3-iodo-2-phenyl-4-(phenylamino)quinoline | 1243585-54-7

• 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: 3-iodo-2-phenyl-4-(phenylamino)quinoline
• CAS: 1243585-54-7
• 化学式: C₂₁H₁₅IN₂
• 分子量: 422.268
• InChiKey: DBTSNYDFLDOADE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.25
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  24.92
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-iodo-2-phenyl-4-(phenylamino)quinoline 、 3-溴丙烯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 以68%的产率得到4-(N-allyl-N-phenylamino)-3-iodo-2-phenylquinoline
  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
• 作为产物：
  描述：

  4-chloro-3-iodo-2-phenylquinoline 、 苯胺 以 乙醇 为溶剂， 反应 18.0h， 以86%的产率得到3-iodo-2-phenyl-4-(phenylamino)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

• One-pot palladium-catalyzed C–I and C–H bond activation and subsequent Suzuki–Miyaura cross-coupling of 2-aryl-3-iodo-4-(phenylamino)quinolines with arylboronic acids
  作者：Malose J. Mphahlele、Mamasegare M. Mphahlele

  DOI：10.1016/j.tet.2011.04.040

  日期：2011.6

  The 2-aryl-3-iodo-4-(phenylamino)quinolines undergo one-pot palladium-mediated C–I and C–H bond activation and subsequent Suzuki–Miyaura cross-coupling with arylboronic acids under anhydrous conditions to afford mixture of 2,3-diaryl-4-(phenylamino)quinolines (minor) and 2-aryl-4-([(1,1′-biaryl)-2-yl]amino)quinoline derivatives (major). The 2,3-diaryl-4-(phenylamino)quinolines were isolated as major

  2-芳基-3-碘-4-（苯基氨基）喹啉经过一锅钯介导的C–I和C–H键活化，随后在无水条件下与芳基硼酸进行Suzuki–Miyaura交叉偶联，得到2的混合物，3-二芳基-4-（苯基氨基）喹啉（次要）和2-芳基-4-（[（（1,1'-联芳基-2-基）氨基]喹啉）衍生物（主要）。当以2 MK 2 CO 3为碱时，分离出2,3-二芳基-4-（苯基氨基）喹啉为主要产物。提出了一种可能的机制，该机制涉及六元的palladacycle中间体，用于形成观察到的产物混合物。结合光谱学和X射线晶体学技术对制备的化合物进行表征。