5-benzyl-3-phenyl-5H-pyrido[4,3-b]indole

• 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: 5-benzyl-3-phenyl-5H-pyrido[4,3-b]indole
• 英文别名: 5-Benzyl-3-phenylpyrido[4,3-b]indole
• 化学式: C₂₄H₁₈N₂
• 分子量: 334.42
• InChiKey: WADAJVUGBODUOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-溴-1H-吲哚-3-甲醛 在 2percent PdCl₂(PPh₃)2 叔丁胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 5-benzyl-3-phenyl-5H-pyrido[4,3-b]indole
  参考文献：
  名称：

  Synthesis of β- and γ-Carbolines by the Palladium/Copper-Catalyzed Coupling and Cyclization of Terminal Acetylenes

  摘要：

  A variety of 3-substituted beta- and gamma-carbolines have been synthesized from N-substituted 3-iodoindole-2-carboxaldehydes and 2-bromoindole-3-carboxaldehydes, respectively. The coupling of these aldehydes with various terminal acetylenes with PdCl2(PPh3)(2)/CuI as the catalyst readily affords the corresponding alkynylindole carboxaldehydes, which have subsequently been converted to the corresponding tert-butylimines and cyclized to beta- and gamma-carbolines by either copper-catalyzed or thermal processes.

  DOI：

  10.1021/jo0258857

文献信息

• Synthesis of β- and γ-Carbolines by the Palladium/Copper-Catalyzed Coupling and Cyclization of Terminal Acetylenes
  作者：Haiming Zhang、Richard C. Larock

  DOI：10.1021/jo0258857

  日期：2002.10.1

  A variety of 3-substituted beta- and gamma-carbolines have been synthesized from N-substituted 3-iodoindole-2-carboxaldehydes and 2-bromoindole-3-carboxaldehydes, respectively. The coupling of these aldehydes with various terminal acetylenes with PdCl2(PPh3)(2)/CuI as the catalyst readily affords the corresponding alkynylindole carboxaldehydes, which have subsequently been converted to the corresponding tert-butylimines and cyclized to beta- and gamma-carbolines by either copper-catalyzed or thermal processes.