1-phenyl-N-prop-2-ynyl-3-tri(propan-2-yl)silylprop-2-yn-1-imine | 713524-89-1

• 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: 1-phenyl-N-prop-2-ynyl-3-tri(propan-2-yl)silylprop-2-yn-1-imine
• CAS: 713524-89-1
• 化学式: C₂₁H₂₉NSi
• 分子量: 323.553
• InChiKey: OHLBBTCODZVZKE-UHFFFAOYSA-N

物化性质

• 沸点：
  382.9±44.0 °C(Predicted)
• 密度：
  0.85±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.33
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-phenyl-N-prop-2-ynyl-3-tri(propan-2-yl)silylprop-2-yn-1-imine 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 氘代氯仿 为溶剂， 反应 12.08h， 生成 6-苯基吡啶-3-甲醛
  参考文献：
  名称：

  α,5-Didehydro-3-picoline Diradicals from Skipped Azaenediynes:  Computational and Trapping Studies of an Aza-Myers−Saito Cyclization

  摘要：

  On the basis of density functional calculations, the isomerization of skipped azaenediynes (C-alkynyl-N-propargylimines) to azaenyne allenes and subsequent rapid aza-Myers-Saito cyclization to alpha,5-didehydro-3-picoline were predicted. We prepared the N-propargylimine of 1-phenyl-3-tri(isopropyl)silylprop-2-yn-1-one, which undergoes proto-clesilylation and isomerization to an azaenyne allene when treated with tetrabutylammonium fluoride. In the presence of 1,4-cyclohexadiene, this azaenyne allene affords 6-phenyl-3-picoline and other products corresponding to the trapping of an alpha,5-didehydro-3-picoline diradical.

  DOI：

  10.1021/ol049266r
• 作为产物：
  描述：

  炔丙胺 、 1-phenyl-3-(triisopropylsilyl)prop-2-yn-1-one 在 titanium(IV) tetraethanolate 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以52%的产率得到1-phenyl-N-prop-2-ynyl-3-tri(propan-2-yl)silylprop-2-yn-1-imine
  参考文献：
  名称：

  α,5-Didehydro-3-picoline Diradicals from Skipped Azaenediynes:  Computational and Trapping Studies of an Aza-Myers−Saito Cyclization

  摘要：

  On the basis of density functional calculations, the isomerization of skipped azaenediynes (C-alkynyl-N-propargylimines) to azaenyne allenes and subsequent rapid aza-Myers-Saito cyclization to alpha,5-didehydro-3-picoline were predicted. We prepared the N-propargylimine of 1-phenyl-3-tri(isopropyl)silylprop-2-yn-1-one, which undergoes proto-clesilylation and isomerization to an azaenyne allene when treated with tetrabutylammonium fluoride. In the presence of 1,4-cyclohexadiene, this azaenyne allene affords 6-phenyl-3-picoline and other products corresponding to the trapping of an alpha,5-didehydro-3-picoline diradical.

  DOI：

  10.1021/ol049266r