N,N'-bis(alanine-2-benzimidazolyl) hexanediamide | 790666-04-5

• 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: N,N'-bis(alanine-2-benzimidazolyl) hexanediamide
• 英文别名: N,N'-bis[1-(1H-benzimidazol-2-yl)ethyl]hexanediamide
• CAS: 790666-04-5
• 化学式: C₂₄H₂₈N₆O₂
• 分子量: 432.525
• InChiKey: WGSSGRYROQDGTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  32.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  115.56
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N,N'-bis(alanine-2-benzimidazolyl) hexanediamide 、 copper(II) nitrate trihydrate 以 甲醇 为溶剂， 生成 [Cu(NO3)(N,N'-bis(alanine-2-benzimidazolyl)hexanediamide)](NO3)*2H2O
  参考文献：
  名称：

  Synthesis, spectral and oxidase studies of a new diamide copper(II) complex with pendant benzimidazolyl groups

  摘要：

  A new benzimidazole-based diamide ligand-N,N '-bis(alanine-2-benzimidazolyl) hexanediamide (ABHA) has been synthesized and utilized to prepare Cu(II) complexes of general composition [Cu(ABHA)X-2](nH2O)-H-center dot, where X is an exogenous anionic ligand (X = Cl-, NO3-). Low temperature EPR spectra has been obtained that shows g(parallel to) > g(perpendicular to) > 2.0024, indicating a tetragonal geometry in the solution state. The complexes display a quasi-reversible redox wave due to the Cu(II)/Cu(I) reduction process. E-1/2 values shift anodically as NO3- < Cl-, indicating that the bound NO3 stabilizes the Cu(II) ion while the bonded Cl- destabilizes it. The complex [Cu(ABHA)Cl-2] has been found to oxidize dopamine to dopachrome or aminochrome, both in a methanolic and a reverse-miceller system. The oxidation of dopamine to aminochrome is reminiscent of the functioning of Prostglandin H-synthetase in brain cells which requires dopamine as a cofactor for catalytic activity. (c) 2006 Elsevier B.V.. All rights reserved.

  DOI：

  10.1016/j.saa.2006.03.002
• 作为产物：
  描述：

  1-(1H-benzimidazol-2-yl)-ethylamine; dihydrochloride 、 己二酸 在 亚磷酸三苯酯 作用下， 以 吡啶 为溶剂， 以31%的产率得到N,N'-bis(alanine-2-benzimidazolyl) hexanediamide
  参考文献：
  名称：

  Synthesis, spectral and oxidase studies of a new diamide copper(II) complex with pendant benzimidazolyl groups

  摘要：

  A new benzimidazole-based diamide ligand-N,N '-bis(alanine-2-benzimidazolyl) hexanediamide (ABHA) has been synthesized and utilized to prepare Cu(II) complexes of general composition [Cu(ABHA)X-2](nH2O)-H-center dot, where X is an exogenous anionic ligand (X = Cl-, NO3-). Low temperature EPR spectra has been obtained that shows g(parallel to) > g(perpendicular to) > 2.0024, indicating a tetragonal geometry in the solution state. The complexes display a quasi-reversible redox wave due to the Cu(II)/Cu(I) reduction process. E-1/2 values shift anodically as NO3- < Cl-, indicating that the bound NO3 stabilizes the Cu(II) ion while the bonded Cl- destabilizes it. The complex [Cu(ABHA)Cl-2] has been found to oxidize dopamine to dopachrome or aminochrome, both in a methanolic and a reverse-miceller system. The oxidation of dopamine to aminochrome is reminiscent of the functioning of Prostglandin H-synthetase in brain cells which requires dopamine as a cofactor for catalytic activity. (c) 2006 Elsevier B.V.. All rights reserved.

  DOI：

  10.1016/j.saa.2006.03.002