4-{3-[2-amino-4-(trifluoromethyl)phenyl]prop-2-ynoyl}benzonitrile | 1035989-22-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4-{3-[2-amino-4-(trifluoromethyl)phenyl]prop-2-ynoyl}benzonitrile
• 英文别名: 4-[3-[2-Amino-4-(trifluoromethyl)phenyl]prop-2-ynoyl]benzonitrile；4-[3-[2-amino-4-(trifluoromethyl)phenyl]prop-2-ynoyl]benzonitrile
• CAS: 1035989-22-0
• 化学式: C₁₇H₉F₃N₂O
• 分子量: 314.266
• InChiKey: KTWDMVGZSUIZLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-{3-[2-amino-4-(trifluoromethyl)phenyl]prop-2-ynoyl}benzonitrile 、 3-甲氧基苯硼酸 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 3.0h， 以70%的产率得到4-[4-(3-methoxyphenyl)-7-(trifluoromethyl)quinolin-2-yl]benzonitrile
  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
• 作为产物：
  描述：

  一氧化碳 、 2-ethynyl-5-(trifluoromethyl)aniline 、 alkaline earth salt of/the/ methylsulfuric acid 在 palladium dichloride 1,1'-双(二苯基膦)二茂铁 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 20.0 ℃ 、1.0 MPa 条件下， 以60%的产率得到4-{3-[2-amino-4-(trifluoromethyl)phenyl]prop-2-ynoyl}benzonitrile
  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.