4-(4-(trifluoromethyl)phenyl)pyrrolo[1,2-a]quinoline | 1146543-10-3

• 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-(trifluoromethyl)phenyl)pyrrolo[1,2-a]quinoline
• 英文别名: 4-(4-trifluoromethyl-phenyl)-pyrrolo[1,2-a]quinoline；4-[4-(Trifluoromethyl)phenyl]pyrrolo[1,2-a]quinoline
• CAS: 1146543-10-3
• 化学式: C₁₉H₁₂F₃N
• 分子量: 311.306
• InChiKey: BBAUAIRYEVVZSS-UHFFFAOYSA-N

物化性质

• 熔点：
  63-65 °C
• 沸点：
  379.3±42.0 °C(predicted)
• 密度：
  1.24±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  4.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(2-溴苯基)-1H-吡咯 、 4-乙炔基-α,α,α-三氟甲苯 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium acetate 、 lithium chloride 作用下， 以 二甲胺 为溶剂， 反应 40.0h， 以31%的产率得到4-(4-(trifluoromethyl)phenyl)pyrrolo[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

• Tandem Pd-Catalyzed Double C−C Bond Formation: Effect of Water
  作者：David I. Chai、Mark Lautens

  DOI：10.1021/jo900053b

  日期：2009.4.17

  A highly efficient water-accelerated palladium-catalyzed reaction of gem-dibromoolefins with a boronic acid via a tandem Suzuki−Miyaura coupling and direct arylation is reported. A wide range of aryl, alkenyl, and alkyl boronic acids, as well as a variety of substitution patterns on the phenyl ring, are tolerated. Additionally, mechanistic studies were conducted to ascertain the order of the couplings

  据报道，通过串联的Suzuki-Miyaura偶联和直接芳基化反应，宝石-二溴代烯烃与硼酸进行了高效的水促进钯催化反应。宽范围的芳基，烯基和烷基硼酸，以及苯环上的各种取代方式都可以使用。此外，进行了机械研究，以确定耦合的顺序以及水的作用。这项研究的结果表明，主要途径是Suzuki-Miyaura偶联/直接芳基化序列，水加速了Pd（0）的形成和Suzuki-Miyaura偶联。
• 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.