6-(1-Ethyl-5-{1-ethyl-2-[6-(1-ethyl-5-(mercaptomethyl)-1H-benzoimidazol-2-yl)-pyridin-2-yl]-1H-benzoimidazol-5-ylmethyl}-1H-benzoimidazol-2-yl)-pyridine-2-carboxylic acid diethylamide | 1396893-65-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 6-(1-Ethyl-5-{1-ethyl-2-[6-(1-ethyl-5-(mercaptomethyl)-1H-benzoimidazol-2-yl)-pyridin-2-yl]-1H-benzoimidazol-5-ylmethyl}-1H-benzoimidazol-2-yl)-pyridine-2-carboxylic acid diethylamide
• CAS: 1396893-65-4
• 化学式: C₄₄H₄₅N₉OS
• 分子量: 747.967
• InChiKey: QVDCMSHRVKEACC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.09
• 重原子数：
  55.0
• 可旋转键数：
  12.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  99.55
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  6-(1-Ethyl-5-{1-ethyl-2-[6-(1-ethyl-5-(mercaptomethyl)-1H-benzoimidazol-2-yl)-pyridin-2-yl]-1H-benzoimidazol-5-ylmethyl}-1H-benzoimidazol-2-yl)-pyridine-2-carboxylic acid diethylamide 、 1,5-dichloro-3-(2-chloroethyl)-3-methylpentane 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以53%的产率得到6-[5-[[2-[6-[5-[[5-[[2-[6-[5-[[2-[6-(diethylcarbamoyl)pyridin-2-yl]-1-ethylbenzimidazol-5-yl]methyl]-1-ethylbenzimidazol-2-yl]pyridin-2-yl]-1-ethylbenzimidazol-5-yl]methylsulfanyl]-3-[2-[[2-[6-[5-[[2-[6-(diethylcarbamoyl)pyridin-2-yl]-1-ethylbenzimidazol-5-yl]methyl]-1-ethylbenzimidazol-2-yl]pyridin-2-yl]-1-ethylbenzimidazol-5-yl]methylsulfanyl]ethyl]-3-methylpentyl]sulfanylmethyl]-1-ethylbenzimidazol-2-yl]pyridin-2-yl]-1-ethylbenzimidazol-5-yl]methyl]-1-ethylbenzimidazol-2-yl]-N,N-diethylpyridine-2-carboxamide
  参考文献：
  名称：

  Allosteric Effects in Binuclear Homo- and Heterometallic Triple-Stranded Lanthanide Podates

  摘要：

  This work illustrates a simple approach for deciphering and exploiting the various free energy contributions to the global complexation process leading to the binuclear triple-stranded podates [Ln(2)(L9)](6+) (Ln is a trivalent lanthanide). Despite the larger microscopic affinities exhibited by the binding sites for small Ln(3+), the stability constants measured for [Ln(2)(L9)](6+) decrease along the lanthanide series; a phenomenon which can be ascribed to the severe enthalpic penalty accompanying the intramolecular cyclization around small Ln(III), combined with increasing anticooperative allosteric interligand interactions. Altogether, the microscopic thermodynamic characteristics predict beta(La,Lu,L9)(1,1,1)/beta(Lu,La,L9)(1,1,1) = 145 for the ratio of the formation constants of the target heterobimetallic [LaLu(L9)](6+) and [LuLa(L9)](6+) microspecies, a value in line with the quantitative preparation (>90%) of [LaLu(L9)](6+) at millimolar concentrations. Preliminary NMR titrations indeed confirm the rare thermodynamic programming of a pure heterometallic f-f' complex.

  DOI：

  10.1021/ic301631n
• 作为产物：
  描述：

  2,6-吡啶二羧酸单甲酯 在 盐酸 、 氯化亚砜 、 三氟化硼乙醚 、 乙酸酐 、 铁粉 、 N,N-二甲基甲酰胺 、 lithium hydroxide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 81.0h， 生成 6-(1-Ethyl-5-{1-ethyl-2-[6-(1-ethyl-5-(mercaptomethyl)-1H-benzoimidazol-2-yl)-pyridin-2-yl]-1H-benzoimidazol-5-ylmethyl}-1H-benzoimidazol-2-yl)-pyridine-2-carboxylic acid diethylamide
  参考文献：
  名称：

  Allosteric Effects in Binuclear Homo- and Heterometallic Triple-Stranded Lanthanide Podates

  摘要：

  This work illustrates a simple approach for deciphering and exploiting the various free energy contributions to the global complexation process leading to the binuclear triple-stranded podates [Ln(2)(L9)](6+) (Ln is a trivalent lanthanide). Despite the larger microscopic affinities exhibited by the binding sites for small Ln(3+), the stability constants measured for [Ln(2)(L9)](6+) decrease along the lanthanide series; a phenomenon which can be ascribed to the severe enthalpic penalty accompanying the intramolecular cyclization around small Ln(III), combined with increasing anticooperative allosteric interligand interactions. Altogether, the microscopic thermodynamic characteristics predict beta(La,Lu,L9)(1,1,1)/beta(Lu,La,L9)(1,1,1) = 145 for the ratio of the formation constants of the target heterobimetallic [LaLu(L9)](6+) and [LuLa(L9)](6+) microspecies, a value in line with the quantitative preparation (>90%) of [LaLu(L9)](6+) at millimolar concentrations. Preliminary NMR titrations indeed confirm the rare thermodynamic programming of a pure heterometallic f-f' complex.

  DOI：

  10.1021/ic301631n