1-benzyl-2-(3,4-dimethoxyphenyl)-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-(3,4-dimethoxyphenyl)-4,5-diphenyl-1H-imidazole
• 英文别名: 1-Benzyl-2-(3,4-dimethoxyphenyl)-4,5-diphenylimidazole
• 化学式: C₃₀H₂₆N₂O₂
• 分子量: 446.549
• InChiKey: NMKATEPLVXEJQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  氯化苄 、 2-(3,4-二甲氧基苯基)-4,5-二苯基-1H-咪唑 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以42%的产率得到1-benzyl-2-(3,4-dimethoxyphenyl)-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。
• Green synthesis of tri/tetrasubstituted 1H-imidazoles and 2,3-dihydroquinazolin-4(1H)-ones using nano aluminium nitride as solid source of ammonia
  作者：MARYAM HAJJAMI、ARASH GHORBANI-CHOGHAMARANI、ZAKIEH YOUSOFVAND、MASOOMEH NOROUZI

  DOI：10.1007/s12039-015-0890-2

  日期：2015.7

  A simple, green and cost-effective protocol was achieved for the synthesis of tri/tetrasubstituted-1H-imidazoles and 2,3-dihydroquinazolin-4(1H)-ones using nano aluminium nitride. The reaction was carried out under catalyst-free conditions and the products were isolated in good to excellent yield.

  采用纳米氮化铝实现了一种简单、绿色且经济高效的合成三/四取代-1H-咪唑和2,3-二氢喹唑啉-4(1H)-酮的新方法。反应在无催化剂的条件下进行，产物的收率良好到优秀。
• Copper(I) complex of 1,3-DimethylBarbituric acid modified SBA-15 and its catalytic role for the synthesis of 2,3-Dihydroquinazolin-4(1H)-ones and Imidazoles
  作者：Maryam Hajjami、Farshid Ghorbani、Zakieh Yousofvand

  DOI：10.1002/aoc.3843

  日期：2017.12

  An efficient one‐pot method for synthesis of 2,3‐dihydroquinazolin‐4(1H)‐ones and tri/tetra substituted‐1H‐imidazoles has been accomplished in the presence of catalytic amounts of Cu(I)‐1,3‐dimethylbarbituric acid modified SBA‐15 as heterogeneous catalyst with good to excellent yields. The catalyst is reusable and can be applied several times without any decrease in product yield. The synthesized catalyst

  在催化量的Cu（I）-1,3-二甲基巴比妥酸存在下，已经完成了一种高效的一锅法合成2,3-二氢喹唑啉-4（1H）-酮和三/四取代-1H-咪唑的方法。酸改性的SBA-15作为非均相催化剂，具有良好或优异的收率。该催化剂是可重复使用的，并且可以多次使用而不会降低产品收率。通过扫描电子显微镜（SEM），X射线衍射（XRD），能量色散X射线光谱（EDS），热重分析（TGA），N 2吸附/解吸等温线（BET），傅里叶变换对催化剂进行表征红外光谱（FT-IR）和原子吸收光谱（AAS）。
• β–Cyclodextrin–Propyl Sulfonic Acid Catalysed One-Pot Synthesis of 1,2,4,5-Tetrasubstituted Imidazoles as Local Anesthetic Agents
  作者：Yan Ran、Ming Li、Zong-Ze Zhang

  DOI：10.3390/molecules201119696

  日期：——

  local anesthetic effect of these derivatives was assessed in comparison to lidocaine as a standard using a rabbit corneal and mouse tail anesthesia model. The three most potent promising compounds were subjected to a rat sciatic nerve block assay where they showed considerable local anesthetic activity, along with minimal toxicity. Among the tested analogues, 4-(1-benzyl-4,5-diphenyl-1H-imidazol-2-yl)-N

  使用一锅，四组分反应合成了一些官能化的1,2,4,5-四取代的咪唑衍生物，该反应涉及1,2-二酮，芳基醛，乙酸铵和取代的芳族胺。使用β-环糊精-丙基磺酸作为催化剂，在无溶剂介质中有效地进行了合成，从而以优异的收率得到了目标化合物。使用兔角膜和小鼠尾巴麻醉模型，与利多卡因作为标准品相比，评估了这些衍生物的局部麻醉作用。对三种最有希望的化合物进行了大鼠坐骨神经阻滞试验，结果显示它们具有相当大的局部麻醉活性，并且毒性最小。在测试的类似物中，4-（1-苄基-4,5-二苯基-1H-咪唑-2-基）-N，N-二甲基苯胺（5g）被确定为最有效的类似物，毒性最小。其特征还在于比标准更有利的治疗指数。