4,4'-dibromo-6,6'-di-tert-butyl-2,2'-bibenzimidazole | 1353014-51-3

• 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: 4,4'-dibromo-6,6'-di-tert-butyl-2,2'-bibenzimidazole
• CAS: 1353014-51-3
• 化学式: C₂₂H₂₄Br₂N₄
• 分子量: 504.267
• InChiKey: HBPCMVSEKKORHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.23
• 重原子数：
  28.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  57.36
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4,4'-dibromo-6,6'-di-tert-butyl-2,2'-bibenzimidazole 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 30.25h， 生成 1,1,1'-bis(tert-butoxycarbonyl)-4,4'-bis(triptycen-9-ylethynyl)-6,6'-di-tert-butyl-2,2'-bibenzimidazole
  参考文献：
  名称：

  Molecular Spur Gears Comprising Triptycene Rotators and Bibenzimidazole-Based Stators

  摘要：

  Dynamic gearing of molecular spur gears, the most common type of mechanical gear, is elucidated. Molecular design and conformational analysis show that derivatives of 4,4-bis(triptycen-9-ylethynyl)bibenzimidazole represent suitable constructs to investigate gearing behavior of collateral triptycene (Tp) groups. To test this design, DFT calculations (B97-D/Def2-TZVP) were employed and the results suggest that these molecules undergo geared rotation preferentially to gear slippage. Synthesis of derivatives was carried out, providing a series of molecular spur gears, including the first desymmetrized spur gear molecules, which were subsequently subjected to stereochemical analysis.

  DOI：

  10.1021/ja2063346
• 作为产物：
  描述：

  4-叔丁基乙酰苯胺 在 盐酸 、 溴 、 硝酸 、 乙酸酐 、 溶剂黄146 、 tin(ll) chloride 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 3.75h， 生成 4,4'-dibromo-6,6'-di-tert-butyl-2,2'-bibenzimidazole
  参考文献：
  名称：

  Molecular Spur Gears Comprising Triptycene Rotators and Bibenzimidazole-Based Stators

  摘要：

  Dynamic gearing of molecular spur gears, the most common type of mechanical gear, is elucidated. Molecular design and conformational analysis show that derivatives of 4,4-bis(triptycen-9-ylethynyl)bibenzimidazole represent suitable constructs to investigate gearing behavior of collateral triptycene (Tp) groups. To test this design, DFT calculations (B97-D/Def2-TZVP) were employed and the results suggest that these molecules undergo geared rotation preferentially to gear slippage. Synthesis of derivatives was carried out, providing a series of molecular spur gears, including the first desymmetrized spur gear molecules, which were subsequently subjected to stereochemical analysis.

  DOI：

  10.1021/ja2063346