1-Phenyl-1,2-propanediol [C9H12O2]

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2018-08-07 14h:39m:47s (UTC)

HO

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HO

Search as: As drawn ) AND (IDE.XRN=2044500))

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Reaxys ID 2044500 View in Reaxys

1/1 CAS Registry Number: 1855-09-0 Chemical Name: 1-phenyl-1,2-propandiol; 1-phenyl-1,2-propanediol; 1-phenylpropane-1,2-diol; (α.α-Dioxy-propyl)-benzol; α-Phenyl-propylenglykol; 11.12-Dioxy-1-propyl-benzol; α-Methyl-α'-phenyl-aethylenglykol Linear Structure Formula: C9H12O2 Molecular Formula: C9H12O2 Molecular Weight: 152.193 Type of Substance: isocyclic InChI Key: MZQZXSHFWDHNOW-UHFFFAOYSA-N Note:

HO

HO

Substance Label (14) Label References 1e

Matsusaki, Yoko; Yamaguchi, Tomoaki; Tada, Norihiro; Miura, Tsuyoshi; Itoh, Akichika; Synlett; vol. 23; nb. 14; (2012); p. 2059 - 2062, View in Reaxys; Escande, Vincent; Lam, Chun Ho; Coish, Philip; Anastas, Paul T.; Angewandte Chemie - International Edition; vol. 56; nb. 32; (2017); p. 9561 - 9565; Angew. Chem.; vol. 129; nb. 32; (2017); p. 9689 - 9693,5, View in Reaxys

10k

Wang, Jun-Li; Li, Hui-Jing; Wang, Hong-Shuang; Wu, Yan-Chao; Organic Letters; vol. 19; nb. 14; (2017); p. 3811 3814, View in Reaxys

S26

Borrell, Margarida; Costas, Miquel; Journal of the American Chemical Society; vol. 139; nb. 36; (2017); p. 12821 12829, View in Reaxys

2z

Yang, Bo; Lu, Zhan; Chemical Communications; vol. 53; nb. 94; (2017); p. 12634 - 12637, View in Reaxys

4c

Wusiman, Abudureheman; Lu, Chong-Dao; Applied Organometallic Chemistry; vol. 29; nb. 4; (2015); p. 254 - 258, View in Reaxys

13

Shi, Yan-Ni; Yang, Lian; Zhao, Jin-Hua; Shi, Yi-Ming; Qu, Yan; Zhu, Hong-Tao; Wang, Dong; Yang, ChongRen; Li, Xing-Cong; Xu, Min; Zhang, Ying-Jun; Natural Product Research; vol. 29; nb. 14; (2015); p. 1372 - 1375, View in Reaxys

7

Sivakumari, Thakkellapati; Chadha, Anju; RSC Advances; vol. 4; nb. 105; (2014); p. 60526 - 60533, View in Reaxys

2e

Zhang, Min; Xie, Feng; Wang, Xiaoting; Yan, Fengxia; Wang, Ting; Chen, Mengmeng; Ding, Yuqiang; RSC Advances; vol. 3; nb. 17; (2013); p. 6022 - 6029, View in Reaxys

3c

Shaikh, Tanveer Mahammadali; Hong, Fung-E; Tetrahedron; vol. 69; nb. 42; (2013); p. 8929 - 8935, View in Reaxys

2d

Santi, Claudio; Di Lorenzo, Rosalia; Tidei, Caterina; Bagnoli, Luana; Wirth, Thomas; Tetrahedron; vol. 68; nb. 51; (2012); p. 10530 - 10535,6, View in Reaxys

T.1, 3 (R1=Ph, R2=Me)

Kamochi, Yasuko; Kudo, Tadahiro; Masuda, Toshinobu; Takadate, Akira; Chemical and Pharmaceutical Bulletin; vol. 53; nb. 8; (2005); p. 1017 - 1020, View in Reaxys

Scheme 3

Jana, Samaresh; Guin, Chandrani; Roy, Subhas Chandra; Tetrahedron Letters; vol. 45; nb. 35; (2004); p. 6575 6577, View in Reaxys

entry 4 (Table S1)

Choudary; Chowdari; Kantam; Raghavan; Journal of the American Chemical Society; vol. 123; nb. 37; (2001); p.

