2-(4-methoxyphenyl)-1,4-diphenyl-1H-imidazole | 1602636-73-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-methoxyphenyl)-1,4-diphenyl-1H-imidazole
• 英文别名: 2-(4-Methoxyphenyl)-1,4-diphenyl-imidazole；2-(4-methoxyphenyl)-1,4-diphenylimidazole
• CAS: 1602636-73-6
• 化学式: C₂₂H₁₈N₂O
• 分子量: 326.398
• InChiKey: RAVXRELGFKHKBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  苯甲酰氯 在 potassium tert-butylate 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 14.0h， 生成 2-(4-methoxyphenyl)-1,4-diphenyl-1H-imidazole
  参考文献：
  名称：

  通过N-苯基苯甲酰胺和环氧化亚砜ox的酸催化合成咪唑衍生物

  摘要：

  在这项研究中报道了一种直接的方法，该方法由酸催化的am和sulf基磺酸盐合成咪唑衍生物。具体而言，在DCE溶剂中由三氟乙酸催化可提高无金属条件下的合成效率。生产了一系列咪唑支架，收率良好至优异。

  DOI：

  10.1016/j.tet.2019.04.004

文献信息

• One-Pot Protocol for the Synthesis of Imidazoles and Quinoxalines using<i>N</i>-Bromosuccinimide
  作者：Sachin D. Pardeshi、Pratima A. Sathe、Kamlesh S. Vadagaonkar、Atul C. Chaskar

  DOI：10.1002/adsc.201700900

  日期：2017.12.11

  N‐bromosuccinimide (NBS)‐mediated one‐pot, green, efficient and practical synthesis of substituted imidazoles and quinoxalines has been achieved by the reaction of styrenes with N‐arylbenzamidines and o‐phenylenediamines, respectively, in a water:1,4‐dioxane mixture. The reaction involves formation of an α‐bromo ketone as an intermediate in the presence of NBS and water, followed by condensation with

  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。
• Facile Synthesis of 1,2,4-trisubstituted Imidazoles via Aerobic Copper Catalyzed Ligand-free [3+2] Cycloaddition
  作者：Wei Li、Weixiang Tian、Ming Lei

  DOI：10.2174/1570178611666140207221202

  日期：2014.4

  A simple and facile approach to highly functionalized imidazole derivatives in moderate to good yields has been developed. This method involves copper catalyzed aerobic [3+2] cycloaddition of amidines with nitroolefins in absence of ligand. Based on observation of the intermediates, possible reaction mechanism different from the same reported approach was proposed.

  一种简单易行的方法被开发用于在中等到良好的产率下合成高度功能化的咪唑衍生物。该方法涉及在没有配体的情况下，铜催化的有氧[3+2]环加成反应，其中氨基脲与亚硝基烯反应。基于对中间体的观察，提出了一种不同于已有报道的方法的可能反应机制。
• 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。
• 10.1021/acs.orglett.4c01534
  作者：Li, Zhi、He, Zhengjun、Huang, Qiang、Kan, Mei、Li, Hongji

  DOI：10.1021/acs.orglett.4c01534

  日期：——

  amidines in the absence of any transition metal catalyst is first reported. This methodology involves sequential addition/cyclization that is perfectly tuned by stepwise addition of K2CO3, affording a plethora of valuable 1,2,4- and 1,2,5-trisubstituted imidazoles in good yields with high regioselectivity. Importantly, trapping and isolation of the reactive intermediate unveiled the reaction mechanism

  首次报道了在不存在任何过渡金属催化剂的情况下炔基锍盐与双亲核N-芳基脒的可调反应流形。该方法涉及顺序添加/环化，通过逐步添加K 2 CO 3进行完美调整，以良好的产率和高区域选择性提供大量有价值的1,2,4-和1,2,5-三取代咪唑。重要的是，反应中间体的捕获和分离揭示了[3 + 2]环加成反应中三键β-攻击的反应机制。
• Discovery of new leads against Mycobacterium tuberculosis using scaffold hopping and shape based similarity
  作者：Ravindra D. Wavhale、Elvis A.F. Martis、Premlata K. Ambre、Baojie Wan、Scott G. Franzblau、Krishna R. Iyer、Kavita Raikuvar、Katarzyna Macegoniuk、Łukasz Berlicki、Santosh R. Nandan、Evans C. Coutinho

  DOI：10.1016/j.bmc.2017.07.034

  日期：2017.9

  BM212 [1,5-diaryl-2-methyl-3-(4-methylpiperazin-1-yl)-methyl-pyrrole] is a pyrrole derivative with strong inhibitory activity against drug resistant Mycobacterium tuberculosis and mycobacteria residing in macrophages. However, it was not pursued because of its poor pharmacokinetics and toxicity profile. Our goal was to design and synthesize new antimycobacterial BM212 analogs with lower toxicity and better pharmacokinetic profile. Using the scaffold hopping approach, three structurally diverse heterocycles - 2,3-disubstituted imidazopyridines, 2,3-disubstituted benzimidazoles and 1,2,4-trisubstituted imidazoles emerged as promising antitubercular agents. All compounds were synthesized through easy and convenient methods and their structures confirmed by IR, H-1 NMR, C-11 NMR and MS. In-vitro cytotoxicity studies on normal kidney monkey cell lines and HepG2 cell lines, as well as metabolic stability studies on rat liver microsomes for some of the most active compounds, established that these compounds have negligible cytotoxicity and are metabolically stable. Interestingly the benzimidazole compound (4a) is as potent as the parent molecule BM212 (MIC 2.3 mu g/ml vs 0.7-1.5 mu g/ml), but is devoid of the toxicity against HepG2 cell lines (IC50 203.10 mu M vs 7.8 mu M). (C) 2017 Elsevier Ltd. All rights reserved.