(1S,2S,4R,5S)-(-)-4-hydroxy-6-oxabicyclo<3.1.0>hex-2-yl acetate | 137820-14-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (1S,2S,4R,5S)-(-)-4-hydroxy-6-oxabicyclo<3.1.0>hex-2-yl acetate
• 英文别名: [(1R,2S,4R,5S)-4-hydroxy-6-oxabicyclo[3.1.0]hexan-2-yl] acetate
• CAS: 137820-14-5
• 化学式: C₇H₁₀O₄
• 分子量: 158.154
• InChiKey: CIHXKEGIMFVUOV-JRTVQGFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-(+)-α-甲氧基-α-(三氟甲基)苯乙酸 、 (1S,2S,4R,5S)-(-)-4-hydroxy-6-oxabicyclo<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-6-oxa-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：

  顺式-4-环戊烯-1,3-二醇 在 吡啶 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 碳酸氢钠 、 potassium carbonate 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 97.3h， 生成 (1S,2S,4R,5S)-(-)-4-hydroxy-6-oxabicyclo<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

• Chiral induction in cyclopentyl-derived 1,3-meso-diesters: enantioselective hydrolyses with electric eel acetylcholinesterase
  作者：Donald R Deardorff、Roberto B Amador、James W Morton、Henry Y Kim、Cullen M Taniguchi、Arnel A Balbuena、Sam A Warren、Vadim Fanous、S.W.Tina Choe

  DOI：10.1016/s0957-4166(99)00236-0

  日期：1999.6

  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.
• A correlation of configuration and19F-NMR Chemical Shifts of (R)-(+)-Mosher Esters of Chiral Cyclopentanediol Derivatives
  作者：F. Theil、B. Costisella、H. Schick

  DOI：10.1002/prac.19923340116

  日期：——