3-(4,5-diphenyl-1H-imidazol-2-yl)phenol | 95815-86-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4,5-diphenyl-1H-imidazol-2-yl)phenol
• 英文别名: 2-(3-hydroxyphenyl)-4,5-diphenyl-1H-imidazole；2-(3-hydroxyphenyl)-4,5-diphenylimidazole
• CAS: 95815-86-4
• 化学式: C₂₁H₁₆N₂O
• mdl: MFCD00845094
• 分子量: 312.371
• InChiKey: UPJQFPBIFZYRLB-UHFFFAOYSA-N

物化性质

• 熔点：
  259 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  568.8±38.0 °C(Predicted)
• 密度：
  1.223±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 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：
  48.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4,5-diphenyl-1H-imidazol-2-yl)phenol 在 氧气 、 亚甲兰 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 4-hydroperoxy-2-(m-hydroxyphenyl)-4,5-diphenyl-4H-isoimidazole
  参考文献：
  名称：

  Location effect of an OH group on the chemiluminescence efficiency of 4-hydroperoxy-2-(o-, m-, or p-hydroxyphenyl)-4,5-diphenyl-4H-isoimidazoles

  摘要：

  In studying the location effect of an OH group on the chemiluminescence efficiency of 4-hydroperoxy-2-(o-, m-, or p-hydroxyphenyl)-4,5-diphenyl-4H-isoimidazoles 4, we found that the efficiency of 4a with o-OH was 0.28 times that of lophine peroxide on initiation with KOH/MeOH. When the trigger base was changed to TBAF/THF, efficiency was 530-fold in dry DMF. The efficiency of 4b with m-OH or 4c with p-OH showed no such dramatic change. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.01.084
• 作为产物：
  描述：

  3-(4,5-diphenyl-1H-imidazol-2-yl)-aniline 生成 3-(4,5-diphenyl-1H-imidazol-2-yl)phenol
  参考文献：
  名称：

  Troeger; Thomas, Journal fur praktische Chemie (Leipzig 1954), 1925, vol. <2> 110, p. 48

  摘要：

  DOI：

文献信息

• Zinc (II) [tetra(4-methylphenyl)] Porphyrin: a Novel and Reusable Catalyst for Efficient Synthesis of 2,4,5-trisubstituted Imidazoles Under Ultrasound Irradiation
  作者：Javad Safari、Shiva Dehghan Khalili、Sayed Hossein Banitaba、Hossein Dehghani

  DOI：10.5012/jkcs.2011.55.5.787

  日期：2011.10.20

  An efficient three-component one-step synthesis of 2,4,5-trisubstituted imidazoles by condensation reaction of 1,2-diketones or α-hydroxyketones with aromatic aldehydes and ammonium acetate using Zinc (II) (tetra (4-methylphenyl)) porphyrin as a novel and reusable catalyst under ultrasound irradiation at ambient temperature is described. In this method, α-hydroxyketones as well as 1,2-diketones were

  使用锌（II）（四（4-甲基苯基））使1,2-二酮或α-羟基酮与芳族醛和乙酸铵缩合反应，可有效地三步合成2,4,5-三取代的咪唑描述了在室温下超声辐射下卟啉作为新型可重复使用的催化剂。在这种方法中，α-羟基酮以及1,2-二酮以优异的产率转化为它们相应的2,4,5-三取代的咪唑。
• One-pot synthesis of 2,4,5-trisubstituted imidazole derivatives catalyzed by btppc under solvent-free conditions
  作者：M. Alikarami、M. Amozad

  DOI：10.4314/bcse.v31i1.16

  日期：——

  one-pot synthesis of lophine derivatives (2,4,5-trisubstituted imidazoles) by using the benzyltriphenylphosphonium chloride (BTPPC), as a catalyst, under solvent-free conditions is described. BTPPC is an available and inexpensive catalyst; also, it can be easily supplied. This procedure led to the corresponding 2,4,5-trisubstituted imidazoles products in high yields. KEY WORDS : Lophine derivatives, BTPPC

