tribenzylamine hemicryptophane | 1268451-56-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: tribenzylamine hemicryptophane
• 英文别名: 10,17,24-Trimethoxy-8,26,39-trioxa-1-azanonacyclo[16.14.7.312,25.23,6.228,31.234,37.19,13.015,20.022,45]nonatetraconta-3(49),4,6(48),9,11,13(47),15,17,19,22,24,28,30,34(41),35,37(40),42,44-octadecaene
• CAS: 1268451-56-4
• 化学式: C₄₈H₄₅NO₆
• 分子量: 731.888
• InChiKey: CPQQEGREZQMEJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  55
• 可旋转键数：
  3
• 环数：
  22.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  58.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-羟基-3-甲氧基苄醇 在 氨 、 potassium carbonate 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 甲醇 、 丙酮 、 乙腈 为溶剂， 反应 56.0h， 生成 tribenzylamine hemicryptophane
  参考文献：
  名称：

  Multiple Hindered Rotators in a Gyroscope-Inspired Tribenzylamine Hemicryptophane

  摘要：

  A gyroscope-inspired tribenzylamine hemicryptophane provides a vehicle for exploring the structure and properties of multiple p-phenylene rotators within one molecule. The hemicryptophane was synthesized in three steps in good overall yield using mild conditions. Three rotator-forming linkers were cyclized to form a rigid cyclotriveratrylene (CTV) stator framework, which was then closed with an amine. The gyroscope-like molecule was characterized by H-1 NMR and C-13 NMR spectroscopy, and the structure was solved by X-ray crystallography. The rigidity of the two-component CTV-trismethylamine stator was investigated by H-1 variable-temperature (VT) NMR experiments and molecular dynamics simulations. These techniques identified gyration of the three p-phenylene rotators on the millisecond time scale at -93 degrees C, with more dynamic but still hindered motion at room temperature (27 degrees C). The activation energy for the p-phenylene rotation was determined to be similar to 10 kcal mol(-1). Due to the propeller arrangement of the p-phenylenes, their rotation is hindered but not strongly correlated. The compact size, simple synthetic route, and molecular motions of this gyroscope-inspired tribenzylamine hemicryptophane make it an attractive starting point for controlling the direction and coupling of rotators within molecular systems.

  DOI：

  10.1021/jo102480s

文献信息

• Multiple Hindered Rotators in a Gyroscope-Inspired Tribenzylamine Hemicryptophane
  作者：Najat S. Khan、Jose Manuel Perez-Aguilar、Tara Kaufmann、P. Aru Hill、Olena Taratula、One-Sun Lee、Patrick J. Carroll、Jeffery G. Saven、Ivan J. Dmochowski

  DOI：10.1021/jo102480s

  日期：2011.3.4

  A gyroscope-inspired tribenzylamine hemicryptophane provides a vehicle for exploring the structure and properties of multiple p-phenylene rotators within one molecule. The hemicryptophane was synthesized in three steps in good overall yield using mild conditions. Three rotator-forming linkers were cyclized to form a rigid cyclotriveratrylene (CTV) stator framework, which was then closed with an amine. The gyroscope-like molecule was characterized by H-1 NMR and C-13 NMR spectroscopy, and the structure was solved by X-ray crystallography. The rigidity of the two-component CTV-trismethylamine stator was investigated by H-1 variable-temperature (VT) NMR experiments and molecular dynamics simulations. These techniques identified gyration of the three p-phenylene rotators on the millisecond time scale at -93 degrees C, with more dynamic but still hindered motion at room temperature (27 degrees C). The activation energy for the p-phenylene rotation was determined to be similar to 10 kcal mol(-1). Due to the propeller arrangement of the p-phenylenes, their rotation is hindered but not strongly correlated. The compact size, simple synthetic route, and molecular motions of this gyroscope-inspired tribenzylamine hemicryptophane make it an attractive starting point for controlling the direction and coupling of rotators within molecular systems.