1H-吡咯并[1,2-a]苯并咪唑-1-酮 | 95897-43-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 1H-吡咯并[1,2-a]苯并咪唑-1-酮
• 英文名称: 1H-benzo[d]pyrrolo[1,2-a]imidazol-1-one
• 英文别名: 1H-Pyrrolo[1,2-a]benzimidazol-1-one；pyrrolo[1,2-a]benzimidazol-1-one
• CAS: 95897-43-1
• 化学式: C₁₀H₆N₂O
• 分子量: 170.17
• InChiKey: UWQVWPZBJCDVQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  methyl 3-(1-benzimidazolyl)acrylate 反应 1.75h， 以71%的产率得到1H-吡咯并[1,2-a]苯并咪唑-1-酮
  参考文献：
  名称：

  A Thermal Cascade Route to Pyrroloisoindolone and Pyrroloimidazolones

  摘要：

  Flash vacuum pyrolysis (FVP) of indol-1-ylacrylate derivatives 11 and 15 or the isomeric indol-3ylacrylates 21, 22, and 24 at 925 degrees C (0.05 Torr) provides pyrrolo[1,2-alpha]indol-3-ones 2, 18, 28, and 29 in 53-90% yield by a cascade mechanism that involves a sigmatropic migration, elimination, electrocyclization sequence. Pyrrolo[1,2-a]imidazol-5-ones 3 and pyrrolo[1,2-c]imidazol-5-ones 4 were similarly obtained by FVP of corresponding 2,5-unsubstituted imidazol-1-ylacrylates (e.g., 33), with the former isomer predominating in ca. 80:20 ratio. Migration to the 2-position is therefore favored in the initial sigmatropic shift. FVP of 2-substituted imidazol-1-ylacrylates 35, 37, and 51 (825-875 C) instead give pyrrolo[l,2-c]imidazol-5-ones 56-58 only (88-91%), and that of 4,5-disubstituted imidazol-1-ylacrylates 39 and 41 (825-850 degrees C) provide pyrrolo[1,2-a]imidazol-5-ones 59 and 60 exclusively (93-95%), and thus the selectivity of the initial shift can be controlled by the presence of substituents on the imidazole 2- and 5-positions. FVP of the benzimidazole analogues 61 and 62 at 950 C gave the pyrrolo[1,2-a]benzimidazol-l-ones 6 (71%) and 63 (36%), respectively.

  DOI：

  10.1021/jo0712502