(3-phenoxypropionyl)carbamic acid (1R,2S)-2-phenylcyclohex-1-yl ester | 374778-25-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (3-phenoxypropionyl)carbamic acid (1R,2S)-2-phenylcyclohex-1-yl ester
• 英文别名: [(1R,2S)-2-phenylcyclohexyl] N-(3-phenoxypropanoyl)carbamate
• CAS: 374778-25-3
• 化学式: C₂₂H₂₅NO₄
• 分子量: 367.445
• InChiKey: MQOMDSOCEAZYFI-VQTJNVASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3-phenoxypropionyl)carbamic acid (1R,2S)-2-phenylcyclohex-1-yl ester 在 三氟化硼乙醚 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 chroman-4-yl-carbamic acid (1R,2S)-2-phenyl cyclohex-1-yl ester
  参考文献：
  名称：

  The Preparation and Intra- and Intermolecular Addition Reactions of Acyclic N-Acylimines:  Application to the Synthesis of (±)-Sertraline

  摘要：

  Intramolecular endo-cyclization reactions of N-acyliminium ions have seen wide application for the synthesis of heterocyclic compounds. The corresponding exocyclic variant, which would provide 1-aminotetralin derivatives, for example, has little precedent. We have discovered that acyclic N-acylcarbamates can be readily reduced to the corresponding N-acylhemiaminal derivatives in high yield using DIBAL as the reducing agent. These intermediates are remarkably stable and, if desired, can be purified and stored. The acyclic N-acylhemiaminals undergo both intra- and intermolecular nucleophilic addition reactions mediated by strong Lewis acids, such as TiCl4. Diastereoselectivity, induced either by a substituent on the newly formed ring, or by utilizing a chiral ester on the carbamic acid, was disappointingly low. This methodology was successfully applied to the synthesis of the racemic form of the marketed antidepressant sertraline.

  DOI：

  10.1021/jo010370l
• 作为产物：
  描述：

  3-苯氧基丙酰氯 、 trans-2-phenylcyclohexyl carbamate 以 甲苯 为溶剂， 反应 6.0h， 以93%的产率得到(3-phenoxypropionyl)carbamic acid (1R,2S)-2-phenylcyclohex-1-yl ester
  参考文献：
  名称：

  The Preparation and Intra- and Intermolecular Addition Reactions of Acyclic N-Acylimines:  Application to the Synthesis of (±)-Sertraline

  摘要：

  Intramolecular endo-cyclization reactions of N-acyliminium ions have seen wide application for the synthesis of heterocyclic compounds. The corresponding exocyclic variant, which would provide 1-aminotetralin derivatives, for example, has little precedent. We have discovered that acyclic N-acylcarbamates can be readily reduced to the corresponding N-acylhemiaminal derivatives in high yield using DIBAL as the reducing agent. These intermediates are remarkably stable and, if desired, can be purified and stored. The acyclic N-acylhemiaminals undergo both intra- and intermolecular nucleophilic addition reactions mediated by strong Lewis acids, such as TiCl4. Diastereoselectivity, induced either by a substituent on the newly formed ring, or by utilizing a chiral ester on the carbamic acid, was disappointingly low. This methodology was successfully applied to the synthesis of the racemic form of the marketed antidepressant sertraline.

  DOI：

  10.1021/jo010370l

文献信息

• The Preparation and Intra- and Intermolecular Addition Reactions of Acyclic <i>N</i>-Acylimines:  Application to the Synthesis of (±)-Sertraline
  作者：Michael P. DeNinno、Cynthia Eller、John B. Etienne

  DOI：10.1021/jo010370l

  日期：2001.10.1

  Intramolecular endo-cyclization reactions of N-acyliminium ions have seen wide application for the synthesis of heterocyclic compounds. The corresponding exocyclic variant, which would provide 1-aminotetralin derivatives, for example, has little precedent. We have discovered that acyclic N-acylcarbamates can be readily reduced to the corresponding N-acylhemiaminal derivatives in high yield using DIBAL as the reducing agent. These intermediates are remarkably stable and, if desired, can be purified and stored. The acyclic N-acylhemiaminals undergo both intra- and intermolecular nucleophilic addition reactions mediated by strong Lewis acids, such as TiCl4. Diastereoselectivity, induced either by a substituent on the newly formed ring, or by utilizing a chiral ester on the carbamic acid, was disappointingly low. This methodology was successfully applied to the synthesis of the racemic form of the marketed antidepressant sertraline.