3-(chloromethyl)-1-methylindole-2-carbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-(chloromethyl)-1-methylindole-2-carbonitrile
• 化学式: C₁₁H₉ClN₂
• 分子量: 204.659
• InChiKey: ZLQBDCCIWOWBEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  28.7
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(chloromethyl)-1-methylindole-2-carbonitrile 在 偶氮二异丁腈 、 三正丁基氢锡 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 18.0h， 生成 1'-methyl-1-<(1-methyl-2-cyano-3-indolyl)methyl>spiro-2'-carbonitrile
  参考文献：
  名称：

  Nucleophilic-type radical cyclizations of indoles: conversion of 2-cyano 3-substituted indoles to spiro-annelated indolines and tetrahydrocarbazolones

  摘要：

  Oxidative photocyclizations of appropriate 2-anilino alkenenitriles (6) afforded a series of indole-2-carbonitriles (7) having bromoalkyl substituents at the C-3 positions. Upon treatment with Bu3SnH, these indolecarbonitriles underwent intramolecular cyclizations either by attack at the C-3 positions of the indole rings to give the spiro-annelated indolinecarbonitriles or by attack at the cyano group to give carbazolone derivatives.

  DOI：

  10.1021/jo00063a032

文献信息

• Yang Chau-Chen, Chang Han-Ting, Fang Jim-Min, J. Org. Chem., 58 (1993) N 11, S 3100-3105
  作者：Yang Chau-Chen, Chang Han-Ting, Fang Jim-Min

  DOI：——

  日期：——
• Nucleophilic-type radical cyclizations of indoles: conversion of 2-cyano 3-substituted indoles to spiro-annelated indolines and tetrahydrocarbazolones
  作者：Chau Chen Yang、Han Ting Chang、Jim Min Fang

  DOI：10.1021/jo00063a032

  日期：1993.5

  Oxidative photocyclizations of appropriate 2-anilino alkenenitriles (6) afforded a series of indole-2-carbonitriles (7) having bromoalkyl substituents at the C-3 positions. Upon treatment with Bu3SnH, these indolecarbonitriles underwent intramolecular cyclizations either by attack at the C-3 positions of the indole rings to give the spiro-annelated indolinecarbonitriles or by attack at the cyano group to give carbazolone derivatives.