9220 - 9221, View in Reaxys

11e

Ji, Shun-Jun; Matsushita, Masatoshi; Takahashi, T. Tomoyoshi; Horiuchi, C. Akira; Tetrahedron Letters; vol. 40; nb. 37; (1999); p. 6791 - 6794, View in Reaxys

Patent-Specific Data (2) Prophetic ComLocation in Patent pound

References Patent; Bayer Aktiengesellschaft; US6825377; (2004); (B1) English, View in Reaxys

prophetic product

Claim

Patent; BROWN, DAVID A.; KHORLIN, ALEXANDER A.; LESIAK, KRYSTYNA; REN, WU YUN; US2002/141952; (2002); (A1) English, View in Reaxys; Patent; Applied Genetics Incorporated Dermatics; US6110975; (2000); (A) English, View in Reaxys; Patent; Codon Pharmaceuticals, Inc.; US5990177; (1999); (A) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.065

H Bond Donors

2

H Bond Acceptors

2

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Rotatable Bonds

2

TPSA

40.46

Lipinski Number

4

Veber Number

2

Related Structure (1) References Colonge et al.; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 259; (1964); p. 3566, View in Reaxys Derivative (1) Comment (Derivative)

References

Monoacetylverb.: Struktur (NMR)

Lavrova; Zalesskaya; Journal of Organic Chemistry USSR (English Translation); vol. 10; (1974); p. 1803; Zhurnal Organicheskoi Khimii; vol. 10; (1974); p. 1788, View in Reaxys

Melting Point (10) 1 of 10

Melting Point [°C]

56 - 58

Location

supporting information

Wang, Jun-Li; Li, Hui-Jing; Wang, Hong-Shuang; Wu, Yan-Chao; Organic Letters; vol. 19; nb. 14; (2017); p. 3811 - 3814, View in Reaxys 2 of 10

Melting Point [°C]

91 - 92

Ogibin, Yu. N.; Ilovaiskii, A. I.; Nikishin, G. I.; Russian Chemical Bulletin; vol. 42; nb. 1; (1993); p. 126 - 128; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 1; (1993); p. 140 - 143, View in Reaxys 3 of 10

Melting Point [°C]

54 - 55

Marshall; Prager; Australian Journal of Chemistry; vol. 30; (1977); p. 141,144. 150, View in Reaxys 4 of 10

Melting Point [°C]

52 - 53

Solvent (Melting Point)

diethyl ether

Bratchanskii,P.E.; Komissarova,G.G.; Zhurnal Organicheskoi Khimii; vol. 11; (1975); p. 1661 - 1665,1650 - 1654, View in Reaxys 5 of 10

Melting Point [°C]

90 - 92

Sinsheimer; Dring; Williams; Biochemical Journal; vol. 136; nb. 3; (1973); p. 763 - 771, View in Reaxys 6 of 10

Melting Point [°C]

93 - 94

Zalesskaja; Lavrova; Zhurnal Organicheskoi Khimii; vol. 5; (1969); p. 454,441, View in Reaxys 7 of 10

Melting Point [°C]

90.5

Solvent (Melting Point)

benzene

Colonge et al.; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 259; (1964); p. 3566, View in Reaxys 8 of 10

Melting Point [°C]

70 - 73

Neuberg; Komarewsky; Biochemische Zeitschrift; vol. 182; (1927); p. 287, View in Reaxys 9 of 10

Melting Point [°C]

92 - 93

Solvent (Melting Point)

diethyl ether

Comment (Melting Point)

high-melting form

Zincke; Chemische Berichte; vol. 17; (1884); p. 709, View in Reaxys 10 of 10

Melting Point [°C]

52 - 53

Solvent (Melting Point)

diethyl ether; petroleum ether

Comment (Melting Point)

low-melting form

Zincke; Chemische Berichte; vol. 17; (1884); p. 709, View in Reaxys Boiling Point (5) Boiling Point [°C]

Pressure (Boiling Point) [Torr]

References

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99

1

Miyaura, N.; Kochi, J. K.; Journal of the American Chemical Society; vol. 105; nb. 8; (1983); p.

