CAS 112068-01-6|CAS 22348-32-9|(S)-(-)-Alpha,alpha-Diphenyl-2-pyrrolidinemethanol|diphenyl(2S)-pyrrolidin-2-ylmethanol|diphenyl(2S)-pyrrolidin-2-ylmethanol|Diphenyl[(2R)-(+)-pyrrolidin-2-yl]methanol...

General Information

Structure

Molecular Formula

C₁₇H₁₉NO

Molecular Mass

253.33886

Exact Mass

253.14666423

Charge

InChI

InChI=1S/C17H19NO/c19-17(16-12-7-13-18-16,14-8-3-1-4-9-14)15-10-5-2-6-11-15/h1-6,8-11,16,18-19H,7,12-13H2/t16-/m0/s1

InChIKey

OGCGXUGBDJGFFY-INIZCTEOSA-N

Canonic Smiles

OC(c1ccccc1)(c1ccccc1)[C@@H]1CCCN1

Isomeric Smiles

N1[C@@H](CCC1)C(O)(c1ccccc1)c1ccccc1

Calculated Properties

JChem

Acid pKa

12.901563

H Acceptors

H Donor

LogD (pH = 5.5)

-0.35732114

LogD (pH = 7.4)

0.039381664

Log P

2.8763463

Molar Refractivity

77.1829

Polarizability

30.58561

Polar Surface Area

32.26

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC Traditional name

diphenyl(2S)-pyrrolidin-2-ylmethanol

Synonyms

(S)-(-)-Alpha,alpha-Diphenyl-2-pyrrolidinemethanol(2R)-(+)-2-[Hydroxy(diphenyl)methyl]pyrrolidineDiphenyl[(2R)-(+)-pyrrolidin-2-yl]methanol(R)-(+)-alpha,alpha-Diphenylprolinol(S)-(-)-α,α-二苯基脯氨醇(S)-(-)-alpha,alpha-Diphenyl-2-pyrrolidinemethanol(S)-(-)-alpha,alpha-Diphenylprolinol(S)-α,α-二苯基-2-吡咯烷甲醇α,α-Diphenyl-L-prolinol(S)-2-(Diphenylhydroxymethyl)pyrrolidine(S)-α,α-Diphenyl-2-pyrrolidinemethanol(S)-(+)-α,α-二苯基脯氨醇(S)-2-(二苯基羟甲基)吡咯烷(S)-Diphenyl(pyrrolidin-2-yl)methanol(S)-(-)-2-(二苯基羟甲基)吡咯烷(S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanolα,α-Diphenyl-L-prolinolα,α-二苯基-L-脯氨醇(S)-(-)-2-(Diphenylhydroxymethyl)pyrrolidine

IUPAC name

diphenyl(2S)-pyrrolidin-2-ylmethanol

Names and Identifiers

Registration numbers

CAS Number

112068-01-622348-32-9

Beilstein Number

171036060893

MDL Number

MFCD00075506

PubChem SID

2486289924879275162035060

PubChem CID

2724899

Registration numbers

Properties

Product Information

Physical Property

Properties

Related Proteins

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Molecular Spectra

No Data Available

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Molecule Details

Sigma Aldrich

552526

Legal Information
A Product of Onyx Scientific, U.K.

368199

Packaging
1, 5 g in glass bottle
Application
Used to prepare the corresponding oxazaborolidines for the borane-mediated asymmetric reduction of ketones.1

43182

Other Notes
The cyclic borane adduct, an oxazaborolidine, is an efficient catalyst for enantioselective reductions of ketones with borane (CBS-reduction)1,2,3,4

Molecule Details

References

PubChem Literature

From Data Sources

• For reviews of oxazaborolidines as enantioselective catalysts, see: Angew. Chem. Int. Ed., 31, 729 (1992); 37, 1986 (1998); Tetrahedron: Asymmetry, 3, 1475 (1992). For reviews of the asymmetric reduction of ketones, see: Synthesis, 605 (1992); Chem. Ind. (London), 552 (1994).

• Precursor of Corey, Bakshi and Shibata's oxazaborolidine derivatives (CBS catalysts) for enantioselective reduction of prochiral ketones: J. Am. Chem. Soc., 109, 5551 (1987). Ketones are not reduced rapidly by either borane-THF or the oxazaborolidine alone but together they form a complex which reduces ketones rapidly and stereoselectively, permitting reduction with very high ee in the presence of a catalytic amount of the oxazaborolidine: J. Am. Chem. Soc., 109, 7925 (1987).

• For use in conjunction with borane generated in situ using NaBH₄ and iodine, see: Tetrahedron, 50, 6411 (1994). For an optimized in situ procedure for generation and use of the oxazaborolidine from BMS, see: Tetrahedron: Asymmetry, 7, 3147 (1996). In a comparison with other oxazaborolidine precursors, diphenylprolinol gave the best results (same ref.). For in situ generation of an asymmetric reduction system using trimethyl borate and BMS, see: Synlett, 273 (1997). For the generation and use of the phenyl oxazaborolidine, using Benzeneboronic acid, A14257, see: Tetrahedron Lett., 31, 7415 (1990); 32, 7175 (1991); J. Org. Chem., 57, 7115 (1992). For a detailed comparative study of various alkyl- and aryl-substituted borolidines, see: J. Org. Chem., 56, 763 (1991). For a process for the in situ formation of butyl oxazaborolidines using 1-Butylboronic acid, A13725, see: Tetrahedron Lett., 33, 4141 (1992). For use for the catalytic enantioselective synthesis of chiral monosubstituted oxiranes, see: Tetrahedron Lett., 34, 5227 (1993).

• See also the preformed catalyst (S)-2-Methyl-CBS-oxazaborolidine, L14583, and (S)-2-Methyl-CBS-oxazaborolidine monohydrate, L09219.

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

diphenyl(2S)-pyrrolidin-2-ylmethanol

Synonyms

IUPAC name

diphenyl(2S)-pyrrolidin-2-ylmethanol

Registration numbers

CAS Number

112068-01-622348-32-9

Beilstein Number

171036060893

MDL Number

MFCD00075506

PubChem SID

2486289924879275162035060

PubChem CID

2724899

Properties

Product Information

Physical Property

Molecule Details

Sigma Aldrich

552526

Legal Information
A Product of Onyx Scientific, U.K.

368199

Packaging
1, 5 g in glass bottle
Application
Used to prepare the corresponding oxazaborolidines for the borane-mediated asymmetric reduction of ketones.1

43182

Other Notes
The cyclic borane adduct, an oxazaborolidine, is an efficient catalyst for enantioselective reductions of ketones with borane (CBS-reduction)1,2,3,4

References

PubChem Literature

From Data Sources

• See also the preformed catalyst (S)-2-Methyl-CBS-oxazaborolidine, L14583, and (S)-2-Methyl-CBS-oxazaborolidine monohydrate, L09219.

Bioactivity

PubChem BioAssay

Molecule

ID:69333