  描述了一种简单有效的方法，该方法通过在无溶剂条件下，使用苄基三苯基氯化TP（BTPPC）作为催化剂，一锅合成木素衍生物（2,4,5-三取代的咪唑）。BTPPC是一种可用的廉价催化剂。而且，它可以很容易地提供。该方法以高收率得到了相应的2,4,5-三取代的咪唑产物。关键词：Lophine衍生物，BTPPC，无溶剂，一锅法合成，多组分合成Bull。化学 Soc。埃塞俄比亚。2017，31（1），177-184。DOI：http：//dx.doi.org/10.4314/bcse.v31i1.16
• One-Pot Three-Component Synthesis of 2,4,5-Triaryl-1H-imidazoles Using Mn2+ Complex of [7-Hydroxy-4-methyl-8-coumarinyl] Glycine as a Heterogeneous Catalyst
  作者：Hashem Sharghi、Seyyede Faeze Razavi、Mahdi Aberi

  DOI：10.1007/s10562-021-03717-2

  日期：2022.6

  A highly efficient and simple synthesis of 2,4,5-trisubstituted imidazoles has been developed using highly reusable support‐free Mn2+complex of [7-hydroxy-4-methyl-8-coumarinyl] glycine as a heterogeneous catalyst via a one-pot three-component reaction of benzil, aldehydes and ammonium acetate as a nitrogen source. Moreover, this catalyst was characterized by various techniques such as field emission

  使用高度可重复使用的 [7-hydroxy-4-methyl-8-coumarinyl] 甘氨酸的 Mn 2+ 配合物作为非均相催化剂，开发了一种高效且简单的 2,4,5-三取代咪唑合成方法。- 苯偶酰、醛类和乙酸铵作为氮源的锅三组分反应。此外，该催化剂通过场发射扫描电子显微镜（FE-SEM）、能量色散X射线光谱（EDX）、FT-IR光谱、粉末X射线衍射（XRD）、电感耦合等离子体（ ICP）和热重分析（TGA）。此外，该催化剂是稳定的，可以重复使用至少六次而不会显着丧失活性。 图形摘要
• Crystal structures and solution spectroscopy of lophine derivatives
  作者：Natalya Fridman、Menahem Kaftory、Yoav Eichen、Shammai Speiser

  DOI：10.1016/j.molstruc.2008.07.003

  日期：2009.1

  Abstract Lophine (2,4,5-triphenylimidazole) derivatives were synthesized and their physicochemical properties were determined. Spectroscopic and fluorescence behavior of lophine derivatives in methanol at different pH and various solvents were presented. The observed spectroscopic features in the solution are determined by specific interactions of the NH hydrogen. These kinds of interactions are manifested

  摘要 合成了洛芬(2,4,5-三苯基咪唑)衍生物并测定了其理化性质。介绍了在不同 pH 值和各种溶剂下，洛啡因衍生物在甲醇中的光谱和荧光行为。溶液中观察到的光谱特征是由 NH 氢的特定相互作用决定的。这些类型的相互作用在固态和溶液中都表现出来。介绍和讨论了具有不同结晶溶剂的洛啡因衍生物的晶体和分子结构。在所有溶剂化物中，溶剂分子通过氢键连接主体分子。
• In silico studies, synthesis and pharmacological evaluation to explore multi-targeted approach for imidazole analogues as potential cholinesterase inhibitors with neuroprotective role for Alzheimer’s disease
  作者：Archana S. Gurjar、Mrunali N. Darekar、Keng Yoon Yeong、Luyi Ooi

  DOI：10.1016/j.bmc.2018.01.029

  日期：2018.5

  employed to study interactions within the AChE active site. In silico ADME study was performed to estimate pharmacokinetic parameters. Based on computational studies, some analogues were synthesized and subjected to pharmacological evaluation involving antioxidant activity, toxicity and memory model studies in animals followed by detailed mechanistic in vitro cholinesterase inhibition study. Amongst the

  阿尔茨海默氏病（AD）是一种进行性神经退行性疾病，其发病机理涉及多种因素。我们的抗AD策略涉及设计多目标的2-取代-4,5-二苯基-1H-咪唑类似物，这些类似物可以相互作用并抑制AChE，从而增加ACh的突触可用性，抑制BuChE，减轻诱导的氧化应激并赋予AChE。神经保护作用。分子对接用于研究AChE活性位点内的相互作用。在计算机上进行ADME研究以估计药代动力学参数。在计算研究的基础上，合成了一些类似物，并进行了药理学评估，包括在动物体内进行抗氧化剂活性，毒性和记忆模型研究，随后进行了详细的体外机理研究。胆碱酯酶抑制研究。在该系列中，类似物13和20是最有前途的多目标候选物，可以潜在地增加记忆力，降低自由基水平并保护神经元免受认知缺陷的困扰。