[(E)-[(2S)-2-methoxycyclohexylidene]methyl]benzene | 187404-40-6

• 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: [(E)-[(2S)-2-methoxycyclohexylidene]methyl]benzene
• CAS: 187404-40-6
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: XNHINWRWMDZYDX-CMPYXILNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [(E)-[(2S)-2-methoxycyclohexylidene]methyl]benzene 在 氧气 、 臭氧 、 三苯基膦 作用下， 生成 (S)-2-甲氧基环己酮
  参考文献：
  名称：

  Microbially-aided preparation of (S)-2-Methoxycyclohexanone key intermediate in the synthesis of Sanfetrinem

  摘要：

  (S) 2-Methoxycyclohexanone 1, useful intermediate in the synthesis of Sanfetrinem 2, is obtained from (S) alpha-benzylidene cyclohexanol 4, derived from the ketone 3 through a short sequence involving as key step yeast reduction of the carbonyl group. The (R) enantiomer of 1 is similarly accessible from the (R) enantiomer of 4 obtained either upon Candida lipolytica-mediated reduction of 3 or from (R,S)-4 by porcine pancreatic lipase catalyzed acetylation with vinyl acetate. Also the saturated carbinols 7 and 8, which accompany 4 in the microbial reduction of 3, are converted into 1 through unexceptional steps. Nocardia opaca, Pichia etchelsii and Mucor subtilissimus provide from 3 upon reduction (S)-configurated 4, 7 and 8 possessing moderate-high ee values. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01152-0
• 作为产物：
  描述：

  (E)-2-benzylidenecyclohexanone 在 sodium hydride 作用下， 反应 28.0h， 生成 [(E)-[(2S)-2-methoxycyclohexylidene]methyl]benzene
  参考文献：
  名称：

  Microbially-aided preparation of (S)-2-Methoxycyclohexanone key intermediate in the synthesis of Sanfetrinem

  摘要：

  (S) 2-Methoxycyclohexanone 1, useful intermediate in the synthesis of Sanfetrinem 2, is obtained from (S) alpha-benzylidene cyclohexanol 4, derived from the ketone 3 through a short sequence involving as key step yeast reduction of the carbonyl group. The (R) enantiomer of 1 is similarly accessible from the (R) enantiomer of 4 obtained either upon Candida lipolytica-mediated reduction of 3 or from (R,S)-4 by porcine pancreatic lipase catalyzed acetylation with vinyl acetate. Also the saturated carbinols 7 and 8, which accompany 4 in the microbial reduction of 3, are converted into 1 through unexceptional steps. Nocardia opaca, Pichia etchelsii and Mucor subtilissimus provide from 3 upon reduction (S)-configurated 4, 7 and 8 possessing moderate-high ee values. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01152-0

文献信息

• Microbially-aided preparation of (S)-2-Methoxycyclohexanone key intermediate in the synthesis of Sanfetrinem
  作者：Claudio Fuganti、Piero Grasselli、Monica Mendozza、Stefano Servi、Gioia Zucchi

  DOI：10.1016/s0040-4020(96)01152-0

  日期：1997.2

  (S) 2-Methoxycyclohexanone 1, useful intermediate in the synthesis of Sanfetrinem 2, is obtained from (S) alpha-benzylidene cyclohexanol 4, derived from the ketone 3 through a short sequence involving as key step yeast reduction of the carbonyl group. The (R) enantiomer of 1 is similarly accessible from the (R) enantiomer of 4 obtained either upon Candida lipolytica-mediated reduction of 3 or from (R,S)-4 by porcine pancreatic lipase catalyzed acetylation with vinyl acetate. Also the saturated carbinols 7 and 8, which accompany 4 in the microbial reduction of 3, are converted into 1 through unexceptional steps. Nocardia opaca, Pichia etchelsii and Mucor subtilissimus provide from 3 upon reduction (S)-configurated 4, 7 and 8 possessing moderate-high ee values. (C) 1997, Elsevier Science Ltd.