4-(1-(4-hydroxy-3-methoxybenzyl)-1H-benzo[d]imidazol-2-yl)-2-methoxyphenol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 4-(1-(4-hydroxy-3-methoxybenzyl)-1H-benzo[d]imidazol-2-yl)-2-methoxyphenol
• 英文别名: 4-[1-(4-Hydroxy-3-methoxybenzyl)-1H-benzimidazol-2-yl]-2-methoxyphenol；4-[[2-(4-hydroxy-3-methoxyphenyl)benzimidazol-1-yl]methyl]-2-methoxyphenol
• 化学式: C₂₂H₂₀N₂O₄
• mdl: MFCD01952969
• 分子量: 376.412
• InChiKey: SBVOOAOEAYENPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  二苯氨基甲酰氯 、 4-(1-(4-hydroxy-3-methoxybenzyl)-1H-benzo[d]imidazol-2-yl)-2-methoxyphenol 在 吡啶 作用下， 反应 12.0h， 以97%的产率得到
  参考文献：
  名称：

  聚集诱导发射（AIE）活性咪唑的简便合成，用于三氟拉林的灵敏检测

  摘要：

  由香草醛，邻苯二胺和N，N-二苯基氨基甲酰氯合成了新型咪唑荧光探针（2）。其结构的特征在于荧光光谱，UV-Vis光谱，1 H NMR，13 C NMR和高分辨率质谱（HRMS）。此外，在THF / MeOH溶液中研究了其聚集诱导的发射（AIE）功能。此外，荧光猝灭实验结果表明，化合物2是潜在的小有机分子荧光探针，对硝基芳香族化合物显示出高选择性和敏感性。此外，该探针可用于三氟拉林的测定，具有快速响应和稳定的特点。探针的荧光响应与三氟拉林的浓度在10至100μM之间表现出良好的线性相关性，并且检出限（LOD）低至5.066μM。最终，该探针成功地用于测定实际样品中三氟拉林的含量，回收率为91.1％至111.2％，表明该探针的适用性和可靠性。

  DOI：

  10.1016/j.saa.2021.119880
• 作为产物：
  描述：

  N,N'-bis(4-hydroxy-3-methoxybenzylidene)-1,2-phenylenediamine 在 对甲苯磺酸 作用下， 以 neat (no solvent) 为溶剂， 以92%的产率得到4-(1-(4-hydroxy-3-methoxybenzyl)-1H-benzo[d]imidazol-2-yl)-2-methoxyphenol
  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

• 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。
• Nano indium oxide: an efficient catalyst for the synthesis of 1,2-disubstituted benzimidazoles in aqueous media
  作者：Sougata Santra、Adinath Majee、Alakananda Hajra

  DOI：10.1016/j.tetlet.2012.02.021

  日期：2012.4

  Synthesis of 1,2-disubstituted benzimidazoles has been developed by the condensation of diamine with aldehydes using nano In2O3 as an efficient catalyst under mild reaction conditions in aqueous media. The procedure is applicable to aryl, aliphatic, heteroaryl aldehydes. In2O3 nanoparticles are recyclable without the loss of significant catalytic activity.

  通过在水介质中温和的反应条件下，使用纳米In 2 O 3作为有效的催化剂，通过二胺与醛的缩合反应，开发了1,2-二取代的苯并咪唑的合成方法。该方法适用于芳基，脂族，杂芳基醛。In 2 O 3中的纳米颗粒是可回收的，而不会损失明显的催化活性。
• Efficient Synthesis of 2-Aryl-1-arylmethyl-1<i>H</i>-benzimidazoles in Ball Mill without Solvent
  作者：Meihong Jin、Guowei Song、Zhenjiang Li、Feng Zhou、Bo Fan、Pingkai Ouyang

  DOI：10.1002/jhet.1113

  日期：2014.11

  2‐Aryl‐1‐arylmethyl‐1H‐benzimidazoles were prepared in excellent yields by the condensation of o‐phenylenediamine with aldehydes under mechanically activated solvent‐free conditions in ball mill using FeCl3·6H2O as the catalyst.

  通过在球磨机中使用FeCl 3 ·6H 2 O作为催化剂，在机械活化的无溶剂条件下，邻苯二胺与醛的缩合，可以制备出高收率的2-芳基-1-芳基甲基-1 H-苯并咪唑。
• A Cu (NO3)2.3H2O catalysed facile synthesis of substituted 4(3H)-quinazolinones and benzimidazoles
  作者：G A N K DURGAREDDY、R RAVIKUMAR、S RAVI、SRINIVAS R ADAPA

  DOI：10.1007/s12039-012-0343-0

  日期：2013.1

  One pot synthesis of alkyl, aryl, heteroaryl mono(2)substituted 4(3H)-quinazolinones and 2-aryl or heteroaryl, 1-arylmethyl or heteroarylmethyl -1H-benzimidazoles using a water soluble Cu (NO3)2.3H2O catalyst at room/ambient temperature in excellent yield. One pot synthesis of alkyl, aryl, heteroaryl mono(2)substituted 4(3H)-quinazolinones and 2-aryl or heteroaryl, 1-arylmethyl or heteroarylmethyl-1H-benzimidazoles

  使用水溶性Cu（NO 3）2 .3H 2 O一锅合成烷基，芳基，杂芳基单（2）取代的4（3H）-喹唑啉酮和2-芳基或杂芳基，1-芳基甲基或杂芳基甲基-1H-苯并咪唑在室温/环境温度下以优异的收率得到催化剂。 使用水溶性Cu（NO 3）2 .3H 2 O一锅合成烷基，芳基，杂芳基单（2）取代的4（3H）-喹唑啉酮和2-芳基或杂芳基，1-芳基甲基或杂芳基甲基-1H-苯并咪唑据报道，该催化剂在室温/环境温度下具有优异的产率。

表征谱图