISG-UHFFFAOYSA-N Note:

N O

Cl

Substance Label (4) Label References 2b

Choudhary, Manoj K.; Rao Ganga, Venkata Subba; Menapara, Tusharkumar; Kureshy, Rukhsana I.; Khan, Noor-Ul H.; Abdi, Sayed H. R.; Suresh, Eringathodi; RSC Advances; vol. 6; nb. 106; (2016); p. 104148 - 104153, View in Reaxys

2i

Wu, Hao; Sheng, Wei-Jian; Chen, Bin; Liu, Ren-Rong; Gao, Jian-Rong; Jia, Yi-Xia; Synlett; vol. 26; nb. 20; (2015); p. 2817 - 2820; Art.No: ST-2015-S0581-C, View in Reaxys

3cc

Creech, Gardner S.; Kwon, Ohyun; Chemical Science; vol. 4; nb. 6; (2013); p. 2670 - 2674, View in Reaxys

1c

Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb.

11; (2008); p. 4295 - 4298, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.3

H Bond Donors

0

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H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

Reaxys ID 18552737 View in Reaxys

28/65

O

CAS Registry Number: 1029124-37-5 Chemical Name: (Z)-2-(4'-chlorophenyl)-1-nitropropene; (Z)-2-(4chlorophenyl)-1-nitropropene Linear Structure Formula: C9H8ClNO2 Molecular Formula: C9H8ClNO2 Molecular Weight: 197.621 InChI Key: TZMYDRHHJHGISG-SREVYHEPSA-N Note:

N O

Cl

Substance Label (2) Label References (Z)-1h

Bertolotti, Mattia; Brenna, Elisabetta; Crotti, Michele; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Santangelo, Sara; ChemCatChem; vol. 8; nb. 3; (2016); p. 577 - 583, View in Reaxys

(Z)-1c

Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb.

11; (2008); p. 4295 - 4298, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.3

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

NMR Spectroscopy (5) 1 of 5

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 400 scopy) [MHz] Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys 2 of 5

Description (NMR Spectroscopy)

Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 400 scopy) [MHz]

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Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys 3 of 5

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 100 scopy) [MHz] Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys 4 of 5

Description (NMR Spectroscopy)

Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 100 scopy) [MHz] Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys 5 of 5

Description (NMR Spectroscopy)

2D-NMR

Nucleus (NMR Spectroscopy)

1H; 13C

Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat liquid

Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum; electron impact (EI)

Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb.

11; (2008); p. 4295 - 4298, View in Reaxys

UV/VIS Spectroscopy (1) 1 of 1

Absorption Maxima (UV/ VIS) [nm]

221

Toogood, Helen S.; Fryszkowska, Anna; Hare, Victoria; Fisher, Karl; Roujeinikova, Anna; Leys, David; Gardiner, John M.; Stephens, Gill M.; Scrutton, Nigel S.; Advanced Synthesis and Catalysis; vol. 350; nb. 17; (2008); p. 2789 - 2803, View in Reaxys

Reaxys ID 19761858 View in Reaxys

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

29/65

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O

Linear Structure Formula: C9H8ClNO2 Molecular Formula: C9H8ClNO2 Molecular Weight: 197.621 InChI Key: QAAPSWCQZSSQAU-UHFFFAOYSA-N Note:

N O Cl

Druglikeness (1) 1 of 1

LogP

3.3

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

Reaxys ID 23875299 View in Reaxys

30/65 O

Chemical Name: (E)-1-chloro-2-(1-nitroprop-1-en-2-yl)benzene Linear Structure Formula: C9H8ClNO2 Molecular Formula: C9H8ClNO2 Molecular Weight: 197.621 InChI Key: IIIRZSBBECCJBK-VOTSOKGWSA-N Note:

N Cl

O

Substance Label (2) Label References (E)-1f

Bertolotti, Mattia; Brenna, Elisabetta; Crotti, Michele; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Santangelo, Sara; ChemCatChem; vol. 8; nb. 3; (2016); p. 577 - 583, View in Reaxys

1q

Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol.

19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.3

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

NMR Spectroscopy (2) 1 of 2

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

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Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb.

33; (2013); p. 10840 - 10844, View in Reaxys 2 of 2

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb.

33; (2013); p. 10840 - 10844, View in Reaxys

Reaxys ID 12096246 View in Reaxys

31/65 O

Chemical Name: 1-(4-((E)-1-nitroprop-1-en-2-yl)phenyl)ethanone; (E)-2-(4-acetylphenyl)-1-nitro-1-propene Linear Structure Formula: C11H11NO3 Molecular Formula: C11H11NO3 Molecular Weight: 205.213 InChI Key: GARWDHIDGVUMRZ-BQYQJAHWSA-N Note:

N O

O

Patent-Specific Data (1) References Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; CARREIRA, Erick, M.; WO2004/103951; (2004); (A1) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

2.555

H Bond Donors

0

H Bond Acceptors

1

Rotatable Bonds

3

TPSA

62.89

Lipinski Number

4

Veber Number

2

Melting Point (1) 1 of 1

Melting Point [°C]

53

Czekelius, Constantin; Carreira, Erick M.; Organic Process Research and Development; vol. 11; nb. 3; (2007); p. 633 - 636, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Temperature (NMR Spectroscopy) [°C]

25

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Frequency (NMR Spectro- 300 scopy) [MHz] Czekelius, Constantin; Carreira, Erick M.; Organic Process Research and Development; vol. 11; nb. 3; (2007); p. 633 - 636, View in Reaxys 2 of 2

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Temperature (NMR Spectroscopy) [°C]

