6-([1,1'-biphenyl]-4-yl)-7-methylindolo[1,2-a]quinoline | 1404454-08-5

• 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: 6-([1,1'-biphenyl]-4-yl)-7-methylindolo[1,2-a]quinoline
• 英文别名: 7-Methyl-6-(4-phenylphenyl)indolo[1,2-a]quinoline；7-methyl-6-(4-phenylphenyl)indolo[1,2-a]quinoline
• CAS: 1404454-08-5
• 化学式: C₂₉H₂₁N
• 分子量: 383.492
• InChiKey: ADFIAJKSJMCTQB-UHFFFAOYSA-N

物化性质

• 熔点：
  82-85 °C
• 沸点：
  590.5±50.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  4.4
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  邻碘溴苯 在 T406石油添加剂 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium tert-butylate 、 sodium acetate 、 lithium chloride 作用下， 以 二甲基亚砜 、 二甲胺 为溶剂， 反应 25.0h， 生成 6-([1,1'-biphenyl]-4-yl)-7-methylindolo[1,2-a]quinoline
  参考文献：
  名称：

  Palladium-Catalyzed Sonogashira-Coupling Conjoined C–H Activation: A Regioselective Tandem Strategy to Access Indolo- and Pyrrolo[1,2-a]quinolines

  摘要：

  An operationally simple approach for the regioselective tandem synthesis of indolo[1,2-a]quinolines 4a-v and pyrrolo[1,2-a]quinolines 5a-k from 1-(2-bromophenyl)-1H-indole/pyrrole/imidazole 1a-c, 2a,b by the palladium-catalyzed sequential C-C bond formation is described. The developed approach involves the palladium-catalyzed Sonogashira coupling followed by the intramolecular C-C bond formation via C-H activation, which leads to the formation of 6-endo-dig cyclized product. This synthetic methodology accommodates wide functional group variation on alkyne, which proves to be advantageous for the structural and biological activity assessments.

  DOI：

  10.1021/jo302112a

文献信息

• Palladium-Catalyzed Sonogashira-Coupling Conjoined C–H Activation: A Regioselective Tandem Strategy to Access Indolo- and Pyrrolo[1,2-<i>a</i>]quinolines
  作者：Satya Prakash Shukla、Rakesh K. Tiwari、Akhilesh K. Verma

  DOI：10.1021/jo302112a

  日期：2012.11.16

  An operationally simple approach for the regioselective tandem synthesis of indolo[1,2-a]quinolines 4a-v and pyrrolo[1,2-a]quinolines 5a-k from 1-(2-bromophenyl)-1H-indole/pyrrole/imidazole 1a-c, 2a,b by the palladium-catalyzed sequential C-C bond formation is described. The developed approach involves the palladium-catalyzed Sonogashira coupling followed by the intramolecular C-C bond formation via C-H activation, which leads to the formation of 6-endo-dig cyclized product. This synthetic methodology accommodates wide functional group variation on alkyne, which proves to be advantageous for the structural and biological activity assessments.