2-(1H-indol-3-yl)-7,7-dimethyl-5-oxo-4-phenyl-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile | 1315505-91-9

• 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: 2-(1H-indol-3-yl)-7,7-dimethyl-5-oxo-4-phenyl-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile
• CAS: 1315505-91-9
• 化学式: C₂₆H₂₃N₃O
• 分子量: 393.488
• InChiKey: MLIIOTITKWZWTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.43
• 重原子数：
  30.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  68.68
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  苯甲醛 、 3-氨基-5,5-二甲基-2-环己烯-1-酮 、 3-(1H-吲哚-3-基)-3-氧丙腈 在 ammonium acetate 作用下， 以 正丁醇 为溶剂， 反应 12.0h， 以83%的产率得到2-(1H-indol-3-yl)-7,7-dimethyl-5-oxo-4-phenyl-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile
  参考文献：
  名称：

  A convergent construction of 1,4-dihydropyridine scaffold containing indole fragment

  摘要：

  Accompanying with the construction of 1,4-dihydropyridine scaffold, indol-3-yl-5-oxo-1,4,5,6,7,8-hexahydroquinoline, and indol-3-yl-1,4-dihydropyridine derivatives were facilely synthesized through three-component reactions of aromatic aldehydes, 3-cyanoacetyl indoles with 3-amino-2-enones in the presence of ammonium acetate. The 1,4-dihydropyridine core structure can be efficiently aromatized in the presence of stoichiometric 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). This chemistry provides an efficient and promising synthetic strategy to diversity-oriented construction of unaromatized and aromatized desired products. The advantages of the present protocol are atom-economy, simple work-up and easy purification of products by non-chromatographic methods. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.065