Methyl (phthalimidomethyl)phosphonochloridate | 159395-31-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: Methyl (phthalimidomethyl)phosphonochloridate
• 英文别名: 2-[[Chloro(methoxy)phosphoryl]methyl]isoindole-1,3-dione
• CAS: 159395-31-0
• 化学式: C₁₀H₉ClNO₄P
• 分子量: 273.613
• InChiKey: KQWCFFMYKUAXDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  L-丙氨酸甲酯盐酸盐 、 Methyl (phthalimidomethyl)phosphonochloridate 在 三乙胺 作用下， 以 氯仿 为溶剂， 以35%的产率得到N- methyl (phthalimidomethyl)phosphonamidate
  参考文献：
  名称：

  The Chemistry of Phosphapeptides: Formation of Functionalized Phosphonochloridates under Mild Conditions and Their Reaction with Alcohols and Amines

  摘要：

  A variety of methods have been explored for the convergent synthesis of phosphonamidates and phosphonates via phosphonochloridates. In the absence of complex functionality, phosphorus pentachloride is an effective reagent for the conversion of diethyl and diisopropyl phosphonates to phosphonochloridates. Subsequent reaction with amines and alcohols provides good yields of the phosphonamidates and mixed phosphonates, respectively. However, in the presence of more complex functionality, a milder method utilizing oxalyl chloride to generate the phosphonochloridate from a monomethyl phosphonic acid is required. Aminolysis of the dimethyl phosphonates generates the requisite monomethyl phosphonic acids which are cleanly converted to phosphonochloridates and reacted with amines and primary alcohols.

  DOI：

  10.1021/jo00104a016
• 作为产物：
  描述：

  monomethyl phthalimidomethylphosphonate 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 Methyl (phthalimidomethyl)phosphonochloridate
  参考文献：
  名称：

  The Chemistry of Phosphapeptides: Formation of Functionalized Phosphonochloridates under Mild Conditions and Their Reaction with Alcohols and Amines

  摘要：

  A variety of methods have been explored for the convergent synthesis of phosphonamidates and phosphonates via phosphonochloridates. In the absence of complex functionality, phosphorus pentachloride is an effective reagent for the conversion of diethyl and diisopropyl phosphonates to phosphonochloridates. Subsequent reaction with amines and alcohols provides good yields of the phosphonamidates and mixed phosphonates, respectively. However, in the presence of more complex functionality, a milder method utilizing oxalyl chloride to generate the phosphonochloridate from a monomethyl phosphonic acid is required. Aminolysis of the dimethyl phosphonates generates the requisite monomethyl phosphonic acids which are cleanly converted to phosphonochloridates and reacted with amines and primary alcohols.

  DOI：

  10.1021/jo00104a016

文献信息

• The Chemistry of Phosphapeptides: Formation of Functionalized Phosphonochloridates under Mild Conditions and Their Reaction with Alcohols and Amines
  作者：William P. Malachowski、James K. Coward

  DOI：10.1021/jo00104a016

  日期：1994.12

  A variety of methods have been explored for the convergent synthesis of phosphonamidates and phosphonates via phosphonochloridates. In the absence of complex functionality, phosphorus pentachloride is an effective reagent for the conversion of diethyl and diisopropyl phosphonates to phosphonochloridates. Subsequent reaction with amines and alcohols provides good yields of the phosphonamidates and mixed phosphonates, respectively. However, in the presence of more complex functionality, a milder method utilizing oxalyl chloride to generate the phosphonochloridate from a monomethyl phosphonic acid is required. Aminolysis of the dimethyl phosphonates generates the requisite monomethyl phosphonic acids which are cleanly converted to phosphonochloridates and reacted with amines and primary alcohols.