[1-Cyclopentylmethoxy-2-methyl-2-phenyl-1,2-dihydro-indol-(3E)-ylidene]-phenyl-amine | 134736-56-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: [1-Cyclopentylmethoxy-2-methyl-2-phenyl-1,2-dihydro-indol-(3E)-ylidene]-phenyl-amine
• 英文别名: 1-(cyclopentylmethoxy)-2-methyl-N,2-diphenylindol-3-imine
• CAS: 134736-56-4
• 化学式: C₂₇H₂₈N₂O
• 分子量: 396.532
• InChiKey: USYAXOGBSPMIRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.66
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  24.83
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1,2-dihydro-2-methyl-2-phenyl-3H-indole-3-phenylimino-1-oxyl 、 溴甲基环戊烷 生成 (2-methyl-2-phenyl-1,2-dihydroindol-3-ylidene)-phenylamine 、 [1-Cyclopentylmethoxy-2-methyl-2-phenyl-1,2-dihydro-indol-(3E)-ylidene]-phenyl-amine
  参考文献：
  名称：

  Electron-transfer reactions. Oxidation of Grignard reagents in the presence of an aminoxyl as a radical-trapping agent

  摘要：

  The indole bisnitrone 1 (E1/2red = -0.125 V vs NHE in DMF) reacts with a series of Grignard reagents (RMgX) including primary, secondary, and tertiary alkyls and benzyl and phenyl derivatives, which show different E(OX), by single electron transfer to form C-centered radicals corresponding to the Grignard used. The radicals produced in the reaction were trapped by the (arylimino)indolinone nitroxide 5 to form the alkylated hydroxylamines 6. When the reaction is carried out with a ''cyclizing Grignard'' such as 5-hexenylmagnesium bromide, the uncyclized (5-hexen-1-yl) 6g and cyclized (methylcyclopentyl) 6h alkylated hydroxylamines are both isolated. In all cases, the Marcus theory treatment predicts high electron-transfer rate constants.

  DOI：

  10.1021/jo00015a029