2368 - 2378, View in Reaxys

121 - 121.5

3

Bratchanskii,P.E.; Komissarova,G.G.; Zhurnal Organicheskoi Khimii; vol. 11; (1975); p. 1661 1665,1650 - 1654, View in Reaxys

127 - 127.5

3.5

v. Falkenhausen; Biochemische Zeitschrift; vol. 219; (1930); p. 242,247, View in Reaxys

154 - 156

17

v. Falkenhausen; Biochemische Zeitschrift; vol. 219; (1930); p. 242,247, View in Reaxys

118

1

Neuberg; Komarewsky; Biochemische Zeitschrift; vol. 182; (1927); p. 287, View in Reaxys

Refractive Index (1) Refractive Index Wavelength (ReTemperature (Refractive Index) [nm] fractive Index) [°C] 1.5374

589

20

References Bratchanskii,P.E.; Komissarova,G.G.; Zhurnal Organicheskoi Khimii; vol.

11; (1975); p. 1661 - 1665,1650 - 1654, View in Reaxys

Density (1) 1 of 1

Density [g·cm-3]

1.1003

Reference Temperature [°C]

4

Measurement Temperature 20 [°C] Bratchanskii,P.E.; Komissarova,G.G.; Zhurnal Organicheskoi Khimii; vol. 11; (1975); p. 1661 - 1665,1650 - 1654, View in Reaxys Crystal Property Description (4) Colour & Other Location Properties

Comment (Crystal Property Description)

References

white

supporting information

Wang, Jun-Li; Li, Hui-Jing; Wang, Hong-Shuang; Wu, Yan-Chao; Organic Letters; vol. 19; nb. 14; (2017); p. 3811 - 3814, View in Reaxys

colourless

supporting information

Yang, Bo; Lu, Zhan; Chemical Communications; vol. 53; nb. 94; (2017); p.

12634 - 12637, View in Reaxys

Tafeln

low-melting form

Zincke; Chemische Berichte; vol. 17; (1884); p. 709, View in Reaxys

Tafeln

high-melting form

Zincke; Chemische Berichte; vol. 17; (1884); p. 709, View in Reaxys

Further Information (1) Description (FurReferences ther Information) Further information Pascal; Annales de Chimie (Cachan, France); vol. 3; nb. 14; (1968); p. 247,272, View in Reaxys Optical Rotatory Power (2) 1 of 2

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

c=10

Solvent (Optical Rotatory Power)

ethanol

Optical Rotatory Power [deg]

-17

Wavelength (Optical Rota- 589 tory Power) [nm] v. Falkenhausen; Biochemische Zeitschrift; vol. 219; (1930); p. 242,247, View in Reaxys 2 of 2

Type (Optical Rotatory Power)

alpha

Length of Path [cm]

10

Solvent (Optical Rotatory Power)

neat (no solvent)

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Optical Rotatory Power [deg]

-15.15

Wavelength (Optical Rota- 589 tory Power) [nm] Neuberg; Komarewsky; Biochemische Zeitschrift; vol. 182; (1927); p. 287, 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

Wang, Jun-Li; Li, Hui-Jing; Wang, Hong-Shuang; Wu, Yan-Chao; Organic Letters; vol. 19; nb. 14; (2017); p. 3811 - 3814, View in Reaxys; Yang, Bo; Lu, Zhan; Chemical Communications; vol. 53; nb. 94; (2017); p. 12634 - 12637, 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

Wang, Jun-Li; Li, Hui-Jing; Wang, Hong-Shuang; Wu, Yan-Chao; Organic Letters; vol. 19; nb. 14; (2017); p. 3811 - 3814, View in Reaxys 3 of 7

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Erathodiyil, Nandanan; Gu, Hongwei; Shao, Huilin; Jiang, Jiang; Ying, Jackie Y.; Green Chemistry; vol. 13; nb. 11; (2011); p. 3070 - 3074, View in Reaxys 4 of 7

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Comment (NMR Spectroscopy)

single stereoisomer

Bales; Horner; Huang; Newcomb; Crich; Greenberg; Journal of the American Chemical Society; vol. 123; nb. 16; (2001); p.