25

Frequency (NMR Spectro- 75 scopy) [MHz] Czekelius, Constantin; Carreira, Erick M.; Organic Process Research and Development; vol. 11; nb. 3; (2007); p. 633 - 636, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

film

Czekelius, Constantin; Carreira, Erick M.; Organic Process Research and Development; vol. 11; nb. 3; (2007); p. 633 - 636, View in Reaxys

Reaxys ID 32892853 View in Reaxys

32/65 O

Linear Structure Formula: C11H13NO3 Molecular Formula: C11H13NO3 Molecular Weight: 207.229 InChI Key: LIXHGHRADMZONS-UHFFFAOYSA-N Note:

N O

O

Druglikeness (1) 1 of 1

LogP

2.833

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

3

TPSA

55.05

Lipinski Number

4

Veber Number

2

Reaxys ID 5536991 View in Reaxys

33/65 O

CAS Registry Number: 109757-72-4 Chemical Name: (E)-1-nitro-4-(1-nitroprop-1-en-2-yl)benzene Linear Structure Formula: C9H8N2O4 Molecular Formula: C9H8N2O4 Molecular Weight: 208.174 Type of Substance: isocyclic InChI Key: XDEIADAZNKSZOG-VOTSOKGWSA-N

N O O N O

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Note: Substance Label (2) Label References 1h

Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb.

26; (2016); p. 4812 - 4815, View in Reaxys

1d

Ohta, Hiromichi; Ozaki, Kazuhiko; Tsuchihashi, Gen-ichi; Chemistry Letters; (1987); p. 191 - 192, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.57

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

3

TPSA

91.64

Lipinski Number

4

Veber Number

2

Melting Point (1) 1 of 1

Melting Point [°C]

106 - 108

Location

supporting information

Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys Crystal Property Description (1) Colour & Other Location Properties yellow

References

supporting informa- Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Comtion munications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys 2 of 2

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) high resolution mass spectrometry

References

supporting informa- Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Comtion munications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys

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(HRMS); electrospray ionisation (ESI); spectrum

Reaxys ID 7532429 View in Reaxys

34/65

O

Chemical Name: 2-(4-nitrophenyl)-1-nitro-1-propene Linear Structure Formula: C9H8N2O4 Molecular Formula: C9H8N2O4 Molecular Weight: 208.174 Type of Substance: isocyclic InChI Key: XDEIADAZNKSZOG-SREVYHEPSA-N Note:

N N

O

O

O

Druglikeness (1) 1 of 1

LogP

2.57

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

3

TPSA

91.64

Lipinski Number

4

Veber Number

2

Melting Point (1) 1 of 1

Melting Point [°C]

78 - 80

Barco, Achille; Benetti, Simonetta; De Risi, Carmela; Morelli, Carlo F.; Pollini, Gian P.; Zanirato, Vinicio; Tetrahedron; vol. 52; nb. 27; (1996); p. 9275 - 9288, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Barco, Achille; Benetti, Simonetta; De Risi, Carmela; Morelli, Carlo F.; Pollini, Gian P.; Zanirato, Vinicio; Tetrahedron; vol. 52; nb. 27; (1996); p. 9275 - 9288, View in Reaxys 2 of 2

Description (NMR Spectroscopy)

Spin-spin coupling constants

Solvents (NMR Spectroscopy)

CDCl3

Comment (NMR Spectroscopy)

1H-1H

Barco, Achille; Benetti, Simonetta; De Risi, Carmela; Morelli, Carlo F.; Pollini, Gian P.; Zanirato, Vinicio; Tetrahedron; vol. 52; nb. 27; (1996); p. 9275 - 9288, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CHCl3

Comment (IR Spectroscopy)

1500 - 1330 cm**(-1)

Barco, Achille; Benetti, Simonetta; De Risi, Carmela; Morelli, Carlo F.; Pollini, Gian P.; Zanirato, Vinicio; Tetrahedron; vol. 52; nb. 27; (1996); p. 9275 - 9288, View in Reaxys

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Reaxys ID 19317764 View in Reaxys

35/65 CAS Registry Number: 181058-93-5 Linear Structure Formula: C9H8N2O4 Molecular Formula: C9H8N2O4 Molecular Weight: 208.174 InChI Key: XDEIADAZNKSZOG-UHFFFAOYSA-N Note:

N

O N

O

O

O

Druglikeness (1) 1 of 1

LogP

2.57

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

3

TPSA

91.64

Lipinski Number

4

Veber Number

2

Reaxys ID 8831874 View in Reaxys

36/65 CAS Registry Number: 344832-12-8 Chemical Name: (Z)-3-(4'-chlorophenyl)-2-nitro-2-butene Linear Structure Formula: C10H10ClNO2 Molecular Formula: C10H10ClNO2 Molecular Weight: 211.648 Type of Substance: isocyclic InChI Key: ZCDJEQCPCALYBX-FPLPWBNLSA-N Note:

N Cl

O

O

Substance Label (1) Label References 3e

Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.54

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

NMR Spectroscopy (2) 1 of 2

Nucleus (NMR Spectroscopy)

1H

Coupling Nuclei

1H

Solvents (NMR Spectroscopy)

CDCl3

Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318, View in Reaxys 2 of 2

Description (NMR Spectroscopy)

Chemical shifts

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Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318, View in Reaxys

Reaxys ID 8831912 View in Reaxys

37/65 CAS Registry Number: 344832-11-7 Chemical Name: (Z)-3-(3'-chlorophenyl)-2-nitro-2-butene Linear Structure Formula: C10H10ClNO2 Molecular Formula: C10H10ClNO2 Molecular Weight: 211.648 Type of Substance: isocyclic InChI Key: XOUCAQVDOPSVOG-FPLPWBNLSA-N Note:

Cl

N O

O

Substance Label (1) Label References 3d

Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.54

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

NMR Spectroscopy (2) 1 of 2

Nucleus (NMR Spectroscopy)

