2-(4-bromophenyl)-4,5-bis(4-methoxyphenyl)-1-methyl-1H-imidazole | 1360596-77-5

• 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-(4-bromophenyl)-4,5-bis(4-methoxyphenyl)-1-methyl-1H-imidazole
• 英文别名: 2-(4-Bromophenyl)-4,5-bis(4-methoxyphenyl)-1-methylimidazole；2-(4-bromophenyl)-4,5-bis(4-methoxyphenyl)-1-methylimidazole
• CAS: 1360596-77-5
• 化学式: C₂₄H₂₁BrN₂O₂
• 分子量: 449.347
• InChiKey: BYHXZELWCXGRBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对溴苯甲醛 、 4,4'-二甲氧基苯酚酯 、 甲胺 在 sodium dihydrogenphosphate 、 ammonium acetate 作用下， 以87%的产率得到2-(4-bromophenyl)-4,5-bis(4-methoxyphenyl)-1-methyl-1H-imidazole
  参考文献：
  名称：

  Novel Triarylimidazole Redox Catalysts: Synthesis, Electrochemical Properties, and Applicability to Electrooxidative C–H Activation

  摘要：

  A new class of metal-free, easy to synthesize redox catalysts based on a triarylimidazole framework is described. With those synthesized thus far, one can access a potential range of ca. 410 mV. They proved to be useful mediators for the activation of benzylic C-H bonds under mild conditions.

  DOI：

  10.1021/ol300195c

文献信息

• Triarylimidazole Redox Catalysts: Electrochemical Analysis and Empirical Correlations
  作者：Ni-tao Zhang、Cheng-chu Zeng、Chiu Marco Lam、Randi K. Gbur、R. Daniel Little

  DOI：10.1021/jo302309m

  日期：2013.3.1

  A series of triarylimidazoles was synthesized and characterized electrochemically. The synthetic route is general, providing a pathway to 30 redox mediators that exhibit a > 700 mV range of accessible potentials. Most of the triarylimidazoles display three oxidation peaks where the first redox couple is quasi-reversible. The electronic character of the substituents affects the oxidation potential. This is exemplified by a linear correlation between the first oxidation potential and the sum of the Hammett sigma(+) substituent constants, as well as with a series of calculated ionization potentials. We close by putting forward a rule of thumb stating that for a given mediator, the upper limit of accessible potentials can be extended by at least 500 mV beyond the largest recorded value. A rationale, the conditions under which the rule is likely to apply, and an example are provided.