O,O-diisopropyl S-trifluoromethyl phosphorothioate | 88282-85-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: O,O-diisopropyl S-trifluoromethyl phosphorothioate
• 英文别名: 2-[propan-2-yloxy(trifluoromethylsulfanyl)phosphoryl]oxypropane
• CAS: 88282-85-3
• 化学式: C₇H₁₄F₃O₃PS
• 分子量: 266.221
• InChiKey: VSMMKJFTHIRESH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  O,O-diisopropyl S-trifluoromethyl phosphorothioate 、 三甲基溴硅烷 以 氯仿 为溶剂， 反应 20.0h， 生成 O,O-bistrimethylsilyl S-trifluoromethyl phosphorothioate
  参考文献：
  名称：

  Blackburn, Michael G.; Maciej, Thomas W., Journal of the Chemical Society. Perkin transactions I, 1985, p. 1419 - 1424

  摘要：

  DOI：
• 作为产物：
  描述：

  亚磷酸二异丙酯 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 O,O-diisopropyl S-trifluoromethyl 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

• HAAS, A.;KORTMANN, W., Z. ANORG. UND ALLG. CHEM., 1983, 501, N 6, 79-88
  作者：HAAS, A.、KORTMANN, W.

  DOI：——

  日期：——
• BLACKBURN, G. M.;MACIEJ, TH. W., J. CHEM. SOC. PERKIN TRANS., 1985, N 7, 1419-1423
  作者：BLACKBURN, G. M.、MACIEJ, TH. W.

  DOI：——

  日期：——
• 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.
• Blackburn, Michael G.; Maciej, Thomas W., Journal of the Chemical Society. Perkin transactions I, 1985, p. 1419 - 1424
  作者：Blackburn, Michael G.、Maciej, Thomas W.

  DOI：——

  日期：——