1H

Coupling Nuclei

1H

Solvents (NMR Spectroscopy)

CDCl3

Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318, View in Reaxys 2 of 2

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318, View in Reaxys

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IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318, View in Reaxys

Reaxys ID 8832833 View in Reaxys

38/65 Chemical Name: (Z)-3-(2'-chlorophenyl)-2-nitro-2-butene Linear Structure Formula: C10H10ClNO2 Molecular Formula: C10H10ClNO2 Molecular Weight: 211.648 Type of Substance: isocyclic InChI Key: VBRQSXAKAHOHAK-FPLPWBNLSA-N Note:

Cl

N O

O

Substance Label (1) Label References 3c

Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.54

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

NMR Spectroscopy (2) 1 of 2

Nucleus (NMR Spectroscopy)

1H

Coupling Nuclei

1H

Solvents (NMR Spectroscopy)

CDCl3

Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318, View in Reaxys 2 of 2

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318, View in Reaxys

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Reaxys ID 30915349 View in Reaxys

39/65 O

F

Chemical Name: (E)-1,2,3-trifluoro-5-(1-nitroprop-1-en-2-yl)benzene Linear Structure Formula: C9H6F3NO2 Molecular Formula: C9H6F3NO2 Molecular Weight: 217.147 InChI Key: IZLLTGHTRFNPLF-SNAWJCMRSA-N Note:

N O

F F

Substance Label (1) Label References 1p

Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.161

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

Crystal Property Description (1) Colour & Other Location Properties yellow

References

supporting informa- Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; tion (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5, View in Reaxys

NMR Spectroscopy (3) 1 of 3

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 500 scopy) [MHz] Location

supporting information

Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew.

Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5, View in Reaxys 2 of 3

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 125 scopy) [MHz] Location

supporting information

Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew.

Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5, View in Reaxys 3 of 3

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

19F

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Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 470 scopy) [MHz] Location

supporting information

Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew.

Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5, View in Reaxys

Reaxys ID 19761861 View in Reaxys

40/65 CAS Registry Number: 1187850-66-3 Chemical Name: (E)-1-(tert-butyl)-4-(1-nitroprop-1-en-2-yl)benzene; (E)-1-tert-butyl-4-(1-nitroprop-1-en-2-yl)benzene Linear Structure Formula: C13H17NO2 Molecular Formula: C13H17NO2 Molecular Weight: 219.283 InChI Key: LKLYRKAPIRWVLC-MDZDMXLPSA-N Note:

O N O

Substance Label (1) Label References 1n

Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol.

19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.495

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

3

TPSA

45.82

Lipinski Number

4

Veber Number

2

NMR Spectroscopy (4) 1 of 4

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys; Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys 2 of 4

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz]

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Location

supporting information

Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys; Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys 3 of 4

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 300 scopy) [MHz] Location

supporting information

Soltani, Omid; Ariger, Martin A.; Carreira, Erick M.; Organic Letters; vol. 11; nb. 18; (2009); p. 4196 - 4198, View in Reaxys 4 of 4

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 75 scopy) [MHz] Location

supporting information

Soltani, Omid; Ariger, Martin A.; Carreira, Erick M.; Organic Letters; vol. 11; nb. 18; (2009); p. 4196 - 4198, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Location

supporting information

Comment (IR Spectroscopy)

film

Soltani, Omid; Ariger, Martin A.; Carreira, Erick M.; Organic Letters; vol. 11; nb. 18; (2009); p. 4196 - 4198, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)

References

HRMS (High reso- supporting informa- Soltani, Omid; Ariger, Martin A.; Carreira, Erick M.; Organic Letters; vol. 11; nb. 18; (2009); lution mass spection p. 4196 - 4198, View in Reaxys trometry); EI (Electron impact); Spectrum

Reaxys ID 29042943 View in Reaxys

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

41/65

76/100

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O

Chemical Name: (E)-1-isobutyl-4-(1-nitroprop-1-en-2-yl)benzene Linear Structure Formula: C13H17NO2 Molecular Formula: C13H17NO2 Molecular Weight: 219.283 InChI Key: ZAZQOPXSCUVOMH-PKNBQFBNSA-N Note:

N O

Substance Label (1) Label References 1g

Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb.

18; (2015); p. 3875 - 3879, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.656

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

4

TPSA

45.82

Lipinski Number

4

Veber Number

2

Crystal Property Description (1) Colour & Other Location Properties yellow

References

supporting informa- Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and tion Catalysis; vol. 357; nb. 18; (2015); p. 3875 - 3879, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p. 3875 - 3879, View in Reaxys 2 of 2

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p. 3875 - 3879, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)

References

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

supporting informa- Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and tion Catalysis; vol. 357; nb. 18; (2015); p. 3875 - 3879, View in Reaxys

Reaxys ID 29359749 View in Reaxys

42/65 O

Chemical Name: (E)-methyl 4-(1-nitroprop-1-en-2-yl)benzoate Linear Structure Formula: C11H11NO4 Molecular Formula: C11H11NO4 Molecular Weight: 221.213 InChI Key: CXLXTVXCYPBSHE-BQYQJAHWSA-N Note:

N O O

O

Substance Label (1) Label References 1f

Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb.

