thiophosphoric O,O'-dibenzyl ester S-(3-hydroxypropyl) ester

• 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: thiophosphoric O,O'-dibenzyl ester S-(3-hydroxypropyl) ester
• 英文别名: 3-[Oxido-bis(phenylmethoxy)phosphaniumyl]sulfanylpropan-1-ol；3-[oxido-bis(phenylmethoxy)phosphaniumyl]sulfanylpropan-1-ol
• 化学式: C₁₇H₂₁O₄PS
• 分子量: 352.391
• InChiKey: AIWXGWYFNQLGGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  87
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-thiocyanato-propan-1-ol 、 亚磷酸二苄酯 在 1-叔丁基-4,4,4-三(二甲氨基)-2,2-二[三(二甲氨基)-正膦亚基氨基]-2Λ5,4Λ5-连二(磷氮基化合物) 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 18.0h， 以54%的产率得到thiophosphoric O,O'-dibenzyl ester S-(3-hydroxypropyl) ester
  参考文献：
  名称：

  Easy Access to Phosphonothioates

  摘要：

  A new and particularly mild method for the formation of phosphorus-sulfur bonds has been achieved through base-catalyzed addition of thiocyanate to the corresponding H-phosphine oxide, phosphinate, or phosphonate. This reaction procedure offers many advantages: the use as starting material of a stable and not oxygen-sensitive phosphorus(v) species, particularly mild and nonaqueous reaction conditions and workup (a pivotal point for these sensitive phosphonothioates), and, through optimized access to thiocyanates, a wider scope of substrates. This method has been applied to achieve the synthesis of substrate analogues for the study of antibody-catalyzed hydrolysis of acetylcholinesterase inhibitor PhX (11).

  DOI：

  10.1002/1521-3765(20020703)8:13<2910::aid-chem2910>3.0.co;2-r

文献信息

• Easy Access to Phosphonothioates
  作者：Pierre-Yves Renard、Hervé Schwebel、Philippe Vayron、Ludovic Josien、Alain Valleix、Charles Mioskowski

  DOI：10.1002/1521-3765(20020703)8:13<2910::aid-chem2910>3.0.co;2-r

  日期：2002.7.3

  A new and particularly mild method for the formation of phosphorus-sulfur bonds has been achieved through base-catalyzed addition of thiocyanate to the corresponding H-phosphine oxide, phosphinate, or phosphonate. This reaction procedure offers many advantages: the use as starting material of a stable and not oxygen-sensitive phosphorus(v) species, particularly mild and nonaqueous reaction conditions and workup (a pivotal point for these sensitive phosphonothioates), and, through optimized access to thiocyanates, a wider scope of substrates. This method has been applied to achieve the synthesis of substrate analogues for the study of antibody-catalyzed hydrolysis of acetylcholinesterase inhibitor PhX (11).