11-(p-chlorophenyl)-9-methyl-6H-indolo[2,3-b]quinoline | 1019842-35-3

• 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: 11-(p-chlorophenyl)-9-methyl-6H-indolo[2,3-b]quinoline
• CAS: 1019842-35-3
• 化学式: C₂₂H₁₅ClN₂
• 分子量: 342.827
• InChiKey: ZVVFHGRALMDSGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  25.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  28.68
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  N-[2-[(p-chlorophenyl)ethynyl]-4-methylphenyl]-N'-phenylcarbodiimide 在 1,4-环己二烯 作用下， 以 甲苯 为溶剂， 生成 11-(p-chlorophenyl)-9-methyl-6H-indolo[2,3-b]quinoline
  参考文献：
  名称：

  Thermal C²−C⁶ Cyclization of Enyne−Carbodiimides:  Experimental Evidence Contradicts a Diradical and Suggests a Carbene Intermediate

  摘要：

  Mechanistic details of the thermal C(2)-C(6) cyclization of enyne-carbodiimides are investigated. A variety of product and kinetic studies on solvent and substituent effects open the way for a deeper mechanistic understanding. Nonlinear Hammett correlations suggest that a change of mechanism takes place: the thermal C(2)-C(6) cyclization of enyne-carbodiimides with electron-withdrawing substituents may be best described as a coarctate cyclization to a carbene and with electron-donating substituents as a polar cyclization to a carbene with strong zwitterionic character. Theoretical investigations had originally suggested a diradical intermediate. DFT computations and NBO analysis for the parent diazafulvenediyl are in agreement with a carbene intermediate. While any intermolecular trapping of the intermediate failed, the formation of the C-H insertion product 19 strongly supports the carbene hypothesis.

  DOI：

  10.1021/jo701966h

文献信息

• Thermal C²−C⁶ Cyclization of Enyne−Carbodiimides:  Experimental Evidence Contradicts a Diradical and Suggests a Carbene Intermediate
  作者：Michael Schmittel、Jens-Peter Steffen、David Rodríguez、Bernward Engelen、Elmar Neumann、Mehmet Emin Cinar

  DOI：10.1021/jo701966h

  日期：2008.4.1

  Mechanistic details of the thermal C(2)-C(6) cyclization of enyne-carbodiimides are investigated. A variety of product and kinetic studies on solvent and substituent effects open the way for a deeper mechanistic understanding. Nonlinear Hammett correlations suggest that a change of mechanism takes place: the thermal C(2)-C(6) cyclization of enyne-carbodiimides with electron-withdrawing substituents may be best described as a coarctate cyclization to a carbene and with electron-donating substituents as a polar cyclization to a carbene with strong zwitterionic character. Theoretical investigations had originally suggested a diradical intermediate. DFT computations and NBO analysis for the parent diazafulvenediyl are in agreement with a carbene intermediate. While any intermolecular trapping of the intermediate failed, the formation of the C-H insertion product 19 strongly supports the carbene hypothesis.