(S)-α-hydroxy(m-phenoxy)benzylphosphonic acid | 536739-14-7

• 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)-α-hydroxy(m-phenoxy)benzylphosphonic acid
• 英文别名: [(S)-hydroxy-(3-phenoxyphenyl)methyl]phosphonic acid
• CAS: 536739-14-7
• 化学式: C₁₃H₁₃O₅P
• 分子量: 280.217
• InChiKey: CEGGQDAMAWMUIM-ZDUSSCGKSA-N

物化性质

• 沸点：
  516.8±60.0 °C(Predicted)
• 密度：
  1.446±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  四甲基氢氧化铵 、 (S)-α-hydroxy(m-phenoxy)benzylphosphonic acid 以 水 、 丙酮 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Chiral, non-racemic α-hydroxyphosphonates and phosphonic acids via stereoselective hydroxylation of diallyl benzylphosphonates

  摘要：

  Chiral, non-racemic alpha-hydroxyphosphonates have been prepared in high enantiomeric excess (96-98% ee), via stereoselective oxaziridine-mediated hydroxylation of diallyl benzylphosphonates. The enantiomeric purity and absolute configuration of the alpha-hydroxyphosphonates was established from H-1 and P-31 NMR spectroscopy of the (S)-O-methylmandelate esters. Deprotection of the diallyl alpha-hydroxyphosphonates under neutral conditions furnished the corresponding free phosphonic acids, retaining a high degree of stereochemical purity (90 to >98% ee). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00786-3
• 作为产物：
  描述：

  diallyl (S)-α-hydroxy(m-phenoxy)benzylphosphonate 在 四(三苯基膦)钯 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以51%的产率得到(S)-α-hydroxy(m-phenoxy)benzylphosphonic acid
  参考文献：
  名称：

  Chiral, non-racemic α-hydroxyphosphonates and phosphonic acids via stereoselective hydroxylation of diallyl benzylphosphonates

  摘要：

  Chiral, non-racemic alpha-hydroxyphosphonates have been prepared in high enantiomeric excess (96-98% ee), via stereoselective oxaziridine-mediated hydroxylation of diallyl benzylphosphonates. The enantiomeric purity and absolute configuration of the alpha-hydroxyphosphonates was established from H-1 and P-31 NMR spectroscopy of the (S)-O-methylmandelate esters. Deprotection of the diallyl alpha-hydroxyphosphonates under neutral conditions furnished the corresponding free phosphonic acids, retaining a high degree of stereochemical purity (90 to >98% ee). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00786-3

文献信息

• Chiral, non-racemic α-hydroxyphosphonates and phosphonic acids via stereoselective hydroxylation of diallyl benzylphosphonates
  作者：Danielle Skropeta、Richard R. Schmidt

  DOI：10.1016/s0957-4166(02)00786-3

  日期：2003.1

  Chiral, non-racemic alpha-hydroxyphosphonates have been prepared in high enantiomeric excess (96-98% ee), via stereoselective oxaziridine-mediated hydroxylation of diallyl benzylphosphonates. The enantiomeric purity and absolute configuration of the alpha-hydroxyphosphonates was established from H-1 and P-31 NMR spectroscopy of the (S)-O-methylmandelate esters. Deprotection of the diallyl alpha-hydroxyphosphonates under neutral conditions furnished the corresponding free phosphonic acids, retaining a high degree of stereochemical purity (90 to >98% ee). (C) 2003 Elsevier Science Ltd. All rights reserved.