1-benzyl-2-(4-bromophenyl)-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-(4-bromophenyl)-4,5-diphenyl-1H-imidazole
• 英文别名: 1-Benzyl-2-(4-bromophenyl)-4,5-diphenylimidazole
• 化学式: C₂₈H₂₁BrN₂
• 分子量: 465.392
• InChiKey: DKUYAKCRFVTQTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 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-(4-bromophenyl)-4,5-diphenyl-1H-imidazole 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以64%的产率得到1-benzyl-2-(4-bromophenyl)-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

• An Effective and New Method for the Synthesis of Polysubstituted Imidazoles by the Use of CrCl₃.6H₂O as a Green and Reusable Catalyst: Synthasis of Some Novel Imidazole Derivatives
  作者：Bahador Karami、Khalil Eskandari、Mahnaz Farahi、Akram Barmas

  DOI：10.1002/jccs.201100555

  日期：2012.4

  environmentally adapted synthesis of polysubstituted imidazoles in one‐pot is found. The multicomponent reaction of various aldehydes, benzil, aliphatic and aromatic primary amines and ammonium acetate under solvent‐free condition is explained. The highly efficient role of CrCl3.6H2O as catalyst in this synthesis was shown. By this advantage, several polysubstituted imidazoles as pharmaceutical important

  发现了一种新的，高效且环保的单锅合成多取代咪唑的方法。解释了在无溶剂条件下各种醛，苄基，脂肪族和芳香族伯胺与乙酸铵的多组分反应。显示了CrCl 3 .6H 2 O在该合成中作为催化剂的高效作用。利用这一优点，可以高产率和高纯度制备几种作为药物重要分子的多取代的咪唑。该方法是合成咪唑衍生物的非常容易且快速的反应。粗产物重结晶，得到结晶纯产物。此外，催化剂表现出显着的可重复使用活性。
• One-Pot Synthesis of Polysubstituted Imidazoles Based on Pd(OAc)2/Ce(SO4)2/Bi(NO3)3 Trimetallic Cascade of Decarboxylation/Wacker-Type Oxidation/Debus–Radziszewski Reaction
  作者：Wei Sun、Mingjuan Zhang、Peilang Li、Yiqun Li

  DOI：10.1055/s-0037-1611835

  日期：2019.9

  Abstract A novel and highly efficient one-pot synthesis of polysubstituted imidazoles from α-hydroxyphenylacetic acids, diphenylacetylene, and amines has been achieved by Pd(OAc)2/Ce(SO4)2/Bi(NO3)3 trimetallic catalytic system. A series of control experiments showed that this overall reaction occurs through a one-pot cascade process combining the steps of decarboxylation of α-hydroxyphenylacetic acids

  抽象的 通过Pd（OAc）2 / Ce（SO 4）2 / Bi（NO 3）3从α-羟基苯基乙酸，二苯乙炔和胺中合成新颖高效的一锅合成咪唑三金属催化体系。一系列对照实验表明，整个反应是通过一锅级联过程完成的，该过程结合了α-羟基苯基乙酸的脱羧步骤，二苯基乙炔的Wacker型氧化步骤以及原位生成的芳基醛和苯的Debus-Radziszewski环合反应，以及胺。该反应代表使用α-羟基苯基乙酸和二苯乙炔作为芳基醛和β-二酮的来源的新颖的多组分反应。该方法具有宽泛的底物范围和良好的官能团耐受性，可在温和条件下以优异的收率（72–88％）组装相应的多取代的咪唑。 通过Pd（OAc）2 / Ce（SO 4）2 / Bi（NO 3）3从α-羟基苯基乙酸，二苯乙炔和胺中合成新颖高效的一锅合成咪唑三金属催化体系。一系列对照实验表明，整个反应是通过一锅级联过程完成的，该过程结合了α-羟基苯基乙酸的脱羧步骤，二
• Facile and rapid synthesis of some novel polysubstituted imidazoles by employing magnetic Fe_3O_4 nanoparticles as a high efficient catalyst
  作者：BAHADOR KARAMI、KHALIL ESKANDARI、ABDOLMOHAMMAD GHASEMI

