N-Hydroxy-1-phenyl-2-propanimine (1-Phenylpropan-2-one oxime) [C9H11NO]

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8 substances in Reaxys

2017-12-12 00h:17m:52s (EST)

5 substances in Reaxys

2017-12-12 00h:19m:36s (EST)

N OH

1. Query

Search as: As drawn 2. Query

(1. Query) AND NOT itemno in (7,6,5)

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Reaxys ID 2255425 View in Reaxys

(v1)

O

1/5 CAS Registry Number: 38989-82-1 Linear Structure Formula: C9H10NO Molecular Formula: C9H10NO Molecular Weight: 148.184 Type of Substance: isocyclic InChI Key: WVXLTPXFNVMBOY-UHFFFAOYSA-N Note:

N

Druglikeness (1) 1 of 1

LogP

1.957

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

12.36

Lipinski Number

4

Veber Number

2

ESR Spectroscopy (4) 1 of 4

Description (ESR Spectroscopy)

ESR-hyperfine coupling constants

Solvents (ESR Spectroscopy)

toluene

Temperature (ESR Spectroscopy) [°C]

21.9

Comment (ESR Spectroscopy)

14N, 1H.

Jezierski, Adam; Magnetic Resonance in Chemistry; vol. 27; nb. 2; (1989); p. 130 - 133, View in Reaxys 2 of 4

Description (ESR Spectroscopy)

g-factor

Jezierski, Adam; Magnetic Resonance in Chemistry; vol. 27; nb. 2; (1989); p. 130 - 133, View in Reaxys 3 of 4

Description (ESR Spectroscopy)

Signals

Solvents (ESR Spectroscopy)

toluene

Temperature (ESR Spectroscopy) [°C]

21.9

Jezierski, Adam; Magnetic Resonance in Chemistry; vol. 27; nb. 2; (1989); p. 130 - 133, View in Reaxys 4 of 4

Description (ESR Spectroscopy)

Signals

Brokenshire,J.L. et al.; Journal of the American Chemical Society; vol. 94; nb. 20; (1972); p. 7040 - 7049, View in Reaxys

Reaxys ID 508872 View in Reaxys

HO

2/5 CAS Registry Number: 13213-36-0 Chemical Name: 1-phenylpropan-2-one oxime; phenylacetone oxime Linear Structure Formula: C9H11ON Molecular Formula: C9H11NO Molecular Weight: 149.192 Type of Substance: isocyclic InChI Key: AUYFJUMCPAMOKN-UHFFFAOYSA-N

N

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Note: Substance Label (34) Label References 5

Wessling, Michael; Schäfer, Hans J.; Beilstein Journal of Organic Chemistry; vol. 11; (2015); p. 1163 1174, View in Reaxys

1i

Xuan, Jun; Xia, Xu-Dong; Zeng, Ting-Ting; Feng, Zhu-Jia; Chen, Jia-Rong; Lu, Liang-Qiu; Xiao, WenJing; Angewandte Chemie - International Edition; vol. 53; nb. 22; (2014); p. 5653 - 5656; Angew. Chem.; vol.

126; nb. 22; (2014); p. 5759 - 5762,4, View in Reaxys

T1, E5, Ketoxime

Sardarian; Shahsavari-Fard; Shahsavari; Ebrahimi; Tetrahedron Letters; vol. 48; nb. 14; (2007); p. 2639 2643, View in Reaxys

5b

Bures, Jordi; Isart, Carles; Vilarrasa, Jaume; Organic Letters; vol. 9; nb. 22; (2007); p. 4635 - 4638, View in Reaxys

T.4, Entry 16,Sub- Shirini; Esm-Hosseini; Hejazi; Mohammadpoor-Baltork; Journal of Chemical Research; nb. 1; (2006); p. strate 29 - 31, View in Reaxys 13

Wipf, Peter; Fletcher, Joan M.; Scarone, Laura; Tetrahedron Letters; vol. 46; nb. 33; (2005); p. 5463 5466, View in Reaxys

Table I, entry 7

Kiasat, Ali Reza; Kazemi, Foad; Nourbakhsh, Kazem; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 179; nb. 6; (2004); p. 1193 - 1196, View in Reaxys

Tab. 1., Ent. 3., educt

Dongare, Mohan K.; Bhagwat, Vivekanand V.; Ramana; Gurjar, Mukund K.; Tetrahedron Letters; vol. 45; nb. 24; (2004); p. 4759 - 4762, View in Reaxys

3b

Torii, Sigeru; Tanaka, Hideo; Katoh, Tetsuo; Chemistry Letters; (1983); p. 607 - 610, View in Reaxys; Hwu, Jih Ru; Tseng, Wen Nan; Patel, Himatkumar V.; Wong, Fong Fuh; Horng, Den-Nan; Liaw, Ben Ruey; Lung Ching, Lin; Journal of Organic Chemistry; vol. 64; nb. 7; (1999); p. 2211 - 2218, View in Reaxys

4, R=C6H5

Kim, Kil Joong; Kim, Kyongtae; Heterocycles; vol. 50; nb. 1; (1999); p. 147 - 157, View in Reaxys

2; AMPH oxime

Cashman, John R.; Xiong, Yeng N.; Lifen, Xu; Janowsky, Aaron; Journal of Pharmacology and Experimental Therapeutics; vol. 288; nb. 3; (1999); p. 1251 - 1260, View in Reaxys

2e

Tomioka, Hideo; Ueda, Koichi; Ohi, Hirofumi; Izawa, Yasuji; Chemistry Letters; (1986); p. 1359 - 1362, View in Reaxys; Iesce, M. Rosaria; Cermola, Flavio; Guitto, Antonio; Synthesis; nb. 6; (1997); p. 657 660, View in Reaxys

PhCH2(CH3)C=N Marques, C. A.; Selva, M.; Tundo, P.; Montanari, F.; Journal of Organic Chemistry; vol. 58; nb. 21; (1993); OH p. 5765 - 5770, View in Reaxys 53a

Hall, J. Herbert; Chien, Joseph Yuming; Kauffman, Joel M.; Litak, Peter T.; Adams, Jeffrey K.; et al.; Journal of Heterocyclic Chemistry; vol. 29; nb. 5; (1992); p. 1245 - 1273, View in Reaxys

entry 2

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

12

Felix, C.; Laurent, A.; Lesniak, S.; Mison, P.; Journal of Chemical Research, Miniprint; nb. 2; (1991); p. 301 - 323, View in Reaxys

entry 4

Ranu, Brindaban C.; Chakraborty, Rupak; Tetrahedron Letters; vol. 32; nb. 29; (1991); p. 3579 - 3582, View in Reaxys

