2-(3,5-dimethoxyphenyl)-4,5-diphenyl-1H-imidazole | 1262023-44-8

• 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-(3,5-dimethoxyphenyl)-4,5-diphenyl-1H-imidazole
• CAS: 1262023-44-8
• 化学式: C₂₃H₂₀N₂O₂
• 分子量: 356.424
• InChiKey: BYHDPACSNXFGPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  47.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,5-二甲氧基苯甲醛 、 联苯甲酰 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 3.5h， 以98%的产率得到2-(3,5-dimethoxyphenyl)-4,5-diphenyl-1H-imidazole
  参考文献：
  名称：

  Fe₃O₄@chitosan nanoparticles: a valuable heterogeneous nanocatalyst for the synthesis of 2,4,5-trisubstituted imidazoles

  摘要：

  壳聚糖包被的Fe3O4纳米颗粒（Fe3O4@CS）通过在壳聚糖水溶液中通过NH4OH的原位共沉淀Fe2+和Fe3+离子简单制备而成，其催化活性在苯二酮衍生物、芳基醛和醋酸铵在乙醇中的一锅缩合合成2,4,5-三取代咪唑中进行了研究。

  DOI：

  10.1039/c4ra03176h

文献信息

• Zinc (II) [tetra(4-methylphenyl)] Porphyrin: a Novel and Reusable Catalyst for Efficient Synthesis of 2,4,5-trisubstituted Imidazoles Under Ultrasound Irradiation
  作者：Javad Safari、Shiva Dehghan Khalili、Sayed Hossein Banitaba、Hossein Dehghani

  DOI：10.5012/jkcs.2011.55.5.787

  日期：2011.10.20

  An efficient three-component one-step synthesis of 2,4,5-trisubstituted imidazoles by condensation reaction of 1,2-diketones or α-hydroxyketones with aromatic aldehydes and ammonium acetate using Zinc (II) (tetra (4-methylphenyl)) porphyrin as a novel and reusable catalyst under ultrasound irradiation at ambient temperature is described. In this method, α-hydroxyketones as well as 1,2-diketones were

  使用锌（II）（四（4-甲基苯基））使1,2-二酮或α-羟基酮与芳族醛和乙酸铵缩合反应，可有效地三步合成2,4,5-三取代的咪唑描述了在室温下超声辐射下卟啉作为新型可重复使用的催化剂。在这种方法中，α-羟基酮以及1,2-二酮以优异的产率转化为它们相应的2,4,5-三取代的咪唑。
• Catalytic activity of Cu nanoparticles supported on Fe₃O₄–polyethylene glycol nanocomposites for the synthesis of substituted imidazoles
  作者：Zohre Zarnegar、Javad Safari

  DOI：10.1039/c4nj00645c

  日期：——

  In the present study, we carried out chemical synthesis and characterization for a Fe3O4–polyethylene glycol–Cu nanocomposite (Fe3O4–PEG–Cu). Firstly, poly(ethylene glycol) was functionalized using cyanuric chloride (PEG-Cl4). Then PEG-Cl4 was linked with Fe3O4 nanoparticles via formation of covalent bonds (Fe3O4–PEG). The Cu nanoparticles were supported by reducing copper ammonia complexes with hydrazine hydrate on the surface of this nanocomposite. Nanoparticles have been characterized by FT-IR, XRD, SEM, EDAX, TGA-DTA, AAS and VSM techniques. The catalytic activity of the Fe3O4–PEG–Cu catalyst was evaluated for the synthesis of highly substituted imidazoles. This new catalyst was found to be a highly active and green catalyst for the synthesis of 2,4,5-trisubstituted imidazoles and 1,2,4,5-substituted imidazoles. The synthesized catalysts displayed magnetic properties, which allowed their fast separation from the reaction medium using a simple magnet.

  在本研究中，我们进行了Fe3O4-聚乙烯醇-Cu纳米复合材料（ -PEG-Cu）的化学合成和表征。首先，聚乙烯醇通过氰尿酸氯化物（PEG-Cl4）进行了功能化。然后，PEG-Cl4通过形成共价键与 纳米粒子连接（ -PEG）。铜纳米粒子通过在该纳米复合材料表面用肼水合物还原氨铜络合物来支持。纳米粒子通过FT-IR、XRD、SEM、EDAX、TGA-DTA、AAS和VSM技术进行表征。 -PEG-Cu催化剂的催化活性在合成高度取代的咪唑时进行了评估。发现这款新催化剂在合成2,4,5-三取代咪唑和1,2,4,5-取代咪唑方面表现出很高的活性且环保。合成的催化剂显示出磁性特性，这使得它们能够通过简单的磁铁快速从反应介质中分离出来。
• Identification and Mechanistic Evaluation of Hemozoin-Inhibiting Triarylimidazoles Active against <i>Plasmodium falciparum</i>
  作者：Kathryn J. Wicht、Jill M. Combrinck、Peter J. Smith、Roger Hunter、Timothy J. Egan

  DOI：10.1021/acsmedchemlett.6b00416

  日期：2017.2.9

  In a previous study, target based screening was carried out for inhibitors of β-hematin (synthetic hemozoin) formation, and a series of triarylimidazoles were identified as active against Plasmodium falciparum. Here, we report the subsequent synthesis and testing of derivatives with varying substituents on the three phenyl rings for this series. The results indicated that a 2-hydroxy-1,3-dimethoxy

  在先前的研究中，针对β-血凝素（合成血红蛋白）形成的抑制剂进行了基于靶点的筛选，并且鉴定出了一系列三芳基咪唑对恶性疟原虫具有活性。在这里，我们报告了该系列三个苯环上具有不同取代基的衍生物的后续合成和测试。结果表明，亚微摩尔寄生虫活性需要环A上的2-羟基-1,3-二甲氧基取代模式。此外，细胞分离研究显示，恶性疟原虫细胞内可交换（游离）血红素异常大，剂量依赖性增加，这与β-血红素抑制衍生物的寄生虫存活率降低有关。
• Nanocrystalline magnesium oxide: a novel and efficient catalyst for facile synthesis of 2,4,5-trisubstituted imidazole derivatives
  作者：Javad Safari、Shiva Dehghan Khalili、Mehran Rezaei、Sayed Hossein Banitaba、Fereshteh Meshkani

  DOI：10.1007/s00706-010-0397-y

  日期：2010.12

  area has been used as a novel and efficient catalyst for an improved and rapid synthesis of biologically active 2,4,5-trisubstituted imidazoles, by three-component, one-pot condensation of 1,2-diketones and aryl aldehydes, in excellent yields under solvent-free and conventional heating conditions. The method has several advantages, for example excellent yields, shorter reaction time, and use of a non-toxic

  摘要具有高比表面积的纳米晶氧化镁已被用作新型，有效的催化剂，用于通过三组分一锅缩合的1,2-二酮来改进和快速合成具有生物活性的2,4,5-三取代的咪唑和芳基醛，在无溶剂和常规加热条件下，收率极高。该方法具有多个优点，例如优异的产率，较短的反应时间以及使用无毒且可回收的催化剂。 图形概要
• 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，