(+)-cis-1-(N-pyrrolidine-1'-carbonyloxy)-2-cyclopentyl isobutyrate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (+)-cis-1-(N-pyrrolidine-1'-carbonyloxy)-2-cyclopentyl isobutyrate
• 英文别名: (-)-cis-1-(N-pyrrolidine-1'-carbonyloxy)-2-cyclopentyl isobutyrate；cis-1-(N-pyrrolidine-1'-carbonyloxy)-2-cyclopentyl isobutyrate；[(1R,2S)-2-(2-methylpropanoyloxy)cyclopentyl] pyrrolidine-1-carboxylate
• 化学式: C₁₄H₂₃NO₄
• 分子量: 269.341
• InChiKey: STGAWZUKJWBESA-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  cis-1,2-cyclohexane 在 吡啶 、 (S)-N-2,4,6-iPr3PhSO2-N(ϖ)Me-histidinol tBuPh2 ether 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (+)-cis-1-(N-pyrrolidine-1'-carbonyloxy)-2-cyclopentyl isobutyrate
  参考文献：
  名称：

  Rational Design of an l-Histidine-Derived Minimal Artificial Acylase for the Kinetic Resolution of Racemic Alcohols

  摘要：

  This communication describes the rational design of an l-histidine-derived minimal artificial acylase. Our new artificial acylase, tert-butyldiphenylsilyl ether of N-(2,4,6-triisopropylbenzenesulfonyl)-pi(Me)-l-histidinol, is a simple and small molecule (molecular weight = 660) that contains only one chiral carbon center that originates from natural l-histidine. The kinetic acylation of racemic secondary alcohols induced by this compound showed an S (kfast/kslow) value of up to 93. A reusable polystyrene-bound artificial acylase was also developed to examine its practical usability.

  DOI：

  10.1021/ja045850j

文献信息

• Rational Design of an <scp>l</scp>-Histidine-Derived Minimal Artificial Acylase for the Kinetic Resolution of Racemic Alcohols
  作者：Kazuaki Ishihara、Yuji Kosugi、Matsujiro Akakura

  DOI：10.1021/ja045850j

  日期：2004.10.1

  This communication describes the rational design of an l-histidine-derived minimal artificial acylase. Our new artificial acylase, tert-butyldiphenylsilyl ether of N-(2,4,6-triisopropylbenzenesulfonyl)-pi(Me)-l-histidinol, is a simple and small molecule (molecular weight = 660) that contains only one chiral carbon center that originates from natural l-histidine. The kinetic acylation of racemic secondary alcohols induced by this compound showed an S (kfast/kslow) value of up to 93. A reusable polystyrene-bound artificial acylase was also developed to examine its practical usability.