4c

Wessling, Michael; Schaefer, Hans J.; Chemische Berichte; vol. 124; nb. 10; (1991); p. 2303 - 2306, View in Reaxys

Table entry 6 column 1

Barton, H. R. Derek; Bowles, Timothy; Husinec, Suren; Forbes, Judith E.; Llobera, Antonia; et al.; Tetrahedron Letters; vol. 29; nb. 27; (1988); p. 3343 - 3346, View in Reaxys

educt for 6e

Jennings, W. Brian; Watson, Stephen P.; Boyd, Derek R.; Journal of the Chemical Society, Chemical Communications; (1988); p. 931 - 932, View in Reaxys

Table 1, entry 26,col.1

Firouzabadi, H.; Iranpoor, N.; Kiaeezadeh, F.; Toofan, J.; Tetrahedron; vol. 42; nb. 2; (1986); p. 719 - 726, View in Reaxys

1, table, entry 9

Monti, D.; Gramatica, P.; Speranza, G.; Tagliapietra, S.; Manitto, P.; Synthetic Communications; vol. 16; nb. 7; (1986); p. 803 - 808, View in Reaxys

19

Lozynski, Marek; Rusinska-Roszak, Danuta; Polish Journal of Chemistry; vol. 60; nb. 4-6; (1986); p. 625 630, View in Reaxys

2a

Beckett,A.H. et al.; Tetrahedron; vol. 32; (1976); p. 1267 - 1276, View in Reaxys; Varma, Rajender S.; Varma, Manju; Kabalka, George W.; Tetrahedron Letters; vol. 26; nb. 49; (1985); p. 6013 - 6014, View in Reaxys

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5a

Shono, Tatsuya; Hamaguchi, Hiroshi; Mikami, Hiroshi; Nogusa, Hideo; Kashimura, Shigenori; Journal of Organic Chemistry; vol. 48; nb. 12; (1983); p. 2103 - 2105, View in Reaxys

2a (syn/anti)

Beckett,A.H. et al.; Tetrahedron; vol. 32; (1976); p. 1267 - 1276, View in Reaxys

VIa

Beckett; Coutts; Ogunbona; Journal of Pharmacy and Pharmacology; vol. 26; nb. 5; (1974); p. 312 - 316, View in Reaxys

10

Beckett; Coutts; Ogunbona; Tetrahedron; vol. 29; nb. 24; (1973); p. 4189 - 4193, View in Reaxys; Humbert; Laurent; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 272; (1971); p. 1165, View in Reaxys

IIa

Coutts; Malicky; Organic Mass Spectrometry; vol. 7; (1973); p. 985,986, View in Reaxys

(E)-Oxim 1a

Busser,U.; Haller,R.; Tetrahedron Letters; (1973); p. 231 - 232, View in Reaxys

14

Warren,R.G. et al.; Journal of the Chemical Society [Section] D: Chemical Communications; (1971); p. 1521 - 1522, View in Reaxys

VII

Fox et al.; Journal of Organic Chemistry; vol. 35; (1970); p. 4234, View in Reaxys

Va

Dornow,A.; Mueller,A.; Chemische Berichte; vol. 93; (1960); p. 32 - 40, View in Reaxys

1

Benington,F. et al.; Journal of Medicinal Chemistry; vol. 8; (1965); p. 100 - 104, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.957

H Bond Donors

1

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

32.59

Lipinski Number

4

Veber Number

2

Related Structure (1) References Alvernhe; Laurent; Bulletin de la Societe Chimique de France; (1970); p. 3003,3004,3007, View in Reaxys Derivative (1) Derivative 1-phenyl-acetone

References Varma, Rajender S.; Varma, Manju; Kabalka, George W.; Synthetic Communications; vol. 16; nb. 1; (1986); p. 91 - 96, View in Reaxys

Melting Point (8) 1 of 8

Melting Point [°C]

69 - 71

Kiasat, Ali Reza; Javaherian, Mohammad; Daei, Mina; Farbod, Mansoor; Revue Roumaine de Chimie; vol. 60; nb. 9; (2015); p. 875 - 880, View in Reaxys 2 of 8

Melting Point [°C]

87 - 88

Solvent (Melting Point)

hexane

Yamamoto, Yutaro; Hasegawa, Hiroto; Yamataka, Hiroshi; Journal of Organic Chemistry; vol. 76; nb. 11; (2011); p. 4652 - 4660, View in Reaxys 3 of 8

Melting Point [°C]

56 - 57

Solvent (Melting Point)

hexane

Langhals, Heinz; Range, Guenter; Wistuba, Eckehardt; Ruechardt, Christoph; Chemische Berichte; vol. 114; nb. 12; (1981); p. 3813 - 3830, View in Reaxys 4 of 8

Melting Point [°C]

69

Mezheritskaya, L. V.; Matsovskaya, E. S.; Dorofeenko, G. N.; Journal of Organic Chemistry USSR (English Translation); vol. 16; (1980); p. 174 - 178; Zhurnal Organicheskoi Khimii; vol. 16; nb. 1; (1980); p. 183 - 188, View in Reaxys 5 of 8

Melting Point [°C]

68 - 69

Solvent (Melting Point)

diethyl ether

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Dornow,A.; Mueller,A.; Chemische Berichte; vol. 93; (1960); p. 32 - 40, View in Reaxys 6 of 8

Melting Point [°C]

68 - 68.5

Jaeger; van Dijk; Pr. Acad. Amsterdam; vol. 44; (1941); p. 26,27, View in Reaxys 7 of 8

Melting Point [°C]

70

Hey; Journal of the Chemical Society; (1930); p. 18,20, View in Reaxys 8 of 8

Melting Point [°C]

68 - 70

Neber; v. Friedolsheim; Justus Liebigs Annalen der Chemie; vol. 449; (1926); p. 129, View in Reaxys Boiling Point (4) Boiling Point [°C]

Pressure (Boiling Point) [Torr]

References

109

0.4

Langhals, Heinz; Range, Guenter; Wistuba, Eckehardt; Ruechardt, Christoph; Chemische Berichte; vol. 114; nb. 12; (1981); p. 3813 - 3830, View in Reaxys

107

0.7

Alvernhe; Laurent; Bulletin de la Societe Chimique de France; (1970); p.

