4-(4,5-diphenyl-1H-imidazol-2-yl)benzene-1,3-diol | 488787-64-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4,5-diphenyl-1H-imidazol-2-yl)benzene-1,3-diol
• 英文别名: 4,5-Diphenyl-2-(2,4-dihydroxyphenyl)-1H-imidazole
• CAS: 488787-64-0
• 化学式: C₂₁H₁₆N₂O₂
• 分子量: 328.37
• InChiKey: YKZFBYGKWSTWIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4,5-diphenyl-1H-imidazol-2-yl)benzene-1,3-diol 、 4-二乙氨基酮酸 在 甲烷磺酸 作用下， 反应 24.0h， 以75%的产率得到6′-(diethylamino)-2′-(4,5-diphenyl-1H-imidazol-2-yl)-3′-hydroxy-3H-spiro [isobenzofuran-1,9′-xanthen]-3-one
  参考文献：
  名称：

  ESIPT-rhodol derivatives with enhanced Stokes shift: Synthesis, photophysical properties, viscosity sensitivity and DFT studies

  摘要：

  Three rhodol derivatives, namely spirolactamized phenanthrene-imidazole, diphenyl-imidazole and benzothiazole substituted N, N-diethylamine rhodols were designed, synthesized and characterized. Their photophysical properties were studied in spirocyclic and open form from non-polar to polar solvents. The spirocyclic form exhibited larger Stokes shifts (50-260 nm) due to presence of ESIPT process whereas, open form showed small Stokes shift (10-40 nm) due to the lack of protons. Positive solvatochromism was observed for both the spirocyclic and open forms which is well supported by the linear (Lippert-Mataga and Mac-Rae) and multi-linear (Kamlet-Taft and Catalan parameters) analysis. Solvent polarizability (d(sp)) is the major factor responsible for red shift in absorption/emission and larger Stokes shift for spirocyclic form. Polarity graphs and charge transfer descriptors are in good relation with Generalized Mulliken-Hush (GMH) parameters. From the solvatochromic data we observed that open forms show good TICT characteristics as compared to their respective spirocyclic forms. Open form is highly sensitive to viscosity as compared to spirocyclic form in a mixture of polarprotic solvents (EtOH:PEG 400). The experimental results are well correlated theoretically using Density Functional Theory (DFT) computations. (C) 2019 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molliq.2019.111626
• 作为产物：
  描述：

  联苯甲酰 、 2,4-二羟基苯甲醛 在 ammonium acetate 作用下， 以 乙醇 、 水 为溶剂， 以77 %的产率得到4-(4,5-diphenyl-1H-imidazol-2-yl)benzene-1,3-diol
  参考文献：
  名称：

  2,4,5-三取代和1,2,4,5-四取代咪唑的无催化剂一锅法合成

  摘要：

  目前的工作重点是使用多种醛与苯偶酰、乙酸铵或胺进行无催化剂的 2,4,5-三取代和 1,2,4,5-四取代咪唑合成。乙酸铵作为反应物催化剂发挥着至关重要的作用，它可分解成乙酸，形成亚胺和二胺，从而确定 2,4,5-三取代和 1,2,4,5-四取代咪唑。目前方法的主要优点是高效、绿色、环保、简便，在80°C的温度下，在较短的反应时间内具有中等至优异的产率。乙醇：水作为溶剂使反应过程更加环保。总体而言，所描述的方法为有效和可持续合成取代咪唑提供了一条有前途的途径，其在医药、农用化学品和材料科学等各个领域具有广泛的应用。

  DOI：

  10.1002/jhet.4771

文献信息

• Efficient Multi-component Synthesis of Highly Substituted Imidazoles Utilizing P2O5/SiO2 as a Reusable Catalyst
  作者：Hamid Reza Shaterian、Mohammad Ranjbar、Kobra Azizi

  DOI：10.1002/cjoc.201180293

  日期：2011.8

  gel (P2O5/SiO2) has been used as an efficient and reusable catalyst for the one‐pot pseudo four‐component synthesis of 2,4,5‐trisubstituted imidazoles from benzil or benzoin, aldehydes, and ammonium acetate. It was also used for four‐component preparation of 1,2,4,5‐tetrasubstituted imidazoles from benzil or benzoin, aldehydes, primary amine, and ammonium acetate under thermal solvent‐free conditions

