(S)-(-)-α,α-二苯基脯氨醇

• 产品号: L09217
• CAS号: 112068-01-6
• 分子式: C17H19NO
• 分子量: 253.33886
• 纯 度: 98%

产品别名

• 标题: (S)-(-)-alpha,alpha-Diphenylprolinol
• IUPAC标准名: diphenyl(2S)-pyrrolidin-2-ylmethanol
• IUPAC传统名: diphenyl(2S)-pyrrolidin-2-ylmethanol
• 别名: (S)-(-)-alpha,alpha-Diphenyl-2-pyrrolidinemethanol

产品登记号

• Beilstein号: 17103
• CAS号: 112068-01-6
• MDL号: MFCD00075506

产品性质

• 纯度: 98%
• 熔点: 76-78°C
• 比旋光度: -57.5 (c=3 in methanol)
• GHS危险声明: H315-H319-H335
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• GHS警示性声明: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 危险公开号: 36/37/38
• 安全公开号: 26-37
• TSCA收录: 否

参考文献

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