N,N'-bis(glycine-2-benzimidazolyl)hexanediamide | 330945-64-7

• 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(glycine-2-benzimidazolyl)hexanediamide
• 英文别名: N,N'-bis(benzimidazol-2-ylmethyl)hexanediamide；N,N'-bis(2-methylbenzimidazolyl)hexanediamine；GBHA；N,N'-bis(1H-benzimidazol-2-ylmethyl)hexanediamide
• CAS: 330945-64-7
• 化学式: C₂₂H₂₄N₆O₂
• 分子量: 404.472
• InChiKey: KHQNBAPNDAMWHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氯甲基吡啶 、 N,N'-bis(glycine-2-benzimidazolyl)hexanediamide 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 N,N'-bis((N-picolylbenzimidazol-2-yl)methyl)hexanediamide
  参考文献：
  名称：

  Copper(II) complexes of a new N-picolylated bis benzimidazolyl diamide ligand: Synthesis, crystal structure and catechol oxidase studies

  摘要：

  Copper(II) complexes of a new bis benzimidazole diamide ligand N-picolyl-N,N'-bis(2-methylbenzimidazolyl) hexanediamide [Pic-GBHA = L(2)] have been synthesized and characterized. One of the compound [Cu(L(2))(NO(3))(2)] has been structurally characterized. The copper atom is bound to two benzimidazolyl nitrogen atoms, two amide carbonyl oxygen atoms and a bidentate nitrate ion, resulting in a distorted octahedral geometry. EPR spectra obtained at low temperature indicate a tetragonal geometry in the solution state. Complexes display a quasi-reversible redox wave due to the Cu(II)/Cu(I) reduction process having fairly cathodic E(1/2). These Cu(II) complexes were utilized to carry out oxidation of ditertbutylcatechol (DTBC) in methanol using molecular oxygen as the oxidant in. Low temperature EPR study of the oxidation reaction implicates the formation of an active copper species with fairly low A(parallel to) value. The presence of picolyl groups on the ligand also serve as a proton sponge giving 2-3 times higher rates of reaction in comparison to the non-picolylated ligand, implying a role of free basic groups in the pH control of enzymatic oxidation of catechols by catechol oxidase and tyrosinase. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.06.013

文献信息

• Synthesis, Crystal Structure, Spectral Studies, and Catechol Oxidase Activity of Trigonal Bipyramidal Cu(II) Complexes Derived from a Tetradentate Diamide Bisbenzimidazole Ligand
  作者：Manisha Gupta、Pavan Mathur、Ray J. Butcher

  DOI：10.1021/ic000313v

  日期：2001.2.1

  quasi-reversible redox wave due to the Cu(II)/Cu(I) reduction process. E(1/2) values shift anodically from Cl(-) < NO(3)(-) < SCN(-), indicating that the bound Cl(-) ion stabilizes the Cu(II) ion while the N-bonded SCN(-) ion destabilizes the Cu(II) state in the complex. When calculated against NHE, the redox potentials turn out to be quite positive as compared to other copper(II) benzimidazole bound complexes (Nakao

  合成了一种新的基于苯并咪唑的二酰胺配体-N，N'-双（甘氨酸-2-苯并咪唑基）己二酰胺（GBHA），并用于制备具有一般成分[Cu（GBHA）X] X的Cu（II）配合物，其中X是外源性阴离子配体（X = Cl（-），NO（3）（-），SCN（-））。获得了其中一种配合物[Cu（GBHA）Cl] Cl.H（2）O.CH（3）OH的X射线结构。该化合物在单斜晶空间群C2 / c中结晶，晶胞尺寸为a = 26.464（3）A，b = 10.2210（8）A，c = 20.444（2）A，alpha = 90度，beta = 106.554（7）度，伽玛= 90度，V = 5300.7（9）A（3），Z =8。据我们所知，[Cu（GBHA）Cl] Cl.H（2）O.CH（3） OH配合物是第一个具有配位酰胺羰基氧的结构特征的单核三角双锥体金字塔形铜（II）双苯并咪唑二酰胺配合物。Cu（II）离子周围的配位几何是扭曲的三角双锥体（tau
• Bakshi, Ruchi; Kumar, Ravinder; Mathur, Pavan, Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 2011, vol. 50, # 5, p. 658 - 663
  作者：Bakshi, Ruchi、Kumar, Ravinder、Mathur, Pavan

  DOI：——

  日期：——