2-(2-methoxyphenyl)-1,4,5-triphenyl-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: 2-(2-methoxyphenyl)-1,4,5-triphenyl-1H-imidazole
• 英文别名: 2-(2-Methoxyphenyl)-1,4,5-triphenylimidazole；2-(2-methoxyphenyl)-1,4,5-triphenylimidazole
• 化学式: C₂₈H₂₂N₂O
• 分子量: 402.495
• InChiKey: SMXKRQKHDFZCOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 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：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  邻甲基苄醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 乙酸铵 、 potassium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 2-(2-methoxyphenyl)-1,4,5-triphenyl-1H-imidazole
  参考文献：
  名称：

  Imidazole-Based Excited-State Intramolecular Proton-Transfer Materials:  Synthesis and Amplified Spontaneous Emission from a Large Single Crystal

  摘要：

  We have synthesized a novel class of imidazole-based excited-state intramolecular proton-transfer (ESIPT) materials, i.e., hydroxy-substituted tetraphenylimidazole (HPI) and its derivative HPI-Ac, which formed large single crystals exhibiting intense blue fluorescence and amplified spontaneous emission (ASE). Transparent, clear, and well-defined fluorescent single crystals of HPI-Ac as large as 20 mm x 25 mm x 5 mm were easily grown from its dilute solution. From the X-ray crystallographic analysis and semiempirical molecular orbital calculation, it was deduced that the four phenyl groups substituted into the imidazole ring of HPI and HPI-Ac allowed the crystals free from concentration quenching of fluorescence by limiting the excessive tight-stacking responsible for intermolecular vibrational coupling and relevant nonradiative relaxation. Fluorescence spectral narrowing and efficient ASE were observed in the HPI-Ac single crystal even at low excitation levels attributed to the intrinsic four-level ESIPT photocycle.

  DOI：

  10.1021/ja0508727

文献信息

• 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
• An efficient green protocol for the synthesis of tetra-substituted imidazoles catalyzed by zeolite BEA: effect of surface acidity and polarity of zeolite
  作者：Jenifer J. Gabla、Sunil R. Mistry、Kalpana C. Maheria

  DOI：10.1039/c7cy01398a

  日期：——

  controlled dealumination. The synthesized materials were characterized by various characterization techniques such as XRD, ICP-OES, BET, NH3-TPD, FT-IR, pyridine FT-IR, 27Al and 1H MAS NMR. It has been observed that the dealumination of the parent zeolite H-BEA (12) results in the enhanced strength of Brønsted acidity up to a certain Si/Al ratio which is attributed to the inductive effect of Lewis acidic

  在本研究中，研究了各种介质（H-ZSM-5）和大孔（H-BEA，HY，H-MOR）沸石作为固体酸催化剂的催化活性。发现H-BEA沸石是一种可通过NH-苄基苯之间的一锅，四组分反应（4-CR）合成1-苄基-2,4,5-三苯基-1 H-咪唑的有效催化剂4 OAc，取代的芳族醛和苄基胺。通过控制脱铝可以很好地改善BEA分子筛的疏水性，Si / Al比和酸性。合成的材料通过各种表征技术进行表征，例如XRD，ICP-OES，BET，NH 3 -TPD，FT-IR，吡啶FT-IR，27 Al和1H MAS NMR。据观察，母体H-BEA沸石（12）的脱铝导致布朗斯台德酸度的强度提高到一定的Si / Al比，这归因于路易斯酸性EFAl物质的诱导作用，导致较高的沸石BEA（15）催化剂对1-苄基2,4,5-三苯-1 H合成的催化活性;-咪唑类在无热溶剂的条件下具有良好至极好的收率。使用本发明的催化合成方案
• Immobilized ionic liquid on superparamagnetic nanoparticles as an effective catalyst for the synthesis of tetrasubstituted imidazoles under solvent-free conditions and microwave irradiation
  作者：Javad Safari、Zohre Zarnegar

