3a-(4-chlorophenyl)-2,3,3a,4-tetrahydro-1H-pyrrolo<1,2-a>benzimidazol-1-one | 116910-57-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 3a-(4-chlorophenyl)-2,3,3a,4-tetrahydro-1H-pyrrolo<1,2-a>benzimidazol-1-one
• 英文别名: 3a-(4-chlorophenyl)-2,3,3a,4-tetrahydro-1H-pyrrolo[1,2-a]benzimidazol-1-one；3a-(4-chlorophenyl)-3,4-dihydro-2H-pyrrolo[1,2-a]benzimidazol-1-one
• CAS: 116910-57-7
• 化学式: C₁₆H₁₃ClN₂O
• 分子量: 284.745
• InChiKey: ZLNZEIFAAWZJFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3a-(4-chlorophenyl)-2,3,3a,4-tetrahydro-1H-pyrrolo<1,2-a>benzimidazol-1-one 生成 (R)-3a-(4-Chloro-phenyl)-2,3,3a,4-tetrahydro-benzo[d]pyrrolo[1,2-a]imidazol-1-one
  参考文献：
  名称：

  Separation of the enantiomers of anticonvulsant tricyclic pyrroloimidazolones by enantioselective HPLC. A chiral recognition model and a chiroptical study

  摘要：

  The enantiomers of several pyrrolobenzimidazolone and pyrroloimidazopyridine derivatives have been successfully resolved by HPLC on a Whelk-O 1 Chiral Stationary Phase superior to other CSPs. A chiral recognition model explained the substituent effects on the enantioselectivity and afforded correlation of the elution order of the enantiomers to their absolute configuration. The exciton coupling method was applied to the CD spectra of the isolated enantiomers to confirm their absolute configuration. Copyright (C) 1996 Published by Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00331-x
• 作为产物：
  描述：

  3-(4-氯苯甲酰)丙酸 、 邻苯二胺 以 甲苯 为溶剂， 反应 6.0h， 以52%的产率得到3a-(4-chlorophenyl)-2,3,3a,4-tetrahydro-1H-pyrrolo<1,2-a>benzimidazol-1-one
  参考文献：
  名称：

  Synthesis and anticonvulsant properties of 2,3,3a,4-tetrahydro-1H-pyrrolo[1,2-a]benzimidazol-1-ones

  摘要：

  A series of 2,3,3a,4-tetrahydro-1H-pyrrolo[1,2-a]benzimidazol-1-ones were synthesized and evaluated for anticonvulsant activity in DBA/2 mice against sound-induced seizures and in rats against maximal electroshock-induced seizures. Most of the derivatives showed an anticonvulsant effect better than that of valproate, a commonly used anticonvulsant drug. Compound 3 possessed an anticonvulsant activity comparable to that of diphenylhydantoin in both tests and was selected for further studies. Structure-activity relationships are discussed.

  DOI：

  10.1021/jm00121a019