o-(diethylphosphoryl)phenylphosphonic Acid Ethyl EsterN,N-Diethylamide | 1398805-34-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: o-(diethylphosphoryl)phenylphosphonic Acid Ethyl EsterN,N-Diethylamide
• 英文别名: N-[(2-diethoxyphosphorylphenyl)-ethoxyphosphoryl]-N-ethylethanamine
• CAS: 1398805-34-9
• 化学式: C₁₆H₂₉NO₅P₂
• 分子量: 377.357
• InChiKey: SOGWMPYUIQXBGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  氯磷酸二乙酯 、 ethyl P-phenyl-N,N-diethylaminophosphinate 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.92h， 以70%的产率得到o-(diethylphosphoryl)phenylphosphonic Acid Ethyl EsterN,N-Diethylamide
  参考文献：
  名称：

  Two-Fold Modification of the Phenyl Substituent in Phenylphosphonic Acid Monoester Monoamides

  摘要：

  Phenylphosphonic acid ethyl ester N,N-diethylamide was subjected to a double modification of its phenyl substituent through directed ortho-metalation followed by dearomatization of the aryl substituent under Birch reduction conditions. Application of the same methodology to a diastereomerically pure phenylphosphonic acid monoester monoamide led to the formation of P-stereogenic cyclohexadienyl-phosphonic acid derivatives. The method offers a simple and efficient modification of phenyl substituent in organophosphorus compounds.

  DOI：

  10.1021/jo301526k

文献信息

• Two-Fold Modification of the Phenyl Substituent in Phenylphosphonic Acid Monoester Monoamides
  作者：Marek Stankevič、Jolanta Bazan

  DOI：10.1021/jo301526k

  日期：2012.9.21

  Phenylphosphonic acid ethyl ester N,N-diethylamide was subjected to a double modification of its phenyl substituent through directed ortho-metalation followed by dearomatization of the aryl substituent under Birch reduction conditions. Application of the same methodology to a diastereomerically pure phenylphosphonic acid monoester monoamide led to the formation of P-stereogenic cyclohexadienyl-phosphonic acid derivatives. The method offers a simple and efficient modification of phenyl substituent in organophosphorus compounds.