phenylphosphonic acid L-menthyl ester N,N-diethylamide | 1228361-75-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: phenylphosphonic acid L-menthyl ester N,N-diethylamide
• 英文别名: N-ethyl-N-[[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxy-phenylphosphoryl]ethanamine
• CAS: 1228361-75-8
• 化学式: C₂₀H₃₄NO₂P
• 分子量: 351.469
• InChiKey: MZWMZQKHZOFYSG-SSYAZSBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  phenylphosphonic acid L-menthyl ester N,N-diethylamide 在 正丁基锂 、 碘 作用下， 以 四氢呋喃 为溶剂， 反应 0.92h， 以82%的产率得到o-iodophenylphosphonic acid L-menthyl 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：

  二乙胺 、 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl phenylphosphinate 在 三乙胺 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 以77%的产率得到phenylphosphonic acid L-menthyl ester N,N-diethylamide
  参考文献：
  名称：

  H-膦酸酯和仲膦氧化物与胺和醇的立体定向偶联：制备旋光有机磷酸衍生物的通用方法†

  摘要：

  H-次膦酸酯和仲膦氧化物与胺和醇的反应高度立体定向，在阿瑟顿-托德反应条件下，磷中心的构型转化得到相应的偶联产物。该发现导致建立一种通用且有效的方法，该方法用于由容易获得的手性H-次膦酸酯和仲膦氧化物合成多种光学活性的有机磷酸衍生物。

  DOI：

  10.1021/jo100473s

文献信息

• Stereospecific Coupling of <i>H</i>-Phosphinates and Secondary Phosphine Oxides with Amines and Alcohols: A General Method for the Preparation of Optically Active Organophosphorus Acid Derivatives
  作者：Gang Wang、Ruwei Shen、Qing Xu、Midori Goto、Yufen Zhao、Li-Biao Han

  DOI：10.1021/jo100473s

  日期：2010.6.4

  secondary phosphine oxides with amines and alcohols proceeds highly stereospecifically to give the corresponding coupling products with inversion of configuration at the phosphorus center under the Atherton−Todd reaction conditions. This finding leads to the establishment of a general and efficient method for the synthesis of a variety of optically active organophosphorus acid derivatives from the easily

  H-次膦酸酯和仲膦氧化物与胺和醇的反应高度立体定向，在阿瑟顿-托德反应条件下，磷中心的构型转化得到相应的偶联产物。该发现导致建立一种通用且有效的方法，该方法用于由容易获得的手性H-次膦酸酯和仲膦氧化物合成多种光学活性的有机磷酸衍生物。
• 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.