26; (2016); p. 4812 - 4815, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.614

H Bond Donors

0

H Bond Acceptors

2

Rotatable Bonds

4

TPSA

72.12

Lipinski Number

4

Veber Number

2

Melting Point (1) 1 of 1

Melting Point [°C]

98 - 100

Location

supporting information

Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys Crystal Property Description (1) Colour & Other Location Properties yellow

References

supporting informa- Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Comtion munications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys 2 of 2

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

78/100

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Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

References

supporting informa- Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Comtion munications; vol. 52; nb. 26; (2016); p. 4812 - 4815, View in Reaxys

Reaxys ID 20668536 View in Reaxys

43/65 CAS Registry Number: 1314240-23-7 Chemical Name: ((Z)-1-methyl-2-nitrovinyl)-2,4-dimethoxybenzene Linear Structure Formula: C11H13NO4 Molecular Formula: C11H13NO4 Molecular Weight: 223.229 InChI Key: KRMCHNHKZRGIQH-FPLPWBNLSA-N Note:

O

N O

O

O

Druglikeness (1) 1 of 1

LogP

2.508

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

4

TPSA

64.28

Lipinski Number

4

Veber Number

2

Crystal Property Description (1) Colour & Other Location Properties yellow

References

supporting informa- Zhang, Min; Zhou, Jun; Kan, Jian; Wang, Min; Su, Weiping; Hong, Maochun; Chemical tion Communications; vol. 46; nb. 30; (2010); p. 5455 - 5457, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Zhang, Min; Zhou, Jun; Kan, Jian; Wang, Min; Su, Weiping; Hong, Maochun; Chemical Communications; vol. 46; nb. 30; (2010); p. 5455 - 5457, View in Reaxys

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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2 of 2

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Zhang, Min; Zhou, Jun; Kan, Jian; Wang, Min; Su, Weiping; Hong, Maochun; Chemical Communications; vol. 46; nb. 30; (2010); p. 5455 - 5457, View in Reaxys

Reaxys ID 20668537 View in Reaxys

44/65

O

CAS Registry Number: 1242462-13-0 Chemical Name: ((E)-1-methyl-2-nitrovinyl)-2,4-dimethoxybenzene Linear Structure Formula: C11H13NO4 Molecular Formula: C11H13NO4 Molecular Weight: 223.229 InChI Key: KRMCHNHKZRGIQH-BQYQJAHWSA-N Note:

O N O

O

Druglikeness (1) 1 of 1

LogP

2.508

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

4

TPSA

64.28

Lipinski Number

4

Veber Number

2

Crystal Property Description (1) Colour & Other Location Properties yellow

References

supporting informa- Zhang, Min; Zhou, Jun; Kan, Jian; Wang, Min; Su, Weiping; Hong, Maochun; Chemical tion Communications; vol. 46; nb. 30; (2010); p. 5455 - 5457, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Zhang, Min; Zhou, Jun; Kan, Jian; Wang, Min; Su, Weiping; Hong, Maochun; Chemical Communications; vol. 46; nb. 30; (2010); p. 5455 - 5457, View in Reaxys 2 of 2

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

80/100

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Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Zhang, Min; Zhou, Jun; Kan, Jian; Wang, Min; Su, Weiping; Hong, Maochun; Chemical Communications; vol. 46; nb. 30; (2010); p. 5455 - 5457, View in Reaxys

Reaxys ID 20778445 View in Reaxys

45/65 O

O

CAS Registry Number: 1252644-41-9 Linear Structure Formula: C11H13NO4 Molecular Formula: C11H13NO4 Molecular Weight: 223.229 InChI Key: ZHEFPWOWJCNGLO-BQYQJAHWSA-N Note:

N O

O

Druglikeness (1) 1 of 1

LogP

2.24

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

4

TPSA

64.28

Lipinski Number

4

Veber Number

2

Reaxys ID 2460331 View in Reaxys

46/65 O

CAS Registry Number: 32636-63-8 Linear Structure Formula: C10H8F3NO2 Molecular Formula: C10H8F3NO2 Molecular Weight: 231.174 Type of Substance: isocyclic InChI Key: AIFYVJFOHADBJL-UHFFFAOYSA-N Note:

N O

F F F

Substance Label (1) Label References 2g

Wu, Hao; Sheng, Wei-Jian; Chen, Bin; Liu, Ren-Rong; Gao, Jian-Rong; Jia, Yi-Xia; Synlett; vol. 26; nb. 20; (2015); p. 2817 - 2820; Art.No: ST-2015-S0581-C, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.603

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

3

TPSA

45.82

Lipinski Number

4

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

81/100

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Veber Number

2

Reaxys ID 22818499 View in Reaxys

47/65 O

CAS Registry Number: 1402166-83-9 Chemical Name: (E)-1-(1-nitroprop-1-en-2-yl)-3-(trifluoromethyl)benzene Linear Structure Formula: C10H8F3NO2 Molecular Formula: C10H8F3NO2 Molecular Weight: 231.174 InChI Key: AIFYVJFOHADBJL-VOTSOKGWSA-N Note:

N O

F

F F

Substance Label (2) Label References 1j

Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5, View in Reaxys

1c

Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol.

19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.603

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

3

TPSA

45.82

Lipinski Number

4

Veber Number

2

NMR Spectroscopy (4) 1 of 4

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys; Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys 2 of 4

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Coupling Nuclei

19F

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb.

33; (2013); p. 10840 - 10844, View in Reaxys 3 of 4

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys 4 of 4

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

19F

Solvents (NMR Spectroscopy)

chloroform-d1

Location

supporting information

Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys

Reaxys ID 22818501 View in Reaxys

48/65 O

CAS Registry Number: 1402166-86-2 Chemical Name: (E)-1-(1-nitroprop-1-en-2-yl)-4-(trifluoromethyl)benzene Linear Structure Formula: C10H8F3NO2 Molecular Formula: C10H8F3NO2 Molecular Weight: 231.174 InChI Key: QRWVNLRECAXCCK-VOTSOKGWSA-N Note:

N O

F F F

Substance Label (2) Label References 1k

Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5, View in Reaxys

1h

Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol.

19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.603

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

3

TPSA

45.82

Lipinski Number

4

Veber Number

2

NMR Spectroscopy (3) 1 of 3

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

83/100

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Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys; Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys 2 of 3

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Coupling Nuclei

19F

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb.