3003,3004,3007, View in Reaxys

101 - 103

3

Biela,R. et al.; Journal fuer Praktische Chemie (Leipzig); vol. 33; (1966); p. 282 - 292, View in Reaxys

142 - 143

15

Prajsnar; Zeszyty Naukowe Politechniki Slaskiej, Chemia; vol. 20; (1963); p. 1,72, View in Reaxys

Refractive Index (1) Refractive Index Wavelength (Refractive Index) [nm]

Temperature (Refractive Index) [°C]

References

1.5454

20

Prajsnar; Zeszyty Naukowe Politechniki Slaskiej, Chemia; vol. 20; (1963); p. 1,72, View in Reaxys

589

Density (1) 1 of 1

Density [g·cm-3]

1.23

Type (Density)

crystallographic

Jaeger; van Dijk; Pr. Acad. Amsterdam; vol. 44; (1941); p. 26,27, View in Reaxys Conformation (1) Object of Investi- References gation Conformation

Alvernhe; Laurent; Bulletin de la Societe Chimique de France; (1970); p. 3003,3004,3007, View in Reaxys

Crystal Phase (2) Description (Crys- Comment (Crystal References tal Phase) Phase) Crystal structure determination

β=89.5 grad, a=8.65 Angstroem, b=16.58 Angstroem, c=5.46 Angstroem, n=4.; aus dem RoentgenDiagramm ermittelt.

Crystal structure determination

Jaeger; van Dijk; Pr. Acad. Amsterdam; vol. 44; (1941); p. 26,27, View in Reaxys

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

Jaeger; van Dijk; Pr. Acad. Amsterdam; vol. 44; (1941); p. 26,27, View in Reaxys

supporting information

References Moran, Joseph; Pfeiffer, Jennifer Y.; Gorelsky, Serge I.; Beauchemin, Andre M.; Organic Letters; vol. 11; nb. 9; (2009); p. 1895 - 1898, View in Reaxys

Crystal System (1) Crystal System References monoclinic

Jaeger; van Dijk; Pr. Acad. Amsterdam; vol. 44; (1941); p. 26,27, View in Reaxys

Further Information (1)

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Description (Further Information)

References

Further information

Coutts; Malicky; Organic Mass Spectrometry; vol. 7; (1973); p. 985,986, View in Reaxys

NMR Spectroscopy (15) 1 of 15

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Yamamoto, Yutaro; Hasegawa, Hiroto; Yamataka, Hiroshi; Journal of Organic Chemistry; vol. 76; nb. 11; (2011); p. 4652 - 4660, View in Reaxys 2 of 15

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

75

Comment (NMR Spectroscopy)

two stereoisomers

Beauchemin, Andre M.; Moran, Joseph; Lebrun, Marie-Eve; Seguin, Catherine; Dimitrijevic, Elena; Zhang, Lili; Gorelsky, Serge I.; Angewandte Chemie - International Edition; vol. 47; nb. 8; (2008); p. 1410 - 1413, View in Reaxys 3 of 15

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

75

Beauchemin, Andre M.; Moran, Joseph; Lebrun, Marie-Eve; Seguin, Catherine; Dimitrijevic, Elena; Zhang, Lili; Gorelsky, Serge I.; Angewandte Chemie - International Edition; vol. 47; nb. 8; (2008); p. 1410 - 1413, View in Reaxys 4 of 15

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Comment (NMR Spectroscopy)

two stereoisomers

Beauchemin, Andre M.; Moran, Joseph; Lebrun, Marie-Eve; Seguin, Catherine; Dimitrijevic, Elena; Zhang, Lili; Gorelsky, Serge I.; Angewandte Chemie - International Edition; vol. 47; nb. 8; (2008); p. 1410 - 1413, View in Reaxys 5 of 15

Description (NMR Spec- Chemical shifts troscopy)

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Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Portela-Cubillo, Fernando; Lymer, James; Scanlan, Eoin M.; Scott, Jackie S.; Walton, John C.; Tetrahedron; vol. 64; nb. 52; (2008); p. 11908 - 11916, View in Reaxys 6 of 15

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- CDCl3 scopy) Wessling, Michael; Schaefer, Hans J.; Chemische Berichte; vol. 124; nb. 10; (1991); p. 2303 - 2306, View in Reaxys; Hwu, Jih Ru; Tseng, Wen Nan; Patel, Himatkumar V.; Wong, Fong Fuh; Horng, Den-Nan; Liaw, Ben Ruey; Lung Ching, Lin; Journal of Organic Chemistry; vol. 64; nb. 7; (1999); p. 2211 - 2218, View in Reaxys 7 of 15

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Hwu, Jih Ru; Tseng, Wen Nan; Patel, Himatkumar V.; Wong, Fong Fuh; Horng, Den-Nan; Liaw, Ben Ruey; Lung Ching, Lin; Journal of Organic Chemistry; vol. 64; nb. 7; (1999); p. 2211 - 2218, View in Reaxys 8 of 15

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- CCl4 scopy) Ranu; Chakraborty; Tetrahedron; vol. 48; nb. 25; (1992); p. 5317 - 5322, View in Reaxys 9 of 15

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Beckett,A.H. et al.; Tetrahedron; vol. 32; (1976); p. 1267 - 1276, View in Reaxys 10 of 15

Description (NMR Spec- NMR troscopy) Beckett; Coutts; Ogunbona; Journal of Pharmacy and Pharmacology; vol. 26; nb. 5; (1974); p. 312 - 316, View in Reaxys

11 of 15

Description (NMR Spec- NMR troscopy) Comment (NMR Spectroscopy)

syn-anti-Gemisch

Lindeke et al.; Acta Pharmaceutica Suecica; vol. 10; (1973); p. 493,500, View in Reaxys 12 of 15

Description (NMR Spec- NMR troscopy) Comment (NMR Spectroscopy)

1H- ( anti/syn = 7/3 )

Alvernhe; Laurent; Bulletin de la Societe Chimique de France; (1970); p. 3003,3004,3007, View in Reaxys

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13 of 15

Description (NMR Spec- NMR troscopy) Comment (NMR Spectroscopy)

1H; Einfluss v. HCl auf chemical shift; Konzentr.-abhaengigkeit

Fox et al.; Journal of Organic Chemistry; vol. 35; (1970); p. 4234, View in Reaxys 14 of 15

Description (NMR Spec- Spectrum troscopy) Comment (NMR Spectroscopy)

Bzl., CCl4

Lustig; Journal of Physical Chemistry; vol. 65; (1961); p. 491,493,494; Chem.Abstr.; nb. 22183; (1959), View in Reaxys 15 of 15

Description (NMR Spec- NMR troscopy) Comment (NMR Spectroscopy)

Unters. zur syn-anti-Isomerie

Lustig; Journal of Physical Chemistry; vol. 65; (1961); p. 491,493,494; Chem.Abstr.; nb. 22183; (1959), View in Reaxys IR Spectroscopy (4) 1 of 4

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

3250 - 922 1/cm

Hwu, Jih Ru; Tseng, Wen Nan; Patel, Himatkumar V.; Wong, Fong Fuh; Horng, Den-Nan; Liaw, Ben Ruey; Lung Ching, Lin; Journal of Organic Chemistry; vol. 64; nb. 7; (1999); p. 2211 - 2218, View in Reaxys 2 of 4

