(-)-(1R,2R,4S)-4-hydroxy-2-methyl-2-p-tolylcyclopentanecarboxylic acid ethyl ester | 613669-92-4

• 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: (-)-(1R,2R,4S)-4-hydroxy-2-methyl-2-p-tolylcyclopentanecarboxylic acid ethyl ester
• 英文别名: ethyl (1R,2R,4S)-4-hydroxy-2-methyl-2-(4-methylphenyl)cyclopentane-1-carboxylate
• CAS: 613669-92-4
• 化学式: C₁₆H₂₂O₃
• 分子量: 262.349
• InChiKey: JJDQAJRMSOPOLB-DZKIICNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-(1R,2R,4S)-4-hydroxy-2-methyl-2-p-tolylcyclopentanecarboxylic acid ethyl ester 在 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.67h， 生成 (-)-(1R,2R)-2-methyl-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：

  乙酸乙烯酯 、 (+)-(1S,2S,4R)-4-羟基-2-甲基-2-对甲苯基环戊烷羧酸乙酯 在 Candida antartica B lipase 作用下， 反应 7.0h， 以792 mg的产率得到(-)-(1R,2R,4S)-4-hydroxy-2-methyl-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

文献信息

• Enantioselective synthesis of natural (−)-tochuinyl acetate, (−)-dihydrotochuinyl acetate and (+)-β-cuparenone using both enantiomers of the same building block
  作者：Samir Acherar、Gérard Audran、Fabrice Cecchin、Honoré Monti

  DOI：10.1016/j.tet.2004.05.037

  日期：2004.7

  The first enantioselective synthesis of tochuinyl acetate and dihydrotochuinyl acetate, two natural marine products isolated from Tochuina tetraquetra and Gersemia rubiformis, has been achieved starting from an enantiopure building block. The key feature of the present synthesis is complete control of two vicinal quaternary stereogenic centers present in the natural products and elucidation of their

  从对映体纯净的结构单元开始，实现了乙酸甲苯酯和乙酸二氢甲苯酯的首次对映体选择性合成，这两种天然水产品是从四叶草（Tochuina tetraquetra）和红叶Gersemia分离得到的。本合成的关键特征是完全控制天然产物中存在的两个邻近的季生立体中心，并阐明了它们的绝对立体化学，这在以前是未知的。此外，从相同构件的对映异构体开始，所应用的方法为天然（R）-（+）-β-cuparenone提供了一种新方法。