cis-2-phenyl-cyclohexyl acetate

• 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: cis-2-phenyl-cyclohexyl acetate
• 英文别名: (+/-)-acetic acid-(cis-2-phenyl-cyclohexyl ester)；(+/-)-Essigsaeure-(cis-2-phenyl-cyclohexylester)；[(1R,2R)-2-phenylcyclohexyl] acetate
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: OCJKSUSNMXDOGL-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cis-2-phenyl-cyclohexyl acetate 生成 1-苯基-1-环已烯 、 3-phenyl-1-cyclohexene
  参考文献：
  名称：

  Studies on the Mechanism of Chugaev and Acetate Thermal Decompositions. I. cis- and trans-2-Phenylcyclohexanol

  摘要：

  DOI：

  10.1021/ja01160a115
• 作为产物：
  描述：

  2-苯基环己烷-1-醇 、 乙酰氯 在 吡啶 作用下， 生成 cis-2-phenyl-cyclohexyl acetate
  参考文献：
  名称：

  Studies on the Mechanism of Chugaev and Acetate Thermal Decompositions. I. cis- and trans-2-Phenylcyclohexanol

  摘要：

  DOI：

  10.1021/ja01160a115

文献信息

• Diastereoselective and enantioselective alkaline-hydrolysis of 2-aryl-1-cyclohexyl acetate: a CAL-B catalyzed deacylation/acylation tandem process
  作者：Fatma Zahra Belkacemi、Mounia Merabet-Khelassi、Louisa Aribi-Zouioueche、Olivier Riant

  DOI：10.1016/j.tetasy.2017.09.010

  日期：2017.11

  Candida antarctica lipase proved to be a particularly efficient lipase for the resolution of racemic 2-aryl-cyclohexyl acetate in hydrolysis reaction with Na2CO3 in an organic medium. The (1R,2S)-trans-2-arylcy-clohexanols 2a-2d were obtained with high ee values (up to >99%) and the selectivity reached E > 200. The influence of the enol ester and the solvent on (+/-)-trans-2-arylcyclohexanol in the CAL-B catalyzed acylation was also studied and compared with the deacylation. The CAL-B exhibits a better affinity for the alkaline hydrolysis reaction compared with acylation with the enol esters in the same organic solvents. The best conditions were applied to resolve a stereoisomeric mixture cis/trans-2-phenyl-1-cyclohexanol and its corresponding acetate by acylation and deacylation. The obtained results show a highly enantio- and diastereoselectivity of the CAL-B during the acylation and the deacylation in favor of the trans-(R)-enantiomer product. The resolution of a mixture of cis/trans-2-arylcyclohexanols was an easy, convenient approach to provide only one stereoisomer of a mixture of four with high enantiomeric excess. (C) 2017 Elsevier Ltd. All rights reserved.
• Youssef, Abdel-Hamid A.; Sharaf, Saber M.; Hegazy, Fatma M. El, Journal fur praktische Chemie (Leipzig 1954), 1982, vol. 324, # 5, p. 725 - 734
  作者：Youssef, Abdel-Hamid A.、Sharaf, Saber M.、Hegazy, Fatma M. El

  DOI：——

  日期：——
• Studies on the Mechanism of Chugaev and Acetate Thermal Decompositions. I. cis- and trans-2-Phenylcyclohexanol
  作者：Elliot R. Alexander、Anton Mudrak

  DOI：10.1021/ja01160a115

  日期：1950.4