2-(2,2,3,3-tetramethylcyclopropyl)-1H-benzimidazole | 154050-33-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(2,2,3,3-tetramethylcyclopropyl)-1H-benzimidazole
• CAS: 154050-33-6
• 化学式: C₁₄H₁₈N₂
• 分子量: 214.31
• InChiKey: QSRORTKGEIATCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(2,2,3,3-tetramethylcyclopropyl)-1H-benzimidazole 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 4.5h， 生成 1,1,2,2-tetramethyl-2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazole
  参考文献：
  名称：

  Synthesis of 2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazoles via the cyclopropyliminium rearrangement of substituted 2-cyclopropylbenzimidazoles

  摘要：

  2-Cyclopropylbenzimidazole derivatives with various substituents in the small ring undergo cyclopropyliminium rearrangement into 2,3-dihydropyrrolobenzimidazoles substituted at positions 1, 2 or 3. The substrates containing a functional group in position 1 of the cyclopropane ring form products substituted at position 3. Substituents at position 2 in most cases lead to the formation of a mixture of isomers. The reaction can be directed to yield one of the isomers predominantly by varying the solvent polarity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.02.021
• 作为产物：
  描述：

  2,2,3,3-四甲基环丙烷羧酸酰氯 在 三乙胺 作用下， 以 溶剂黄146 、 乙腈 为溶剂， 反应 5.0h， 生成 2-(2,2,3,3-tetramethylcyclopropyl)-1H-benzimidazole
  参考文献：
  名称：

  Synthesis of 2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazoles via the cyclopropyliminium rearrangement of substituted 2-cyclopropylbenzimidazoles

  摘要：

  2-Cyclopropylbenzimidazole derivatives with various substituents in the small ring undergo cyclopropyliminium rearrangement into 2,3-dihydropyrrolobenzimidazoles substituted at positions 1, 2 or 3. The substrates containing a functional group in position 1 of the cyclopropane ring form products substituted at position 3. Substituents at position 2 in most cases lead to the formation of a mixture of isomers. The reaction can be directed to yield one of the isomers predominantly by varying the solvent polarity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.02.021

文献信息

• Synthesis of 2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazoles via the cyclopropyliminium rearrangement of substituted 2-cyclopropylbenzimidazoles
  作者：Rinat F. Salikov、Dmitry N. Platonov、Aleksandr E. Frumkin、Dmitry L. Lipilin、Yury V. Tomilov

  DOI：10.1016/j.tet.2013.02.021

  日期：2013.4

  2-Cyclopropylbenzimidazole derivatives with various substituents in the small ring undergo cyclopropyliminium rearrangement into 2,3-dihydropyrrolobenzimidazoles substituted at positions 1, 2 or 3. The substrates containing a functional group in position 1 of the cyclopropane ring form products substituted at position 3. Substituents at position 2 in most cases lead to the formation of a mixture of isomers. The reaction can be directed to yield one of the isomers predominantly by varying the solvent polarity. (C) 2013 Elsevier Ltd. All rights reserved.