3-iodo-1-methylindole-2-carboxaldehyde tert-butylimine | 372954-82-0

• 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-iodo-1-methylindole-2-carboxaldehyde tert-butylimine
• 英文别名: 3-iodo-1-methylindole-2-methylene-tert-butylamine；N-tert-butyl-1-(3-iodo-1-methylindol-2-yl)methanimine
• CAS: 372954-82-0
• 化学式: C₁₄H₁₇IN₂
• 分子量: 340.207
• InChiKey: YUBAWZJHYPEPNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-iodo-1-methylindole-2-carboxaldehyde tert-butylimine 在 2percent PdCl₂(PPh₃)2 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 9-methyl-3-phenyl-9H-pyrido[3,4-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
• 作为产物：
  描述：

  3-iodo-1H-indole-2-carbaldehyde 反应 24.0h， 生成 3-iodo-1-methylindole-2-carboxaldehyde tert-butylimine
  参考文献：
  名称：

  Synthesis of β- and γ-Carbolines by the Palladium-Catalyzed Iminoannulation of Internal Alkynes

  摘要：

  [GRAPHICS]A variety of substituted beta- and gamma -carbolines have been prepared in good to excellent yields by the annulation of internal acetylenes by the tert-butylimines of N-substituted 3-iodoindole-2-carboxaldehydes and 2-haloindole-3-carboxaldehydes, respectively, in the presence of a palladium catalyst.

  DOI：

  10.1021/ol010124w