(1R,2S,4R,5S)-(-)-4-hydroxybicyclo<3.1.0>hex-2-yl acetate | 137820-16-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S,4R,5S)-(-)-4-hydroxybicyclo<3.1.0>hex-2-yl acetate
• 英文别名: (1S,2R,4S,5R)-(+)-4-Hydroxybicyclo<3.1.0>hex-4-yl acetate；[(1R,2S,4R,5S)-4-hydroxy-2-bicyclo[3.1.0]hexanyl] acetate
• CAS: 137820-16-7
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: LCDAUHCMSYLFIY-OSMVPFSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(+)-α-甲氧基-α-(三氟甲基)苯乙酸 、 (1R,2S,4R,5S)-(-)-4-hydroxybicyclo<3.1.0>hex-2-yl acetate 在 4-二甲氨基吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 生成 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,2R,4S,5R)-4-acetoxy-bicyclo[3.1.0]hex-2-yl ester
  参考文献：
  名称：

  A correlation of configuration and19F-NMR Chemical Shifts of (R)-(+)-Mosher Esters of Chiral Cyclopentanediol Derivatives

  摘要：

  DOI：

  10.1002/prac.19923340116
• 作为产物：
  描述：

  (1RS,2SR,4RS,5SR)-bicyclo<3.1.0>hex-2,4-diyl diacetate 在 sodium dihydrogenphosphate 、 sodium azide 、 Electrophorus electricus acetylcholinesterase 作用下， 以60%的产率得到(1R,2S,4R,5S)-(-)-4-hydroxybicyclo<3.1.0>hex-2-yl acetate
  参考文献：
  名称：

  Chiral induction in cyclopentyl-derived 1,3-meso-diesters: enantioselective hydrolyses with electric eel acetylcholinesterase

  摘要：

  Eight 1,3-meso-diesters derived from a common cyclopentyl backbone were exposed to the hydrolase enzyme acetylcholinesterase from Electrophorus electricus. All eight compounds were hydrolyzed by the enzyme. The overall enantioselectivities were quite high, and the resulting e.e.s were generally >90%. The absolute configurations of the product monoesters were determined through stereochemical correlation. These data revealed that the preferred site for enzymatic hydrolysis in seven of the substrates was the pro-S ester function, with pro-R cleavage detected in the eighth. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00236-0

文献信息

• Lipase-catalyzed transesterification of meso-cyclopentane diols
  作者：Fritz Theil、Hans Schick、Gabriele Winter、Günter Reck

  DOI：10.1016/s0040-4020(01)88281-8

  日期：1991.9

  The lipase-catalyzed transesterification of the meso-cyclopentane diols 1a - 6a with vinyl acetate in tetrahydrofuran/triethylamine in the presence of lipases of different origin has been investigated. Depending on the structure of the substrate and the origin of the lipase chiral cyclopentane derivatives with high enantiomeric excess could be obtained in good to excellent chemical yields.