2,4,5-triphenyl-1-p-tolylimidazole | 16112-36-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2,4,5-triphenyl-1-p-tolylimidazole
• 英文别名: 1-(4-methylphenyl)-2,4,5-triphenyl-1H-imidazole；2,4,5-triphenyl-1-(p-tolyl)-1H-imidazole；1-p-Tolyl-2,4,5-triphenylimidazol；2,4,5-Triphenyl-1-p-tolyl-1H-imidazol；1-p-tolyl-2,4,5-triphenyl-1H-imidazole；1-(4-methylphenyl)-2,4,5-triphenylimidazole
• CAS: 16112-36-0
• 化学式: C₂₈H₂₂N₂
• 分子量: 386.496
• InChiKey: RFZBRFSCRBCSQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  30
• 可旋转键数：
  4
• 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：

  苯甲醛 在 ammonium acetate 、 1,3-bis(octylbenzimidazolium)bromide 、 溶剂黄146 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.16h， 生成 2,4,5-triphenyl-1-p-tolylimidazole
  参考文献：
  名称：

  ONE-POT SYNTHESIS OF POLYSUBSTITUTED IMIDAZOLES FROM ARYLALDEHYDES IN WATER CATALYZED BY NHC USING MICROWAVE IRRADIATION

  摘要：

  A simple, high yielding synthesis of tri (3a-i) and tetrasubstituted (4a-g) imidazols from aldehydes is described. The cornerstone of this methodology involves the condensation of NH4OAc, substituted aldehydes, and benzoin, which is synthesized in situ from aldehydes catalyzed by N-heterocyclic carbine (NHC), under microwave irradiation in water to afford trisubstituted imidazoles (3a-i). If arylamine is added in the solution, tetrasubstituted imidazoles (4a-g) can be obtained. Lepidilines B and trifenagrel are also synthesized in high yield using this procedure. All the experiment deta are in agreement with the literature.

  DOI：

  10.4067/s0717-97072012000300002

文献信息

• Synthesis of organosilyl compounds-containing 1,2,4,5-tetraaryl imidazoles sonocatalyzed by M/SAPO-34 (M = Fe, Co, Mn, and Cu) nanostructures
  作者：Kazem D. Safa、Maryam Allahvirdinesbat、Hassan Namazi、Parvaneh Nakhostin Panahi

  DOI：10.1016/j.crci.2015.04.008

  日期：2015.8

  Résumé The one-step synthesis of silylated 1,2,4,5-tetraaryl imidazoles by use of a series of M/SAPO-34 (M: Fe, Co, Mn, and Cu) nanocatalysts and subsequent silylation reactions is described. Cu/SAPO-34 catalyst has the highest activity in improving the efficiency of the heterogeneous cyclo-condensation of an aldehyde, benzil, ammonium acetate and a primary aromatic amine in water under ultrasonic irradiation. Some of imidazole derivatives are studied with a view to the synthesis of a series of new, multi-substituted imidazoles containing organosilyl groups including carbosilanes (Si–C) and silyl ethers (Si–O). Supplementary Materials: Supplementary material for this article is supplied as a separate file: mmc1.docx

  简历 本文描述了使用一系列 M/SAPO-34（M: Fe、Co、Mn 和 Cu）纳米催化剂一步合成硅烷化 1,2,4,5-四芳基咪唑及其随后的硅烷化反应。Cu/SAPO-34 催化剂在水下超声辐射中对醛、二苯乙二酮、乙酸铵和初级芳香胺的异质环缩合反应效率的提高活性最高。一些咪唑衍生物被研究，旨在合成一系列新的、多取代的咪唑，这些咪唑含有有机硅基团，包括碳硅烷（Si–C）和硅醚（Si–O）。 补充材料： 本文的补充材料以单独文件形式提供： mmc1.docx
• Visible light-emitting diode light-driven one-pot four component synthesis of poly-functionalized imidazoles under catalyst- and solvent-free conditions
  作者：Geetika Patel、Ashok Raj Patel、Subhash Banerjee

  DOI：10.1039/d0nj02527e

  日期：——

  A visible light-emitting diode light-driven green and sustainable protocol has been demonstrated for the one-pot four component synthesis of poly-functionalized imidazoles under catalyst- and solvent-free conditions.

