1-benzyl-3-phenyl-4,5,6,7-tetrahydro-1H-indole | 230287-26-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-benzyl-3-phenyl-4,5,6,7-tetrahydro-1H-indole
• 英文别名: 1-Benzyl-3-phenyl-4,5,6,7-tetrahydroindole
• CAS: 230287-26-0
• 化学式: C₂₁H₂₁N
• 分子量: 287.404
• InChiKey: IUCRNTQVLAVVJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-benzyl-3-phenyl-4,5,6,7-tetrahydro-1H-indole 在 palladium on activated charcoal 作用下， 以 xylene 为溶剂， 反应 48.0h， 以76%的产率得到1-benzyl-3-phenyl-1H-indole
  参考文献：
  名称：

  Reaction of cyclohexanones imines with substituted nitroolefins. New synthesis of tetrahydroindole derivatives

  摘要：

  The Michael-type addition of cyclohexanones imines, reacting as their secondary enamine tautomers. to beta-substituted nitroolefins is followed by a cyclization reaction with elimination of the nitro group to afford substituted tetrahydroindoles. When a 2-methylcyclohexanone imine is reacted, an unexpected inversion of the regioselectivity is observed when compared with beta-substituted ethylenic eaters. thus allowing to obtain also substituted tetrahydroindoles (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00708-x
• 作为产物：
  描述：

  反式硝基苯乙烯 、 N-benzylcyclohexylimine 以 甲苯 为溶剂， 以70%的产率得到1-benzyl-3-phenyl-4,5,6,7-tetrahydro-1H-indole
  参考文献：
  名称：

  Reaction of cyclohexanones imines with substituted nitroolefins. New synthesis of tetrahydroindole derivatives

  摘要：

  The Michael-type addition of cyclohexanones imines, reacting as their secondary enamine tautomers. to beta-substituted nitroolefins is followed by a cyclization reaction with elimination of the nitro group to afford substituted tetrahydroindoles. When a 2-methylcyclohexanone imine is reacted, an unexpected inversion of the regioselectivity is observed when compared with beta-substituted ethylenic eaters. thus allowing to obtain also substituted tetrahydroindoles (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00708-x

文献信息

• Three-Component Ordered Annulation of Amines, Ketones, and Nitrovinylarenes: Access to Fused Pyrroles and Substituted Indoles under Metal-Free Conditions
  作者：Jinjin Chen、Dan Chang、Fuhong Xiao、Guo-Jun Deng

  DOI：10.1021/acs.joc.8b02410

  日期：2019.1.18

  An efficient synthesis of pyrroles and indoles has been developed via three-component ordered annulation of amines, ketones, and nitrovinylarenes. The reaction selectivity can be well controlled under metal-free conditions to afford the corresponding heterocyclic products in good yields.

  通过胺，酮和硝基乙烯基芳烃的三组分有序环化，已开发出吡咯和吲哚的有效合成方法。可以在无金属的条件下很好地控制反应选择性，从而以高收率得到相应的杂环产物。