4-(4-chlorophenyl)-3-methyl-1-phenyl-1H-pyrrolo[3,2-c]quinoline | 1243585-83-2

• 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-chlorophenyl)-3-methyl-1-phenyl-1H-pyrrolo[3,2-c]quinoline
• 英文别名: 4-(4-Chlorophenyl)-3-methyl-1-phenylpyrrolo[3,2-c]quinoline；4-(4-chlorophenyl)-3-methyl-1-phenylpyrrolo[3,2-c]quinoline
• CAS: 1243585-83-2
• 化学式: C₂₄H₁₇ClN₂
• 分子量: 368.865
• InChiKey: QWRRWRSNZWHOGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  27
• 可旋转键数：
  2
• 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：

  4-(N-allyl-N-phenylamino)-2-(4-chlorophenyl)-3-iodo-quinoline 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以81%的产率得到4-(4-chlorophenyl)-3-methyl-1-phenyl-1H-pyrrolo[3,2-c]quinoline
  参考文献：
  名称：

  Synthesis of 1H-pyrrolo[3,2-c]quinoline derivatives via palladium-catalyzed heteroannulation of 2-aryl-3-iodo-4-(phenylamino)quinolines and 4-(N,N-allylphenylamino)-2-aryl-3-iodoquinolines

  摘要：

  Palladium(0)/copper iodide catalyzed Sonogashira cross-coupling of 2-aryl-3-iodo-4-(phenylamino) quinolines with terminal alkynes afforded series of 1,2,4-trisubstituted 1H-pyrrolo[3,2-c]quinolines in a single-step operation. Conversely, the 4-(N,N-allylphenylamino)-2-aryl-3-iodoquinoline derivatives were found to undergo PdCl2(PPh3)(2)/CuI catalyzed intramolecular Heck reaction to yield the corresponding 1,3,4-trisubstituted 1H-pyrrolo[3,2-c]quinolines. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.018

文献信息

• Synthesis of 1H-pyrrolo[3,2-c]quinoline derivatives via palladium-catalyzed heteroannulation of 2-aryl-3-iodo-4-(phenylamino)quinolines and 4-(N,N-allylphenylamino)-2-aryl-3-iodoquinolines
  作者：Malose J. Mphahlele、Lehlohonolo G. Lesenyeho、Hlamulo R. Makelane

  DOI：10.1016/j.tet.2010.06.018

  日期：2010.8

  Palladium(0)/copper iodide catalyzed Sonogashira cross-coupling of 2-aryl-3-iodo-4-(phenylamino) quinolines with terminal alkynes afforded series of 1,2,4-trisubstituted 1H-pyrrolo[3,2-c]quinolines in a single-step operation. Conversely, the 4-(N,N-allylphenylamino)-2-aryl-3-iodoquinoline derivatives were found to undergo PdCl2(PPh3)(2)/CuI catalyzed intramolecular Heck reaction to yield the corresponding 1,3,4-trisubstituted 1H-pyrrolo[3,2-c]quinolines. (c) 2010 Elsevier Ltd. All rights reserved.