N-(6'-bromo-2'-pyridyl)-N'-(6''-benzylamino-2''-pyridyl)-2,6-diaminopyridine | 427900-22-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(6'-bromo-2'-pyridyl)-N'-(6''-benzylamino-2''-pyridyl)-2,6-diaminopyridine
• 英文别名: 2-N-benzyl-6-N-[6-[(6-bromopyridin-2-yl)amino]pyridin-2-yl]pyridine-2,6-diamine
• CAS: 427900-22-9
• 化学式: C₂₂H₁₉BrN₆
• 分子量: 447.337
• InChiKey: NZXPNIFZMFAPAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  74.8
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N²-benzylpyridine-2,6-diamine 、 N-(6'-bromo-2'-pyridyl)-N'-(6''-benzylamino-2''-pyridyl)-2,6-diaminopyridine 在 18-冠醚-6 tris(dibenzylideneacetone)dipalladium (0) 、 potassium tert-butylate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 苯 为溶剂， 反应 8.0h， 以64%的产率得到bis{6-[6'-((benzylamino)pyrid-2'-yl)amino]pyrid-2-yl}amine
  参考文献：
  名称：

  Self-Complementarity of Oligo-2-aminopyridines:  A New Class of Hydrogen-Bonded Ladders

  摘要：

  A new class of hydrogen-bonded ladders based on hydrogen-bonded dimerization of oligo-alpha-aminopryidines has been demonstrated. Jorgensen's model can be successfully applied to this hydrogen-bonding system in nonpolar solvents. The results show the competitive enthalpy/entropy compensation relationship upon dimerization, Although increasing the number of hydrogen-bonding interactions would enhance the hydrogen-bonding stabilization enthalpy, this stabilization enthalpy per unit would be partially sacrificed to compensate for the entropy loss due to dimerization. These results clearly support the importance of preorganization in designing hydrogen-bonding guest-host molecules.

  DOI：

  10.1021/ja011679p
• 作为产物：
  描述：

  2,6-二溴吡啶 在 18-冠醚-6 tris(dibenzylideneacetone)dipalladium (0) 、 potassium tert-butylate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 苯 为溶剂， 反应 8.0h， 生成 N-(6'-bromo-2'-pyridyl)-N'-(6''-benzylamino-2''-pyridyl)-2,6-diaminopyridine
  参考文献：
  名称：

  Self-Complementarity of Oligo-2-aminopyridines:  A New Class of Hydrogen-Bonded Ladders

  摘要：

  A new class of hydrogen-bonded ladders based on hydrogen-bonded dimerization of oligo-alpha-aminopryidines has been demonstrated. Jorgensen's model can be successfully applied to this hydrogen-bonding system in nonpolar solvents. The results show the competitive enthalpy/entropy compensation relationship upon dimerization, Although increasing the number of hydrogen-bonding interactions would enhance the hydrogen-bonding stabilization enthalpy, this stabilization enthalpy per unit would be partially sacrificed to compensate for the entropy loss due to dimerization. These results clearly support the importance of preorganization in designing hydrogen-bonding guest-host molecules.

  DOI：

  10.1021/ja011679p

文献信息

• Self-Complementarity of Oligo-2-aminopyridines:  A New Class of Hydrogen-Bonded Ladders
  作者：Man-kit Leung、Ashis B. Mandal、Chih-Chieh Wang、Gene-Hsiang Lee、Shie-Ming Peng、Hsing-Ling Cheng、Guor-Rong Her、Ito Chao、Hsiu-Feng Lu、Ying-Chieh Sun、Mei-Ying Shiao、Pi-Tai Chou

  DOI：10.1021/ja011679p

  日期：2002.4.1

  A new class of hydrogen-bonded ladders based on hydrogen-bonded dimerization of oligo-alpha-aminopryidines has been demonstrated. Jorgensen's model can be successfully applied to this hydrogen-bonding system in nonpolar solvents. The results show the competitive enthalpy/entropy compensation relationship upon dimerization, Although increasing the number of hydrogen-bonding interactions would enhance the hydrogen-bonding stabilization enthalpy, this stabilization enthalpy per unit would be partially sacrificed to compensate for the entropy loss due to dimerization. These results clearly support the importance of preorganization in designing hydrogen-bonding guest-host molecules.