N-[1-(diphenylphosphinoyl)-2-oxopropyl]benzamide | 475040-38-1

• 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: N-[1-(diphenylphosphinoyl)-2-oxopropyl]benzamide
• 英文别名: N-(1-diphenylphosphoryl-2-oxopropyl)benzamide
• CAS: 475040-38-1
• 化学式: C₂₂H₂₀NO₃P
• 分子量: 377.379
• InChiKey: VXZIVNMZWBIIMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  63.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[1-(diphenylphosphinoyl)-2-oxopropyl]benzamide 在 六氯乙烷 、 三苯基膦 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 20.08h， 以79%的产率得到(5-methyl-2-phenyloxazol-4-yl)diphenylphosphine oxide
  参考文献：
  名称：

  Asymmetric Synthesis of 2H-Azirines Derived from Phosphine Oxides Using Solid-Supported Amines. Ring Opening of Azirines with Carboxylic Acids

  摘要：

  A simple and efficient asymmetric synthesis of 2H-azirine-2-phosphine oxides 3 is described. The key step is a solid-phase bound achiral or chiral amine-mediated Neber reaction of beta-ketoxime tosylates derived from phosphine oxides 1. Reaction of 2H-azirines 3 and 11 with carboxylic acids 4 gives phosphorylated ketamides 5 and 12. Ring closure of ketamides 5 and 12 with triphenylphosphine and hexachloroethane in the presence of triethylamine leads to the formation of phosphorylated oxazoles 8 and 13.

  DOI：

  10.1021/jo025995d
• 作为产物：
  描述：

  β-(N-p-toluenesulfonyloxyimino)propyldiphenylphosphine oxide 在 diethylamine polystyrene resine 作用下， 以 四氢呋喃 、 苯 为溶剂， 生成 N-[1-(diphenylphosphinoyl)-2-oxopropyl]benzamide
  参考文献：
  名称：

  Asymmetric Synthesis of 2H-Azirines Derived from Phosphine Oxides Using Solid-Supported Amines. Ring Opening of Azirines with Carboxylic Acids

  摘要：

  A simple and efficient asymmetric synthesis of 2H-azirine-2-phosphine oxides 3 is described. The key step is a solid-phase bound achiral or chiral amine-mediated Neber reaction of beta-ketoxime tosylates derived from phosphine oxides 1. Reaction of 2H-azirines 3 and 11 with carboxylic acids 4 gives phosphorylated ketamides 5 and 12. Ring closure of ketamides 5 and 12 with triphenylphosphine and hexachloroethane in the presence of triethylamine leads to the formation of phosphorylated oxazoles 8 and 13.

  DOI：

  10.1021/jo025995d