diallyl (S)-α-hydroxybenzylphosphonate | 536739-06-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diallyl (S)-α-hydroxybenzylphosphonate
• 英文别名: (S)-[oxido-bis(prop-2-enoxy)phosphaniumyl]-phenylmethanol
• CAS: 536739-06-7
• 化学式: C₁₃H₁₇O₄P
• 分子量: 268.249
• InChiKey: JPEFKDGUBMHMMZ-ZDUSSCGKSA-N

物化性质

• 沸点：
  385.4±42.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  61.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diallyl (S)-α-hydroxybenzylphosphonate 在 四(三苯基膦)钯 、 5,5-二甲基-1,3-环己二酮 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以100%的产率得到(-)-(S)-1-phenyl-1-hydroxymethylphosphonic 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
• 作为产物：
  描述：

  benzylphosphonic dichloride 在 吡啶 、 4-二甲氨基吡啶 、 sodium hexamethyldisilazane 、 (+)-8,8-二氯樟脑磺哑嗪 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 diallyl (S)-α-hydroxybenzylphosphonate
  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

• Stereoselective synthesis of phosphoramidate α(2-6)Sialyltransferase transition-State analogue inhibitors
  作者：Danielle Skropeta、Ralf Schwörer、Richard R. Schmidt

  DOI：10.1016/s0960-894x(03)00672-3

  日期：2003.10

  The asymmetric synthesis of novel, potent phosphoramidate alpha(2-6)sialyltransferase transition-state analogue inhibitors such as (R)-9 (K-i - 68 muM) is described, via condensation of cytidine phosphitamide 6 with key chiral, non-racemic alpha-aminophosphonates, prepared in > 98 % ee by Mitsunobu azidation followed by Staudinger reduction of the corresponding chiral, non-racemic alpha-hydroxyphosphonates. (C) 2003 Elsevier Ltd. All rights reserved.
• 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.