33; (2013); p. 10840 - 10844, View in Reaxys 3 of 3

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys

Reaxys ID 28862760 View in Reaxys

49/65 O

Linear Structure Formula: C10H8F3NO2 Molecular Formula: C10H8F3NO2 Molecular Weight: 231.174 InChI Key: QRWVNLRECAXCCK-UHFFFAOYSA-N Note:

N O F F F

Substance Label (1) Label References 2h

Wu, Hao; Sheng, Wei-Jian; Chen, Bin; Liu, Ren-Rong; Gao, Jian-Rong; Jia, Yi-Xia; Synlett; vol. 26; nb. 20; (2015); p. 2817 - 2820; Art.No: ST-2015-S0581-C, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.603

H Bond Donors

0

H Bond Acceptors

0

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

84/100

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Rotatable Bonds

3

TPSA

45.82

Lipinski Number

4

Veber Number

2

Reaxys ID 21214380 View in Reaxys

50/65 O

Linear Structure Formula: C9H7Cl2NO2 Molecular Formula: C9H7Cl2NO2 Molecular Weight: 232.066 InChI Key: BNOUJPAZROZBHW-UHFFFAOYSA-N Note:

N O Cl

Cl

Druglikeness (1) 1 of 1

LogP

3.922

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

Reaxys ID 3354062 View in Reaxys

51/65 Chemical Name: α-Nitro-α-(5-nitro-2-oxy-4-methyl-phenyl)-α-propylen; 5.α-Dinitro-2-oxy-4.α-dimethyl-styrol; 5-Methyl-4-nitro-2-(2-nitro-1methyl-vinyl)-phenol Linear Structure Formula: C10H10N2O5 Molecular Formula: C10H10N2O5 Molecular Weight: 238.2 Type of Substance: isocyclic InChI Key: GJYPNMDYYMKMFY-FNORWQNLSA-N Note:

O N O

O

N O

OH

Druglikeness (1) 1 of 1

LogP

2.39

H Bond Donors

1

H Bond Acceptors

0

Rotatable Bonds

3

TPSA

111.87

Lipinski Number

4

Veber Number

2

Melting Point (1) 1 of 1

Melting Point [°C]

120 - 121

Solvent (Melting Point)

benzene

Clayton; Journal of the Chemical Society; vol. 97; (1910); p. 1407, View in Reaxys Crystal Property Description (1)

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Colour & Other Properties

References

gelbbraun

Clayton; Journal of the Chemical Society; vol. 97; (1910); p. 1407, View in Reaxys

Reaxys ID 4989272 View in Reaxys

52/65 CAS Registry Number: 119880-57-8; 109757-71-3 Chemical Name: (E)-1-bromo-4-(1-nitroprop-1-en-2-yl)benzene; (E)-2-(4'-bromophenyl)-1-nitropropene; (E)-2-(4-bromophenyl)-1-nitropropene Linear Structure Formula: C9H8BrNO2 Molecular Formula: C9H8BrNO2 Molecular Weight: 242.072 Type of Substance: isocyclic InChI Key: MLCXHNYYLCTFIW-VOTSOKGWSA-N Note:

O N O

Br

Substance Label (5) Label References 1c

Ohta, Hiromichi; Ozaki, Kazuhiko; Tsuchihashi, Gen-ichi; Chemistry Letters; (1987); p. 191 - 192, View in Reaxys; Lei, Xue; Zheng, Lei; Zhang, Chuanxin; Shi, Xiaodong; Chen, Yunfeng; Journal of Organic Chemistry; vol. 83; nb.

4; (2018); p. 1772 - 1778, View in Reaxys

1o

Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5, View in Reaxys

1d

Ohta, Hiromichi; Kobayashi, Naoki; Ozaki, Kazuhiko; Journal of Organic Chemistry; vol. 54; nb. 8; (1989); p. 1802 - 1804, View in Reaxys; Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys; Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p. 3875 - 3879, View in Reaxys

1k

Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol.

19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys

2e

Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; nb. 39; (2013); p.

6713 - 6716, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.476

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

Chromatographic Data (1) Chromatographic Location data TLC (Thin layer chromatography)

supporting informa- Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; tion nb. 39; (2013); p. 6713 - 6716, View in Reaxys

Crystal Property Description (3) Colour & Other Location Properties yellow yellow

References

References Lei, Xue; Zheng, Lei; Zhang, Chuanxin; Shi, Xiaodong; Chen, Yunfeng; Journal of Organic Chemistry; vol. 83; nb. 4; (2018); p. 1772 - 1778, View in Reaxys

supporting informa- Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; tion nb. 39; (2013); p. 6713 - 6716, View in Reaxys; Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p. 3875 3879, View in Reaxys

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yellow

Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys

NMR Spectroscopy (8) 1 of 8

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 500 scopy) [MHz] Location

supporting information

Lei, Xue; Zheng, Lei; Zhang, Chuanxin; Shi, Xiaodong; Chen, Yunfeng; Journal of Organic Chemistry; vol. 83; nb. 4; (2018); p. 1772 - 1778, View in Reaxys 2 of 8

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 125 scopy) [MHz] Location

supporting information

Lei, Xue; Zheng, Lei; Zhang, Chuanxin; Shi, Xiaodong; Chen, Yunfeng; Journal of Organic Chemistry; vol. 83; nb. 4; (2018); p. 1772 - 1778, View in Reaxys 3 of 8

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys; Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys; Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; nb. 39; (2013); p. 6713 - 6716, View in Reaxys; Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol.

