2-benzyl-4,5-diphenyl-1H-imidazole | 56796-43-1

• 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-benzyl-4,5-diphenyl-1H-imidazole
• 英文别名: 2-Benzyl-4,5-diphenylimidazole
• CAS: 56796-43-1
• 化学式: C₂₂H₁₈N₂
• 分子量: 310.398
• InChiKey: ZXOIVAXCYUMPLN-UHFFFAOYSA-N

物化性质

• 熔点：
  239-240 °C
• 沸点：
  544.2±29.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 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：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  8-溴辛酸乙酯 、 2-benzyl-4,5-diphenyl-1H-imidazole 在 silica gel 、 二氯甲烷 、 乙醇 、 正己烷 作用下， 200.0 ℃ 、1.78 kPa 条件下， 以gave 2-benzyl-1-(7-ethoxycarbonylheptyl)-4,5-diphenylimidazole (2.69 g, 52.6%) as a white solid, m.p. 82°-3°的产率得到2-benzyl-1-(7-ethoxycarbonylheptyl)-4,5-diphenylimidazole
  参考文献：
  名称：

  Inhibition of inflammatory lipid mediators

  摘要：

  需要Coenzyme A独立的转酰基酶来释放游离的花生四烯酸，并产生花生四烯酸代谢产物和血小板激活因子。阻断这种酶的作用可以抑制这些炎症介质的产生，在广泛的过敏和炎症性疾病和障碍的治疗中具有治疗用途。本文描述了抑制CoA-IT作用的化合物，因此在治疗由此引起的疾病状态中有用。

  公开号：

  US05663053A1
• 作为产物：
  描述：

  N-(2-氧代-1,2-二苯基乙基)-2-苯基乙酰胺 在 乙酸铵 、 溶剂黄146 作用下， 生成 2-benzyl-4,5-diphenyl-1H-imidazole
  参考文献：
  名称：

  Acetic Acid—Ammonium Acetate Reactions. 2-Isoimidazoles as Intermediates in Imidazole Formation¹

  摘要：

  DOI：

  10.1021/ja01140a063

文献信息

• Synthesis of 2,4,5-trisubstituted imidazoles catalyzed by [Hmim]HSO₄ as a powerful Brönsted acidic ionic liquid
  作者：Ahmad R Khosropour

  DOI：10.1139/v08-009

  日期：2008.3.1

  An efficient and green procedure for the synthesis of 2,4,5-trisubstituted imidazoles with various aldehydes using a catalytic amount of 1-methylimidazolium hydrogenesulfate as an active and low cost Brönsted acidic room temperature ionic liquid has been developed. The ionic liquid was easily separated from the reaction mixture and was recycled five times without any loss in activity.Key words: ionic liquid, 2,4,5-trisubstituted imidazoles, [Hmim]HSO₄, aldehyde, benzil.

  利用催化量的 1-甲基咪唑硫酸氢盐作为活性低、成本低的勃氏酸性室温离子液体，开发了一种高效、绿色的 2,4,5-三取代咪唑与各种醛的合成方法。该离子液体很容易从反应混合物中分离出来，并且可以循环使用五次，活性没有任何损失。关键词：离子液体、2,4,5-三取代咪唑、[Hmim]HSO4、醛、苯齐尔。
• An efficient and one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles catalyzed by InCl3·3H2O
  作者：Saikat Das Sharma、Parasa Hazarika、Dilip Konwar

  DOI：10.1016/j.tetlet.2008.02.053

  日期：2008.3

  InCl3·3H2O was found to be a mild and effective catalyst for the efficient, one-pot, three component synthesis of 2,4,5-trisubstituted imidazoles at room temperature. Moreover, the utility of this protocol was further explored conveniently for the one-pot, four component synthesis of 1,2,4,5-tetrasubstituted imidazoles in high yields.

  发现InCl 3 ·3H 2 O是在室温下高效，一锅，三组分合成2,4,5-三取代的咪唑的温和有效的催化剂。此外，可以方便地进一步探索该方案的实用性，以高产率一锅，四组分合成1,2,4,5-四取代的咪唑。
• CoA-IT and PAF inhibitors
  申请人：SmithKline Beecham Corporation

  公开号：US05648373A1

  公开（公告）日：1997-07-15

  Coenzyme A-independent transacylase is required for the release of free arachidonic acid, and the production of arachidonic acid metabolites and platelet activation factor. Blocking of this enzyme inhibits the production of these inflammatory mediators and will be of therapeutic utility in a broad range of allergic and inflammatory diseases and disorders. Compounds are described herein which inhibit the action of CoA-IT and are therefore useful in the treatment of disease states caused thereby.

  无需辅酶A的转酰基酶在释放游离花生四烯酸、产生花生四烯酸代谢产物和血小板活化因子时起作用。阻断该酶会抑制这些炎症介质的产生，在广泛的过敏和炎症性疾病和障碍中具有治疗效用。本文描述的化合物可以抑制CoA-IT的作用，因此在治疗由此引起的疾病状态中是有用的。
• Highly efficient one-pot synthesis of trisubstituted imidazoles under catalyst-free conditions
  作者：Najmadin Azizi、Nairreh Dado、Alireza Khajeh Amiri

  DOI：10.1139/v11-141

  日期：2012.2

  Operationally simple, atom economical, and scalable synthesis of 2,4,5-trisubstituted imidazoles from benzil, aldehydes, and ammonium acetate is shown to proceed readily in methanol with high yield. The scope of the reaction is quite broad; a variety of aromatic and aliphatic activated and unactivated aldehydes have all been shown to be viable substrates for this reaction. Excellent yields and purity were obtained by washing the products with hot ethanol.

  操作简单，原子经济，可扩展的合成2,4,5-三取代咪唑的方法从苯二酮、醛和醋酸铵开始，在甲醇中迅速进行，产率高。该反应的范围非常广泛；各种芳香族和脂肪族活化和未活化的醛都被证明是这种反应的可行底物。通过用热乙醇洗涤产物，得到了优异的产率和纯度。
• TMSOTf-catalyzed synthesis of trisubstituted imidazoles using hexamethyldisilazane as a nitrogen source under neat and microwave irradiation conditions
  作者：Kesatebrhan Haile Asressu、Chieh-Kai Chan、Cheng-Chung Wang

  DOI：10.1039/d1ra05802a

  日期：——

  In the process of drug discovery and development, an efficient and expedient synthetic method for imidazole-based small molecules from commercially available and cheap starting materials has great significance. Herein, we developed a TMSOTf-catalyzed synthesis of trisubstituted imidazoles through the reaction of 1,2-diketones and aldehydes using hexamethyldisilazane as a nitrogen source under microwave

  在药物发现和开发过程中，一种高效便捷的以市售廉价起始原料合成咪唑基小分子的方法具有重要意义。在此，我们利用六甲基二硅氮烷作为氮源，在微波加热和无溶剂条件下，通过 1,2-二酮和醛的反应开发了 TMSOTf 催化合成三取代咪唑。使用 X 射线单晶衍射分析证实了代表性三取代咪唑的化学结构。这种合成方法有几个优点，包括温和的路易斯酸的参与，不含金属和添加剂，底物范围广，收率好至极好，反应时间短。此外，