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

3280 - 1665 cm**(-1)

Ranu; Chakraborty; Tetrahedron; vol. 48; nb. 25; (1992); p. 5317 - 5322, View in Reaxys 3 of 4

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

3500 - 1660 cm**(-1)

Wessling, Michael; Schaefer, Hans J.; Chemische Berichte; vol. 124; nb. 10; (1991); p. 2303 - 2306, View in Reaxys 4 of 4

Description (IR Spectroscopy)

Bands

Warren,R.G. et al.; Journal of the Chemical Society [Section] D: Chemical Communications; (1971); p. 1521 - 1522, View in Reaxys Mass Spectrometry (3) Description (Mass References Spectrometry) spectrum

Hwu, Jih Ru; Tseng, Wen Nan; Patel, Himatkumar V.; Wong, Fong Fuh; Horng, Den-Nan; Liaw, Ben Ruey; Lung Ching, Lin; Journal of Organic Chemistry; vol. 64; nb. 7; (1999); p. 2211 - 2218, View in Reaxys

spectrum; electron impact (EI)

Wessling, Michael; Schaefer, Hans J.; Chemische Berichte; vol. 124; nb. 10; (1991); p. 2303 - 2306, View in Reaxys Coutts; Malicky; Organic Mass Spectrometry; vol. 7; (1973); p. 985,986, View in Reaxys

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UV/VIS Spectroscopy (1) 1 of 1

Description (UV/VIS Spectroscopy)

Absorption maxima

Warren,R.G. et al.; Journal of the Chemical Society [Section] D: Chemical Communications; (1971); p. 1521 - 1522, View in Reaxys Medchem (8) 1 of 8

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Bioassay Details

Effect : |receptor blocking agent Target : HEK cell membranes expressing human dopamine transporterBioassay : non-specific binding was defined in presence of mazindol; Krebs-HEPES buffer, room temp., darkness radioligand binding assay; membranes were isolated; preincubated with title comp. for 10 min before addition of <125I>RTI-55; incubated for 90 min; filtered; radioactivity remaining on the filter was measured by liquid scintillation counting

Substance RN

508872View in Reaxys

Substance Name

1429114

Measurement Parameter

Ki

Unit

nM

Quantitative value

10000

Measurement pX

5

Cashman, John R.; Xiong, Yeng N.; Lifen, Xu; Janowsky, Aaron; Journal of Pharmacology and Experimental Therapeutics; vol. 288; nb. 3; (1999); p. 1251 - 1260, View in Reaxys 2 of 8

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Bioassay Details

Effect : |receptor blocking agent Target : HEK cell membranes expressing human serotonin transporterBioassay : non-specific binding was defined in presence of imipramine; Krebs-HEPES buffer, room temp., darkness radioligand binding assay; membranes were isolated; preincubated with title comp. for 10 min before addition of <125I>RTI-55; incubated for 90 min; filtered; radioactivity remaining on the filter was measured by liquid scintillation counting

Substance RN

508872View in Reaxys

Substance Name

1429114

Measurement Parameter

Ki

Unit

nM

Quantitative value

10000

Measurement pX

5

Cashman, John R.; Xiong, Yeng N.; Lifen, Xu; Janowsky, Aaron; Journal of Pharmacology and Experimental Therapeutics; vol. 288; nb. 3; (1999); p. 1251 - 1260, View in Reaxys 3 of 8

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : |receptor blocking agent Target : HEK cell membranes expressing human NETBioassay : non-specific binding was defined in presence of mazindol; Krebs-HEPES buffer, room temp., darkness; NET: norepinephrine transporter radioligand binding assay; membranes were isolated; preincubated with title comp. for 10 min before addition of <125I>RTI-55; incubated for 90 min; filtered; radioactivity remaining on the filter was measured by liquid scintillation counting

Substance RN

508872View in Reaxys

Substance Name

1429114

Measurement Parameter

Ki

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Unit

nM

Quantitative value

10000

Measurement pX

5

Cashman, John R.; Xiong, Yeng N.; Lifen, Xu; Janowsky, Aaron; Journal of Pharmacology and Experimental Therapeutics; vol. 288; nb. 3; (1999); p. 1251 - 1260, View in Reaxys 4 of 8

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : transport; inhibition fTarget : C6 glioma cells expressing human dopamine transporterBioassay : <3H>MPP(1+): <3H>1-methyl-4-phenylpyridinium was used as radiolabel; non-specific uptake was defined in presence of mazindol; Krebs-HEPES buffer, pH 7.4; release was stimulated with trichloroacetic acid cells were pre-incubated with <3H>MPP(1+) for 20 min; room temp.; washed; pre-incubated with release buffer for 10 min before title comp. was added; 37 deg C; radioactivity remaining in the cells was measured by liquid scintillation spectrometry

Substance RN

508872View in Reaxys

Substance Name

1429114

Measurement Parameter

IC50

Unit

nM

Quantitative value

100

Measurement pX

7

Cashman, John R.; Xiong, Yeng N.; Lifen, Xu; Janowsky, Aaron; Journal of Pharmacology and Experimental Therapeutics; vol. 288; nb. 3; (1999); p. 1251 - 1260, View in Reaxys 5 of 8

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : transport; inhibition ofTarget : HEK cells expressing human dopamine transporterBioassay : DA: dopamine; <3H>DA was used as radiolabel; non-specific uptake was defined in presence of mazindol; Krebs-HEPES buffer; 25 deg C, water bath cells were preincubated with title comp. for 10 min before addition of <3H>DA; then incubated for 10 min; filtered; radioactivity remaining on the filter was measured by liquid scintillation counting

Substance RN

508872View in Reaxys

Substance Name

1429114

Measurement Parameter

IC50

Unit

nM

Quantitative value

10000

Measurement pX

5

Cashman, John R.; Xiong, Yeng N.; Lifen, Xu; Janowsky, Aaron; Journal of Pharmacology and Experimental Therapeutics; vol. 288; nb. 3; (1999); p. 1251 - 1260, View in Reaxys 6 of 8

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : transport; inhibition ofBioassay : <3H>MPP(1+): <3H>1-methyl-4-phenylpyridinium was used as radiolabel; non-specific uptake was defined in presence of mazindol; KrebsHEPES buffer, pH 7.4; release was stimulated with trichloroacetic acid cells were pre-incubated with <3H>MPP(1+) for 20 min; room temp.; washed; pre-incubated with release buffer for 10 min before title comp. was added; 37 deg C; radioactivity remaining in the cells was measured by liquid scintillation spectrometry

