2-(4-tert-butyl-cycloxeh-1-enyl)-4-phenyl-quinoline | 1035989-51-5

• 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: 2-(4-tert-butyl-cycloxeh-1-enyl)-4-phenyl-quinoline
• 英文别名: 2-(4-Tert-butylcyclohexen-1-yl)-4-phenylquinoline；2-(4-tert-butylcyclohexen-1-yl)-4-phenylquinoline
• CAS: 1035989-51-5
• 化学式: C₂₅H₂₇N
• 分子量: 341.496
• InChiKey: KAJDOJILBMBRRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-(2-aminophenyl)-1-(4-tert-butylcyclohex-1-en-1-yl)prop-2-yn-1-one 、 苯基三氟硼酸钾 在 palladium diacetate 溶剂黄146 、 1,2-双(二苯基膦)乙烷 作用下， 以 乙醇 为溶剂， 反应 30.0h， 以60%的产率得到2-(4-tert-butyl-cycloxeh-1-enyl)-4-phenyl-quinoline
  参考文献：
  名称：

  Pd-catalyzed regioselective hydroarylation of α-(2-aminoaryl)-α,β-ynones with organoboron derivatives as a tool for the synthesis of quinolines: experimental evidence and quantum-chemical calculations

  摘要：

  The Pd-catalyzed hydroarylation of beta-(2-aminoaryl)-alpha,beta-ynones with organoboron derivatives, leading to 2,4-diarylquinolines in good to excellent yields through sequential cycloamination, has been investigated. The reaction is catalyzed by both Pd(II) and Pd(0) precatalysts, and can be carried out even under neutral conditions. The regiochemical outcome is inverted with respect to the Pd-catalyzed hydroarylation of beta-(2-aminoaryl)-alpha,beta-ynones with aryl iodides. This aspect has been rationalized using quantum-chemical calculations, which show significant differences between the energy barriers of the regioisomeric transition states for the migratory insertion (hydropalladation) step, and are consistent with the charge density of the pi complex that undergoes such insertion. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.03.015

文献信息

• Pd-catalyzed regioselective hydroarylation of α-(2-aminoaryl)-α,β-ynones with organoboron derivatives as a tool for the synthesis of quinolines: experimental evidence and quantum-chemical calculations
  作者：Antonio Arcadi、Massimiliano Aschi、Fabio Marinelli、Mirella Verdecchia

  DOI：10.1016/j.tet.2008.03.015

  日期：2008.5

  The Pd-catalyzed hydroarylation of beta-(2-aminoaryl)-alpha,beta-ynones with organoboron derivatives, leading to 2,4-diarylquinolines in good to excellent yields through sequential cycloamination, has been investigated. The reaction is catalyzed by both Pd(II) and Pd(0) precatalysts, and can be carried out even under neutral conditions. The regiochemical outcome is inverted with respect to the Pd-catalyzed hydroarylation of beta-(2-aminoaryl)-alpha,beta-ynones with aryl iodides. This aspect has been rationalized using quantum-chemical calculations, which show significant differences between the energy barriers of the regioisomeric transition states for the migratory insertion (hydropalladation) step, and are consistent with the charge density of the pi complex that undergoes such insertion. (C) 2008 Elsevier Ltd. All rights reserved.