2-(2,2-dimethylcyclopropyl)-1H-benzimidazole | 1428555-68-3

• 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-dimethylcyclopropyl)-1H-benzimidazole
• 英文别名: 2-(2,2-dimethylcyclopropyl)-1H-benzo[d]imidazole
• CAS: 1428555-68-3
• 化学式: C₁₂H₁₄N₂
• 分子量: 186.257
• InChiKey: YYFBAFUYBVBGAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 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-dimethylcyclopropyl)-1H-benzimidazole 在 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 2-[2,2-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopropyl]-1-methyl-1H-benzo[d]imidazole
  参考文献：
  名称：

  立体选择性C ？二氧化硅负载的单膦-Ir催化剂对环丙烷和环戊二烯的氢硼化作用

  摘要：

  杂原子-定向Ç  ħ环丙烷和环丁烷用二氧化硅负载monophosphane-IR催化剂实现的硼基化。硼化发生在C 位于H键γ到具有卓越的定向N或O原子的顺式相对于所述定位基团的立体选择性。该协议被加到叔C的硼化一个稠环环丙烷的H键。

  DOI：

  10.1002/chem.201404362
• 作为产物：
  描述：

  2,2-二甲基环丙烯羧酸 在 吡啶 、 氯化亚砜 、 三乙胺 作用下， 以 乙醚 、 溶剂黄146 、 乙腈 为溶剂， 反应 6.0h， 生成 2-(2,2-dimethylcyclopropyl)-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.
• Stereoselective CH Borylations of Cyclopropanes and Cyclobutanes with Silica-Supported Monophosphane-Ir Catalysts
  作者：Ryo Murakami、Kiyoshi Tsunoda、Tomohiro Iwai、Masaya Sawamura

  DOI：10.1002/chem.201404362

  日期：2014.10.6

  Heteroatom‐directed CH borylation of cyclopropanes and cyclobutanes was achieved with silica‐supported monophosphane–Ir catalysts. Borylation occurred at the CH bonds located γ to the directing N or O atoms with exceptional cis stereoselectivity relative to the directing groups. This protocol was applied to the borylation of a tertiary CH bond of a ring‐fused cyclopropane.

  杂原子-定向Ç  ħ环丙烷和环丁烷用二氧化硅负载monophosphane-IR催化剂实现的硼基化。硼化发生在C 位于H键γ到具有卓越的定向N或O原子的顺式相对于所述定位基团的立体选择性。该协议被加到叔C的硼化一个稠环环丙烷的H键。