Cells/Cell Lines

C6

Substance RN

508872View in Reaxys

Substance Name

1429114

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Measurement Parameter

IC50

Unit

nM

Quantitative value

1640

Measurement pX

5.79

Cashman, John R.; Xiong, Yeng N.; Lifen, Xu; Janowsky, Aaron; Journal of Pharmacology and Experimental Therapeutics; vol. 288; nb. 3; (1999); p. 1251 - 1260, View in Reaxys 7 of 8

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : transport; inhibition ofBioassay : <3H>5-HT: <3H>5-hydroxytryptamine was used as radiolabel; non-specific uptake was defined in presence of imipramine; Krebs-HEPES buffer; 25 deg C, water bath cells were pre-incubated with title comp. for 10 min before addition of <3H>5-HT; then incubated for 10 min; filtered; radioactivity remaining on the filter was measured by liquid scintillation counting

Cells/Cell Lines

HEK 293

Substance RN

508872View in Reaxys

Substance Name

1429114

Measurement Parameter

IC50

Unit

nM

Quantitative value

10000

Measurement pX

5

Cashman, John R.; Xiong, Yeng N.; Lifen, Xu; Janowsky, Aaron; Journal of Pharmacology and Experimental Therapeutics; vol. 288; nb. 3; (1999); p. 1251 - 1260, View in Reaxys 8 of 8

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : transport; inhibition ofBioassay : NE: norepinephrine; <3H>NE was used as radiolabel; non-specific uptake was defined in presence of mazindol; Krebs-HEPES buffer; 25 deg C, water bath cells were pre-incubated with title comp. for 10 min before addition of <3H>NE; then incubated for 10 min; filtered; radioactivity remaining on the filter was measured by liquid scintillation counting

Cells/Cell Lines

HEK 293

Substance RN

508872View in Reaxys

Substance Name

1429114

Measurement Parameter

IC50

Unit

nM

Quantitative value

10000

Measurement pX

5

Cashman, John R.; Xiong, Yeng N.; Lifen, Xu; Janowsky, Aaron; Journal of Pharmacology and Experimental Therapeutics; vol. 288; nb. 3; (1999); p. 1251 - 1260, View in Reaxys

Reaxys ID 2043527 View in Reaxys

3/5 CAS Registry Number: 10048-65-4 Chemical Name: oxime de la 1-phenyl-2-propanone (cis); (Z)-1-phenylpropan-2-one oxime; anti-methyl benzyl ketoxime; cis-phenylpropanone oxime; Z-phenylacetone oxime; benzylmethylketoxime; anti-1-Phenyl-propanon-(2)-oxim

OH NZ

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Linear Structure Formula: C9H11NO Molecular Formula: C9H11NO Molecular Weight: 149.192 Type of Substance: isocyclic InChI Key: AUYFJUMCPAMOKN-NTMALXAHSA-N Note: Substance Label (12) Label References 1a

Kline, Mike; Pierce, Dawn; Cheatham, Steve; Magnetic Resonance in Chemistry; vol. 55; nb. 2; (2017); p.

154 - 156, View in Reaxys

(Z)-2a

Yadav; Subba Reddy; Srinivas; Ramalingam; Synlett; nb. 10; (2000); p. 1447 - 1449, View in Reaxys

2a

Cashman, John R.; Xiong, Yeng N.; Lifen, Xu; Janowsky, Aaron; Journal of Pharmacology and Experimental Therapeutics; vol. 288; nb. 3; (1999); p. 1251 - 1260, View in Reaxys

VII-(Z)

Krivdin, L. B.; Shcherbakov, V. V.; Kalabin, G. A.; Journal of Organic Chemistry USSR (English Translation); (1986); p. 300 - 305; Zhurnal Organicheskoi Khimii; vol. 22; nb. 2; (1986); p. 342 - 348, View in Reaxys

2b (Z isomer)

Varma, Rajender S.; Varma, Manju; Gai, Yuan-Zhu; Kabalka, George W.; Heterocycles; vol. 24; nb. 9; (1986); p. 2581 - 2586, View in Reaxys

2c

Hiroi, Kunio; Otsuka, Masahiko; Sato, Shuko; Chemistry Letters; (1985); p. 1907 - 1910, View in Reaxys

2b-Z

Varma, Rajender S.; Varma, Manju; Kabalka, George W.; Synthetic Communications; vol. 15; nb. 14; (1985); p. 1325 - 1332, View in Reaxys

syn-Isomer

Lindeke et al.; Acta Pharmaceutica Suecica; vol. 12; (1975); p. 183,192, 193, View in Reaxys

18

Hawkes,G.E. et al.; Journal of Organic Chemistry; vol. 39; (1974); p. 1017 - 1028, View in Reaxys

anti-Isomer

Alvernhe; Laurent; Bulletin de la Societe Chimique de France; (1970); p. 3003,3004,3007, View in Reaxys

IIa

Kotera,K. et al.; Tetrahedron; vol. 24; (1968); p. 5677 - 5690, View in Reaxys

II

Huitric et al.; Journal of Organic Chemistry; vol. 32; (1967); p. 1661, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.957

H Bond Donors

1

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

32.59

Lipinski Number

4

Veber Number

2

Melting Point (2) 1 of 2

Melting Point [°C]

70

Alvernhe; Laurent; Bulletin de la Societe Chimique de France; (1970); p. 3003,3004,3007, View in Reaxys 2 of 2

Melting Point [°C]

62 - 63

Kotera et al.; Tetrahedron Letters; (1967); p. 841, View in Reaxys Conformation (1) Object of Investi- References gation Conformation

Alvernhe; Laurent; Bulletin de la Societe Chimique de France; (1970); p. 3003,3004,3007, View in Reaxys

NMR Spectroscopy (15) 1 of 15

Description (NMR Spec- 2D-NMR troscopy) Nucleus (NMR Spectroscopy)

1H; 15N

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy)

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Kline, Mike; Pierce, Dawn; Cheatham, Steve; Magnetic Resonance in Chemistry; vol. 55; nb. 2; (2017); p. 154 156, View in Reaxys 2 of 15

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

15N

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Kline, Mike; Pierce, Dawn; Cheatham, Steve; Magnetic Resonance in Chemistry; vol. 55; nb. 2; (2017); p. 154 156, View in Reaxys 3 of 15

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- CD2Cl2 scopy) Hanquet, Gilles; Lusinchi, Xavier; Tetrahedron; vol. 50; nb. 42; (1994); p. 12185 - 12200, View in Reaxys 4 of 15

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- acetone-d6 scopy) Temperature (NMR Spectroscopy) [°C]

25 - 30

Krivdin, L. B.; Shcherbakov, V. V.; Kalabin, G. A.; Journal of Organic Chemistry USSR (English Translation); (1986); p. 300 - 305; Zhurnal Organicheskoi Khimii; vol. 22; nb. 2; (1986); p. 342 - 348, View in Reaxys 5 of 15

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- CDCl3 scopy) Varma, Rajender S.; Varma, Manju; Gai, Yuan-Zhu; Kabalka, George W.; Heterocycles; vol. 24; nb. 9; (1986); p.

