O,O-bis(2-chloroethyl) S-hydrogen phosphorothioate | 29918-64-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫代磷酸及其衍生物
• 英文名称: O,O-bis(2-chloroethyl) S-hydrogen phosphorothioate
• 英文别名: Bis(2-chloroethoxy)-hydroxy-sulfanylidene-lambda5-phosphane；bis(2-chloroethoxy)-hydroxy-sulfanylidene-λ5-phosphane
• CAS: 29918-64-7
• 化学式: C₄H₉Cl₂O₃PS
• 分子量: 239.059
• InChiKey: BTHJWPKAXAKMAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,3-二甲基-1-(三氟甲基)-1,2-苯并碘氧杂戊环 、 O,O-bis(2-chloroethyl) S-hydrogen phosphorothioate 以 氘代氯仿 为溶剂， 反应 23.0h， 以8%的产率得到1-Chloro-2-[2-chloroethoxy(trifluoromethylsulfanyl)phosphoryl]oxyethane
  参考文献：
  名称：

  Electrophilic Trifluoromethylation of S-Hydrogen Phosphorothioates

  摘要：

  A series of S-hydrogen phosphorothioates have been converted to the corresponding S-trifluoromethyl derivatives upon reaction with the electrophilic trifluoromethylation reagent 1 (trifluoromethyl 1,3-dihydro-3,3-dimethyl-1,2-benziodoxole). Relative rate data were obtained by F-19 NMR monitoring of competition experiments and were evaluated by means of the Taft equation. A high positive polar sensitivity factor of 2.55 was found for electron-rich substrates and a negative one of -0.37 for electron-poor ones, implying the involvement of two different rate-determining steps. Furthermore, the reaction was found to be unaffected by steric factors.

  DOI：

  10.1021/jo200522w
• 作为产物：
  描述：

  二(2-氯乙基)亚磷酸氢酯 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 三乙胺 、 盐酸 作用下， 以 乙醚 、 水 为溶剂， 以62%的产率得到O,O-bis(2-chloroethyl) S-hydrogen phosphorothioate
  参考文献：
  名称：

  Electrophilic Trifluoromethylation of S-Hydrogen Phosphorothioates

  摘要：

  A series of S-hydrogen phosphorothioates have been converted to the corresponding S-trifluoromethyl derivatives upon reaction with the electrophilic trifluoromethylation reagent 1 (trifluoromethyl 1,3-dihydro-3,3-dimethyl-1,2-benziodoxole). Relative rate data were obtained by F-19 NMR monitoring of competition experiments and were evaluated by means of the Taft equation. A high positive polar sensitivity factor of 2.55 was found for electron-rich substrates and a negative one of -0.37 for electron-poor ones, implying the involvement of two different rate-determining steps. Furthermore, the reaction was found to be unaffected by steric factors.

  DOI：

  10.1021/jo200522w

文献信息

• Electrophilic Trifluoromethylation of <i>S</i>-Hydrogen Phosphorothioates
  作者：Nico Santschi、Antonio Togni

  DOI：10.1021/jo200522w

  日期：2011.5.20

  A series of S-hydrogen phosphorothioates have been converted to the corresponding S-trifluoromethyl derivatives upon reaction with the electrophilic trifluoromethylation reagent 1 (trifluoromethyl 1,3-dihydro-3,3-dimethyl-1,2-benziodoxole). Relative rate data were obtained by F-19 NMR monitoring of competition experiments and were evaluated by means of the Taft equation. A high positive polar sensitivity factor of 2.55 was found for electron-rich substrates and a negative one of -0.37 for electron-poor ones, implying the involvement of two different rate-determining steps. Furthermore, the reaction was found to be unaffected by steric factors.