dibenzyl (2S)-2-[[methyl(phenylmethoxy)phosphoryl]amino]pentanedioate | 200941-07-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: dibenzyl (2S)-2-[[methyl(phenylmethoxy)phosphoryl]amino]pentanedioate
• CAS: 200941-07-7
• 化学式: C₂₇H₃₀NO₆P
• 分子量: 495.512
• InChiKey: OBAXWWGYJXCORN-LLIHCOLESA-N

物化性质

• 沸点：
  616.964±65.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.221±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  35
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dibenzyl (2S)-2-[[methyl(phenylmethoxy)phosphoryl]amino]pentanedioate 在 钯 氢气 作用下， 生成 C₁₃H₁₈NO₆P
  参考文献：
  名称：

  Evaluation of phosphorus-containing inhibitors of γ-glutamyl hydrolase

  摘要：

  Several putative, phosphorus-containing inhibitors of gamma-glutamyl hydrolase were synthesized and evaluated for inhibitory activity. The phosphonamidoic acids were shown to be weak competitive inhibitors while both a phosphoramidate diester and a phosphonamidate ester were shown to be potent time-dependent inactivators, presumably through irreversible phosphorylation of an active site nucleophile. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00253-4
• 作为产物：
  描述：

  dibenzyl L-glutamate 、 benzyl methylphosphonochloridate 在 二乙醇胺 作用下， 生成 dibenzyl (2S)-2-[[methyl(phenylmethoxy)phosphoryl]amino]pentanedioate
  参考文献：
  名称：

  Evaluation of phosphorus-containing inhibitors of γ-glutamyl hydrolase

  摘要：

  Several putative, phosphorus-containing inhibitors of gamma-glutamyl hydrolase were synthesized and evaluated for inhibitory activity. The phosphonamidoic acids were shown to be weak competitive inhibitors while both a phosphoramidate diester and a phosphonamidate ester were shown to be potent time-dependent inactivators, presumably through irreversible phosphorylation of an active site nucleophile. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00253-4

文献信息

• Alternatives to 1-H-tetrazole in the preparation of phosphonate diesters and phosphonamidates from phosphonyl dichlorides
  作者：Jack Maung、Jeremy P. Mallari、Cindy J. Choy、Clifford E. Berkman

  DOI：10.1016/j.tetlet.2004.06.083

  日期：2004.8

  5-Ethylthio-1-H-tetrazole (SET) and 4,5-dicyanoimidazole (DCI) were examined as alternatives to 1-H-tetrazole to mediate the synthesis of phosphonate diesters and phosphonamidates from phosphonyl dichlorides through a two-step one-pot reaction in various organic solvents. SET and DCI were comparable to 1-H-tetrazole for catalyzing these reactions. SET afforded slightly greater yields than DCI while

  研究了5-乙硫基-1 - H-四唑（SET）和4,5-二氰基咪唑（DCI）作为1- H-四唑的替代品，以通过两步式一价反应从膦酰二氯化物介导膦酸酯二酯和膦酰胺的合成。在各种有机溶剂中进行罐式反应。SET和DCI在催化这些反应方面与1- H-四唑相当。SET的收率略高于DCI，而苯通常是该反应的最佳溶剂。
• A convenient two-step one-pot synthesis of phosphonamidates
  作者：Karyn L. Mlodnosky、H. Michael Holmes、Vinh Q. Lam、Clifford E. Perkman

  DOI：10.1016/s0040-4039(97)10421-x

  日期：1997.12

  Phosphonamidates are formed in high yield from a one-pot sequential reaction of a phosphonyl dichloride with an alcohol and then an amine in the presence of catalytic 1H-tetrazole. Undesired disubstitution of the phoshphonyl dichloride by the alcohol or the amine is minimal due to the presence of tetrazole. (C) 1997 Elsevier Science Ltd.
• Evaluation of phosphorus-containing inhibitors of γ-glutamyl hydrolase
  作者：Chester E. Rodriguez、H. Michael Holmes、Karyn L. Mlodnosky、Vinh Q. Lam、Clifford E. Berkman

  DOI：10.1016/s0960-894x(98)00253-4

  日期：1998.6

  Several putative, phosphorus-containing inhibitors of gamma-glutamyl hydrolase were synthesized and evaluated for inhibitory activity. The phosphonamidoic acids were shown to be weak competitive inhibitors while both a phosphoramidate diester and a phosphonamidate ester were shown to be potent time-dependent inactivators, presumably through irreversible phosphorylation of an active site nucleophile. (C) 1998 Elsevier Science Ltd. All rights reserved.