7-benzyl-3,11-di-tert-butyl-1,13-bis(triptycen-9-ylethynyl)-6H-benzamidazo[2',1':3,4]pyrrolo[3',4':5,6]pyrazino[1,2-a]benzimidazole-6,8(7H)-dione | 1353014-57-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 7-benzyl-3,11-di-tert-butyl-1,13-bis(triptycen-9-ylethynyl)-6H-benzamidazo[2',1':3,4]pyrrolo[3',4':5,6]pyrazino[1,2-a]benzimidazole-6,8(7H)-dione
• CAS: 1353014-57-9
• 化学式: C₇₇H₅₅N₅O₂
• 分子量: 1082.32
• InChiKey: ACJXEUMXQQWYGC-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C
• 密度：
  1.29±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.43
• 重原子数：
  84.0
• 可旋转键数：
  2.0
• 环数：
  19.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  73.67
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  7-benzyl-1,13-dibromo-3,11-di-tert-butyl-6H-benzamidazo[2',1':3,4]pyrrolo[3',4':5,6]-pyrazino[1,2-a]benzimidazole-6,8(7H)-dione 、 9-ethynyltriptycene 在 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以52%的产率得到7-benzyl-3,11-di-tert-butyl-1,13-bis(triptycen-9-ylethynyl)-6H-benzamidazo[2',1':3,4]pyrrolo[3',4':5,6]pyrazino[1,2-a]benzimidazole-6,8(7H)-dione
  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