1-methyl-3-phenyl-2-propyl-1H-indole

• 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-methyl-3-phenyl-2-propyl-1H-indole
• 英文别名: 1-Methyl-3-phenyl-2-propylindole
• 化学式: C₁₈H₁₉N
• 分子量: 249.356
• InChiKey: OPWYXJPQTXUAHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  N'-[1-Benzyl-but-(E)-ylidene]-N-methyl-N-phenyl-hydrazine 在 diethyl(2,2,6,6-tetramethylpiperidino)aluminium 作用下， 以 正己烷 、 甲苯 为溶剂， 生成 1-methyl-3-phenyl-2-propyl-1H-indole 、 2-Benzyl-3-ethyl-1-methyl-1H-indole
  参考文献：
  名称：

  Regioselective Fischer indole synthesis mediated by organoaluminum amides

  摘要：

  Amphiphilic reagents such as organoaluminum amides are found to be highly effective for the Fischer indole synthesis. In particular, diethylaluminum 2,2,6,6-tetramethylpiperidide (DATMP) is the reagent of choice for regioselective Fischer indole synthesis. For example, treatment of the (E)-N-methyl-N-phenylhydrazone of 5-methyl-3-heptanone with DATMP affords 3-sec-butyl-2-ethyl-1-methylindole as the sole isolable product; its Z-isomer affords 1,3-dimethyl-2-(2-methylbutyl)indole with high regioselectivity under similar reaction conditions.

  DOI：

  10.1021/jo00079a005

文献信息

• The First Regioselective Palladium-Catalyzed Indolization of 2-Bromo- or 2-Chloroanilines with Internal Alkynes:  A New Approach to 2,3-Disubstituted Indoles
  作者：Ming Shen、Guisheng Li、Bruce Z. Lu、Azad Hossain、Frank Roschangar、Vittorio Farina、Chris H. Senanayake

  DOI：10.1021/ol048114t

  日期：2004.10.1

  The first practical and economical process for synthesis of 2,3-disubstituted indole compounds has been developed with high regioselectivity by palladium-catalyzed indolization of 2-bromo- or chloroanilines and their derivatives with internal alkynes.