{1-ethyl-2-[6-(1-ethyl-5-methyl-1H-benzoimidazol-2-yl)pyridin-2-yl]-1H-benzoimidazol-5-yl}methanethiol | 1006587-92-3

• 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: {1-ethyl-2-[6-(1-ethyl-5-methyl-1H-benzoimidazol-2-yl)pyridin-2-yl]-1H-benzoimidazol-5-yl}methanethiol
• CAS: 1006587-92-3
• 化学式: C₂₅H₂₅N₅S
• 分子量: 427.573
• InChiKey: RQSPJLRLXKCUQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.89
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  48.53
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  {1-ethyl-2-[6-(1-ethyl-5-methyl-1H-benzoimidazol-2-yl)pyridin-2-yl]-1H-benzoimidazol-5-yl}methanethiol 、 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77%的产率得到1-Ethyl-2-[6-[1-ethyl-5-[[5-[[1-ethyl-2-[6-(1-ethyl-5-methylbenzimidazol-2-yl)pyridin-2-yl]benzimidazol-5-yl]methylsulfanyl]-3-[2-[[1-ethyl-2-[6-(1-ethyl-5-methylbenzimidazol-2-yl)pyridin-2-yl]benzimidazol-5-yl]methylsulfanyl]ethyl]-3-methylpentyl]sulfanylmethyl]benzimidazol-2-yl]pyridin-2-yl]-5-methylbenzimidazole
  参考文献：
  名称：

  Effective Concentration as a Tool for Quantitatively Addressing Preorganization in Multicomponent Assemblies:  Application to the Selective Complexation of Lanthanide Cations

  摘要：

  The beneficial entropic effect, which may be expected from the connection of three tridentate binding units to a strain-free covalent tripod for complexing nine-coordinate cations (Mz(+) = Ca2+, La3+, Eu3+, Lu3+), is quantitatively analyzed by using a simple thermodynamic additive model. The switch from pure intermolecular binding processes, characterizing the formation of the triple-helical complexes [M(L2)(3)](z+), to a combination of inter- and intramolecular complexation events in [M(L8)](z+) shows that the ideal structural fit observed in [M(L8)](z+) indeed masks large energetic constraints. This limitation is evidenced by the faint effective concentrations, c(eff), which control the intramolecular ring-closing reactions operating in [M(L8)](z+). This predominence of the thermodynamic approach over the usual structural analysis agrees with the hierarchical relationships linking energetics and structures. Its simple estimation by using a single microscopic parameter, c(eff), opens novel perspectives for the molecular tuning of specific receptors for the recognition of large cations, a crucial point for the programming of heterometallic f-f complexes under thermodynamic control.

  DOI：

  10.1021/ja0772290
• 作为产物：
  描述：

  thioacetic acid S-{1-ethyl-2-[6-(1-ethyl-5-methyl-1H-benzoimidazol-2-yl)pyridin-2-yl]-1H-benzoimidazol-5-ylmethyl} ester 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以99%的产率得到{1-ethyl-2-[6-(1-ethyl-5-methyl-1H-benzoimidazol-2-yl)pyridin-2-yl]-1H-benzoimidazol-5-yl}methanethiol
  参考文献：
  名称：

  Effective Concentration as a Tool for Quantitatively Addressing Preorganization in Multicomponent Assemblies:  Application to the Selective Complexation of Lanthanide Cations

  摘要：

  The beneficial entropic effect, which may be expected from the connection of three tridentate binding units to a strain-free covalent tripod for complexing nine-coordinate cations (Mz(+) = Ca2+, La3+, Eu3+, Lu3+), is quantitatively analyzed by using a simple thermodynamic additive model. The switch from pure intermolecular binding processes, characterizing the formation of the triple-helical complexes [M(L2)(3)](z+), to a combination of inter- and intramolecular complexation events in [M(L8)](z+) shows that the ideal structural fit observed in [M(L8)](z+) indeed masks large energetic constraints. This limitation is evidenced by the faint effective concentrations, c(eff), which control the intramolecular ring-closing reactions operating in [M(L8)](z+). This predominence of the thermodynamic approach over the usual structural analysis agrees with the hierarchical relationships linking energetics and structures. Its simple estimation by using a single microscopic parameter, c(eff), opens novel perspectives for the molecular tuning of specific receptors for the recognition of large cations, a crucial point for the programming of heterometallic f-f complexes under thermodynamic control.

  DOI：

  10.1021/ja0772290