6,7-dihydro-1,12-bis[4-(trifluoromethyl)triptycen-9-ylethynyl]-3,10-di-tertbutylbenzimidazo[2',1':3,4][1,4]diazino[1,2-a]benzimidazole | 1353014-70-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 6,7-dihydro-1,12-bis[4-(trifluoromethyl)triptycen-9-ylethynyl]-3,10-di-tertbutylbenzimidazo[2',1':3,4][1,4]diazino[1,2-a]benzimidazole
• 英文别名: 7,16-Ditert-butyl-5,18-bis[2-[6-(trifluoromethyl)-1-pentacyclo[6.6.6.02,7.09,14.015,20]icosa-2(7),3,5,9,11,13,15,17,19-nonaenyl]ethynyl]-3,10,13,20-tetrazapentacyclo[11.7.0.02,10.04,9.014,19]icosa-1(20),2,4,6,8,14,16,18-octaene；7,16-ditert-butyl-5,18-bis[2-[6-(trifluoromethyl)-1-pentacyclo[6.6.6.02,7.09,14.015,20]icosa-2(7),3,5,9,11,13,15,17,19-nonaenyl]ethynyl]-3,10,13,20-tetrazapentacyclo[11.7.0.02,10.04,9.014,19]icosa-1(20),2,4,6,8,14,16,18-octaene
• CAS: 1353014-70-6
• 化学式: C₇₀H₅₀F₆N₄
• 分子量: 1061.18
• InChiKey: IVALUQUXAKZGMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.3
• 重原子数：
  80
• 可旋转键数：
  6
• 环数：
  17.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  35.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  、 1-溴-2-氯乙烷 在 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以21 mg的产率得到6,7-dihydro-1,12-bis[4-(trifluoromethyl)triptycen-9-ylethynyl]-3,10-di-tertbutylbenzimidazo[2',1':3,4][1,4]diazino[1,2-a]benzimidazole
  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

文献信息

• Molecular Spur Gears Comprising Triptycene Rotators and Bibenzimidazole-Based Stators
  作者：Derik K. Frantz、Anthony Linden、Kim K. Baldridge、Jay S. Siegel

  DOI：10.1021/ja2063346

  日期：2012.1.25

  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.