(3aS,6aS)-1-[(1S)-1-phenylethyl]hexahydrocyclopenta[b]pyrrole-6a(1H)-carbonitrile | 1268852-13-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (3aS,6aS)-1-[(1S)-1-phenylethyl]hexahydrocyclopenta[b]pyrrole-6a(1H)-carbonitrile
• 英文别名: (3aS,6aS)-1-[(1S)-1-phenylethyl]-2,3,3a,4,5,6-hexahydrocyclopenta[b]pyrrole-6a-carbonitrile
• CAS: 1268852-13-6
• 化学式: C₁₆H₂₀N₂
• 分子量: 240.348
• InChiKey: ZKWKLDSERVQKMJ-CWRNSKLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3aS,6aS)-1-[(1S)-1-phenylethyl]hexahydrocyclopenta[b]pyrrole-6a(1H)-carbonitrile 在 硫酸 作用下， 以 正己烷 为溶剂， 反应 54.0h， 以89%的产率得到(3aS,6aS)-1-[(1S)-1-phenylethyl]hexahydrocyclopenta[b]pyrrole-6a(1H)-carboxylic acid amide
  参考文献：
  名称：

  Synthesis of enantiopure (R,R)- and (S,S)-cis-2,3-propanoprolines

  摘要：

  A novel approach to the synthesis of an enantiopure bicyclic proline analogue, hexahydrocyclopentalb]pyrrole-6a(1H)-carboxylic acid ('2,3-propanoproline'), has been developed. The method relied on tandem Strecker-nucleophilic cyclization reaction of 2-(2-bromoethyl)cyclopentanone. The overall synthetic scheme included six steps and resulted in 18% overall yield of both enantiomers of the title amino acid. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.11.017
• 作为产物：
  描述：

  2-methyl-2-((1-phenylethyl)amino)propane-nitrile 、 2-(2-bromoethyl)cyclopentanone 以 乙腈 为溶剂， 反应 48.0h， 以30%的产率得到(3aS,6aS)-1-[(1S)-1-phenylethyl]hexahydrocyclopenta[b]pyrrole-6a(1H)-carbonitrile
  参考文献：
  名称：

  Synthesis of enantiopure (R,R)- and (S,S)-cis-2,3-propanoprolines

  摘要：

  A novel approach to the synthesis of an enantiopure bicyclic proline analogue, hexahydrocyclopentalb]pyrrole-6a(1H)-carboxylic acid ('2,3-propanoproline'), has been developed. The method relied on tandem Strecker-nucleophilic cyclization reaction of 2-(2-bromoethyl)cyclopentanone. The overall synthetic scheme included six steps and resulted in 18% overall yield of both enantiomers of the title amino acid. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.11.017