ethyl P-phenyl-N,N-diethylaminophosphinate | 100525-32-4

• 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: ethyl P-phenyl-N,N-diethylaminophosphinate
• 英文别名: phenylphosphonic acid ethyl ester N,N-diethylamide；ethyl N,N-diethyl-P-phenylphosphonamidate；Phosphonamidic acid, N,N-diethyl-P-phenyl-, ethyl ester；N-[ethoxy(phenyl)phosphoryl]-N-ethylethanamine
• CAS: 100525-32-4
• 化学式: C₁₂H₂₀NO₂P
• 分子量: 241.27
• InChiKey: RNXXCGPDKIXFNO-UHFFFAOYSA-N

物化性质

• 沸点：
  311.2±25.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  ethyl P-phenyl-N,N-diethylaminophosphinate 在 正丁基锂 、 碘 作用下， 以 四氢呋喃 为溶剂， 反应 0.92h， 以67%的产率得到o-iodophenylphosphonic acid ethyl ester N,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
• 作为产物：
  描述：

  溴苯 在 碘 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 37.0h， 生成 ethyl P-phenyl-N,N-diethylaminophosphinate
  参考文献：
  名称：

  通过膦酸酯与碘和胺的一锅顺序反应有效合成膦酰胺。

  摘要：

  通过从芳基溴化镁和亚磷酸三乙酯原位生成亚膦酸酯，然后用碘和胺进行处理，已经开发出了一种构建磷酸亚酰胺的顺序方法。从室温容易获得的材料在室温下以良好或优异的产率获得了多种膦酰胺盐。

  DOI：

  10.1002/chem.202002934
• 作为试剂：
  描述：

  氯化苄 在 正丁基锂 、 ethyl P-phenyl-N,N-diethylaminophosphinate 作用下， 以 四氢呋喃 为溶剂， 生成 Chloro-1 diphenyl-1,2 ethane
  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

• Duddeck, Helmut; Lecht, Rainer, Phosphorus and Sulfur and the Related Elements, 1987, vol. 29, p. 169 - 178
  作者：Duddeck, Helmut、Lecht, Rainer

  DOI：——

  日期：——
• Efficient Synthesis of Phosphonamidates through One‐Pot Sequential Reactions of Phosphonites with Iodine and Amines
  作者：Xunwei Chen、Wenjun Luo、Yanlin Wang、Zikang Li、Xiaorui Ma、Ai‐Yun Peng

  DOI：10.1002/chem.202002934

  日期：2020.11.11

  one‐pot sequential strategy to construct phosphonamidates has been developed by generating phosphonites in situ from arylmagnesium bromides and triethyl phosphite followed by treatment with iodine and amines. A variety of phosphonamidates were obtained with good to excellent yields at room temperature from easily available materials.

  通过从芳基溴化镁和亚磷酸三乙酯原位生成亚膦酸酯，然后用碘和胺进行处理，已经开发出了一种构建磷酸亚酰胺的顺序方法。从室温容易获得的材料在室温下以良好或优异的产率获得了多种膦酰胺盐。
• 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.