2581 - 2586, View in Reaxys; Varma, Rajender S.; Varma, Manju; Kabalka, George W.; Synthetic Communications; vol. 15; nb. 14; (1985); p. 1325 - 1332, View in Reaxys 6 of 15

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Varma, Rajender S.; Varma, Manju; Gai, Yuan-Zhu; Kabalka, George W.; Heterocycles; vol. 24; nb. 9; (1986); p.

2581 - 2586, View in Reaxys; Varma, Rajender S.; Varma, Manju; Kabalka, George W.; Synthetic Communications; vol. 15; nb. 14; (1985); p. 1325 - 1332, View in Reaxys 7 of 15

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- acetone-d6 scopy) Temperature (NMR Spectroscopy) [°C]

25 - 30

Comment (NMR Spectroscopy)

13C-13C.

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Krivdin, L. B.; Shcherbakov, V. V.; Kalabin, G. A.; Journal of Organic Chemistry USSR (English Translation); (1986); p. 300 - 305; Zhurnal Organicheskoi Khimii; vol. 22; nb. 2; (1986); p. 342 - 348, View in Reaxys 8 of 15

Description (NMR Spec- NMR with shift reagents troscopy) Krivdin, L. B.; Shcherbakov, V. V.; Kalabin, G. A.; Journal of Organic Chemistry USSR (English Translation); (1986); p. 300 - 305; Zhurnal Organicheskoi Khimii; vol. 22; nb. 2; (1986); p. 342 - 348, View in Reaxys

9 of 15

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- benzene scopy) Trofimov, B. A.; Korostova, S. E.; Sobenina, L. N.; Mikhaleva, A. I.; Bzhezovskii, V. M.; et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 18; nb. 2; (1982); p. 148 - 152; Khimiya Geterotsiklicheskikh Soedinenii; vol. 18; nb. 2; (1982); p. 193 - 198, View in Reaxys 10 of 15

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- CCl4 scopy) Trofimov, B. A.; Korostova, S. E.; Sobenina, L. N.; Mikhaleva, A. I.; Bzhezovskii, V. M.; et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 18; nb. 2; (1982); p. 148 - 152; Khimiya Geterotsiklicheskikh Soedinenii; vol. 18; nb. 2; (1982); p. 193 - 198, View in Reaxys 11 of 15

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- nitrobenzene scopy) Trofimov, B. A.; Korostova, S. E.; Sobenina, L. N.; Mikhaleva, A. I.; Bzhezovskii, V. M.; et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 18; nb. 2; (1982); p. 148 - 152; Khimiya Geterotsiklicheskikh Soedinenii; vol. 18; nb. 2; (1982); p. 193 - 198, View in Reaxys 12 of 15

Description (NMR Spec- NMR troscopy) Huitric et al.; Journal of Organic Chemistry; vol. 32; (1967); p. 1661, View in Reaxys; Lindeke et al.; Acta Pharmaceutica Suecica; vol. 12; (1975); p. 183,192, 193, View in Reaxys; Karabatsos; Taller; Tetrahedron; vol. 24; (1968); p. 3347,3353, View in Reaxys

13 of 15

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Hawkes,G.E. et al.; Journal of Organic Chemistry; vol. 39; (1974); p. 1017 - 1028, View in Reaxys 14 of 15

Description (NMR Spec- NMR troscopy) Comment (NMR Spectroscopy)

1H-

Alvernhe; Laurent; Bulletin de la Societe Chimique de France; (1970); p. 3003,3004,3007, View in Reaxys 15 of 15

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Kotera,K. et al.; Tetrahedron; vol. 24; (1968); p. 5677 - 5690, View in Reaxys

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Mass Spectrometry (1) References Lindeke et al.; Acta Pharmaceutica Suecica; vol. 12; (1975); p. 183,192, 193, View in Reaxys

Reaxys ID 2207040 View in Reaxys

HO

4/5 CAS Registry Number: 10048-64-3 Chemical Name: (E)-1-phenylpropan-2-one oxime; trans-phenylpropanone oxime; syn-methyl benzyl ketoxime; E-phenylacetone oxime; Phenylacetone oxime; phenyl-acetone-(E)-oxime; Phenyl-aceton-(E)-oxim Linear Structure Formula: C9H11NO Molecular Formula: C9H11NO Molecular Weight: 149.192 Type of Substance: isocyclic InChI Key: AUYFJUMCPAMOKN-CSKARUKUSA-N Note:

NE

Substance Label (15) Label References 1b

Kline, Mike; Pierce, Dawn; Cheatham, Steve; Magnetic Resonance in Chemistry; vol. 55; nb. 2; (2017); p.

154 - 156, View in Reaxys

6

Eshghi, Hossein; Hassankhani, Asadollah; Organic Preparations and Procedures International; vol. 37; nb. 6; (2005); p. 575 - 579, View in Reaxys

(E)-2a

Yadav; Subba Reddy; Srinivas; Ramalingam; Synlett; nb. 10; (2000); p. 1447 - 1449, View in Reaxys

2b

Coutts; Jones; Liu; Biomedical Mass Spectrometry; vol. 5; nb. 6; (1978); p. 418 - 422, View in Reaxys; Cashman, John R.; Xiong, Yeng N.; Lifen, Xu; Janowsky, Aaron; Journal of Pharmacology and Experimental Therapeutics; vol. 288; nb. 3; (1999); p. 1251 - 1260, View in Reaxys

10

Lantos; Zhang; Shui; Eggleston; Journal of Organic Chemistry; vol. 58; nb. 25; (1993); p. 7092 - 7095, View in Reaxys

VII-(E)

Krivdin, L. B.; Shcherbakov, V. V.; Kalabin, G. A.; Journal of Organic Chemistry USSR (English Translation); (1986); p. 300 - 305; Zhurnal Organicheskoi Khimii; vol. 22; nb. 2; (1986); p. 342 - 348, View in Reaxys

2b (E isomer)

Varma, Rajender S.; Varma, Manju; Gai, Yuan-Zhu; Kabalka, George W.; Heterocycles; vol. 24; nb. 9; (1986); p. 2581 - 2586, View in Reaxys

2b-E

Varma, Rajender S.; Varma, Manju; Kabalka, George W.; Synthetic Communications; vol. 15; nb. 14; (1985); p. 1325 - 1332, View in Reaxys

9E

Krivdin, Leonid B.; Kalabin, Gennady A.; Nesterenko, Raisa N.; Trofimov, Boris A.; Tetrahedron Letters; vol. 25; nb. 42; (1984); p. 4817 - 4820, View in Reaxys

