1-methyl-2,4,5-tris(4-methoxyphenyl)-1H-imidazole | 1278587-19-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-methyl-2,4,5-tris(4-methoxyphenyl)-1H-imidazole
• 英文别名: 2,4,5-tris(4-methoxyphenyl)-1-methyl-1H-imidazole；2,4,5-Tris(4-methoxyphenyl)-1-methylimidazole
• CAS: 1278587-19-1
• 化学式: C₂₅H₂₄N₂O₃
• 分子量: 400.477
• InChiKey: NEISFNRJQKFMMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对甲苯甲醚 在 2,6-二甲基吡啶 、 sodium dihydrogenphosphate 、 ammonium acetate 、 lithium perchlorate 、 2-(4-bromophenyl)-1-methyl-4,5-diphenyl-1H-imidazole 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 1-methyl-2,4,5-tris(4-methoxyphenyl)-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

• Direct Arylation of Simple Azoles Catalyzed by 1,10-Phenanthroline Containing Palladium Complexes: An Investigation of C4 Arylation of Azoles and the Synthesis of Triarylated Azoles by Sequential Arylation
  作者：Fumitoshi Shibahara、Eiji Yamaguchi、Toshiaki Murai

  DOI：10.1021/jo200067y

  日期：2011.4.15

  amounts of azoles, selective C5 monoarylation was achieved by using the same catalytic system. Subsequent efforts demonstrated that C5 arylated azoles undergo exclusive C2 arylation using [Pd(phen)2]PF6 as the catalyst with galvinoxyl as an additive. Finally, unprecedented C4 arylation reactions of 2,5-diaryl-azoles occur by using the new catalytic system to give the corresponding triarylated products in

  描述了由[Pd（phen）2 ] PF 6催化的简单唑的直接三芳基化和顺序三芳基化反应。在[Pd（phen）2 ] PF 6作为催化剂和化学计量的存在下，当使用芳基碘化物处理时，即使是简单的唑类，例如N-甲基咪唑，噻唑和恶唑，即使在其C4位上也发生三芳基化反应。150°C下DMA中Cs 2 CO 3的摩尔数。使用过量的唑类，使用相同的催化系统可实现选择性的C5单芳基化。随后的研究表明，C5芳基化的吡咯使用[Pd（phen）2 ] PF 6进行排他的C2芳基化作为催化剂，加尔维诺尔为添加剂。最后，通过使用新的催化体系，发生了前所未有的2,5-二芳基-唑的C4芳基化反应，从而以良好或优异的收率得到了相应的三芳基化产物。机理研究的结果表明，芳基化C2过程由电芳族取代（S的方式发生ë AR）palladation通路，而在C4位的芳基化反应经由A S发生ë氩palladation和/或自由基机理。
• 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.
• Novel Triarylimidazole Redox Catalysts: Synthesis, Electrochemical Properties, and Applicability to Electrooxidative C–H Activation
  作者：Cheng-chu Zeng、Ni-tao Zhang、Chiu Marco Lam、R. Daniel Little

  DOI：10.1021/ol300195c

  日期：2012.3.2

  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.