  已经展示了一种可见光发光二极管驱动的绿色可持续协议，用于在无催化剂和无溶剂条件下进行一锅式四组分合成多官能基咪唑。
• 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
• An Efficient, Solvent Free One Pot Synthesis of Tetra substitue dimidazoles Catalyzed by Nanocrystalline γ-alumina
  作者：Pallavi Shelke、Anjali Rajbhoj、Madhav Nimase、Gangaram Tikone、Bhaskar Zaware、Shridhar Jadhav

  DOI：10.13005/ojc/320427

  日期：2016.8.25

  spectrophotometer and high- resolution transmission electron microscopy These synthesized γ-Al 2 O 3 NPs were tested used as a catalyst for one pot synthesis of tetraaryl imidazole derivatives from the cyclodehydration and condensation of benzil, aromatic aldehyde, anilines and ammonium acetate under solvent free condition. This method has various advantages like convenient work-up procedure, environmentally

  通过电化学还原法成功地合成了γ-氧化铝纳米粒子（γ-Al2 O 3 NPs）。溴化四丙基铵的水溶液用作电解质和稳定剂。为了防止自发团聚并控制纳米颗粒的尺寸，对各种参数（例如电流密度，电极之间的距离和电解质浓度）进行了优化。由此合成的γ-Al2O3NPs通过复杂的分析技术进行了表征，包括X射线衍射，扫描电子显微镜，能量色散分光光度计和高分辨率透射电子显微镜。这些合成的γ-Al2 O 3 NPs被用作一锅催化剂。由苯甲醚，芳族醛的环脱水和缩合反应合成四芳基咪唑衍生物 无溶剂条件下的苯胺和乙酸铵。该方法具有多种优点，如后处理方便，对环境无害，反应时间短以及产率高。纳米晶γ-Al2 O 3催化剂具有易于获得，多次循环利用，非常简单的分离和生态友好的特点。
• Cu(II) immobilized on guanidinated epibromohydrin‐functionalized γ‐Fe₂O₃@TiO₂(γ‐Fe₂O₃@TiO₂‐EG‐Cu(II)): A highly efficient magnetically separable heterogeneous nanocatalyst for one‐pot synthesis of highly substituted imidazoles
  作者：Mahdi Nejatianfar、Batool Akhlaghinia、Roya Jahanshahi

  DOI：10.1002/aoc.4095

  日期：2018.2

  A simple, efficient and eco‐friendly procedure has been developed using Cu(II) immobilized on guanidinated epibromohydrin‐functionalized γ‐Fe2O3@TiO2 (γ‐Fe2O3@TiO2‐EG‐Cu(II)) for the synthesis of 2,4,5‐trisubstituted and 1,2,4,5‐tetrasubstituted imidazoles, via the condensation reactions of various aldehydes with benzil and ammonium acetate or ammonium acetate and amines, under solvent‐free conditions

  一种简单，高效和环境友好的程序已被使用的Cu（II）固定于显影胍基化表溴醇-官能化了γ-Fe 2 ö 3 @TiO 2（γ-的Fe 2 ö 3 @TiO 2 -EG-的Cu（II））在无溶剂条件下，通过各种醛与苯甲酰和乙酸铵或乙酸铵和胺的缩合反应，合成2,4,5-三取代和1,2,4,5-四取代的咪唑。这种催化剂的高分辨率透射电子显微镜分析明确肯定一个形成了γ-Fe 2 ö 3芯和的TiO 2外壳，平均大小分别约为10–20 nm和5–10 nm。这些数据与X射线晶体学测量（13和7 nm）非常吻合。此外，磁化测量结果表明，这两种了γ-Fe 2 ö 3 @TiO 2和γ-的Fe 2 ö 3 @TiO 2 -EG-的Cu（II）具有超顺磁性与22.12鸸鹋克23.79饱和磁化强度和行为-1分别。了γ-Fe 2 ö 3 @TiO 2‐EG‐Cu（II）被发现是一种绿色高效的纳米催化剂，可以容易地