I

Huitric et al.; Journal of Organic Chemistry; vol. 32; (1967); p. 1661, View in Reaxys; Trofimov, B. A.; Korostova, S. E.; Sobenina, L. N.; Mikhaleva, A. I.; Bzhezovskii, V. M.; et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 18; nb. 2; (1982); p. 148 - 152; Khimiya Geterotsiklicheskikh Soedinenii; vol. 18; nb. 2; (1982); p. 193 - 198, View in Reaxys

1 (R&1%=CH3 , R&2%=Ph)

Reddy, Gaddam Subba; Bhatt, M. Vivekananda; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. <B> 20; nb. 4; (1981); p. 322 - 323, View in Reaxys

8

Kim,S.-G. et al.; Bulletin of the Chemical Society of Japan; vol. 52; (1979); p. 1115 - 1120, View in Reaxys

anti-Isomer Ia

Lindeke et al.; Acta Pharmaceutica Suecica; vol. 12; (1975); p. 183,192, 193, View in Reaxys

17

Hawkes,G.E. et al.; Journal of Organic Chemistry; vol. 39; (1974); p. 1017 - 1028, View in Reaxys

Ia

Kotera,K. et al.; Tetrahedron; vol. 24; (1968); p. 5677 - 5690, View in Reaxys

Patent-Specific Data (1) Location in Patent References Claim

Patent; Bramucci, Michael G.; Nagarajan, Vasantha; Chen, Mario W.; US2003/215929; (2003); (A1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.957

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H Bond Donors

1

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

32.59

Lipinski Number

4

Veber Number

2

Related Structure (2) Related Structure References The author inves- Krivdin, Leonid B.; Kalabin, Gennady A.; Nesterenko, Raisa N.; Trofimov, Boris A.; Tetrahedron Letters; tigated the config- vol. 25; nb. 42; (1984); p. 4817 - 4820, View in Reaxys uration Diese Verb. hat in Kotera,K. et al.; Tetrahedron; vol. 24; (1968); p. 5677 - 5690, View in Reaxys; Huitric et al.; Journal of Orden frueher (s. E ganic Chemistry; vol. 32; (1967); p. 1661, View in Reaxys II 234; E III 1039) beschrieb. kristallinen Praeparaten vorgelegen; Gemische dieser Verb. mit Phenyl(#Z!)-oxim (C9H11NO) haben dagegen in den frueher (s. H 304; E II 234) beschrieb. Praeparaten vorgelegen.

Melting Point (4) 1 of 4

Melting Point [°C]

69.5 - 70.5

Kim,S.-G. et al.; Bulletin of the Chemical Society of Japan; vol. 52; (1979); p. 1115 - 1120, View in Reaxys 2 of 4

Melting Point [°C]

69

Solvent (Melting Point)

hexane

Foreman; Siegel; Mrtek; Journal of pharmaceutical sciences; vol. 58; nb. 2; (1969); p. 189 - 192, View in Reaxys 3 of 4

Melting Point [°C]

62 - 63

Solvent (Melting Point)

petroleum ether

Kotera,K. et al.; Tetrahedron; vol. 24; (1968); p. 5677 - 5690, View in Reaxys 4 of 4

Melting Point [°C]

69 - 71

Solvent (Melting Point)

petroleum ether

Huitric et al.; Journal of Organic Chemistry; vol. 32; (1967); p. 1661, View in Reaxys Boiling Point (1) Boiling Point [°C] 81 - 84

Pressure (Boiling Point) [Torr]

References

0.1

Foreman; Siegel; Mrtek; Journal of pharmaceutical sciences; vol. 58; nb. 2; (1969); p.

189 - 192, View in Reaxys

Electrochemical Characteristics (1) 1 of 1

Description (Electrochemical Characteristics)

polarographic half-wave potential

Comment (Electrochem- (wss.-aethanol. Loesungen vom pH 1 und pH 4). ical Characteristics) Nakaya et al.; Nippon Kagaku Zasshi; vol. 80; (1959); p. 1282; Chem.Abstr.; (1961); p. 5192, View in Reaxys NMR Spectroscopy (21)

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1 of 21

Description (NMR Spec- 2D-NMR troscopy) Nucleus (NMR Spectroscopy)

1H; 15N

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Kline, Mike; Pierce, Dawn; Cheatham, Steve; Magnetic Resonance in Chemistry; vol. 55; nb. 2; (2017); p. 154 156, View in Reaxys 2 of 21

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

15N

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Kline, Mike; Pierce, Dawn; Cheatham, Steve; Magnetic Resonance in Chemistry; vol. 55; nb. 2; (2017); p. 154 156, View in Reaxys 3 of 21

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- CDCl3 scopy) Temperature (NMR Spectroscopy) [°C]

25

Frequency (NMR Spectroscopy) [MHz]

100

Eshghi, Hossein; Hassankhani, Asadollah; Organic Preparations and Procedures International; vol. 37; nb. 6; (2005); p. 575 - 579, View in Reaxys 4 of 21

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- CD2Cl2 scopy) Hanquet, Gilles; Lusinchi, Xavier; Tetrahedron; vol. 50; nb. 42; (1994); p. 12185 - 12200, View in Reaxys 5 of 21

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- acetone-d6 scopy) Temperature (NMR Spectroscopy) [°C]

25 - 30

Krivdin, L. B.; Shcherbakov, V. V.; Kalabin, G. A.; Journal of Organic Chemistry USSR (English Translation); (1986); p. 300 - 305; Zhurnal Organicheskoi Khimii; vol. 22; nb. 2; (1986); p. 342 - 348, View in Reaxys 6 of 21

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- CDCl3 scopy)

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Varma, Rajender S.; Varma, Manju; Gai, Yuan-Zhu; Kabalka, George W.; Heterocycles; vol. 24; nb. 9; (1986); p.

2581 - 2586, View in Reaxys; Varma, Rajender S.; Varma, Manju; Kabalka, George W.; Synthetic Communications; vol. 15; nb. 14; (1985); p. 1325 - 1332, View in Reaxys 7 of 21

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Varma, Rajender S.; Varma, Manju; Gai, Yuan-Zhu; Kabalka, George W.; Heterocycles; vol. 24; nb. 9; (1986); p.

2581 - 2586, View in Reaxys; Varma, Rajender S.; Varma, Manju; Kabalka, George W.; Synthetic Communications; vol. 15; nb. 14; (1985); p. 1325 - 1332, View in Reaxys 8 of 21

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- acetone-d6 scopy) Temperature (NMR Spectroscopy) [°C]

25 - 30

Comment (NMR Spectroscopy)

13C-13C.

