2-(4-methoxyphenyl)-1-methyl-4,5-diphenyl-1H-imidazole | 38696-81-0

• 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-(4-methoxyphenyl)-1-methyl-4,5-diphenyl-1H-imidazole
• 英文别名: 2-(4-Methoxyphenyl)-1-methyl-4,5-diphenylimidazole；2-(4-methoxyphenyl)-1-methyl-4,5-diphenylimidazole
• CAS: 38696-81-0
• 化学式: C₂₃H₂₀N₂O
• 分子量: 340.425
• InChiKey: SDZGYMUEWDNOJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

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 2-(4-methoxyphenyl)-1-methyl-4,5-diphenyl-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

• Synthesis and biological evaluation of 1,2,4,5-tetrasubstituted imidazoles
  作者：Yue Fang、Rui Yuan、Wen-hui Ge、Yuan-jiang Wang、Gui-xiang Liu、Ming-qi Li、Jiang-biao Xu、Yu Wan、Sheng-liang Zhou、Xi-guang Han、Peng Zhang、Jin-juan Liu、Hui Wu

  DOI：10.1007/s11164-017-2886-7

  日期：2017.8

  Tetrasubstituted imidazoles were synthesized in high yields via the four-component reaction of aromatic aldehydes, amines, substituted benzils and ammonium acetate catalyzed by a porous CeO2 nanorod. Their anti-cancer activities on the Huh-7 hepatocellular carcinoma cell and antibacterial activities on four bacterial species (wild-type Escherichia coli, wild-type Staphylococcus aureus, Pseudomonas

  通过多孔CeO 2纳米棒催化的芳族醛，胺，取代的苯甲酰胺和乙酸铵的四组分反应，高产率合成了四取代的咪唑。评估了它们对Huh-7肝癌细胞的抗癌活性以及对四种细菌种类（野生型大肠杆菌，野生型金黄色葡萄球菌，铜绿假单胞菌PAM1032和大肠杆菌-NMD-1）的抗菌活性。筛选出一种化合物（5p）是因为它对所有四种细菌的100μg/ mL的高抑制率。三种产品（5p，5t和5y）在10μg/ mL的浓度下对Huh-7肝癌细胞具有较高的抑制率。结果表明了它们在新药开发中的潜力。
• Acid-Catalyzed 1,3-Dipolar Cycloaddition of 2<i>H</i>-Azirines with Nitrones: An Unexpected Access to 1,2,4,5-Tetrasubstituted Imidazoles
  作者：Anikó Angyal、András Demjén、János Wölfling、László G. Puskás、Iván Kanizsai

  DOI：10.1021/acs.joc.9b03288

  日期：2020.3.6

  The first 1,3-dipolar cycloaddition of 2H-azirines with nitrones, a straightforward approach toward the regioselective synthesis of 1,2,4,5-tetrasubstituted imidazoles, is reported. This trifluoroacetic acid-catalyzed protocol tolerates a broad range of aliphatic and aromatic substrates, offering an efficient access to highly diverse, multisubstituted imidazoles in isolated yields up to 83% under mild

  据报道，2H-叠氮基与硝酮的第一个1,3-偶极环加成反应是对1,2,4,5-四取代的咪唑进行区域选择性合成的直接方法。该三氟乙酸催化的方案可耐受多种脂族和芳族底物，在温和条件下，分离出的收率高达83％，可高效获得高度多样化的多取代咪唑。
• 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.