357; nb. 18; (2015); p. 3875 - 3879, View in Reaxys 4 of 8

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys; Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys; Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; nb. 39; (2013); p. 6713 - 6716, View in Reaxys

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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5 of 8

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 400 scopy) [MHz] Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys 6 of 8

Description (NMR Spectroscopy)

Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 400 scopy) [MHz] Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys 7 of 8

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 100 scopy) [MHz] Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys 8 of 8

Description (NMR Spectroscopy)

Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 100 scopy) [MHz] Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys IR Spectroscopy (2) 1 of 2

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat liquid

Location

supporting information

Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; nb. 39; (2013); p. 6713 6716, View in Reaxys 2 of 2

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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Mass Spectrometry (2) Description (Mass Location Spectrometry) high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); time-offlight mass spectra (TOFMS); spectrum

References

supporting informa- Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; tion nb. 39; (2013); p. 6713 - 6716, View in Reaxys

spectrum; electron impact (EI)

Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298, View in Reaxys

UV/VIS Spectroscopy (1) 1 of 1

Absorption Maxima (UV/ VIS) [nm]

314

Toogood, Helen S.; Fryszkowska, Anna; Hare, Victoria; Fisher, Karl; Roujeinikova, Anna; Leys, David; Gardiner, John M.; Stephens, Gill M.; Scrutton, Nigel S.; Advanced Synthesis and Catalysis; vol. 350; nb. 17; (2008); p. 2789 - 2803, View in Reaxys

Reaxys ID 19520127 View in Reaxys

53/65 CAS Registry Number: 1163136-84-2 Chemical Name: (Z)-2-(4'-bromophenyl)-1-nitropropene Linear Structure Formula: C9H8BrNO2 Molecular Formula: C9H8BrNO2 Molecular Weight: 242.072 InChI Key: MLCXHNYYLCTFIW-SREVYHEPSA-N Note:

N Br

O

O

Druglikeness (1) 1 of 1

LogP

3.476

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

Crystal Property Description (1) Colour & Other References Properties yellow

Toogood, Helen S.; Fryszkowska, Anna; Hare, Victoria; Fisher, Karl; Roujeinikova, Anna; Leys, David; Gardiner, John M.; Stephens, Gill M.; Scrutton, Nigel S.; Advanced Synthesis and Catalysis; vol. 350; nb. 17; (2008); p.

2789 - 2803, View in Reaxys

NMR Spectroscopy (3) 1 of 3

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 300 scopy) [MHz] Location

supporting information

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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Toogood, Helen S.; Fryszkowska, Anna; Hare, Victoria; Fisher, Karl; Roujeinikova, Anna; Leys, David; Gardiner, John M.; Stephens, Gill M.; Scrutton, Nigel S.; Advanced Synthesis and Catalysis; vol. 350; nb. 17; (2008); p. 2789 - 2803, View in Reaxys 2 of 3

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 75 scopy) [MHz] Location

supporting information

Toogood, Helen S.; Fryszkowska, Anna; Hare, Victoria; Fisher, Karl; Roujeinikova, Anna; Leys, David; Gardiner, John M.; Stephens, Gill M.; Scrutton, Nigel S.; Advanced Synthesis and Catalysis; vol. 350; nb. 17; (2008); p. 2789 - 2803, View in Reaxys 3 of 3

Description (NMR Spectroscopy)

DEPT (Distorsionless Enhancement by Polarisation Transfer); Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 75 scopy) [MHz] Location

supporting information

Toogood, Helen S.; Fryszkowska, Anna; Hare, Victoria; Fisher, Karl; Roujeinikova, Anna; Leys, David; Gardiner, John M.; Stephens, Gill M.; Scrutton, Nigel S.; Advanced Synthesis and Catalysis; vol. 350; nb. 17; (2008); p. 2789 - 2803, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

neat liquid

Toogood, Helen S.; Fryszkowska, Anna; Hare, Victoria; Fisher, Karl; Roujeinikova, Anna; Leys, David; Gardiner, John M.; Stephens, Gill M.; Scrutton, Nigel S.; Advanced Synthesis and Catalysis; vol. 350; nb. 17; (2008); p. 2789 - 2803, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry) EI (Electron impact); Spectrum

Toogood, Helen S.; Fryszkowska, Anna; Hare, Victoria; Fisher, Karl; Roujeinikova, Anna; Leys, David; Gardiner, John M.; Stephens, Gill M.; Scrutton, Nigel S.; Advanced Synthesis and Catalysis; vol. 350; nb. 17; (2008); p.

2789 - 2803, View in Reaxys

HRMS (High resolution mass spectrometry); ESI (Electrospray ionisation); Spectrum

Toogood, Helen S.; Fryszkowska, Anna; Hare, Victoria; Fisher, Karl; Roujeinikova, Anna; Leys, David; Gardiner, John M.; Stephens, Gill M.; Scrutton, Nigel S.; Advanced Synthesis and Catalysis; vol. 350; nb. 17; (2008); p.

2789 - 2803, View in Reaxys

UV/VIS Spectroscopy (1) 1 of 1

Absorption Maxima (UV/ VIS) [nm]

224

Toogood, Helen S.; Fryszkowska, Anna; Hare, Victoria; Fisher, Karl; Roujeinikova, Anna; Leys, David; Gardiner, John M.; Stephens, Gill M.; Scrutton, Nigel S.; Advanced Synthesis and Catalysis; vol. 350; nb. 17; (2008); p. 2789 - 2803, View in Reaxys

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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Reaxys ID 19761859 View in Reaxys

54/65 CAS Registry Number: 119880-57-8 Chemical Name: 2-(4-bromophenyl)-1-nitropropene Linear Structure Formula: C9H8BrNO2 Molecular Formula: C9H8BrNO2 Molecular Weight: 242.072 InChI Key: MLCXHNYYLCTFIW-UHFFFAOYSA-N Note:

