1-(5-ethoxy-4-hydroxybenzyl)-2-(2-ethoxyphenol-4-yl)-1H-benzo[d]imidazole | 537010-67-6

• 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: 1-(5-ethoxy-4-hydroxybenzyl)-2-(2-ethoxyphenol-4-yl)-1H-benzo[d]imidazole
• 英文别名: 2-ethoxy-4-(1-(3-ethoxy-4-hydroxybenzyl)-1H-benzo[d]imidazol-2-yl)phenol；1-(3-ethoxy-4-hydroxybenzyl)-2-(3-ethoxy-4-hydroxyphenyl)benzimidazole；2-ethoxy-4-[1-(3-ethoxy-4-hydroxybenzyl)-1H-benzimidazol-2-yl]phenol；2-ethoxy-4-[[2-(3-ethoxy-4-hydroxyphenyl)benzimidazol-1-yl]methyl]phenol
• CAS: 537010-67-6
• 化学式: C₂₄H₂₄N₂O₄
• mdl: MFCD03671172
• 分子量: 404.466
• InChiKey: XQDLZTHUOJVLNA-UHFFFAOYSA-N

物化性质

• 熔点：
  127-129 °C
• 沸点：
  648.7±65.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  乙基香兰素 、 邻苯二胺 在 Citrus limonium extract 作用下， 以 乙醇 为溶剂， 反应 0.75h， 以84%的产率得到1-(5-ethoxy-4-hydroxybenzyl)-2-(2-ethoxyphenol-4-yl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Natural Bio-surfactant for Pseudomulticomponent Synthesis of 2-Aryl-1- aryl Methyl-1H-benzimidazoles

  摘要：

  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。

  DOI：

  10.2174/1570178614666170710115331

文献信息

• MWCNTs‐ZrO ₂ as a reusable heterogeneous catalyst for the synthesis of <i>N</i> ‐heterocyclic scaffolds under green reaction medium
  作者：Bipasa Halder、Flora Banerjee、Ahindra Nag

  DOI：10.1002/aoc.5906

  日期：2020.11

  scanning electron microscopy, and X‐ray photoelectron spectroscopy analysis. The heterogeneous nanocomposite has been used for one‐pot synthesis of various N‐heterocyclic compounds like pyrazoles, 1,2‐disubstituted benzimidazoles, 2‐arylbenzazoles, and 2,3‐dihydroquinazolin‐4(1H)‐ones under green reaction medium at room temperature. This novel method has several advantages, such as short reaction time, simple

  使用天然原料椰子汁（água-de-cocodoCeará）合成了一种简单，高效且易用的异质多壁碳纳米管-氧化锆纳米复合材料（MWCNTs-ZrO 2）。通过傅立叶变换红外光谱，X射线衍射，场发射扫描电子显微镜和X射线光电子能谱分析对合成的催化剂进行了表征。异质纳米复合材料已用于一锅合成各种N杂环化合物，如吡唑，1,2-二取代的苯并咪唑，2-芳基苯并唑和2,3-二氢喹唑啉-4（1 H）-在室温下在绿色反应介质下进行。这种新颖的方法具有多个优点，例如反应时间短，后处理简单，产率高以及绿色的反应条件。催化剂循环使用多达四次，而催化活性没有明显损失。
• Natural dolomitic limestone-catalyzed synthesis of benzimidazoles, dihydropyrimidinones, and highly substituted pyridines under ultrasound irradiation
  作者：Kumar Godugu、Venkata Divya Sri Yadala、Mohammad Khaja Mohinuddin Pinjari、Trivikram Reddy Gundala、Lakshmi Reddy Sanapareddy、Chinna Gangi Reddy Nallagondu

  DOI：10.3762/bjoc.16.156

  日期：——

  Natural dolomitic limestone (NDL) is employed as a heterogeneous green catalyst for the synthesis of medicinally valuable benzimidazoles, dihydropyrimidinones, and highly functionalized pyridines via C–N, C–C, and C–S bond formations in a mixture of ethanol and H2O under ultrasound irradiation. The catalyst is characterized by XRD, FTIR, Raman spectroscopy, SEM, and EDAX analysis. The main advantages

  天然白云质石灰石（NDL）被用作异质绿色催化剂，用于通过乙醇和H 2的混合物中C–N，C–C和C–S键的形成来合成具有药用价值的苯并咪唑，二氢嘧啶酮和高度官能化的吡啶O在超声波照射下。该催化剂通过XRD，FTIR，拉曼光谱，SEM和EDAX分析来表征。这种方法的主要优点包括广泛的底物范围，更清洁的反应曲线，较短的反应时间和优异的分离产率。该产品不需要色谱纯化，该催化剂可以重复使用七次。因此，与现有报道的催化剂相比，该催化剂是用于合成上述N-杂环的更绿色的替代物。
• Exploration of in vitro time point quantitative evaluation of newly synthesized benzimidazole and benzothiazole derivatives as potential antibacterial agents
  作者：Prabal Bandyopadhyay、Manisha Sathe、S. Ponmariappan、Arti Sharma、Pratibha Sharma、A.K. Srivastava、M.P. Kaushik

  DOI：10.1016/j.bmcl.2011.10.034

  日期：2011.12

  Present communication deals with the in vitro time point quantitative antibacterial evaluation of newly synthesized 1,2-disubstituted benzimidazoles (3a-p) and 2-substituted benzothiazoles (5a-h) against Gram-positive bacteria Staphylococcus aureus, Bacillus cereus, and Gram-negative bacteria Vibrio cholerae, Shigella dysenteriae and Escherichia coli. These compounds were synthesized under mild reaction conditions using Al(2)O(3)-Fe(2)O(3) nanocrystals as heterogeneous catalyst. Bio-evaluation studies revealed that, compounds 3a, 5a and 5d exhibited moderate to good antibacterial activity against all the tested bacterial stains. The compounds 3a, 3f and 5a have shown enhanced inhibitory activity compared with standard antibacterial drug ciprofloxacin against V. cholerae, B. cereus, and S. dysenteriae, respectively. Additionally, the compounds 3a, 3e, 3f, 3h and 5b displayed complete bactericidal activity within 24 h, whereas ciprofloxacin took 48 h to kill those bacteria completely. (C) 2011 Elsevier Ltd. All rights reserved.
• Mesoporous mixed metal oxide nanocrystals: Efficient and recyclable heterogeneous catalysts for the synthesis of 1,2-disubstituted benzimidazoles and 2-substituted benzothiazoles
  作者：Prabal Bandyopadhyay、Manisha Sathe、G.K. Prasad、Pratibha Sharma、M.P. Kaushik

  DOI：10.1016/j.molcata.2011.03.027

  日期：2011.5

  Present communication elicits the use of mesoporous mixed metal oxide nanocrystals of Al2O3-Fe2O3. Al2O3-V2O5 and Al2O3-CuO as heterogeneous catalysts for the preparation of series of medicinally significant 1,2-disubstituted benzimidazoles and 2-substituted benzothiazoles. These nanocrystalline catalysts exhibited remarkable catalytic activity with a high substrate to catalyst weight ratio (20:1) to achieve the synthetic targets in the range of yield 81-96%. The solvent-free microwave assisted synthesis of these compounds was an advantageous way which resulted in excellent yields in much lesser time (0.75-1.5 min) in comparison to conventional heating. The use of catalyst in eco-friendly green protocol and its reusability up to four cycles with similar catalytic response are the unique features of the heterogeneous catalysis. This protocol provided greater selectivity, cost-efficiency, clean reaction profiles, simple work-up procedure and high yields. (C) 2011 Elsevier B.V. All rights reserved.
• 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。