dibenzyl (+/-) 2-hydroxy-2-phenylethylphosphonate | 1059608-87-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: dibenzyl (+/-) 2-hydroxy-2-phenylethylphosphonate
• 英文别名: dibenzyl 2-hydroxy-2-phenylethylphosphonate
• CAS: 1059608-87-5
• 化学式: C₂₂H₂₃O₄P
• 分子量: 382.396
• InChiKey: SXHWYVSVNNVPFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.35
• 重原子数：
  27.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  dibenzyl (+/-) 2-hydroxy-2-phenylethylphosphonate 在 sodium iodide 作用下， 以 丁酮 为溶剂， 反应 2.5h， 生成 Sodium;(2-hydroxy-2-phenylethyl)-phenylmethoxyphosphinate
  参考文献：
  名称：

  β-Ketophosphonates as β-lactamase inhibitors: Intramolecular cooperativity between the hydrophobic subsites of a class D β-lactamase

  摘要：

  A series of aryl and arylmethyl beta-aryl-beta-ketophosphonates have been prepared as potential beta-lactamase inhibitors. These compounds, as fast, reversible, competitive inhibitors, were most effective ( micromolar K(i) values) against the class D OXA-1 b-lactamase but had less activity against the OXA-10 enzyme. They were also quite effective against the class C b-lactamase of Enterobacter cloacae P99 but less so against the class A TEM-2 enzyme. Reduction of the keto group to form the corresponding beta-hydroxyphosphonates led to reduced inhibitory activity. Molecular modeling, based on the OXA-1 crystal structure, suggested interaction of the aryl groups with the hydrophobic elements of the enzyme's active site and polar interaction of the keto and phosphonate groups with the active site residues Ser 115, Lys 212 and Thr 213 and with the non-conserved Ser 258. Analysis of binding free energies showed that the beta-aryl and phosphonate ester aryl groups interacted cooperatively within the OXA-1 active site. Overall, the results suggest that quite effective inhibitors of class C and some class D beta-lactamases could be designed, based on the beta-ketophosphonate platform. (c) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2008.05.045
• 作为产物：
  描述：

  苯乙烯 、 亚磷酸二苄酯 在 manganese(II) acetate 作用下， 以 甲苯 为溶剂， 生成 dibenzyl (+/-) 2-hydroxy-2-phenylethylphosphonate
  参考文献：
  名称：

  一种β-羟基膦酸酯衍生物的制备方法

  摘要：

  本发明公开了一种β‑羟基膦酸酯衍生物的制备方法，具体为将芳基乙烯衍生物、磷试剂、醋酸锰溶于溶剂中，反应在20～60℃进行，制得β‑羟基膦酸酯衍生物。β‑羟基膦酸酯衍生物在氨水作用下得到β‑氨基膦酸酯衍生物。本发明使用芳基乙烯衍生物为起始物，原料易得、种类很多；利用本发明的方法得到的产物类型多样，既可以直接使用、又可以用于其他进一步的反应；同时，合成路线简短、反应条件温和、反应操作和后处理过程简单、产率较高，适合于规模化生产。

  公开号：

  CN104370960B