(S)-(-)-[methoxy(phenyl)phosphoryl]acetic acid | 18952-17-5

• 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: (S)-(-)-[methoxy(phenyl)phosphoryl]acetic acid
• 英文别名: 2-[Methoxy(phenyl)phosphoryl]acetic acid；2-[methoxy(phenyl)phosphoryl]acetic acid
• CAS: 18952-17-5
• 化学式: C₉H₁₁O₄P
• 分子量: 214.158
• InChiKey: WOMCCRPWMVUWIN-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-(-)-[methoxy(phenyl)phosphoryl]acetic acid 在 三乙胺 作用下， 以 苯 为溶剂， 反应 48.75h， 生成
  参考文献：
  名称：

  Enantiomerically pure P-chiral dicyclohexylammonium 2-(phosphinyl)acrylates as new Michael acceptors. Enantioselective synthesis of α-methylene-δ-valerolactones

  摘要：

  A convenient method for the preparation of enantiomerically pure P-chiral dicyclohexylammonium 2-(phosphinyl)acrylates 6 and 7 is presented. The synthesis of alpha-methylene-delta-valerolactone 5a with enantiomeric excesses of 85% and 80% has been developed. The key step of the synthesis. involves an asymmetric Michael addition of imine 10 to acrylates 6 and 7, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.10.028
• 作为产物：
  描述：

  二甲基苯基膦酸盐 在 porcine liver esterase 、 sodium hydroxide 、 phosphate buffer 作用下， 反应 16.0h， 生成 (S)-(-)-[methoxy(phenyl)phosphoryl]acetic acid
  参考文献：
  名称：

  Enzyme-promoted kinetic resolution of racemic, P-chiral phosphonyl and phosphorylacetates

  摘要：

  A series of racemic methyl phosphonyl- and phosphorylacetates were hydrolyzed in the presence of porcine liver esterase (PLE) under kinetic resolution conditions to give the corresponding P-chiral phosphonyl- and phosphorylacetic acids and recovered esters in moderate to high enantiomeric purity (up to 95% ee). The Jones PLE active site model was applied to explain the enantioselectivity of this reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00258-4

文献信息

• Enantiomerically pure P-chiral dicyclohexylammonium 2-(phosphinyl)acrylates as new Michael acceptors. Enantioselective synthesis of α-methylene-δ-valerolactones
  作者：Henryk Krawczyk、Marcin Śliwiński、Jacek Kędzia

  DOI：10.1016/j.tetasy.2006.10.028

  日期：2006.10

  A convenient method for the preparation of enantiomerically pure P-chiral dicyclohexylammonium 2-(phosphinyl)acrylates 6 and 7 is presented. The synthesis of alpha-methylene-delta-valerolactone 5a with enantiomeric excesses of 85% and 80% has been developed. The key step of the synthesis. involves an asymmetric Michael addition of imine 10 to acrylates 6 and 7, respectively. (c) 2006 Elsevier Ltd. All rights reserved.
• Enzyme-promoted kinetic resolution of racemic, P-chiral phosphonyl and phosphorylacetates
  作者：Piotr Kiełbasiński、Piotr Góralczyk、Marian Mikołajczyk、Michał W. Wieczorek、Wiesław R. Majzner

  DOI：10.1016/s0957-4166(98)00258-4

  日期：1998.8

  A series of racemic methyl phosphonyl- and phosphorylacetates were hydrolyzed in the presence of porcine liver esterase (PLE) under kinetic resolution conditions to give the corresponding P-chiral phosphonyl- and phosphorylacetic acids and recovered esters in moderate to high enantiomeric purity (up to 95% ee). The Jones PLE active site model was applied to explain the enantioselectivity of this reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.