  负载在硅胶（P 2 O 5 / SiO 2）上的五氧化二磷已被用作一种高效且可重复使用的催化剂，用于由苯甲腈或安息香，醛，和醋酸铵。它也可在无热溶剂的条件下用于由苄基或安息香，醛，伯胺和乙酸铵四组分制备1,2,4,5-四取代的咪唑。这种新方法的显着特征是高转化率，更清洁的反应，简单的实验和后处理程序，并且催化剂可以轻松地从反应混合物中分离出来并重复使用几次，而不会损失其活性。
• Synthesis of highly substituted imidazoles using Brønsted acidic ionic liquid, triphenyl(propyl-3-sulphonyl)phosphonium toluenesulfonate, as teusable catalyst
  作者：H. R. Shaterian、M. Ranjbar、K. Azizi

  DOI：10.1007/bf03246570

  日期：2011.12

  Brønsted acidic ionic liquid, triphenyl(propyl-3-sulphonyl)phosphonium toluenesulfonate, has been used as an efficient and reusable catalyst for the one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles under solvent-free conditions in excellent yields.

  布朗斯台德酸性离子液体三苯基（丙基-3-磺酰基）phosph磺酸甲苯磺酸盐已被用作一锅合成2,4,5-三取代和1,2,4,5-四取代的咪唑的有效且可重复使用的催化剂在无溶剂条件下，收率极高。
• An environmental friendly approach for the synthesis of highly substituted imidazoles using Brønsted acidic ionic liquid, N-methyl-2-pyrrolidonium hydrogen sulfate, as reusable catalyst
  作者：Hamid Reza Shaterian、Mohammad Ranjbar

  DOI：10.1016/j.molliq.2011.02.012

  日期：2011.4

  Brønsted acidic ionic liquid, N-methyl-2-pyrrolidonium hydrogen sulfate, has been used as an efficient and reusable catalyst for the one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles under thermal solvent-free conditions in excellent yields.

  布朗斯台德酸性离子液体N-甲基-2-吡咯烷鎓硫酸氢盐已被用作一种高效且可重复使用的催化剂，用于在以下条件下一锅合成2,4,5-三取代和1,2,4,5-四取代的咪唑无溶剂的热条件，产率高。
• An efficient green MCR protocol for the synthesis of 2,4,5-trisubstituted imidazoles by Selectfluor™ under ultrasound irradiation
  作者：Mohammad Reza Poor Heravi、Esmaeil Vessally、Gholam R. Rezaei Behbehani

  DOI：10.1016/j.crci.2012.12.007

  日期：2014.2

  Résumé A simple, efficient and eco-friendly procedure has been developed using Selectfluor™ (15% mol) as a novel catalyst under ultrasound irradiation and solvent-free conditions for the synthesis of 2,4,5-triaryimidazole by a three-component, one-pot condensation of benzil, aryl aldehydes and ammonium acetate. The present methodology offers several advantages such as excellent yields, shorter reaction times (10–15 min) and environmentally benign milder reaction conditions and easy work-up.

  摘要 一种简单、高效且环保的程序已经开发，采用Selectfluor™（15%摩尔）作为新型催化剂，在超声辐照和无溶剂条件下合成2,4,5-三芳基咪唑。该合成方法通过苯基氨、芳基醛和乙酸铵的三组分一锅缩合反应进行。该方法具有多个优势，如优异的产率、更短的反应时间（10-15分钟）、温和的反应条件以及易于处理的优点。
• Copper borate (CuB₄O₇)-promoted multi-component green synthesis of 2,4,5-triarylimidazole derivatives and evidence of <i>in situ</i> conversion of copper borate (CuB₄O₇) into Cu(OAc)₂ in the presence of NH₄OAc
  作者：Sailesh Chettri、Sumiran Tamang、Kiran Pradhan、Biswajit Sinha、Dhiraj Brahman

  DOI：10.1039/d3ra03183g

  日期：——

  5-triarylimidazole has been developed under solvent-free conditions using unconventional CuB4O7 as a promoter. This green approach encouragingly provides access to a library of 2,4,5-tri-arylimidazole. Also, we have been able to isolate the compound (5) and (6) in situ, which provides an insight into the direct conversion of CuB4O7 into copper acetate in the presence of NH4OAc under solvent-free condition. The

  使用非常规 CuB 4 O 7作为促进剂，在无溶剂条件下开发了一种绿色、高效、简单的 2,4,5-三芳基咪唑三组分合成方法。这种绿色方法令人鼓舞地提供了对 2,4,5-三芳基咪唑库的访问。此外，我们还能够原位分离出化合物( 5 ) 和( 6 ) ，这为在NH 4存在下CuB 4 O 7直接转化为乙酸铜提供了深入的了解。OAc在无溶剂条件下。该方案的主要优点包括反应程序简单，反应时间短，并且无需使用任何繁琐的分离方法即可轻松处理产物。