hexamethyl 2,2',2'',2''',2'''',2'''''-[ 1,1′,1′′-(pyridine-2,4,6-triyl)tris(1H-pyrazole-3,1-diyl)]tris(methylene)tris(azanetriyl)hexaacetate | 1439863-85-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: hexamethyl 2,2',2'',2''',2'''',2'''''-[ 1,1′,1′′-(pyridine-2,4,6-triyl)tris(1H-pyrazole-3,1-diyl)]tris(methylene)tris(azanetriyl)hexaacetate
• 英文别名: Methyl 2-[[1-[2,6-bis[3-[[bis(2-methoxy-2-oxoethyl)amino]methyl]pyrazol-1-yl]pyridin-4-yl]pyrazol-3-yl]methyl-(2-methoxy-2-oxoethyl)amino]acetate
• CAS: 1439863-85-0
• 化学式: C₃₅H₄₄N₁₀O₁₂
• 分子量: 796.794
• InChiKey: PHPFJKDBSYHUEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  57
• 可旋转键数：
  27
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  234
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  hexamethyl 2,2',2'',2''',2'''',2'''''-[ 1,1′,1′′-(pyridine-2,4,6-triyl)tris(1H-pyrazole-3,1-diyl)]tris(methylene)tris(azanetriyl)hexaacetate 在 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以78%的产率得到sodium 2,2',2'',2''',2'''',2'''''-[ 1,1′,1′′-(pyridine-2,4,6-triyl)tris(1H-pyrazole-3,1-diyl)]tris(methylene)tris(azanetriyl)hexaacetate
  参考文献：
  名称：

  Nucleophilic Substitution on Polyfluorinated Pyridine and Pyrimidine Rings for Construction of Lanthanide Ligands

  摘要：

  The use of nucleophilic substitution of fluoride attached to azaaromatics has been used to provide polypyrazolyl-substituted pyridine and pyrimidine ligands of potential value as lanthanide ion complexants. Ester substituents on the pyrazolyl groups can be reduced to the corresponding alcohol, which can in turn be converted to the bromide, then reacted with diethyl iminodiacetate to provide highly functionalized derivatives. Base hydrolysis converts these to polyanionic ligands, although the overall process is only efficient in the case of a pyridine core. The pyridine ligand with three pyrazolate and thus six carboxylate substituents forms stable, water-soluble Eu(III) and Tb(III) complexes displaying interesting spectroscopic properties with excited state lifetimes of about 1.6 ms and 1.0 ms, respectively, and quantum yields in the 4.5% to 13% range in water. Uncoordinated carboxylate groups in these complexes can be used for their grafting to polyacrylate polymer beads.

  DOI：

  10.1055/s-0032-1318219
• 作为产物：
  描述：

  triethyl 1,1′,1′′-(pyridine-2,4,6-triyl)tris(1H-pyrazole-3-carboxylate) 在 lithium aluminium tetrahydride 、 五溴化磷 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 36.0h， 生成 hexamethyl 2,2',2'',2''',2'''',2'''''-[ 1,1′,1′′-(pyridine-2,4,6-triyl)tris(1H-pyrazole-3,1-diyl)]tris(methylene)tris(azanetriyl)hexaacetate
  参考文献：
  名称：

  Nucleophilic Substitution on Polyfluorinated Pyridine and Pyrimidine Rings for Construction of Lanthanide Ligands

  摘要：

  The use of nucleophilic substitution of fluoride attached to azaaromatics has been used to provide polypyrazolyl-substituted pyridine and pyrimidine ligands of potential value as lanthanide ion complexants. Ester substituents on the pyrazolyl groups can be reduced to the corresponding alcohol, which can in turn be converted to the bromide, then reacted with diethyl iminodiacetate to provide highly functionalized derivatives. Base hydrolysis converts these to polyanionic ligands, although the overall process is only efficient in the case of a pyridine core. The pyridine ligand with three pyrazolate and thus six carboxylate substituents forms stable, water-soluble Eu(III) and Tb(III) complexes displaying interesting spectroscopic properties with excited state lifetimes of about 1.6 ms and 1.0 ms, respectively, and quantum yields in the 4.5% to 13% range in water. Uncoordinated carboxylate groups in these complexes can be used for their grafting to polyacrylate polymer beads.

  DOI：

  10.1055/s-0032-1318219