1-benzoyl-3-acetyl-4-benzyl-4H-pyrrolo[1,2-a]benzimidazole | 1235306-18-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-benzoyl-3-acetyl-4-benzyl-4H-pyrrolo[1,2-a]benzimidazole
• 英文别名: 1-(1-Benzoyl-4-benzylpyrrolo[1,2-a]benzimidazol-3-yl)ethanone
• CAS: 1235306-18-9
• 化学式: C₂₆H₂₀N₂O₂
• 分子量: 392.457
• InChiKey: DHIZOWWKOFYZPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  43.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-benzyl-1H-benzo[d]imidazole 生成 1-benzoyl-3-acetyl-4-benzyl-4H-pyrrolo[1,2-a]benzimidazole
  参考文献：
  名称：

  Unexpected formation of pyrrolo[1,2-a]quinoxaline derivatives during the multicomponent synthesis of pyrrolo[1,2-a]benzimidazoles

  摘要：

  New pyrrolo[1,2-a]benzimidazole and pyrrolo[1,2-a]quinoxaline derivatives are obtained via one-pot, three-component reactions from 1-benzylbenzimidazoles, alpha-bromocarbonyl compounds, and non-symmetrical activated acetylenic dipolarophiles in propylene oxide as both the reaction medium and acid scavenger, at room temperature. When the same reaction is performed in 1,2-epoxybutane at reflux temperature only the pyrrolo[1,2-a]benzimidazole derivative is obtained. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.01.036

文献信息

• Fine tuning the outcome of 1,3-dipolar cycloaddition reactions of benzimidazolium ylides to activated alkynes
  作者：Emilian Georgescu、Alina Nicolescu、Florentina Georgescu、Florina Teodorescu、Sergiu Shova、Adriana T. Marinoiu、Florea Dumitrascu、Calin Deleanu

  DOI：10.1016/j.tet.2016.03.086

  日期：2016.5

  1,3-Dipolar cycloaddition reactions of benzimidazolium ylides, generated from 3-phenacylbenzimidazolium bromides, to non-symmetrical activated dipolarophiles in various reaction conditions led to complex mixtures of pyrrolo[1,2-a]benzimidazole and pyrrolo[1,2-a]quinoxaline derivatives. In order to explain all experimental results, the influence of reaction conditions on the reaction products was investigated

  在各种反应条件下，由3-苯甲基苯并咪唑鎓溴化物生成的苯并咪唑鎓烷基化物的1,3-偶极环加成反应与非对称活化偶极亲和剂导致吡咯并[1,2- a ]苯并咪唑和吡咯并[1,2- a的复杂混合物]喹喔啉衍生物。为了解释所有实验结果，研究了反应条件对反应产物的影响。首次出现4-羟基-4,5-二氢吡咯并[1,2 - a ]喹喔啉衍生物6，吡咯并[1,2- a ]喹喔啉季盐8以及4-甲氧基-4,5-二氢吡咯并酮[1,2- a ]喹喔啉9被分离出来，被充分表征，并提出它们的相互转化，以及提出的反应机理。
• Unexpected formation of pyrrolo[1,2-a]quinoxaline derivatives during the multicomponent synthesis of pyrrolo[1,2-a]benzimidazoles
  作者：Alina Nicolescu、Calin Deleanu、Emilian Georgescu、Florentina Georgescu、Ana-Maria Iurascu、Sergiu Shova、Petru Filip

  DOI：10.1016/j.tetlet.2013.01.036

  日期：2013.3

  New pyrrolo[1,2-a]benzimidazole and pyrrolo[1,2-a]quinoxaline derivatives are obtained via one-pot, three-component reactions from 1-benzylbenzimidazoles, alpha-bromocarbonyl compounds, and non-symmetrical activated acetylenic dipolarophiles in propylene oxide as both the reaction medium and acid scavenger, at room temperature. When the same reaction is performed in 1,2-epoxybutane at reflux temperature only the pyrrolo[1,2-a]benzimidazole derivative is obtained. (C) 2013 Elsevier Ltd. All rights reserved.