Krivdin, L. B.; Shcherbakov, V. V.; Kalabin, G. A.; Journal of Organic Chemistry USSR (English Translation); (1986); p. 300 - 305; Zhurnal Organicheskoi Khimii; vol. 22; nb. 2; (1986); p. 342 - 348, View in Reaxys 9 of 21

Description (NMR Spec- NMR with shift reagents troscopy) Krivdin, L. B.; Shcherbakov, V. V.; Kalabin, G. A.; Journal of Organic Chemistry USSR (English Translation); (1986); p. 300 - 305; Zhurnal Organicheskoi Khimii; vol. 22; nb. 2; (1986); p. 342 - 348, View in Reaxys

10 of 21

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Comment (NMR Spectroscopy)

13C-13C. Solvent(s): further solvent(s)

Krivdin, Leonid B.; Kalabin, Gennady A.; Nesterenko, Raisa N.; Trofimov, Boris A.; Tetrahedron Letters; vol.

25; nb. 42; (1984); p. 4817 - 4820, View in Reaxys 11 of 21

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- benzene scopy) Trofimov, B. A.; Korostova, S. E.; Sobenina, L. N.; Mikhaleva, A. I.; Bzhezovskii, V. M.; et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 18; nb. 2; (1982); p. 148 - 152; Khimiya Geterotsiklicheskikh Soedinenii; vol. 18; nb. 2; (1982); p. 193 - 198, View in Reaxys 12 of 21

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- CHCl3 scopy) Trofimov, B. A.; Korostova, S. E.; Sobenina, L. N.; Mikhaleva, A. I.; Bzhezovskii, V. M.; et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 18; nb. 2; (1982); p. 148 - 152; Khimiya Geterotsiklicheskikh Soedinenii; vol. 18; nb. 2; (1982); p. 193 - 198, View in Reaxys 13 of 21

Description (NMR Spec- Chemical shifts troscopy)

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Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- dimethylsulfoxide scopy) Trofimov, B. A.; Korostova, S. E.; Sobenina, L. N.; Mikhaleva, A. I.; Bzhezovskii, V. M.; et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 18; nb. 2; (1982); p. 148 - 152; Khimiya Geterotsiklicheskikh Soedinenii; vol. 18; nb. 2; (1982); p. 193 - 198, View in Reaxys 14 of 21

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- CCl4 scopy) Trofimov, B. A.; Korostova, S. E.; Sobenina, L. N.; Mikhaleva, A. I.; Bzhezovskii, V. M.; et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 18; nb. 2; (1982); p. 148 - 152; Khimiya Geterotsiklicheskikh Soedinenii; vol. 18; nb. 2; (1982); p. 193 - 198, View in Reaxys 15 of 21

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- tetradeuteriomethanol scopy) Trofimov, B. A.; Korostova, S. E.; Sobenina, L. N.; Mikhaleva, A. I.; Bzhezovskii, V. M.; et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 18; nb. 2; (1982); p. 148 - 152; Khimiya Geterotsiklicheskikh Soedinenii; vol. 18; nb. 2; (1982); p. 193 - 198, View in Reaxys 16 of 21

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- nitrobenzene scopy) Trofimov, B. A.; Korostova, S. E.; Sobenina, L. N.; Mikhaleva, A. I.; Bzhezovskii, V. M.; et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 18; nb. 2; (1982); p. 148 - 152; Khimiya Geterotsiklicheskikh Soedinenii; vol. 18; nb. 2; (1982); p. 193 - 198, View in Reaxys 17 of 21

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- various solvent(s) scopy) Trofimov, B. A.; Korostova, S. E.; Sobenina, L. N.; Mikhaleva, A. I.; Bzhezovskii, V. M.; et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 18; nb. 2; (1982); p. 148 - 152; Khimiya Geterotsiklicheskikh Soedinenii; vol. 18; nb. 2; (1982); p. 193 - 198, View in Reaxys 18 of 21

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Kotera,K. et al.; Tetrahedron; vol. 24; (1968); p. 5677 - 5690, View in Reaxys; Kim,S.-G. et al.; Bulletin of the Chemical Society of Japan; vol. 52; (1979); p. 1115 - 1120, View in Reaxys 19 of 21

Description (NMR Spec- NMR troscopy) Huitric et al.; Journal of Organic Chemistry; vol. 32; (1967); p. 1661, View in Reaxys; Lindeke et al.; Acta Pharmaceutica Suecica; vol. 12; (1975); p. 183,192, 193, View in Reaxys; Glover; Raaen; Journal of Organic Chemistry; vol. 31; (1966); p. 1987, View in Reaxys; Karabatsos; Taller; Tetrahedron; vol. 24; (1968); p. 3347,3353, View in Reaxys

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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20 of 21

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Hawkes,G.E. et al.; Journal of Organic Chemistry; vol. 39; (1974); p. 1017 - 1028, View in Reaxys 21 of 21

Description (NMR Spec- NMR troscopy) Comment (NMR Spectroscopy)

1H

Foreman; Siegel; Mrtek; Journal of pharmaceutical sciences; vol. 58; nb. 2; (1969); p. 189 - 192, View in Reaxys IR Spectroscopy (3) 1 of 3

Description (IR Spectroscopy)

IR

Lindeke et al.; Acta Pharmaceutica Suecica; vol. 12; (1975); p. 183,192, 193, View in Reaxys 2 of 3

Description (IR Spectroscopy)

Bands

Kotera,K. et al.; Tetrahedron; vol. 24; (1968); p. 5677 - 5690, View in Reaxys 3 of 3

Description (IR Spectroscopy)

Spectrum

Solvent (IR Spectroscopy)

nujol

Comment (IR Spectroscopy)

5000 - 667 cm**(-1)

Gilsdorf; Nord; Journal of the American Chemical Society; vol. 74; (1952); p. 1837,1841, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry) spectrum

Coutts; Jones; Liu; Biomedical Mass Spectrometry; vol. 5; nb. 6; (1978); p. 418 - 422, View in Reaxys Lindeke et al.; Acta Pharmaceutica Suecica; vol. 12; (1975); p. 183,192, 193, View in Reaxys

Reaxys ID 3697506 View in Reaxys

Cl HO

5/5 Chemical Name: phenyl-acetone oxime ; hydrochloride; Phenyl-aceton-oxim; Hydrochlorid Linear Structure Formula: C9H11NO*ClH Molecular Formula: C9H11NO*ClH Molecular Weight: 185.653 Type of Substance: isocyclic InChI Key: JJHUTLWMUABAQJ-UHFFFAOYSA-N Note:

H

N

Druglikeness (1) 1 of 1

LogP

2.469

H Bond Donors

1

H Bond Acceptors

0

Rotatable Bonds

2

TPSA

32.59

Lipinski Number

4

Veber Number

2

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