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

基本信息

化学结构

分子式

C₁₇H₁₉NO

分子量

253.33886

精确质量

253.14666423

电荷

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

计算属性

JChem

Acid pKa

12.901563

质子受体

质子供体

LogD (pH = 5.5)

-0.35732114

LogD (pH = 7.4)

0.039381664

Log P

2.8763463

摩尔折射率

77.1829

极化性

30.58561

极化表面积

32.26

可自由旋转的化学键

里宾斯基五规则

true

数据来源

名称和标识

IUPAC传统名

diphenyl(2S)-pyrrolidin-2-ylmethanol

别名

(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标准名

diphenyl(2S)-pyrrolidin-2-ylmethanol

名称和标识

数据登录号

CAS号

112068-01-622348-32-9

Beilstein号

171036060893

MDL号

MFCD00075506

PubChem SID

2486289924879275162035060

PubChem CID

2724899

数据登录号

化合物性质

分子相关蛋白质

暂无数据

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分子图谱

暂无数据

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描述信息

Sigma Aldrich

552526

Legal Information
英国 Onyx Scientific 产品

368199

包装
1, 5 g in glass bottle
Application
用于制备对应的噁唑硼烷，噁唑硼烷可用于酮的硼烷介导不对称还原反应。1

43182

Other Notes
环硼烷加合物--噁唑硼烷是一种高效催化剂，用于酮与硼烷的不对称还原反应（CBS-还原反应）1,2,3,4

描述信息

参考文献

PubChem文献

数据源提供

• 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.

参考文献

生物活性

PubChem BioAssay

生物活性