O N O

Br

Substance Label (1) Label References 2f

Wu, Hao; Sheng, Wei-Jian; Chen, Bin; Liu, Ren-Rong; Gao, Jian-Rong; Jia, Yi-Xia; Synlett; vol. 26; nb. 20; (2015); p. 2817 - 2820; Art.No: ST-2015-S0581-C, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.476

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

NMR Spectroscopy (2) 1 of 2

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 500 scopy) [MHz] Taniguchi, Tsuyoshi; Fujii, Tatsuya; Ishibashi, Hiroyuki; Journal of Organic Chemistry; vol. 75; nb. 23; (2010); p. 8126 8132, View in Reaxys 2 of 2

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Temperature (NMR Spectroscopy) [°C]

20.4

Frequency (NMR Spectro- 150.9 scopy) [MHz] Location

supporting information

Taniguchi, Tsuyoshi; Fujii, Tatsuya; Ishibashi, Hiroyuki; Journal of Organic Chemistry; vol. 75; nb. 23; (2010); p. 8126 8132, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) HRMS (High resolution mass spectrometry); FAB (Fast atom bombardment); Spectrum

Taniguchi, Tsuyoshi; Fujii, Tatsuya; Ishibashi, Hiroyuki; Journal of Organic Chemistry; vol. 75; nb. 23; (2010); p.

8126 - 8132, View in Reaxys

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Reaxys ID 22818477 View in Reaxys

55/65 CAS Registry Number: 1402166-82-8 Chemical Name: (E)-1-bromo-3-(1-nitroprop-1-en-2-yl)benzene Linear Structure Formula: C9H8BrNO2 Molecular Formula: C9H8BrNO2 Molecular Weight: 242.072 InChI Key: YIRLVXZLZPMIKG-VOTSOKGWSA-N Note:

O Br

N O

Substance Label (2) Label References 1n

Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5, View in Reaxys

1f

Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol.

19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.476

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

NMR Spectroscopy (2) 1 of 2

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys; Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys 2 of 2

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys; Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys

Reaxys ID 22818483 View in Reaxys

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

56/65

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Br

O

CAS Registry Number: 1402166-79-3 Linear Structure Formula: C9H8BrNO2 Molecular Formula: C9H8BrNO2 Molecular Weight: 242.072 InChI Key: WVNZLMATCQQKLT-VOTSOKGWSA-N Note:

N O

Druglikeness (1) 1 of 1

LogP

3.476

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

NMR Spectroscopy (2) 1 of 2

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys 2 of 2

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys

Reaxys ID 23598404 View in Reaxys

57/65 O

Chemical Name: 1-(1-methyl-2-nitrovinyl)-4-(2-nitropropenyl)benzene Linear Structure Formula: C12H12N2O4 Molecular Formula: C12H12N2O4 Molecular Weight: 248.238 InChI Key: KUFAOXAYYYYVTA-DGLUDJRXSA-N Note:

N O

O N O

Substance Label (1)

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Label

References

4o

Chang, Meng-Yang; Lin, Chung-Han; Tai, Hang-Yi; Tetrahedron Letters; vol. 54; nb. 24; (2013); p. 3194 - 3198, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.393

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

4

TPSA

91.64

Lipinski Number

4

Veber Number

2

Melting Point (1) 1 of 1

Melting Point [°C]

122 - 123

Solvent (Melting Point)

hexane; ethyl acetate

Location

supporting information

Chang, Meng-Yang; Lin, Chung-Han; Tai, Hang-Yi; Tetrahedron Letters; vol. 54; nb. 24; (2013); p. 3194 - 3198, View in Reaxys Crystal Property Description (1) Colour & Other Location Properties yellow

References

supporting informa- Chang, Meng-Yang; Lin, Chung-Han; Tai, Hang-Yi; Tetrahedron Letters; vol. 54; nb. 24; tion (2013); p. 3194 - 3198, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Temperature (NMR Spectroscopy) [°C]

25

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Chang, Meng-Yang; Lin, Chung-Han; Tai, Hang-Yi; Tetrahedron Letters; vol. 54; nb. 24; (2013); p. 3194 - 3198, View in Reaxys 2 of 2

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Chang, Meng-Yang; Lin, Chung-Han; Tai, Hang-Yi; Tetrahedron Letters; vol. 54; nb. 24; (2013); p. 3194 - 3198, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)

References

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

supporting informa- Chang, Meng-Yang; Lin, Chung-Han; Tai, Hang-Yi; Tetrahedron Letters; vol. 54; nb. 24; tion (2013); p. 3194 - 3198, View in Reaxys

Reaxys ID 2509360 View in Reaxys

58/65 CAS Registry Number: 24307-22-0 Chemical Name: (Z)-α-Methyl-α-nitro-pentafluorstyrol Linear Structure Formula: C9H4F5NO2 Molecular Formula: C9H4F5NO2 Molecular Weight: 253.128 Type of Substance: isocyclic InChI Key: PARLIFWZAATTIZ-IHWYPQMZSA-N Note:

F F

N

F

F

O

O

F

Substance Label (1) Label References XVIII

Anichkina,S.A. et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 39; nb. 8; (1969); p. 1766 - 1773,1730 - 1736, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.483

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

NMR Spectroscopy (1) 1 of 1

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Anichkina,S.A. et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 39; nb. 8; (1969); p. 1766 - 1773,1730 - 1736, View in Reaxys

Reaxys ID 2509361 View in Reaxys

59/65 O

CAS Registry Number: 24266-24-8 Chemical Name: (E)-α-Methyl-α-nitro-pentafluorstyrol Linear Structure Formula: C9H4F5NO2 Molecular Formula: C9H4F5NO2 Molecular Weight: 253.128 Type of Substance: isocyclic InChI Key: PARLIFWZAATTIZ-NSCUHMNNSA-N Note:

