5,11,17-triamino-25,26,27,28-tetrakis(2-ethoxyethoxy)calix-[4]arene | 1365681-33-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5,11,17-triamino-25,26,27,28-tetrakis(2-ethoxyethoxy)calix-[4]arene
• CAS: 1365681-33-9
• 化学式: C₄₄H₅₉N₃O₈
• 分子量: 757.968
• InChiKey: JRKFWVVJXFBDLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.77
• 重原子数：
  55.0
• 可旋转键数：
  20.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  151.9
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  5,11,17-triamino-25,26,27,28-tetrakis(2-ethoxyethoxy)calix-[4]arene 、 N,N′-二-Boc-硫脲 在 三乙胺 、 mercury dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以50%的产率得到5,11,17-tris[(N,N'-di-Boc)guanidine]-25,26,27,28-tetrakis(2-ethoxyethoxy)calix[4]arene
  参考文献：
  名称：

  Upper Rim Guanidinocalix[4]arenes as Artificial Phosphodiesterases

  摘要：

  Calix[4]arene derivatives, blocked in the cone conformation and functionalized with two to four guanidinium units at the upper rim were synthesized and investigated as catalysts in the cleavage of the RNA model compound 2-hydroxypropyl p-nitrophenyl phosphate. When compared with the behavior of a monofunctional model compound, the catalytic superiority of the calix[4]arene derivatives points to a high level of cooperation between catalytic groups. Combination of acidity measurements with the pH dependence of catalytic rates unequivocally shows that a necessary requisite for effective catalysis is the simultaneous presence, on the same molecular framework, of a neutral guanidine acting as a general base and a protonated guanidine acting as an electrophilic activator. The additional guanidinium (guanidine) group in the diprotonated (monoprotonated) trifunctional calix[4]arene acts as a more or less innocent spectator. This is not the case with the tetrasubstituted calix[4]arene, whose mono-, di-, and triprotonated forms are slightly less effective than the corresponding di- and triguanidinocalix[4]arene derivatives, most likely on account of a steric interference with HPNP caused by overcrowding.

  DOI：

  10.1021/jo300193y
• 作为产物：
  描述：

  5,11,17-trinitro-25,26,27,28-tetrakis(2-ethoxyethoxy)calix-[4]arene 在 palladium on activated charcoal 、 一水合肼 作用下， 以 乙醇 为溶剂， 以70%的产率得到5,11,17-triamino-25,26,27,28-tetrakis(2-ethoxyethoxy)calix-[4]arene
  参考文献：
  名称：

  Upper Rim Guanidinocalix[4]arenes as Artificial Phosphodiesterases

  摘要：

  Calix[4]arene derivatives, blocked in the cone conformation and functionalized with two to four guanidinium units at the upper rim were synthesized and investigated as catalysts in the cleavage of the RNA model compound 2-hydroxypropyl p-nitrophenyl phosphate. When compared with the behavior of a monofunctional model compound, the catalytic superiority of the calix[4]arene derivatives points to a high level of cooperation between catalytic groups. Combination of acidity measurements with the pH dependence of catalytic rates unequivocally shows that a necessary requisite for effective catalysis is the simultaneous presence, on the same molecular framework, of a neutral guanidine acting as a general base and a protonated guanidine acting as an electrophilic activator. The additional guanidinium (guanidine) group in the diprotonated (monoprotonated) trifunctional calix[4]arene acts as a more or less innocent spectator. This is not the case with the tetrasubstituted calix[4]arene, whose mono-, di-, and triprotonated forms are slightly less effective than the corresponding di- and triguanidinocalix[4]arene derivatives, most likely on account of a steric interference with HPNP caused by overcrowding.

  DOI：

  10.1021/jo300193y