N-(Phenylmethyl)bis(pentamethylphenyl)acetamide | 137122-88-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-(Phenylmethyl)bis(pentamethylphenyl)acetamide
• 英文别名: N-benzyl-2,2-bis(2,3,4,5,6-pentamethylphenyl)acetamide
• CAS: 137122-88-4
• 化学式: C₃₁H₃₉NO
• 分子量: 441.657
• InChiKey: AGSUNMATHAPFSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.22
• 重原子数：
  33.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-(Phenylmethyl)bis(pentamethylphenyl)acetamide 在 溴 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以62%的产率得到N-(Phenylmethyl)bis(pentamethylphenyl)ketene imine
  参考文献：
  名称：

  Relatively stable N-benzhydryl- and N-benzyldiarylketene imines and their conversion to cyanodiarylmethanes via an isolable radical

  摘要：

  An efficient synthetic route to the sterically hindered ketene imines N-benzyl- and N-benzylhydrylbis(pentamethylphenyl)ketene imines 8 from dipentamethylphenyl ketene 6 is described. The thermal stability of these ketene imines is in marked contrast to the diphenylketene imine analogues which rearrange rapidly to C-tri-substituted nitriles. On heating 8b is converted to the relatively stable free radical 13 which can be reduced to the nitrile 10 in a variety of solvents. These radicals are proposed intermediates in the ketene imine-nitrile rearrangement, and the mechanism of this reaction is considered in in terms of these results.

  DOI：

  10.1021/jo00027a062
• 作为产物：
  描述：

  五甲基苯 在 吡啶 、 氯化亚砜 、 硫酸 作用下， 以 溶剂黄146 、 甲苯 为溶剂， 反应 1.5h， 生成 N-(Phenylmethyl)bis(pentamethylphenyl)acetamide
  参考文献：
  名称：

  Relatively stable N-benzhydryl- and N-benzyldiarylketene imines and their conversion to cyanodiarylmethanes via an isolable radical

  摘要：

  An efficient synthetic route to the sterically hindered ketene imines N-benzyl- and N-benzylhydrylbis(pentamethylphenyl)ketene imines 8 from dipentamethylphenyl ketene 6 is described. The thermal stability of these ketene imines is in marked contrast to the diphenylketene imine analogues which rearrange rapidly to C-tri-substituted nitriles. On heating 8b is converted to the relatively stable free radical 13 which can be reduced to the nitrile 10 in a variety of solvents. These radicals are proposed intermediates in the ketene imine-nitrile rearrangement, and the mechanism of this reaction is considered in in terms of these results.

  DOI：

  10.1021/jo00027a062