N F

O

F

F

F F

Substance Label (1) Label References XVII

Anichkina,S.A. et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 39; nb. 8; (1969); p. 1766 - 1773,1730 - 1736, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.483

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H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

NMR Spectroscopy (1) 1 of 1

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Anichkina,S.A. et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 39; nb. 8; (1969); p. 1766 - 1773,1730 - 1736, View in Reaxys

Reaxys ID 30915346 View in Reaxys

60/65 O

Chemical Name: (E)-2-(cyclopentyloxy)-1-methoxy-4-(1-nitroprop-1-en-2-yl)benzene Linear Structure Formula: C15H19NO4 Molecular Formula: C15H19NO4 Molecular Weight: 277.32 InChI Key: IUSOHBDSUSVGTE-ZHACJKMWSA-N Note:

N O

O O

Substance Label (1) Label References 1g

Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.499

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

5

TPSA

64.28

Lipinski Number

4

Veber Number

2

Crystal Property Description (1) Colour & Other Location Properties yellow

References

supporting informa- Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; tion (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

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Frequency (NMR Spectro- 500 scopy) [MHz] Location

supporting information

Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew.

Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5, View in Reaxys 2 of 2

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 125 scopy) [MHz] Location

supporting information

Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew.

Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5, View in Reaxys

Reaxys ID 22818481 View in Reaxys

61/65 O

CAS Registry Number: 1402166-85-1 Linear Structure Formula: C9H8INO2 Molecular Formula: C9H8INO2 Molecular Weight: 289.073 InChI Key: KMIYTEHKQMFFPC-VOTSOKGWSA-N Note:

N O

I

Substance Label (1) Label References (E)-1i

Bertolotti, Mattia; Brenna, Elisabetta; Crotti, Michele; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Santangelo, Sara; ChemCatChem; vol. 8; nb. 3; (2016); p. 577 - 583, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.746

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

45.82

Lipinski Number

4

Veber Number

2

NMR Spectroscopy (2) 1 of 2

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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2 of 2

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys

Reaxys ID 3453398 View in Reaxys

62/65 O

Chemical Name: 3.5.α-trinitro-6-oxy-2.4.α-trimethyl-styrene; α-Nitroα-(3.5-dinitro-6-oxy-2.4-dimethyl-phenyl)-α-propylen; 3.5.α-Trinitro-6oxy-2.4.α-trimethyl-styrol Linear Structure Formula: C11H11N3O7 Molecular Formula: C11H11N3O7 Molecular Weight: 297.224 Type of Substance: isocyclic InChI Key: ARHZJVXGHINDEK-SNAWJCMRSA-N Note:

N O

O

N O

OH N O

O

Druglikeness (1) 1 of 1

LogP

3.366

H Bond Donors

1

H Bond Acceptors

0

Rotatable Bonds

4

TPSA

157.69

Lipinski Number

4

Veber Number

1

Melting Point (1) 1 of 1

Melting Point [°C]

103

Solvent (Melting Point)

benzene

Jordan; Thorpe; Journal of the Chemical Society; vol. 107; (1915); p. 401, View in Reaxys

Reaxys ID 22818518 View in Reaxys F

63/65 O

CAS Registry Number: 1402166-84-0 Chemical Name: (E)-1-(1-nitroprop-1-en-2-yl)-3,5-bis(trifluoromethyl)benzene Linear Structure Formula: C11H7F6NO2 Molecular Formula: C11H7F6NO2 Molecular Weight: 299.172 InChI Key: SWLFIJDRBCMVIX-AATRIKPKSA-N Note:

F N F

O

F

F F

Substance Label (1) Label References

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1b

Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol.

19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.528

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

4

TPSA

45.82

Lipinski Number

4

Veber Number

2

NMR Spectroscopy (3) 1 of 3

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys; Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844, View in Reaxys 2 of 3

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Coupling Nuclei

19F

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb.

33; (2013); p. 10840 - 10844, View in Reaxys 3 of 3

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576, View in Reaxys

Reaxys ID 3073004 View in Reaxys

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

64/65

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CAS Registry Number: 19937-19-0 Chemical Name: 3,4-Dibenzyloxy-α-methyl-α-nitro-styrol Linear Structure Formula: C23H21NO4 Molecular Formula: C23H21NO4 Molecular Weight: 375.424 Type of Substance: isocyclic InChI Key: ODIVOVYCWPKMKP-UHFFFAOYSA-N Note:

O O

N O

O

Substance Label (1) Label References II

Hohenlohe-Oehringen,K.; Call,L.; Monatshefte fuer Chemie; vol. 99; nb. 4; (1968); p. 1313 - 1319, View in Reaxys

Druglikeness (1) 1 of 1

LogP

5.66

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

8

TPSA

64.28

Lipinski Number

3

Veber Number

2

Melting Point (1) 1 of 1

Melting Point [°C]

117

Solvent (Melting Point)

ethanol

Hohenlohe-Oehringen,K.; Call,L.; Monatshefte fuer Chemie; vol. 99; nb. 4; (1968); p. 1313 - 1319, View in Reaxys

Reaxys ID 11967463 View in Reaxys

65/65 O N O

Cl O

H N

Cl O Cl

O

Cl

CAS Registry Number: 1072274-19-1 Linear Structure Formula: C22H20Cl4N2O5 Molecular Formula: C22H20Cl4N2O5 Molecular Weight: 534.223 InChI Key: NUDVTUJOEULUKZ-BUHFOSPRSA-N Note:

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; SYNGENTA PARTICIPATIONS AG; WO2004/52816; (2004); (A1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

7.035

H Bond Donors

1

H Bond Acceptors

2

Rotatable Bonds

12

TPSA

93.38

Lipinski Number

2

Veber Number

1

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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