2-phenyl-4-(3-(trifluoromethyl)phenyl)-1H-imidazole

• 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-phenyl-4-(3-(trifluoromethyl)phenyl)-1H-imidazole
• 英文别名: 2-phenyl-4-[3-(trifluoromethyl)phenyl]-1H-imidazole；2-phenyl-4(5)-(3-trifluoromethylphenyl)imidazole；2-phenyl-5-[3-(trifluoromethyl)phenyl]-1H-imidazole
• 化学式: C₁₆H₁₁F₃N₂
• 分子量: 288.272
• InChiKey: FFLKPRMUNQCFGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-phenyl-4-(3-(trifluoromethyl)phenyl)-1H-imidazole 在 盐酸 作用下， 以 乙醚 、 乙醇 为溶剂， 生成 2-phenyl-4-[3-(trifluoromethyl)phenyl]imidazole
  参考文献：
  名称：

  Anticonvulsant activity of 2,4(1H)-diarylimidazoles in mice and rats acute seizure models

  摘要：

  2,4(1H)-Diarylimidazoles have been previously shown to inhibit hNaV1.2 sodium (Na) channel currents. Since many of the clinically used anticonvulsants are known to inhibit Na channels as an important mechanism of their action, these compounds were tested in two acute rodent seizure models for anticonvulsant activity (MES and scMet) and for sedative and ataxic side effects. Compounds exhibiting antiepileptic activity were further tested to establish a dose response curve (ED(50)). The experimental data identified four compounds with anticonvulsant activity in the MES acute seizure rodent model (compound 10, ED(50) = 61.7 mg/kg; compound 13, ED(50) = 46.8 mg/kg, compound 17, ED(50) = 129.5 mg/kg and compound 20, ED(50) = 136.7 mg/kg). Protective indexes (PI = TD(50)/ED(50)) ranged from 2.1 (compound 10) to greater than 3.6 (compounds 13, 17 and 20). All four compounds were shown to inhibit hNaV1.2 in a dose dependant manner. Even if a correlation between sodium channel inhibition and anticonvulsant activity was unclear, these studies identify four Na channel antagonists with anticonvulsant activity, providing evidence that these derivatives could be potential drug candidates for development as safe, new and effective antiepileptic drugs (AEDs). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.029
• 作为产物：
  描述：

  间三氟甲基苯乙烯 、 苯甲脒 在 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 以71%的产率得到2-phenyl-4-(3-(trifluoromethyl)phenyl)-1H-imidazole
  参考文献：
  名称：

  使用N-溴代琥珀酰亚胺合成咪唑和喹喔啉的一锅方案

  摘要：

  N-溴代琥珀酰亚胺（NBS）介导的苯乙烯，N-芳基苯甲m和邻苯二胺的单锅，绿色，高效，实用合成取代咪唑和喹喔啉已在水中：1,4-二恶烷混合物。该反应包括在NBS和水存在下形成α-溴代酮作为中间体，然后与N-芳基苯甲m和邻苯二酚缩合。苯二胺。使用廉价的NBS作为溴源以及氧化剂，水作为溶剂和易于获得的起始原料，可以使该方案在环境上无害且在经济上可行。得到的咪唑和喹喔啉取代基的收率好至极好，并具有广泛的官能团相容性。

  DOI：

  10.1002/adsc.201700900

文献信息

• Copper-Catalyzed Simultaneous Activation of C–H and N–H Bonds: Three-Component One-Pot Cascade Synthesis of Multi­substituted Imidazoles
  作者：Lucio Melone、Atul Chaskar、Sachin Pardeshi、Pratima Sathe、Kamlesh Vadagaonkar

  DOI：10.1055/s-0036-1588585

  日期：2018.1

  § Authors contributed equally to this work. Abstract A copper-catalyzed expedient, practical, and straightforward approach for the one-pot three-component modular synthesis of multisubstituted imidazoles has been described by using arylacetic acids, N-arylbenzamidines, and nitroalkanes. The reaction involves simultaneous activation of C–H and N–H bonds of arylacetic acids and N-arylbenzamidines, respectively

  §作者对此工作做出了同等贡献。 抽象的 已经通过使用芳基丙烯酸，N-芳基苯甲m和硝基烷烃描述了铜催化的方便，实用和直接的方法用于多取代的咪唑的一锅三组分模块化合成。该反应涉及同时活化芳基丙烯酸和N-芳基苯甲C的CH键和NH键。使用廉价的硫酸铜作为催化剂，容易获得的起始原料以及无硅藻土的处理，使得该方案在经济上可行。多取代的咪唑以中等至良好的产率获得，具有显着的官能团耐受性和高区域选择性。 已经通过使用芳基丙烯酸，N-芳基苯甲m和硝基烷烃描述了铜催化的方便，实用和直接的方法用于多取代的咪唑的一锅三组分模块化合成。该反应涉及同时活化芳基丙烯酸和N-芳基苯甲C的CH键和NH键。使用廉价的硫酸铜作为催化剂，容易获得的起始原料以及无硅藻土的处理，使得该方案在经济上可行。多取代的咪唑以中等至良好的产率获得，具有显着的官能团耐受性和高区域选择性。
• A Practical Synthesis of 2,4(5)-Diarylimidazoles from Simple Building Blocks
  作者：Valentina Zuliani、Giuseppe Cocconcelli、Marco Fantini、Chiara Ghiron、Mirko Rivara

  DOI：10.1021/jo070187d

  日期：2007.6.1

  A simple and efficient approach to selectively obtain 2,4(5)-diarylimidazoles suppressing formation of 2-aroyl-4(5)-arylimidazoles is described. The yield of each of the two products strongly depends on the reaction conditions employed. This reaction provides a simple method to prepare small libraries of biologically active compounds by parallel synthesis.