2,3,3a,4-tetrahydro-3a-(p-tolyl)-1H-pyrrolo[1,2-a]benzimidazol-1-one

• 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: 2,3,3a,4-tetrahydro-3a-(p-tolyl)-1H-pyrrolo[1,2-a]benzimidazol-1-one
• 英文别名: 3a-(4-methylphenyl)-2,3,3a,4-tetrahydro-1H-benzo[d]pyrrolo[1,2-a]imidazol-1-one；3a-(4-methylphenyl)-3,4-dihydro-2H-pyrrolo[1,2-a]benzimidazol-1-one
• 化学式: C₁₇H₁₆N₂O
• 分子量: 264.327
• InChiKey: ALSPFPKAYQWOMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  2,3,3a,4-tetrahydro-3a-(p-tolyl)-1H-pyrrolo[1,2-a]benzimidazol-1-one 、 碘甲烷 在 三乙胺 作用下， 以 丙酮 为溶剂， 以89%的产率得到
  参考文献：
  名称：

  亲电反应作为吡咯并苯并咪唑酮和吡咯并喹唑啉酮的改性方法

  摘要：

  该出版物提出了基于先前合成的具有生物活性的苯并环吡咯并[1,2-a]咪唑啉酮和吡咯并[2,1-b]喹唑啉酮的亲电反应的许多修饰，这些修饰使广泛改变分子的理化性质成为可能。对所有合成化合物的亲脂性进行了定量评估，在此基础上得出了有关引入烷基和三氟乙酰基以通过将其亲脂性提高至40％来提高化合物生物利用度的结论。

  DOI：

  10.1007/s10593-020-02751-z
• 作为产物：
  描述：

  3-(4-甲基苯甲酰)丙酸 、 邻苯二胺 以 甲苯 为溶剂， 反应 24.0h， 以78%的产率得到2,3,3a,4-tetrahydro-3a-(p-tolyl)-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-one derivatives

  摘要：

  A number of novel 1H-pyrrolo[1,2-a]benzimidazol-1-one derivatives were prepared and their anticonvulsant properties evaluated. The new synthesized compounds proved to possess anticonvulsant effects depending on the nature of substituents at C-6, C-2, and C-3a positions of the polycyclic system. In particular, the 6-chloro-3a-(p-tolyl)-2,3,3a,4-tetrahydro-1H-pyrrolo[1,2a]benzimidazol-l-one derivative (22) displayed potency fivefold higher than unsubstituted compound (13). (C) 2001 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01147-8

文献信息

• Synthesis and anticonvulsant properties of 2,3,3a,4-tetrahydro-1H-pyrrolo[1,2-a]benzimidazol-1-one derivatives
  作者：Alba Chimirri、Angela De Sarro、Giovambattista De Sarro、Rosaria Gitto、Maria Zappalà

  DOI：10.1016/s0014-827x(01)01147-8

  日期：2001.11

  A number of novel 1H-pyrrolo[1,2-a]benzimidazol-1-one derivatives were prepared and their anticonvulsant properties evaluated. The new synthesized compounds proved to possess anticonvulsant effects depending on the nature of substituents at C-6, C-2, and C-3a positions of the polycyclic system. In particular, the 6-chloro-3a-(p-tolyl)-2,3,3a,4-tetrahydro-1H-pyrrolo[1,2a]benzimidazol-l-one derivative (22) displayed potency fivefold higher than unsubstituted compound (13). (C) 2001 Elsevier Science S.A. All rights reserved.
• Reaction of 4-oxocarboxylic acids and 5-substituted 3H-furan-2-ones with 1,2-binucleophiles of aromatic and alicyclic series
  作者：V. S. Grinev、O. A. Amal’chieva、A. Yu. Egorova、E. V. Lyubun’

  DOI：10.1134/s1070428010090198

  日期：2010.9

  Based on reactions of 5-substituted 3H-furan-2-ones or 4-oxocarboxylic acids with 1,2-binucleophiles of aromatic and aliphatic series methods were developed for the synthesis of tricyclic structures containing a pyrrolidine fragment fused with imidazolidine or oxazolidine ring. The pathways of the reactions are considered. It was demonstrated that the nature of the substrate did not affect the reaction direction, but changed the scheme of the interaction. The structures of compounds obtained for the first time were proved using IR and (1)H NMR spectra.
• Electrophilic reactions as methods of modification of pyrrolobenzimidazolones and pyrroloquinazolinones
  作者：Vyacheslav S. Grinev、Alevtina Yu. Egorova

  DOI：10.1007/s10593-020-02751-z

  日期：2020.7

  The publication presents a number of modifications based on electrophilic reactions of previously synthesized biologically active benzannulated pyrrolo[1,2-a]imidazolones and pyrrolo[2,1-b]quinazolinones, which make it possible to widely change the physicochemical properties of molecules. Quantitative assessments of the lipophilicity of all synthesized compounds were carried out, on the basis of which

  该出版物提出了基于先前合成的具有生物活性的苯并环吡咯并[1,2-a]咪唑啉酮和吡咯并[2,1-b]喹唑啉酮的亲电反应的许多修饰，这些修饰使广泛改变分子的理化性质成为可能。对所有合成化合物的亲脂性进行了定量评估，在此基础上得出了有关引入烷基和三氟乙酰基以通过将其亲脂性提高至40％来提高化合物生物利用度的结论。