  DOI：10.1016/j.crci.2013.01.019

  日期：2013.10

  Résumé The ionic liquid 1-methyl-3-(3-trimethoxysilylpropyl) imidazolium chloride was immobilized on superparamagnetic Fe3O4 nanoparticles (IL-MNPs) and used as an efficient heterogeneous catalyst for the one-pot synthesis of 1,2,4,5-tetrasubstituted imidazoles under solvent-free conditions using microwave irradiation. The reactions in conventional heating conditions were compared with the microwave-assisted reactions. The combined merits of microwave irradiation and immobilized ionic liquid on superparamagnetic nanoparticles make the four-component condensation with safe operation, low pollution, and rapid access to products and simple work-up. Supplementary Materials: Supplementary materials for this article are supplied as separate files: mmc1.doc mmc2.docx

  摘要 离子液体1-甲基-3-(3-三甲氧基硅基丙基)咪唑氯化物被固定在超顺磁性Fe3O4纳米颗粒上（IL-MNPs），并用作在无溶剂条件下通过微波辐射高效合成1,2,4,5-四取代咪唑的异相催化剂。将常规加热条件下的反应与微波辅助反应进行了比较。微波辐射和固定离子液体在超顺磁性纳米颗粒上的组合优点使得四组分缩合反应操作安全、污染低、快速获得产物且后处理简单。 补充材料： 本文的补充材料以单独文件提供： mmc1.doc mmc2.docx
• Magnetic nanoparticle supported ionic liquid as novel and effective heterogeneous catalyst for synthesis of substituted imidazoles under ultrasonic irradiation
  作者：Javad Safari、Zohre Zarnegar

  DOI：10.1007/s00706-013-1015-6

  日期：2013.9

  AbstractThe ionic liquid 1-methyl-3-(3-trimethoxysilylpropyl)imidazolium chloride was immobilized on Fe3O4 nanoparticles and used as an efficient and reusable catalyst for the one-pot synthesis of 1,2,4,5-tetrasubstituted imidazoles at room temperature under ultrasonic irradiation. The immobilized ionic liquid catalysts proved to be effective and easily separated from the reaction media by applying

  摘要将离子液体1-甲基-3-（3-三甲氧基甲硅烷基丙基）咪唑鎓氯化物固定在Fe 3 O 4纳米颗粒上，并用作高效，可重复使用的催化剂，用于一锅合成1,2,4,5-四取代的咪唑。室温下超声照射。固定的离子液体催化剂被证明是有效的，并且通过施加外部磁场容易与反应介质分离。与先前文献报道的方法相比，该方法具有许多明显的优势，包括避免使用有害的催化剂，在室温下反应，高收率和方法简单。 图形概要
• Synthesis and biological evaluation of 1,2,4,5-tetrasubstituted imidazoles
  作者：Yue Fang、Rui Yuan、Wen-hui Ge、Yuan-jiang Wang、Gui-xiang Liu、Ming-qi Li、Jiang-biao Xu、Yu Wan、Sheng-liang Zhou、Xi-guang Han、Peng Zhang、Jin-juan Liu、Hui Wu

  DOI：10.1007/s11164-017-2886-7

  日期：2017.8

  Tetrasubstituted imidazoles were synthesized in high yields via the four-component reaction of aromatic aldehydes, amines, substituted benzils and ammonium acetate catalyzed by a porous CeO2 nanorod. Their anti-cancer activities on the Huh-7 hepatocellular carcinoma cell and antibacterial activities on four bacterial species (wild-type Escherichia coli, wild-type Staphylococcus aureus, Pseudomonas

  通过多孔CeO 2纳米棒催化的芳族醛，胺，取代的苯甲酰胺和乙酸铵的四组分反应，高产率合成了四取代的咪唑。评估了它们对Huh-7肝癌细胞的抗癌活性以及对四种细菌种类（野生型大肠杆菌，野生型金黄色葡萄球菌，铜绿假单胞菌PAM1032和大肠杆菌-NMD-1）的抗菌活性。筛选出一种化合物（5p）是因为它对所有四种细菌的100μg/ mL的高抑制率。三种产品（5p，5t和5y）在10μg/ mL的浓度下对Huh-7肝癌细胞具有较高的抑制率。结果表明了它们在新药开发中的潜力。