ethyl 3,5-dimethyl-5H-pyrido[4,3-b]indole-4-carboxylate

• 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: ethyl 3,5-dimethyl-5H-pyrido[4,3-b]indole-4-carboxylate
• 英文别名: Ethyl 3,5-dimethylpyrido[4,3-b]indole-4-carboxylate
• 化学式: C₁₆H₁₆N₂O₂
• 分子量: 268.315
• InChiKey: QNRNWTKDXUDRCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-丁炔酸乙酯 、 tert-butylimine of 2-iodo-1-methylindole-3-carboxaldehyde 在 palladium diacetate 、 sodium carbonate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 ethyl 3,5-dimethyl-5H-pyrido[4,3-b]indole-4-carboxylate 、 ethyl 4,5-dimethyl-5H-pyrido[4,3-b]indole-3-carboxylate
  参考文献：
  名称：

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

  摘要：

  A variety of substituted beta- and gamma-carbolines have been prepared in moderate to excellent yields by the palladium-catalyzed annulation of internal and terminal acetylenes by the tert-butylimines of N-substituted 3-iodoindole-2-carboxaldehydes and 2-haloindole-3-carboxaldehydes, respectively. This annulation chemistry is effective for a wide range of alkynes, including aryl-, alkyl-, hydroxymethyl-, ethoxycarbonyl-, and trimethylsilyl-substituted alkynes. When an unsymmetrical internal alkyne is employed, this method generally gives two regioisomers. When a terminal alkyne is employed, only one regioisomer has been isolated. This palladium-catalyzed annulation chemistry has also been successfully applied to the synthesis of two biologically interesting beta-carboline alkaloids, ZK93423 and abecarnil (ZK112119).

  DOI：

  10.1021/jo026317u

文献信息

• Synthesis of β- and γ-Carbolines by the Palladium-Catalyzed Iminoannulation of Alkynes
  作者：Haiming Zhang、Richard C. Larock

  DOI：10.1021/jo026317u

  日期：2002.12.1

  A variety of substituted beta- and gamma-carbolines have been prepared in moderate to excellent yields by the palladium-catalyzed annulation of internal and terminal acetylenes by the tert-butylimines of N-substituted 3-iodoindole-2-carboxaldehydes and 2-haloindole-3-carboxaldehydes, respectively. This annulation chemistry is effective for a wide range of alkynes, including aryl-, alkyl-, hydroxymethyl-, ethoxycarbonyl-, and trimethylsilyl-substituted alkynes. When an unsymmetrical internal alkyne is employed, this method generally gives two regioisomers. When a terminal alkyne is employed, only one regioisomer has been isolated. This palladium-catalyzed annulation chemistry has also been successfully applied to the synthesis of two biologically interesting beta-carboline alkaloids, ZK93423 and abecarnil (ZK112119).