  DOI：10.3906/kim-1112-49

  日期：——

  Multicomponent, one-pot, highly efficient, and environmentally adapted synthesis of some novel polysubstituted imidazoles by the use of various aldehydes, benzil, aliphatic, and aromatic primary amines and ammonium acetate in the presence of Fe_3O_4 nanoparticles as catalyst under solvent-free condition is explained. A highly efficient role of Fe_3O_4 nanoparticles as catalyst in this synthesis was shown. By this advantage, several polysubstituted imidazoles as pharmaceutical important molecules can be prepared in high yield and high purity. This method is very easy and rapid for the synthesis of imidazole derivatives. All products were deduced from their IR and NMR spectroscopic data. The Fe_3O_4 nanoparticles were characterized by powdered X-ray diffraction (XRD), transmission electron microscopy (TEM), and FT-IR spectroscopy.

  本文阐述了在无溶剂条件下，利用多种醛、苯偶酰、脂肪族和芳香族一级胺以及乙酸铵作为原料，通过Fe_3O_4纳米颗粒作为催化剂，实现多组分、一锅法、高效且环境适应性的新型多取代咪唑合成方法。研究表明，Fe_3O_4纳米颗粒在这一合成过程中表现出高效的催化作用。利用这一优势，可以高产率和高纯度地制备出若干具有重要药学意义的多取代咪唑分子。该方法操作简便、反应迅速，适用于咪唑衍生物的合成。所有产物均通过其红外光谱和核磁共振光谱数据得以推导。Fe_3O_4纳米颗粒则通过粉末X射线衍射（XRD）、透射电子显微镜（TEM）以及傅里叶变换红外光谱（FT-IR）进行表征。
• New Conditions for the Effective Synthesis of Tri and Tetrasubstituted Imidazoles Catalysed by Recyclable Indium (III) Triflate and Magnesium Sulfate Heptahydrate
  作者：Bahador Karami、Roghayeh Ferdosian、Khalil Eskandari

  DOI：10.3184/174751914x13863406090407

  日期：2014.1

  aromatic primary amines and ammonium acetate is reported for the synthesis of tri/tetra-substituted imidazoles under solvent-free conditions. Indium (III) trifluoromethanesulfonate and magnesium sulfate heptahydrate as two highly efficient and recyclable catalysts perform a key factor to synthesis of imidazole derivatives with high yields.

  据报道，在无溶剂条件下合成三/四取代咪唑的范围广泛的芳香醛、苄基、脂肪族和芳香族伯胺和乙酸铵的一锅三或四组分反应。三氟甲磺酸铟 (III) 和七水硫酸镁作为两种高效且可回收的催化剂，是高产率合成咪唑衍生物的关键因素。
• Tungstate Sulfuric Acid (TSA): A Green and Highly Efficient Catalyst for Novel and Known Polysubstituted Imidazoles Synthesis
  作者：Bahador Karami、Khalil Eskandari、Mahboobeh Azizi

  DOI：10.2174/15701786113109990044

  日期：2013.11

  Tungstate sulfuric acid (TSA) was composed of anhydrous sodium tungstate and chlorosulfonic acid with a new modified and efficient method. Catalyst was characterized by powdered X-ray diffraction (XRD), X-ray fluorescence (XRF), FT-IR spectroscopy and titration with NaOH (0.1 N). In the present study, highly efficient role of TSA as a catalyst in polysubstituted imidazoles synthesis as pharmaceuticaly

  钨酸硫酸（TSA）由无水钨酸钠和氯磺酸组成，是一种经过改进的高效新方法。催化剂的特征在于粉末X射线衍射（XRD），X射线荧光（XRF），FT-IR光谱和用NaOH（0.1 N）滴定。在本研究中，据报道，在无溶剂条件下，通过广泛的芳基醛，伯胺，苯甲酰和乙酸铵之间的缩合，TSA作为催化剂在多取代的咪唑合成中作为药学上重要的分子具有高效的作用。因此，介绍了该催化剂在合成某些新型咪唑中的新应用。