1-benzyl-2-(3-methoxyphenyl)-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-methoxyphenyl)-4,5-diphenyl-1H-imidazole
• 英文别名: 1-benzyl-2-(3-methoxyphenyl)-4,5-diphenylimidazole
• 化学式: C₂₉H₂₄N₂O
• 分子量: 416.522
• InChiKey: YVXOTSGFXCKEIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  氯化苄 、 2-(3-methoxyphenyl)-4,5-diphenyl-1H-imidazole 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以42%的产率得到1-benzyl-2-(3-methoxyphenyl)-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

• 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。
• Facile preparation of a nanostructured functionalized catalytically active organosalt
  作者：Ahmad Reza Moosavi-Zare、Mohammad Ali Zolfigol、Vahid Khakyzadeh、Christoph Böttcher、Mohammad Hassan Beyzavi、Abdolkarim Zare、Alireza Hasaninejad、Rafael Luque

  DOI：10.1039/c3ta13484a

  日期：——

  and highly crystalline as supported by TEM, ED and XRD studies, having an average nanoparticle size of 50 nm according to TEM micrographs. The novel nano-organocatalyst was proved to be an efficient catalyst in the synthesis of 1,2,4,5-tetrasubstituted imidazoles by a one-pot multi-component condensation of benzil, a broad range of aldehydes, primary amines and ammonium acetate at 90 °C under solvent-free

  我们报告了一种基于磺酸功能化吡嗪鎓[H-吡嗪–SO 3 H] Cl 2 }的新型纳米结构有机盐，该盐通过多种技术合成并表征，包括傅里叶变换红外（FT-IR）光谱，X射线衍射（ XRD），热重分析（TGA），差示热重分析（DTG），透射电子显微镜（TEM），质谱（MS），质子NMR（1 H NMR），碳13 NMR（13C NMR）以及电子衍射（ED）图谱。结果证明，由TEM，ED和XRD研究证实，史无前例的磺化吡嗪鎓有机盐确实是纳米结构且高度结晶，根据TEM显微照片，其平均纳米粒径为50 nm。新型纳米有机催化剂被证明是通过苯的一锅多组分缩合反应，广泛的醛，伯胺和乙酸铵在1,2,4,5-四取代的咪唑合成中的有效催化剂。在无溶剂条件下为90°C。
• Glutamic Acid as an Efficient and Green Catalyst for the One-Pot Synthesis of 1,2,4,5-Tetrasubstituted Imidazoles under Thermal, Solvent-Free Conditions
  作者：Fahimeh Khazaee Feizabad、Khatereh Khandan-Barani、Alireza Hassanabadi

  DOI：10.3184/174751917x15105690662854

  日期：2017.11

  A high-yielding synthesis of 1,2,4,5-tetrasubstituted imidazoles is described, involving the reaction of 1,2-dicarbonyl compounds, aryl aldehydes, amines and ammonium acetate in the presence of a catalytic amount of glutamic acid under thermal, solvent-free conditions. The salient features of this protocol are aerobic conditions, a non-hazardous green catalyst, short reaction times and mild reaction

  描述了 1,2,4,5-四取代咪唑的高产合成，包括 1,2-二羰基化合物、芳基醛、胺和乙酸铵在催化量的谷氨酸存在下，在加热下反应，无溶剂条件。该协议的显着特点是有氧条件、无害的绿色催化剂、反应时间短和反应条件温和。