1-benzyl-2-(3-hydroxyphenyl)-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-(3-hydroxyphenyl)-4,5-diphenyl-1H-imidazole
• 英文别名: 3-(1-benzyl-4,5-diphenyl-1H-imidazol-2-yl)phenol；3-(1-Benzyl-4,5-diphenylimidazol-2-yl)phenol
• 化学式: C₂₈H₂₂N₂O
• 分子量: 402.495
• InChiKey: GBHOKYOGGYIRIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 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：
  38
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-(4,5-diphenyl-1H-imidazol-2-yl)phenol 、 氯化苄 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以45%的产率得到1-benzyl-2-(3-hydroxyphenyl)-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

• Co(II) anchored glutaraldehyde crosslinked magnetic chitosan nanoparticles (MCS) for synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles
  作者：Harminder Singh、Jaspreet Kaur Rajput

  DOI：10.1002/aoc.3989

  日期：2018.1

  A simple, highly efficient and green synthesis of 2,4,5‐trisubsituted and 1,2,4,5‐tetrasubstituted imidazoles was developed using a novel MCS‐GT@Co(II) magnetically recoverable and recyclable catalyst under refluxing conditions with ethanol as a solvent. The catalyst was prepared by immobilization of chitosan onto Fe3O4 using glutaraldehyde as crosslinker followed by Co(II) ion immobilization via cobalt

  使用新型MCS-GT @ Co（II）磁性可回收和可循环利用的催化剂，在乙醇回流条件下，开发了一种简单，高效且绿色的2,4,5-三取代和1,2,4,5-四取代的咪唑合成方法作为溶剂。通过使用戊二醛作为交联剂将壳聚糖固定在Fe 3 O 4上，然后通过乙酸钴固定Co（II）离子来制备催化剂。使用多种技术表征催化剂。对于有机产物的测定，1 H NMR，13使用13 C NMR和傅立叶变换红外光谱。还尝试了用催化剂的各个组分进行反应，但是在制备的催化剂中组分的协同作用显示出最高的产率和最短的反应时间。
• Silica coated magnetic NiFe₂O₄ nanoparticle supported phosphomolybdic acid; synthesis, preparation and its application as a heterogeneous and recyclable catalyst for the one-pot synthesis of tri- and tetra-substituted imidazoles under solvent free conditions
  作者：Behrooz Maleki、Hossein Eshghi、Amir Khojastehnezhad、Reza Tayebee、Samaneh Sedigh Ashrafi、Golnoosh Esmailian Kahoo、Farid Moeinpour

  DOI：10.1039/c5ra10534j

  日期：——

  A novel heteropolyacid supported on silica coated nickel ferrite nanoparticles (NFS–PMA) was synthesized and used as a green catalyst for one-pot syntheses of tri/tetra-substituted imidazoles. The catalyst could be recycled and reused through application of a magnetic field.

  一种新型的硅包覆镍铁氧化物纳米颗粒负载的杂多酸（NFS-PMA）被合成并用作一锅法合成三/四取代咪唑的绿色催化剂。该催化剂可以通过磁场的应用进行回收和重复使用。
• Green synthesis of tri/tetrasubstituted 1H-imidazoles and 2,3-dihydroquinazolin-4(1H)-ones using nano aluminium nitride as solid source of ammonia
  作者：MARYAM HAJJAMI、ARASH GHORBANI-CHOGHAMARANI、ZAKIEH YOUSOFVAND、MASOOMEH NOROUZI

  DOI：10.1007/s12039-015-0890-2

  日期：2015.7

  A simple, green and cost-effective protocol was achieved for the synthesis of tri/tetrasubstituted-1H-imidazoles and 2,3-dihydroquinazolin-4(1H)-ones using nano aluminium nitride. The reaction was carried out under catalyst-free conditions and the products were isolated in good to excellent yield.

  采用纳米氮化铝实现了一种简单、绿色且经济高效的合成三/四取代-1H-咪唑和2,3-二氢喹唑啉-4(1H)-酮的新方法。反应在无催化剂的条件下进行，产物的收率良好到优秀。
• Copper(I) complex of 1,3-DimethylBarbituric acid modified SBA-15 and its catalytic role for the synthesis of 2,3-Dihydroquinazolin-4(1H)-ones and Imidazoles
  作者：Maryam Hajjami、Farshid Ghorbani、Zakieh Yousofvand

  DOI：10.1002/aoc.3843

  日期：2017.12

  An efficient one‐pot method for synthesis of 2,3‐dihydroquinazolin‐4(1H)‐ones and tri/tetra substituted‐1H‐imidazoles has been accomplished in the presence of catalytic amounts of Cu(I)‐1,3‐dimethylbarbituric acid modified SBA‐15 as heterogeneous catalyst with good to excellent yields. The catalyst is reusable and can be applied several times without any decrease in product yield. The synthesized catalyst

  在催化量的Cu（I）-1,3-二甲基巴比妥酸存在下，已经完成了一种高效的一锅法合成2,3-二氢喹唑啉-4（1H）-酮和三/四取代-1H-咪唑的方法。酸改性的SBA-15作为非均相催化剂，具有良好或优异的收率。该催化剂是可重复使用的，并且可以多次使用而不会降低产品收率。通过扫描电子显微镜（SEM），X射线衍射（XRD），能量色散X射线光谱（EDS），热重分析（TGA），N 2吸附/解吸等温线（BET），傅里叶变换对催化剂进行表征红外光谱（FT-IR）和原子吸收光谱（AAS）。
• Synthesis of 1,2,4,5-tetrasubstituted imidazoles using silica-bonded propylpiperazine N-sulfamic acid as a recyclable solid acid catalyst
  作者：Khodabakhsh Niknam、Abdollah Deris、Fatemeh Naeimi、Fatemeh Majleci

  DOI：10.1016/j.tetlet.2011.06.105

  日期：2011.9

  A simple and efficient procedure for the preparation of silica-bonded propylpiperazine-N-sulfamic acid (SBPPSA) by the reaction of 3-piperazine-N-propylsilica (3-PNPS) and chlorosulfonic acid in chloroform is described. Silica-bonded propylpiperazine-N-sulfamic acid is employed as a recyclable catalyst for the synthesis of highly substituted imidazoles from the reaction of benzil, aromatic aldehydes

  一种制备氧化硅键合的propylpiperazine-简单和有效的程序ñ -氨基磺酸（SBPPSA）3 -哌嗪的反应Ñ -propylsilica（3- PNPS）和氯仿氯磺酸进行说明。二氧化硅键合的丙基哌嗪-N-氨基磺酸被用作可循环利用的催化剂，用于在无溶剂条件下由苯甲腈，芳族醛，乙酸铵和胺的反应合成高度取代的咪唑。在苯甲酰，4-甲基苯甲醛，苄胺和乙酸铵反应后，将多相催化剂循环使用五次，而不会失去其催化活性。