4-(4-bromophenyl)-2-(1H-indol-3-yl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydroquinoline-3-carbonitrile | 1315506-10-5

• 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: 4-(4-bromophenyl)-2-(1H-indol-3-yl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydroquinoline-3-carbonitrile
• CAS: 1315506-10-5
• 化学式: C₂₆H₂₀BrN₃O
• 分子量: 470.368
• InChiKey: FPQXGKIDDKJJPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.69
• 重原子数：
  31.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  69.54
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  4-(4-bromophenyl)-2-(1H-indol-3-yl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 正丁醇 为溶剂， 反应 6.0h， 以88%的产率得到4-(4-bromophenyl)-2-(1H-indol-3-yl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydroquinoline-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