1-甲基-2-(3,4-二氯苯基)-3,4-二(羟甲基)-3-吡咯啉 | 104156-44-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: 1-甲基-2-(3,4-二氯苯基)-3,4-二(羟甲基)-3-吡咯啉
• 英文名称: 1-methyl-2-(3,4-dichlorophenyl)-3,4-bis(hydroxymethyl)-3-pyrroline
• 英文别名: [5-(3,4-dichlorophenyl)-4-(hydroxymethyl)-1-methyl-2,5-dihydropyrrol-3-yl]methanol
• CAS: 104156-44-7
• 化学式: C₁₃H₁₅Cl₂NO₂
• 分子量: 288.174
• InChiKey: HCBFTDZZVXNJFW-UHFFFAOYSA-N

物化性质

• 沸点：
  400.3±45.0 °C(Predicted)
• 密度：
  1.344±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.7
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-甲基-2-(3,4-二氯苯基)-3,4-二(羟甲基)-3-吡咯啉 、 异氰酸异丙酯 在 dibutyltin diacetate 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以64%的产率得到1-methyl-2-(3,4-dichlorophenyl)-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：

  Trifluoro-methanesulfonate[1-(3,4-dichloro-phenyl)-meth-(Z)-ylidene]-methyl-trimethylsilanylmethyl-ammonium; 在 二异丁基氢化铝 、 cesium fluoride 作用下， 以 乙二醇二甲醚 、 甲苯 为溶剂， 反应 18.0h， 生成 1-甲基-2-(3,4-二氯苯基)-3,4-二(羟甲基)-3-吡咯啉
  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

文献信息

• ANDERSON W. K.; MILOWSKY A. S., J. MED. CHEM., 29,(1986) N 11, 2241-2249
  作者：ANDERSON W. K.、 MILOWSKY A. S.

  DOI：——

  日期：——