4-((2-(4-羟基苯基)-1H-苯并咪唑-1-基)甲基)苯酚 | 85573-17-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 4-((2-(4-羟基苯基)-1H-苯并咪唑-1-基)甲基)苯酚
• 英文名称: 1-(4-hydroxybenzyl)-2-(4-hydroxyphenyl)-1H-benzo[d]imidazole
• 英文别名: 4-(1-(4-hydroxybenzyl)-1H-benzo[d]imidazol-2-yl)phenol；1-(4-hydroxybenzyl)-2-(4-hydroxyphenyl)-1H-benzimidazole；4-[1-(4-hydroxybenzyl)-1H-benzimidazol-2-yl]-phenol；Phenol, 4-((2-(4-hydroxyphenyl)-1H-benzimidazol-1-yl)methyl)-；4-[[2-(4-hydroxyphenyl)benzimidazol-1-yl]methyl]phenol
• CAS: 85573-17-7
• 化学式: C₂₀H₁₆N₂O₂
• 分子量: 316.359
• InChiKey: UCPIAPAZIWRDBJ-UHFFFAOYSA-N

物化性质

• 熔点：
  226-228 °C
• 沸点：
  602.2±65.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  58.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  水合三氯化钌 、 4-((2-(4-羟基苯基)-1H-苯并咪唑-1-基)甲基)苯酚 以 丙酮 为溶剂， 生成 [RuCl₃(1-p-hydroxybenzyl-2-p-hydroxyphenylbenzimidazole)2(H₂O)2]
  参考文献：
  名称：

  1,2-二取代苯并咪唑氯化钌（III）配合物的合成，表征及其催化活性

  摘要：

  氯化钌（III）与2-单取代和1,2-二取代的苯并咪唑反应生成式RuCl 3 L y .nH 2 O的配合物[L = 2-o-羟基苯基苯并咪唑（oHPB），y = 3，n = 0; L ＝ 2-对羟基苯基苯并咪唑（pHPB），y ＝ 2，n ＝ 3]和RuCl 3 L 2 .H 2 O [L ＝ 1-o-羟基苄基-2-o-羟基苯基苯并咪唑（oHBPB），1-m -羟基苄基-2-间羟基苯基苯并咪唑（mHBPB）和1-对羟基苄基-2-对羟基苯基苯并咪唑（pHBPB）]。配合物的特征在于元素分析，电导率测量，红外，电子，1 H和13C-NMR光谱研究以及热分析。配合物表现出八面体的几何形状。一些配合物充当转移氢化的潜在催化剂。

  DOI：

  10.1080/15533174.2011.568446
• 作为产物：
  描述：

  4,4′-[1,2-phenylenebis(nitrilomethylidene)]bisphenol 在 对甲苯磺酸 作用下， 以 neat (no solvent) 为溶剂， 以91%的产率得到4-((2-(4-羟基苯基)-1H-苯并咪唑-1-基)甲基)苯酚
  参考文献：
  名称：

  Facile Synthesis of 1,2-Disubstituted Benzimidazoles Usingp-Toluenesulfonic Acid through Grinding Method

  摘要：

  An efficient synthetic method for the highly selective synthesis of pharmacologically active 1,2-disubstituted benzimidazole derivatives fromo-phenylenediamine and various aromatic aldehydes catalyzed byp-toluenesulfonic acid through grinding under solvent-free condition is described. The reaction requires the catalyst only during the conversion of intermediateN,N '-dibenzylidene-o-phenylenediamine into the desired product. The products were obtained within a short time with good yields by using only a mortar and pestle, which makes the proposed method convenient and cost-effective.

  DOI：

  10.1134/s1070428020090201

文献信息

• Synthesis of 1,2-disubstituted benzimidazoles, 2-substituted benzimidazoles and 2-substituted benzothiazoles in SDS micelles
  作者：Kiumars Bahrami、Mohammad M. Khodaei、Akbar Nejati

  DOI：10.1039/c000047g

  日期：——

  A practical and convenient synthetic method has been developed for the facile synthesis of 1,2-disubstituted benzimidazoles, 2-substituted benzimidazoles and 2-substituted benzothiazoles. The method described has the benefits of operational simplicity, excellent yields, and high chemoselectivity.

  开发了一种实用且便捷的合成方法，用于便捷合成1,2-二取代苯并咪唑、2-取代苯并咪唑和2-取代苯并噻唑。所述方法具有操作简单、产率高和化学选择性好的优点。
• [EN] BENZIMIDAZOLES FOR THE TREATMENT OF CANCER<br/>[FR] BENZIMIDAZOLES POUR LE TRAITEMENT D'UN CANCER
  申请人：MAX PLANCK GESELLSCHAFT

  公开号：WO2014027053A1

  公开（公告）日：2014-02-20

  The present invention relates to novel substituted benzimidazoles and stereoisomeric forms, prodrugs, solvates, hydrates and/or pharmaceutically acceptable salts of these compounds as well as pharmaceutical compositions containing at least one of these substituted benzimidazoles together with pharmaceutically acceptable carrier, excipient and/or diluents. Said novel substituted benzimidazoles binding to the prenyl binding pocket of PDEδ have been identified as useful for the prophylaxis and treatment of cancer by the inhibition of the binding of PDEδ to K-Ras and of oncogenic Ras signalling in cells by altering its localization leading to cell death or inhibition of proliferation.

