(1R,2R)-2-(phenylthio)cyclopentyl acetate | 154617-12-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (1R,2R)-2-(phenylthio)cyclopentyl acetate
• 英文别名: (1R, 2R)-2-(phenylthio)cyclopentyl acetate
• CAS: 154617-12-6
• 化学式: C₁₃H₁₆O₂S
• 分子量: 236.335
• InChiKey: SYEZZJHPMMLTRJ-CHWSQXEVSA-N

物化性质

• 沸点：
  336.8±35.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1R,2R)-2-(phenylthio)cyclopentyl acetate 在 sodium periodate 、 calcium carbonate 作用下， 生成 (R)-2-cyclopentenyl acetate
  参考文献：
  名称：

  Synthesis of enantiomerically pure (R)-2-cycloalken-1-ols using highly enantioselective enzymatic transesterification

  摘要：

  Optically pure (R)-2-cycloalken-1-ols were synthesized via highly enantioselective lipase-catalyzed transesterification of 2-substituted cycloalkanols.

  DOI：

  10.1016/s0957-4166(00)80093-2
• 作为产物：
  描述：

  乙酸异丙烯酯 、 trans-(±)-2-(phenylthio)cyclopentanol 以 异丙醚 为溶剂， 反应 24.0h， 以50%的产率得到(1R,2R)-2-(phenylthio)cyclopentyl acetate
  参考文献：
  名称：

  Synthesis of an enantiomerically pure aminoisoquinocarbazole with antiarrhythmic activity via lipase-catalyzed enantioselective transesterification

  摘要：

  Enantiomerically pure (R)-2-cydohexen-1-ol 5 was prepared via lipase-catalyzed enantioselective transesterification of 2-substituted cyclohexanol, and stereospecifically converted to (-)-(2-cyclohexenyl)acetic acid 4. Enantiomerically pure aminoisoquinocarbazole 1 (RS-2135) was synthesized stereoselectively from 4, using an intramolecular Dids-Alder reaction and Curtius rearrangement. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00199-1

文献信息

• Highly enantioselective kinetic resolution of trans-2-(phenylthio)cyclohexanol derivatives by immobilized Candida antartica B lipase
  作者：Swapandeep Singh Chimni、Kirandeep Kaur、Neeraj Bala

  DOI：10.1016/j.molcatb.2013.06.006

  日期：2013.12

  Candida antartica B (immobilized CAL-B) mediated resolutions of trans-2-(phenylthio)cyclohexanol derivatives using vinyl acetate as acylating agent and MTBE as solvent provide excellent enantioselectivity (up to >99%) and high yield of both the enantiomers in short reaction time. (C) 2013 Elsevier B.V. All rights reserved.