1-benzyl-2-(3-chlorophenyl)-4,5-diphenyl-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: 1-benzyl-2-(3-chlorophenyl)-4,5-diphenyl-1H-imidazole
• 英文别名: 1-Benzyl-2-(3-chlorophenyl)-4,5-diphenylimidazole
• 化学式: C₂₈H₂₁ClN₂
• 分子量: 420.941
• InChiKey: CKMMXSAJIHVVKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  氯化苄 、 2-(3-chlorophenyl)-4,5-diphenyl-1H-imidazole 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以54%的产率得到1-benzyl-2-(3-chlorophenyl)-4,5-diphenyl-1H-imidazole
  参考文献：
  名称：

  Synthesis and analgesic activity of some 1-benzyl-2-substituted-4,5-diphenyl-1H-imidazole derivatives

  摘要：

  In this study, derivatives of 1-benzyl-2-substituted-4,5-diphenyl-1H-imidazole were synthesized and their analgesic activity assayed in two tests. 1,2,4,5-Tetrasubstituted imidazole compounds were obtained by the treatment of purified imidazole compounds with benzyl chloride in the presence of sodium hydride. The structure elucidation of the compounds was performed by IR, H-1-NMR and mass spectroscopic data and elemental analysis results. Generally the prepared compound exhibited only moderate analgesic activity in mice at the dose of 100 mg/kg i.p.; however, a few of them exhibited good activity, almost equivalent to that of morphine at 1 mg/kg i.p. was observed. At the above dosage, no toxicity was observed for all compounds. (C) 2001 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01076-x

文献信息

• γ-Alumina Nanoparticle Catalyzed Efficient Synthesis of Highly Substituted Imidazoles
  作者：Bandapalli Reddy、Vijayaparthasarathi Vijayakumar、Mariadhas Arasu、Naif Al-Dhabi

  DOI：10.3390/molecules201019221

  日期：——

  γ-Alumina nano particle catalyzed multi component reaction of benzil, arylaldehyde and aryl amines afforded the highly substituted 1,2,4,5-tetraaryl imidazoles with good to excellent yield in less reaction time under the sonication as well as the conventional methods. Convenient operational simplicity, mild conditions and the reusability of catalyst were the other advantages of this developed protocol

  γ-氧化铝纳米粒子催化的苯甲酰，芳基醛和芳基胺的多组分反应提供了高度取代的1,2,4,5-四芳基咪唑，在超声处理下以及常规方法中，在较短的反应时间内即可获得良好或优异的收率。便利的操作简便性，温和的条件和催化剂的可重复使用性是该开发方案的其他优点。
• Efficient Multi-component Synthesis of Highly Substituted Imidazoles Utilizing P2O5/SiO2 as a Reusable Catalyst
  作者：Hamid Reza Shaterian、Mohammad Ranjbar、Kobra Azizi

  DOI：10.1002/cjoc.201180293

  日期：2011.8

  gel (P2O5/SiO2) has been used as an efficient and reusable catalyst for the one‐pot pseudo four‐component synthesis of 2,4,5‐trisubstituted imidazoles from benzil or benzoin, aldehydes, and ammonium acetate. It was also used for four‐component preparation of 1,2,4,5‐tetrasubstituted imidazoles from benzil or benzoin, aldehydes, primary amine, and ammonium acetate under thermal solvent‐free conditions

  负载在硅胶（P 2 O 5 / SiO 2）上的五氧化二磷已被用作一种高效且可重复使用的催化剂，用于由苯甲腈或安息香，醛，和醋酸铵。它也可在无热溶剂的条件下用于由苄基或安息香，醛，伯胺和乙酸铵四组分制备1,2,4,5-四取代的咪唑。这种新方法的显着特征是高转化率，更清洁的反应，简单的实验和后处理程序，并且催化剂可以轻松地从反应混合物中分离出来并重复使用几次，而不会损失其活性。
• Synthesis of highly substituted imidazoles using Brønsted acidic ionic liquid, triphenyl(propyl-3-sulphonyl)phosphonium toluenesulfonate, as teusable catalyst
  作者：H. R. Shaterian、M. Ranjbar、K. Azizi

  DOI：10.1007/bf03246570

  日期：2011.12

  Brønsted acidic ionic liquid, triphenyl(propyl-3-sulphonyl)phosphonium toluenesulfonate, has been used as an efficient and reusable catalyst for the one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles under solvent-free conditions in excellent yields.