  本发明涉及新型取代苯并咪唑和立体异构体形式，以及这些化合物的前药、溶剂化合物、水合物和/或药学上可接受的盐，以及含有至少一种这些取代苯并咪唑的药物组合物，与药学上可接受的载体、赋形剂和/或稀释剂一起。已经确定这些新型取代苯并咪唑结合到PDEδ的藤黄素结合口袋，对于通过抑制PDEδ与K-Ras的结合以及通过改变其定位导致细胞死亡或抑制增殖而对癌症的预防和治疗是有用的。
• Synthesis and application of silica phenyl sulfonic acid as a solid acid heterogeneous catalyst for one-pot synthesis of 2-aryl-1-arylmethyl-1H-1,3-benzimidazoles and bis(indolyl)methanes in water
  作者：Hojat Veisi、Alireza Sedrpoushan、Mohammad Ali Zolfigol、Farajollah Mohanazadeh

  DOI：10.1002/jhet.765

  日期：2011.11

  Silica phenyl sulfonic acid (SPSA) was prepared and effectively used in the one‐pot synthesis of 2‐aryl‐1‐arylmethyl‐1H‐1,3‐benzimidazoles from o‐phenylenediamine with aldehydes in water in the presence of tetrabutyl ammonium bromide with good to high yield. Also, SPSA was used as a catalyst for the synthesis of bis(indolyl)methanes in water. J. Heterocyclic Chem., (2011).

  制备了二氧化硅苯基磺酸（SPSA）并将其有效地用于在四丁基溴化铵与水存在下，由邻苯二胺和醛在水中一锅法合成2-芳基-1-芳基甲基-1H-1,3-苯并咪唑好到高产。而且，SPSA还用作在水中合成双（吲哚基）甲烷的催化剂。J.杂环化​​学。（2011）。
• Chitosan-supported Fe3O4 nanoparticles: a magnetically recyclable heterogeneous nanocatalyst for the syntheses of multifunctional benzimidazoles and benzodiazepines
  作者：Ali Maleki、Nakisa Ghamari、Maryam Kamalzare

  DOI：10.1039/c3ra47366j

  日期：——

  An environmentally benign and clean biopolymer-based heterogeneous nanocatalyst was prepared and its properties and morphology were characterized using scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDX) and X-ray diffraction (XRD). Then, its catalytic activity was investigated in two important organic reactions. In these reactions, efficient and selective syntheses of 1,2-disubstituted benzimidazole and 1,5-benzodiazepine derivatives were carried out using 1,2-diamines and aldehydes or ketones in the presence of a catalytic amount of magnetically recoverable chitosan-supported iron oxide nanoparticles (Fe3O4/chitosan), as a biodegradable nanocomposite, in ethanol at ambient temperature in high yields. The Fe3O4/chitosan nanocatalyst can be recovered easily and reused without any significant loss of the catalytic activity.

  制备了一种环境友好且清洁的生物聚合物基异质纳米催化剂，并通过扫描电子显微镜（SEM）、能量色散X射线光谱（EDX）和X射线衍射（XRD）对其性质和形态进行了表征。随后，研究了其在两种重要有机反应中的催化活性。在这些反应中，使用1,2-二胺和醛或酮在催化量的可磁回收壳聚糖支持铁氧化物纳米颗粒（Fe3O4/壳聚糖）的存在下，在室温下的乙醇中高效且选择性地合成了1,2-取代的苯并咪唑和1,5-苯并二氮杂卓衍生物。Fe3O4/壳聚糖纳米催化剂可以轻松回收并重复使用，且没有显著的催化活性损失。
• Natural Bio-surfactant for Pseudomulticomponent Synthesis of 2-Aryl-1- aryl Methyl-1H-benzimidazoles
  作者：Smita T. Morbale、Sachin K. Shinde、Shashikant A. Damate、Madhukar B. Deshmukh、Suresh S. Patil

  DOI：10.2174/1570178614666170710115331

  日期：2017.12.11

  Green chemistry emphasizes the development of environmentally benign chemical processes and technologies. Pseudo-multicomponent synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles using o-phenylenediamine and aromatic aldehydes is carried out by Bronsted acid type bio-surfactant as a catalyst. The green features of this method include the use of biodegradable catalyst obtained from renewable resource i.e. Citrus Limonium extract as bio-surfactant type Bronsted acid, which provides a micellar media for effective cyclocondensation. The critical micellar concentration (cmc) of biosurfactant was determined by conductivity method and visualized by light microscopy measurement. Identity of all pure compounds was ascertained on the basis of FT-IR, 1H NMR and 13C NMR spectroscopic techniques.

  绿色化学强调开发环保的化学过程和技术。采用邻苯二胺和芳香醛的伪多组分合成2-芳基-1-芳基甲基-1H-苯并咪唑是通过布朗斯特酸型生物表面活性剂作为催化剂进行的。这种方法的绿色特征包括使用来自可再生资源的生物可降解催化剂，即柠檬提取物，作为生物表面活性剂型布朗斯特酸，提供有效的微胶团介质用于环缩合反应。生物表面活性剂的临界胶束浓度（cmc）通过电导法确定，并通过光学显微镜测量进行可视化。所有纯化合物的身份通过FT-IR、1H NMR和13C NMR光谱技术得以确认。