ethyl (1S,2R)-2-acetoxycyclopentanecarboxylate | 603998-13-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (1S,2R)-2-acetoxycyclopentanecarboxylate
• 英文别名: Ethyl (1S,2R)-2-(acetyloxy)cyclopentane-1-carboxylate；ethyl (1S,2R)-2-acetyloxycyclopentane-1-carboxylate
• CAS: 603998-13-6
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: DVPVDANTGJWPDB-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl (dl)-cis-2-acetoxycyclopentanecarboxylate 在 phosphate buffer 作用下， 反应 1.5h， 以50%的产率得到ethyl (1S,2R)-2-acetoxycyclopentanecarboxylate
  参考文献：
  名称：

  荧光假单胞菌脂肪酶催化的五元环乙酸酯的对映选择性水解

  摘要：

  五元环醇的外消旋乙酸酯已通过荧光假单胞菌脂肪酶成功拆分为具有高光学纯度的旋光醇。

  DOI：

  10.1039/c39870000838

文献信息

• Is the ring conformation the most critical parameter in lipase-catalysed acylation of cycloalkanols?
  作者：Laura M. Levy、Iván Lavandera、Vicente Gotor

  DOI：10.1039/b408861a

  日期：——

  CAL-B catalysed the resolution of several five and six-membered cyclic β-hydroxy esters efficiently with the exception of the cis-cyclohexanol (±)-4. When employing molecular modelling techniques the conformation turned out to be the most important determinant for their reactivity towards O-acetylation. In all cases, the R enantiomers reacted faster than the S enantiomers since the reactive intermediates of the former can adopt more favourable ring conformations and thus experience less steric hindrance in the active site. Furthermore, the minimised structure for the main conformer of R-4 showed that the axial hydrogens in the 3 and 5-positions with respect to the hydroxyl group prevent the enzymatic reaction.

  除了顺式环己醇 (±)-4 外，CAL-B 能有效催化多种五元和六元环状 β-羟基酯的分解。采用分子建模技术后发现，构象是决定其 O-乙酰化反应活性的最重要因素。在所有情况下，R 对映体的反应速度都比 S 对映体快，因为前者的反应中间体可以采用更有利的环构象，从而在活性位点中受到的立体阻碍更小。此外，R-4 主要构象的最小化结构显示，相对于羟基的 3 位和 5 位的轴向氢阻碍了酶反应。
• Lipase-catalysed resolution of cyclic cis- and trans-β-hydroxy esters
  作者：Laura M. Levy、Juan R. Dehli、Vicente Gotor

  DOI：10.1016/s0957-4166(03)00366-5

  日期：2003.7

  Lipases A and B from Candida antarctica are shown to be highly efficient and complementary biocatalysts for the resolution of five- to seven-membered cyclic beta-hydroxy esters by O-acylation. Using this procedure, all four stereoisomers of each one are obtained in enantiopure form and very high yields. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Enantioselective hydrolysis of five-membered-ring acetates catalysed by Pseudomonas fluorescens lipase
  作者：Zhuo-Feng Xie、Hiroshi Suemune、Kiyoshi Sakai

  DOI：10.1039/c39870000838

  日期：——

  The racemic acetates of five-membered-ring alcohols were successfully resolved into the optically active alcohols with high optical purities by Pseudomonas fluorescens lipase.

  五元环醇的外消旋乙酸酯已通过荧光假单胞菌脂肪酶成功拆分为具有高光学纯度的旋光醇。