2,6-bis(4,5-diphenyl-1H-imidazol-2-yl)-4-methylphenol | 1044511-65-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2,6-bis(4,5-diphenyl-1H-imidazol-2-yl)-4-methylphenol
• CAS: 1044511-65-0
• 化学式: C₃₇H₂₈N₄O
• 分子量: 544.656
• InChiKey: OQDZXWHBRMHGIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  42
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  77.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-bis(4,5-diphenyl-1H-imidazol-2-yl)-4-methylphenol 、 palladium diacetate 反应 12.0h， 以75%的产率得到bis[4-methyl-2,6-bis(4,5-diphenyl-1H-imidazol-2-yl)phenolato]palladium(II)
  参考文献：
  名称：

  Cyclometallation, steric and electronic tendencies in a series of Pd(II) complex pre-catalysts bearing imidazole–phenol ligands and effects on Suzuki–Miyaura catalytic efficiencies

  摘要：

  A series of new structurally and electronically diversified palladium complexes derived from seven less sterically crowded 2-(4,5-diinethyl-1H-imidazol-2-yl) pheno1/2-(4,5-diethyl-1H-imidazol-2-yl) phenol ligands and fourteen 2-(4,5-diphenyl-1H-imidazol-2-yl) phenols/2-(1H-phenanthro[9,10-d]imidazol-2-yl) phenols bearing varying degrees of higher steric bulk have been prepared and characterized. While single crystals grown from precipitated products of complexation reactions confirmed the bis-ligand Pd(NO)(2) coordination, few crystals obtained from reaction filtrates involving the 244,5-diphenyl-1H-imidazol-2-yl) phenols provided evidence for formation of N (O) over cap(C) over cap chelation species achieved by cyclometallation. Results from structural analyses and catalytic outcomes generally indicate that desirable variables on the ligand frameworks for obtaining superior catalyst activities either provides hemilabile or sterically strained chelation characters, which would both favour generation of monodentate coordination species at the catalysis temperature. In particular, correlation was observed between tendency for cyclometallation in the palladium complexes and poor Suzuki-Miyaura catalytic prospects. Based on hopeful activity obtained for the complex bearing 4-bromo-2-(4,5-dimethyl-1H-imidazol-2-yl) phenol, it was also concluded that sterically bulky ligand is not a necessity for high coupling efficiency, while presence of potentially cyclometallating substituent moieties in the vicinity of the palladium centre may in fact destroy catalytic prospects. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2015.06.001
• 作为产物：
  描述：

  2,6-二甲酰-4-甲基苯酚 、 联苯甲酰 在 C₉H₁₉N₂O₂⁽¹⁺⁾*C₂H₃O₂^(1-) 、 ammonium acetate 、 水 作用下， 以99%的产率得到2,6-bis(4,5-diphenyl-1H-imidazol-2-yl)-4-methylphenol
  参考文献：
  名称：

  在新型可重复使用的离子液体上合成单和双多取代咪唑的生态相容途径：一种高效且绿色的声化学工艺†

  摘要：

  成功合成了由 DABCO 组成的新型环保离子液体 (ILs)。这些离子液体被用作声化学一锅多组分合成路线的稳健催化剂，用于在水中以优异的收率实现官能化的环化咪唑。与传统程序相比，本协议在收益经济方面得分很高。当前绿色方法的优点包括简单、适用、广泛的官能团耐受性、干净的反应曲线和无需繁琐的后处理，并且可以提供高至定量的产率。从环境角度来看，这些环保的绿色催化剂可以毫不费力地回收和重复使用至少连续七次，而不会显着降低催化活性。

  DOI：

  10.1039/c8ra02755b