N,N-diethyl-P-(3,5-dimethyl-4-methoxyphenyl)-phosphonamidic chloride | 129835-86-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N,N-diethyl-P-(3,5-dimethyl-4-methoxyphenyl)-phosphonamidic chloride
• 英文别名: N-[chloro-(4-methoxy-3,5-dimethylphenyl)phosphoryl]-N-ethylethanamine
• CAS: 129835-86-5
• 化学式: C₁₃H₂₁ClNO₂P
• 分子量: 289.742
• InChiKey: AWCKOERDMJPZTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-P-(3,5-dimethyl-4-methoxyphenyl)-phosphonamidic chloride 在 potassium chloride 、 水 作用下， 以 1,4-二氧六环 为溶剂， 生成
  参考文献：
  名称：

  The E1cB mechanism in the alkaline hydrolysis of N,N-diethyl-P-(3,5-dimethyl-4-hydroxyphenyl)phosphonamidic chloride

  摘要：

  The alkaline hydrolysis of the title compound 1 proceeds via an E1cB mechanism. A tricoordinate phosphorus species intermediate 3, or a metaphosphate-like transition state, constitutes the best hypothesis accounting for the observed kinetic results. The apparent bimolecular rate constant for the attack of hydroxide ion on the neutral 4-hydroxy-substituted chloride (k(a)K(a)/K(w)) is more than 5 orders of magnitude larger than the true bimolecular rate constant for the attack of HO- on the corresponding methoxy chloride 2 which possesses the S(N)2(P) mechanism. Support of the E1cB mechanism proposed for 1 comes also from activation entropy studies and by the effect of added nitrogen nucleophiles on reaction rates.

  DOI：

  10.1021/jo00001a016
• 作为产物：
  描述：

  4-溴-2,6-二甲基苯酚 在 正丁基锂 作用下， 以 乙醚 为溶剂， 反应 90.0h， 生成 N,N-diethyl-P-(3,5-dimethyl-4-methoxyphenyl)-phosphonamidic chloride
  参考文献：
  名称：

  The E1cB mechanism in the alkaline hydrolysis of N,N-diethyl-P-(3,5-dimethyl-4-hydroxyphenyl)phosphonamidic chloride

  摘要：

  The alkaline hydrolysis of the title compound 1 proceeds via an E1cB mechanism. A tricoordinate phosphorus species intermediate 3, or a metaphosphate-like transition state, constitutes the best hypothesis accounting for the observed kinetic results. The apparent bimolecular rate constant for the attack of hydroxide ion on the neutral 4-hydroxy-substituted chloride (k(a)K(a)/K(w)) is more than 5 orders of magnitude larger than the true bimolecular rate constant for the attack of HO- on the corresponding methoxy chloride 2 which possesses the S(N)2(P) mechanism. Support of the E1cB mechanism proposed for 1 comes also from activation entropy studies and by the effect of added nitrogen nucleophiles on reaction rates.

  DOI：

  10.1021/jo00001a016

文献信息

• CEVASCO, GIORGIO;THEA, SERGIO, J. ORG. CHEM., 56,(1991) N, C. 72-74
  作者：CEVASCO, GIORGIO、THEA, SERGIO

  DOI：——

  日期：——