α,α'-bis([(1-methyl-2-benzimidazolyl)methyl][2-(1-methyl-2-benzimidazolyl)ethyl]amino)-m-xylene | 184959-17-9

• 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: α,α'-bis([(1-methyl-2-benzimidazolyl)methyl][2-(1-methyl-2-benzimidazolyl)ethyl]amino)-m-xylene
• 英文别名: 2-(1-methylbenzimidazol-2-yl)-N-[[3-[[2-(1-methylbenzimidazol-2-yl)ethyl-[(1-methylbenzimidazol-2-yl)methyl]amino]methyl]phenyl]methyl]-N-[(1-methylbenzimidazol-2-yl)methyl]ethanamine
• CAS: 184959-17-9
• 化学式: C₄₆H₄₈N₁₀
• 分子量: 740.954
• InChiKey: AZIMGKTYIRMFGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  56
• 可旋转键数：
  14
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  77.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tetrakis(acetonitrile)copper(I) perchlorate 、 α,α'-bis([(1-methyl-2-benzimidazolyl)methyl][2-(1-methyl-2-benzimidazolyl)ethyl]amino)-m-xylene 以 乙腈 为溶剂， 生成 [Cu2(α,α'-bis([(1-methyl-2-benzimidazolyl)methyl][2-(1-methyl-2-benzimidazolyl)ethyl]amino)-m-xylene)](ClO4)2
  参考文献：
  名称：

  Functional Modeling of Tyrosinase. Mechanism of Phenol ortho-Hydroxylation by Dinuclear Copper Complexes

  摘要：

  The copper-mediated oxygenation of methyl 4-hydroxybenzoate (1) in acetonitrile has been investigated by employing a series of dinuclear copper(I) complexes with polybenzimidazole ligands. The reaction mimics the activity of the copper enzyme tyrosinase, since the initial product of the reaction is the o-catechol, methyl 3, 4-dihydroxybenzoate (2). The ligand systems investigated include alpha, alpha'-bis{bis[2-(1-methyl-2-benzimidazolyl)-ethyl]amino}-m-xylene (L-66) alpha, alpha'-bis{bis[2-(1-methyl-2-benzimidazolyl)methyl]amino}-m-xylene (L-55), alpha, alpha'-bis{[(1-methyl-2-benzimidazolyl)methyl][2-(1-methyl-2-benzimidazolyl)ethyl]amino}-m-xylene (L-56), and alpha, alpha'-bis{[(2-pyridyl)methyl][2-(1-methyl-2-benzimidazolyl)ethyl]amino}-m-xylene (L-5p6). The most effective among the dicopper(I) complexes is that derived from L-66, while its mononuclear Cu(I) analogue, with the ligand N, N-bis[2-(1-methyl-2-benzimidazolyl)ethyl]amine is inactive in the monooxygenase reaction. The catechol 2 is the only product of phenol hydroxylation when the reaction is carried out at low temperature (-40 degrees C). As the temperature is increased, methyl 2-[4-(carbomethoxy)phenoxy]-3, 4-dihydroxybenzoate (4), formally resulting from Michael addition of the starting phenol to 4-carbomethoxy-1, 2-benzoquinone (3) and probably resulting from the reaction between free phenolate and some intermediate copper-catecholate species, becomes a major product of the reaction. In order to gain insight into the mechanism of the reaction, the dicopper(I)-phenolate adducts and dicopper(II)-catecholate adducts of the L-66, L-55, and L-6 complexes have been studied, In a few cases the adducts containing catecholate monoanion or catecholate dianion have been isolated and spectrally characterized. It has been shown that the final product of the monooxygenase reaction corresponds to the dicopper(II)-catecholate dianion complex. A mechanism for the biomimetic phenol ortho-hydroxylation has been proposed and its possible relevance for tyrosinase discussed.

  DOI：

  10.1021/ic9601100