  布朗斯台德酸性离子液体三苯基（丙基-3-磺酰基）phosph磺酸甲苯磺酸盐已被用作一锅合成2,4,5-三取代和1,2,4,5-四取代的咪唑的有效且可重复使用的催化剂在无溶剂条件下，收率极高。
• Facile synthesis of imidazoles by an efficient and eco-friendly heterogeneous catalytic system constructed of Fe3O4 and Cu2O nanoparticles, and guarana as a natural basis
  作者：Zahra Varzi、Mir Saeed Esmaeili、Reza Taheri-Ledari、Ali Maleki

  DOI：10.1016/j.inoche.2021.108465

  日期：2021.3

  basis), magnetic iron oxide nanoparticles, and copper(I) oxide nanoparticles (Cu2O NPs) is fabricated and suitably applied for catalyzing the multicomponent (three- and four-component) synthesis reactions of imidazole derivatives. Here, an easy preparation strategy for this novel catalytic system (Cu2O/Fe3O4@guarana) is presented. Then, the application of this catalytic system for the synthesis of imidazole

  在这项研究中，由瓜尔胶（瓜尔那胶，作为自然基础），磁性氧化铁纳米颗粒和氧化铜（I）纳米颗粒（Cu 2 O NPs）制成的高效杂化纳米催化剂被制备并适用于催化多组分（三种）。 -和四组分）咪唑衍生物的合成反应。在这里，提出了一种简便的制备策略，用于这种新型的催化体系（Cu 2 O / Fe 3 O 4 @瓜拉那）。然后，精确研究了该催化体系在合成咪唑衍生物中的应用。为此目的，引入超声波处理是一种有效且快速的方法。综上所述，Cu 2 O / Fe 3 O 4的高催化效率通过在温和条件下在少量这种纳米复合材料的存在下获得的高反应产率，很好地证明了瓜拉纳纳米复合材料。宽的活性表面积，显着的磁性，出色的异质性，合适的稳定性，良好的可重复使用性等，已使该催化体系成为促进复杂合成反应的工具。
• (Carboxy-3-oxopropylamino)-3-propylsilylcellulose as a novel organocatalyst for the synthesis of substituted imidazoles under solvent-free conditions
  作者：Mehri Salimi、Mohammad Ali Nasseri、Tayyebeh Daliran Chapesshloo、Batol Zakerinasab

  DOI：10.1039/c5ra01909e

  日期：——

  organocatalyst, has been prepared by a synthesis grafting of –COOH functionalized organosilanes on a cellulose using surface hydroxyl groups as anchor points. The –CO2H group-functionalized cellulose was synthesized via the consecutive surface functionalization with 3-aminopropyltriethoxysilane (3-APTES) followed by the condensation of the surface –NH2 groups with succinic anhydride. COPAPSC is used as a catalyst

  （羧基-3-氧代丙基氨基）-3-丙基甲硅烷基纤维素（COPAPSC）是一种新型的有机催化剂，它是通过将-COOH官能化的有机硅烷合成接枝到纤维素上而使用表面羟基作为锚定点而制备的。通过用3-氨丙基三乙氧基硅烷（3-APTES）进行连续的表面官能化，然后缩合表面-NH 2，合成了–CO 2 H基团官能化的纤维素。与琥珀酸酐基团。COPAPSC用作催化剂，可在无溶剂条件下由苯甲腈，芳族醛，乙酸铵和胺反应合成三取代和四取代的咪唑。该方法的主要优点是高产率，易于后处理，通过非色谱法纯化产物和催化剂的可重复使用性。