3623 - 3629, View in Reaxys 5 of 7

Nucleus (NMR Spectroscopy)

1H

Coupling Nuclei

1H

Solvents (NMR Spectroscopy)

CDCl3

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Comment (NMR Spectroscopy)

single stereoisomer

Bales; Horner; Huang; Newcomb; Crich; Greenberg; Journal of the American Chemical Society; vol. 123; nb. 16; (2001); p.

3623 - 3629, View in Reaxys 6 of 7

Nucleus (NMR Spectroscopy)

1H

Coupling Nuclei

1H

Solvents (NMR Spectroscopy)

CDCl3

Kise; Hirata; Ueda; Journal of Organic Chemistry; vol. 66; nb. 3; (2001); p. 862 - 867, View in Reaxys 7 of 7

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Ogibin, Yu. N.; Ilovaiskii, A. I.; Nikishin, G. I.; Russian Chemical Bulletin; vol. 42; nb. 1; (1993); p. 126 - 128; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 1; (1993); p. 140 - 143, View in Reaxys; Kise; Hirata; Ueda; Journal of Organic Chemistry; vol. 66; nb. 3; (2001); p. 862 - 867, View in Reaxys IR Spectroscopy (2) 1 of 2

Description (IR Spectroscopy)

Bands

Location

supporting information

Comment (IR Spectroscopy)

film

Wang, Jun-Li; Li, Hui-Jing; Wang, Hong-Shuang; Wu, Yan-Chao; Organic Letters; vol. 19; nb. 14; (2017); p. 3811 - 3814, View in Reaxys 2 of 2

Description (IR Spectroscopy)

Bands

Fedoronko,M.; Collection of Czechoslovak Chemical Communications; vol. 37; (1972); p. 3897 - 3901, View in Reaxys; Bratchanskii,P.E.; Komissarova,G.G.; Zhurnal Organicheskoi Khimii; vol. 11; (1975); p. 1661 - 1665,1650 - 1654, View in Reaxys Mass Spectrometry (3) Description (Mass Location Spectrometry) high resolution mass spectrometry (HRMS); spectrum

References

supporting informa- Wang, Jun-Li; Li, Hui-Jing; Wang, Hong-Shuang; Wu, Yan-Chao; Organic Letters; vol. 19; tion nb. 14; (2017); p. 3811 - 3814, View in Reaxys

Spectrum

Erathodiyil, Nandanan; Gu, Hongwei; Shao, Huilin; Jiang, Jiang; Ying, Jackie Y.; Green Chemistry; vol. 13; nb. 11; (2011); p. 3070 - 3074, View in Reaxys Kawai; Baba; Chemical and Pharmaceutical Bulletin; vol. 23; (1975); p. 289,291, View in Reaxys; Audier et al.; Bulletin de la Societe Chimique de France; (1968); p. 3844, View in Reaxys

UV/VIS Spectroscopy (1) 1 of 1

Description (UV/VIS Spectroscopy)

Spectrum

Fedoronko,M.; Collection of Czechoslovak Chemical Communications; vol. 37; (1972); p. 3897 - 3901, View in Reaxys Isolation from Natural Product (1) Isolation from Nat- Location ural Product

References

stems of Piper wall- supporting informa- Shi, Yan-Ni; Yang, Lian; Zhao, Jin-Hua; Shi, Yi-Ming; Qu, Yan; Zhu, Hong-Tao; Wang, ichii; collected in tion Dong; Yang, Chong-Ren; Li, Xing-Cong; Xu, Min; Zhang, Ying-Jun; Natural Product ReHenan Province, search; vol. 29; nb. 14; (2015); p. 1372 - 1375, View in Reaxys People's Republic of China, June 2012

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