Trifluoro-methanesulfonate[1-(4-fluoro-phenyl)-meth-(Z)-ylidene]-methyl-trimethylsilanylmethyl-ammonium; | 104156-75-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: Trifluoro-methanesulfonate[1-(4-fluoro-phenyl)-meth-(Z)-ylidene]-methyl-trimethylsilanylmethyl-ammonium
• CAS: 104156-75-4
• 化学式: CF₃O₃S*C₁₂H₁₉FNSi
• 分子量: 373.444
• InChiKey: OBGSVVFUJRLLFE-WQRRWHLMSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  60.21
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Trifluoro-methanesulfonate[1-(4-fluoro-phenyl)-meth-(Z)-ylidene]-methyl-trimethylsilanylmethyl-ammonium; 在 dibutyltin diacetate 、 二异丁基氢化铝 、 cesium fluoride 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 33.0h， 生成 1-methyl-2-(4-fluorophenyl)-3,4-bis<<(N-2-propylcarbamoyl)oxy>methyl>-3-pyrroline
  参考文献：
  名称：

  Vinylogous carbinolamine tumor inhibitors. 19. Synthesis and antineoplastic activity of bis[[[(alkylamino)carbonyl]oxy]methyl]-substituted 3-pyrrolines as prodrugs of tumor inhibitory pyrrolebis(carbamates)

  摘要：

  A series of bis[(carbamoyloxy)methyl]pyrrolines 2-4 were synthesized from either the appropriate alpha-silylated iminium salt, or an aziridine, or a 2H-azirine in a sequence involving 1,3-dipolar cycloaddition reactions. The antineoplastic activities of the pyrrolines were compared to the corresponding pyrroles. The C-2 gem-dimethyl-substituted pyrroline, 4, which cannot be converted to the pyrrole in vivo, was inactive. The activity of the 2-phenyl-substituted pyrrolines 3 was markedly dependent on the nature of the phenyl substituent, although the corresponding phenylpyrroles all showed comparable activity. The differences in the activities of the pyrrolines 3 may be due to the rate of metabolic conversion of the pyrroline to the pyrrole. Electron-withdrawing substituents on the phenyl ring appear to retard this process.

  DOI：

  10.1021/jm00161a019
• 作为产物：
  描述：

  (三甲基硅基)甲基三氟甲烷磺酸酯 、 1-(4-fluorophenyl)-N-methylmethanimine 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 Trifluoro-methanesulfonate[1-(4-fluoro-phenyl)-meth-(Z)-ylidene]-methyl-trimethylsilanylmethyl-ammonium;
  参考文献：
  名称：

  Vinylogous carbinolamine tumor inhibitors. 19. Synthesis and antineoplastic activity of bis[[[(alkylamino)carbonyl]oxy]methyl]-substituted 3-pyrrolines as prodrugs of tumor inhibitory pyrrolebis(carbamates)

  摘要：

  A series of bis[(carbamoyloxy)methyl]pyrrolines 2-4 were synthesized from either the appropriate alpha-silylated iminium salt, or an aziridine, or a 2H-azirine in a sequence involving 1,3-dipolar cycloaddition reactions. The antineoplastic activities of the pyrrolines were compared to the corresponding pyrroles. The C-2 gem-dimethyl-substituted pyrroline, 4, which cannot be converted to the pyrrole in vivo, was inactive. The activity of the 2-phenyl-substituted pyrrolines 3 was markedly dependent on the nature of the phenyl substituent, although the corresponding phenylpyrroles all showed comparable activity. The differences in the activities of the pyrrolines 3 may be due to the rate of metabolic conversion of the pyrroline to the pyrrole. Electron-withdrawing substituents on the phenyl ring appear to retard this process.

  DOI：

  10.1021/jm00161a019