dimethyl [(4E)-5,5-bis(trifluoromethyl)-4-(tetrafluoroethylidene)-4,5-dihydro-1,3-thiazol-2-yl]phosphonate

• 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: dimethyl [(4E)-5,5-bis(trifluoromethyl)-4-(tetrafluoroethylidene)-4,5-dihydro-1,3-thiazol-2-yl]phosphonate
• 英文别名: (4E)-2-dimethoxyphosphoryl-4-(1,2,2,2-tetrafluoroethylidene)-5,5-bis(trifluoromethyl)-1,3-thiazole
• 化学式: C₉H₆F₁₀NO₃PS
• 分子量: 429.175
• InChiKey: YRDJKUPOXDWSKL-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  73.2
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  二甲基三甲硅基膦酸酯 、 Perfluoro(3-isothiocyanato-2-methyl-2-pentene) 以 乙腈 为溶剂， 反应 42.0h， 以80%的产率得到dimethyl [(4E)-5,5-bis(trifluoromethyl)-4-(tetrafluoroethylidene)-4,5-dihydro-1,3-thiazol-2-yl]phosphonate
  参考文献：
  名称：

  摘要：

  The reactions of perfluoro-3-isothiocyanato-2-methyl-2-pentene with PPh3 and P(NEt2)(3) in the presence of NaBF4, KI, and NaBPh4 form phosphonium salts with the heterocyclic substituent (4E)-5,5-bis-(trifluoromethyl)-4-(tetrafluoroethylidene)-4,5-dihydro-1,3-thiazol-2-yl, instead of involving desulfurization and formation of P-F-containing products. The reaction with tris(pentafluorophenyl)phosphine fails. The reactions with P(OEt)(3) in the presence of ClSiMe3 or (CH3O)(2)POSiMe3 yield diethyl or dimethyl [(4E)-5,5-bis(trifluoromethyl)-4-(tetrafluoroethylidene)-4,5-dihydro-1,3-thiazol-2-yl]phosphonates and no intramolecular alkylation products. The H-1, C-13, F-19, and P-31 spectra are presented, and the reaction pathways are discussed. Potential mechanisms of the biological and catalytic activity of the reaction products are considered.

  DOI：

  10.1023/a:1020402928139

文献信息

• ——
  作者：A. V. Rogoza、G. G. Furin

  DOI：10.1023/a:1020402928139

  日期：——

  The reactions of perfluoro-3-isothiocyanato-2-methyl-2-pentene with PPh3 and P(NEt2)(3) in the presence of NaBF4, KI, and NaBPh4 form phosphonium salts with the heterocyclic substituent (4E)-5,5-bis-(trifluoromethyl)-4-(tetrafluoroethylidene)-4,5-dihydro-1,3-thiazol-2-yl, instead of involving desulfurization and formation of P-F-containing products. The reaction with tris(pentafluorophenyl)phosphine fails. The reactions with P(OEt)(3) in the presence of ClSiMe3 or (CH3O)(2)POSiMe3 yield diethyl or dimethyl [(4E)-5,5-bis(trifluoromethyl)-4-(tetrafluoroethylidene)-4,5-dihydro-1,3-thiazol-2-yl]phosphonates and no intramolecular alkylation products. The H-1, C-13, F-19, and P-31 spectra are presented, and the reaction pathways are discussed. Potential mechanisms of the biological and catalytic activity of the reaction products are considered.