N-[1-(diphenylphosphinoyl)-2-oxobutyl]malonamic acid | 475040-43-8

• 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-oxobutyl]malonamic acid
• 英文别名: 3-[(1-Diphenylphosphoryl-2-oxobutyl)amino]-3-oxopropanoic acid
• CAS: 475040-43-8
• 化学式: C₁₉H₂₀NO₅P
• 分子量: 373.345
• InChiKey: FPOSNNSRICLKJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[1-(diphenylphosphinoyl)-2-oxobutyl]malonamic acid 在 氯化亚砜 、 六氯乙烷 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 24.08h， 生成 [4-(diphenylphosphinoyl)-5-ethyl-oxazol-2-yl]acetic acid methyl ester
  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)butyldiphenylphosphine oxide 在 diethylamine polystyrene resine 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 96.0h， 生成 N-[1-(diphenylphosphinoyl)-2-oxobutyl]malonamic acid
  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

文献信息

• Asymmetric Synthesis of 2<i>H</i>-Azirines Derived from Phosphine Oxides Using Solid-Supported Amines. Ring Opening of Azirines with Carboxylic Acids
  作者：Francisco Palacios、Domitila Aparicio、Ana María Ochoa de Retana、Jesús M. de los Santos、José Ignacio Gil、José María Alonso

  DOI：10.1021/jo025995d

  日期：2002.10.1

  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.