N-ethyl-N-[[4-(trifluoromethyl)-2-(2-trimethylsilylethynyl)phenyl]diazenyl]ethanamine | 1184730-52-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-ethyl-N-[[4-(trifluoromethyl)-2-(2-trimethylsilylethynyl)phenyl]diazenyl]ethanamine
• CAS: 1184730-52-6
• 化学式: C₁₆H₂₂F₃N₃Si
• 分子量: 341.451
• InChiKey: XBKUVCYNHGULSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  28
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-ethyl-N-[[4-(trifluoromethyl)-2-(2-trimethylsilylethynyl)phenyl]diazenyl]ethanamine 在 甲醇 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 N-ethyl-N-[[2-ethynyl-4-(trifluoromethyl)phenyl]diazenyl]ethanamine
  参考文献：
  名称：

  Synthesis of α-Ketoester- and α-Hydroxyester-Substituted Isoindazoles via the Thermodynamic Coarctate Cyclization of Ester-Terminated Azo-Ene-Yne Systems

  摘要：

  The synthesis of isoindazoles bearing alpha-ketoester and alpha-hydroxyester groups via the coarctate cyclization of ester-terminated azo-ene-yne precursors is described. Whereas previous studies on isoindazole formation have shown the reaction to proceed through a kinetic coarctate pathway, functionalization of the terminal acetylene with a methyl ester sufficiently stabilizes the carbene intermediate to make the coarctate cyclization the thermodynamic pathway. Density functional theory (DFT) computations reveal ca. 8-9 kcal mol(-1) lower energy transition states for the coarctate pathway compared to the parent system.

  DOI：

  10.1021/jo9011283
• 作为产物：
  描述：

  N-ethyl-N-[[2-iodo-4-(trifluoromethyl)phenyl]diazenyl]ethanamine 、 三甲基乙炔基硅 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到N-ethyl-N-[[4-(trifluoromethyl)-2-(2-trimethylsilylethynyl)phenyl]diazenyl]ethanamine
  参考文献：
  名称：

  Synthesis of α-Ketoester- and α-Hydroxyester-Substituted Isoindazoles via the Thermodynamic Coarctate Cyclization of Ester-Terminated Azo-Ene-Yne Systems

  摘要：

  The synthesis of isoindazoles bearing alpha-ketoester and alpha-hydroxyester groups via the coarctate cyclization of ester-terminated azo-ene-yne precursors is described. Whereas previous studies on isoindazole formation have shown the reaction to proceed through a kinetic coarctate pathway, functionalization of the terminal acetylene with a methyl ester sufficiently stabilizes the carbene intermediate to make the coarctate cyclization the thermodynamic pathway. Density functional theory (DFT) computations reveal ca. 8-9 kcal mol(-1) lower energy transition states for the coarctate pathway compared to the parent system.

  DOI：

  10.1021/jo9011283