ethyl (1S,2S,4R)-4-acetyloxy-2-methyl-2-(4-methylphenyl)cyclopentane-1-carboxylate | 613669-91-3

• 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: ethyl (1S,2S,4R)-4-acetyloxy-2-methyl-2-(4-methylphenyl)cyclopentane-1-carboxylate
• CAS: 613669-91-3
• 化学式: C₁₈H₂₄O₄
• 分子量: 304.386
• InChiKey: PDJZTKRWKUFIAU-JFIYKMOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (1S,2S,4R)-4-acetyloxy-2-methyl-2-(4-methylphenyl)cyclopentane-1-carboxylate 在 sodium hydride 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 13.0h， 生成 (+)-(1S,2S,4R)-2-methyl-4-methylsulfanylthiocarbonyloxy-2-p-tolylcyclopentanecarboxylic acid ethyl ester
  参考文献：
  名称：

  Use of lipase-catalyzed kinetic resolution for the enantioselective approach toward sesquiterpenes containing quaternary centers: the cuparane family

  摘要：

  The enzymatic kinetic resolution of a suitable hydroxylated precursor of the deoxygenated molecule 3, a key intermediate in a synthesis of the cuparane skeleton, was investigated by screening a range of lipases for enantioselective transesterification with vinyl acetate. CAL-B proved to be the best lipase, affording both enantiomers in high enantiomeric excess (>98% ee). Single-crystal X-ray diffraction analysis enabled assignment of the absolute configuration and the enantiospecificity of the tested lipases. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00445-2
• 作为产物：
  描述：

  2-methyl-4-oxo-2-p-tolylcyclopentanecarboxylic acid ethyl ester 在 sodium tetrahydroborate 、 cerium(III) chloride 、 Candida antartica B lipase 作用下， 以 乙醇 为溶剂， 反应 17.0h， 生成 ethyl (1S,2S,4R)-4-acetyloxy-2-methyl-2-(4-methylphenyl)cyclopentane-1-carboxylate
  参考文献：
  名称：

  Use of lipase-catalyzed kinetic resolution for the enantioselective approach toward sesquiterpenes containing quaternary centers: the cuparane family

  摘要：

  The enzymatic kinetic resolution of a suitable hydroxylated precursor of the deoxygenated molecule 3, a key intermediate in a synthesis of the cuparane skeleton, was investigated by screening a range of lipases for enantioselective transesterification with vinyl acetate. CAL-B proved to be the best lipase, affording both enantiomers in high enantiomeric excess (>98% ee). Single-crystal X-ray diffraction analysis enabled assignment of the absolute configuration and the enantiospecificity of the tested lipases. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00445-2