(+/-)-trans-2-phenylcyclopentyl methoxyacetate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-trans-2-phenylcyclopentyl methoxyacetate
• 英文别名: [(1S,2R)-2-phenylcyclopentyl] 2-methoxyacetate
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: VWRCOABMLYAEEG-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  甲氧基乙酰氯 、 trans-2-phenylcyclopentan-1-ol 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以91%的产率得到(+/-)-trans-2-phenylcyclopentyl methoxyacetate
  参考文献：
  名称：

  Kinetic resolution of (±)-trans- and (±)-cis-2-phenylcyclopentanamine by CALB-catalyzed aminolysis of esters: the key role of the leaving group

  摘要：

  Kinetic resolution of (+/-)-trans- and (+/-)-cis-2-phenylcyclopentanamine is effectively performed by lipase B from Candida antarctica, (CALB)-catalyzed aminolysis reaction. Whereas reaction between (+/-)-trans-2-phenylcyclopentanamine and ethyl acetate proceeds with a very high E value (>200) and conversion (50%), the corresponding acetylation of ()-cis-2-phenylcyclopentanamine happens with low E value (16) and conversion (28%). Nevertheless, this problem is overcome using other acyl donors such as (+/-)-1-phenylethyl and (+/-)-cis-2-phenylcyclopentyl methoxyacetates. The influence of the acyl donor on the CALB-catalyzed aminolysis of (+/-)-cis-2-phenylcyclopentanamine is also studied. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.11.013

文献信息

• Kinetic resolution of (±)-trans- and (±)-cis-2-phenylcyclopentanamine by CALB-catalyzed aminolysis of esters: the key role of the leaving group
  作者：Javier González-Sabı́n、Vicente Gotor、Francisca Rebolledo

  DOI：10.1016/j.tetasy.2003.11.013

  日期：2004.2

  Kinetic resolution of (+/-)-trans- and (+/-)-cis-2-phenylcyclopentanamine is effectively performed by lipase B from Candida antarctica, (CALB)-catalyzed aminolysis reaction. Whereas reaction between (+/-)-trans-2-phenylcyclopentanamine and ethyl acetate proceeds with a very high E value (>200) and conversion (50%), the corresponding acetylation of ()-cis-2-phenylcyclopentanamine happens with low E value (16) and conversion (28%). Nevertheless, this problem is overcome using other acyl donors such as (+/-)-1-phenylethyl and (+/-)-cis-2-phenylcyclopentyl methoxyacetates. The influence of the acyl donor on the CALB-catalyzed aminolysis of (+/-)-cis-2-phenylcyclopentanamine is also studied. (C) 2003 Elsevier Ltd. All rights reserved.