1-(3,4,5-trimethoxybenzyl)benzimidazole

• 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-(3,4,5-trimethoxybenzyl)benzimidazole
• 英文别名: 1-(3,4,5-Trimethoxybenzyl)benzimidazole；1-[(3,4,5-trimethoxyphenyl)methyl]benzimidazole
• 化学式: C₁₇H₁₈N₂O₃
• 分子量: 298.342
• InChiKey: QOBSSSRVZYNPGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3,4,5-trimethoxybenzyl)benzimidazole 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 dichloro[1,3-bis(3,4,5-methoxybenzyl)benzimidazole-2-ylidene]pyridine palladium(II)
  参考文献：
  名称：

  Synthesis, characterization and the Suzuki–Miyaura coupling reactions of N-heterocyclic carbene–Pd(II)–pyridine (PEPPSI) complexes

  摘要：

  N-heterocyclic carbenes (NHCs) are a significant and powerful class of ligands for transition metals. A new series of air and moisture-stable NHC-PdCl2-pyridine complexes, (2a-f), have been described. With the development of a more efficient catalytic system for the cross-coupling of aryl halides in mind, the catalytic performance of the NHC-PdCl2-pyridine complexes for Suzuki cross-coupling under mild conditions in aqueous N,N-dimethylformamide (DMF) was investigated. Electron-rich and electron-poor aryl chlorides were facilely coupled with boronic acids by NHC-PdCl2-pyridine complexes. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2014.10.047
• 作为产物：
  描述：

  苯并咪唑 、 5-溴甲基-1,2,3-三甲氧基苯 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 1-(3,4,5-trimethoxybenzyl)benzimidazole
  参考文献：
  名称：

  Synthesis, characterization and the Suzuki–Miyaura coupling reactions of N-heterocyclic carbene–Pd(II)–pyridine (PEPPSI) complexes

  摘要：

  N-heterocyclic carbenes (NHCs) are a significant and powerful class of ligands for transition metals. A new series of air and moisture-stable NHC-PdCl2-pyridine complexes, (2a-f), have been described. With the development of a more efficient catalytic system for the cross-coupling of aryl halides in mind, the catalytic performance of the NHC-PdCl2-pyridine complexes for Suzuki cross-coupling under mild conditions in aqueous N,N-dimethylformamide (DMF) was investigated. Electron-rich and electron-poor aryl chlorides were facilely coupled with boronic acids by NHC-PdCl2-pyridine complexes. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2014.10.047

文献信息

• Palladium-Catalyzed Heck Reaction of Aryl Bromides in Aqueous Media Using Tris(N<i>-</i>Heterocyclic Carbene) Ligands
  作者：Ismail Özdemir、Serpil Demir、Bekir Çetinkaya

  DOI：10.1055/s-2007-973860

  日期：2007.4

  highly effective, easy to handle and environmentally benign process for palladium-mediated Heck reaction was developed. The in situ prepared three-component system composed of palladium(II) acetate, a tris(azolinium) bromide and potassium TERT-butoxide, quantitatively catalyzes the Heck reaction of aryl bromides in aqueous media.

  开发了一种高效、易于处理且环境友好的钯介导的 Heck 反应工艺。原位制备的三组分体系由乙酸钯（II）、三（唑啉）溴化物和叔丁醇钾组成，在水性介质中定量催化芳基溴化物的 Heck 反应。
• Synthesis, characterization and antimicrobial activities of novel silver(I) complexes with coumarin substituted N-heterocyclic carbene ligands
  作者：Mert Olgun Karataş、Begüm Olgundeniz、Selami Günal、İlknur Özdemir、Bülent Alıcı、Engin Çetinkaya

  DOI：10.1016/j.bmc.2015.12.032

  日期：2016.2

  Eight new coumarin substituted silver(I) N-heterocyclic carbene (NHC) complexes were synthesized by the interaction of the corresponding imidazolium or benzimidazolium chlorides and Ag2O in dichloromethane at room temperature. Structures of these complexes were established on the basis of elemental analysis, 1H NMR, 13C NMR, IR and mass spectroscopic techniques. The antimicrobial activities of carbene

  通过在室温下二氯甲烷中相应的咪唑鎓或苯并咪唑鎓氯化物与Ag 2 O的相互作用，合成了八种新的香豆素取代的银（I）N杂环卡宾（NHC）配合物。这些配合物的结构是在元素分析，1 H NMR，13 C NMR，IR和质谱技术的基础上建立的。卡宾前体和NHC银配合物的抗微生物活性针对标准菌株进行了测试：粪肠球菌，金黄色葡萄球菌，大肠杆菌，铜绿假单胞菌和真菌白色念珠菌和热带假丝酵母。结果表明，所有化合物均能抑制所有细菌和真菌菌株的生长，并且某些复合物对不同微生物具有良好的活性。在所有化合物中，亲脂性最强的双[1-（4-亚甲基-6,8-二甲基-2 H-铬-2-（one）-3-（萘-2-基甲基）苯并咪唑-2-亚烷基]银（I）银二氯乙酸盐（5e）被发现是最活跃的。
• Palladium(II)NHC complexes containing benzimidazole ligand as a catalyst for CN bond formation
  作者：Öznur Doǧan、Serpil Demir、İsmail Özdemir、Bekir Çetinkaya

  DOI：10.1002/aoc.1731

  日期：2011.3

  (1). The reaction of Pd(OAc)2 with 1,3‐dialkylbenzimidazolium salts (1a–c) yields palladium N‐heterocyclic carbene (NHC) complexes (2a–c). All synthesized compounds were characterized by 1H NMR, 13 C NMR, IR and elemental analysis techniques which support the proposed structures. As catalysts, these new palladium complexes offer a simple and efficient methodology for the synthesis of triarylamines and

  2-（2-溴乙基）-1,3-二恶烷与1-烷基苯并咪唑衍生物的反应导致新的苯并咪唑鎓盐的形成（1）。Pd（OAc）2与1,3-二烷基苯并咪唑鎓盐（1a–c）的反应生成钯N-杂环卡宾（NHC）络合物（2a–c）。所有合成的化合物都通过1 H NMR，13 C NMR，IR和元素分析技术进行了表征，这些技术均支持所提出的结构。这些新型的钯配合物作为催化剂，提供了一种简单有效的方法，可从苯胺和胺类合成叔芳基胺和仲胺，并且一步法以叔丁醇钾为碱。版权所有©2010 John Wiley＆Sons，Ltd.
• Synthesis and investigation of catalytic activity of phenylene – And biphenylene bridged bimetallic Palladium-PEPPSI complexes
  作者：Fatma İmik、Sedat Yaşar、İsmail Özdemir

  DOI：10.1016/j.jorganchem.2019.06.019

  日期：2019.9

  steric properties were used on the synthesis of bridged bimetallic NHC–Pd-PEPPSI (PEPPSI: Pyridine Enhanced Precatalyst Preparation Stabilization Initiation) complexes. The catalytic properties of the bridged bimetallic NHC–Pd-PEPPSI complexes were investigated in the different C–C coupling reaction such as Suzuki-Miyaura reactions of aryl bromides with arylboronic acid, the Heck coupling reactions of

  据报道，一系列苯和联苯桥连的N-杂环卡宾（NHC）及其双金属NHC-Pd-PEPPSI配合物，并通过1 H NMR进行了全面表征，1313 C NMR，HRMS，FTIR和元素分析。具有不同电子和空间特性的N标签被用于合成桥联的双金属NHC-Pd-PEPPSI（PEPPSI：吡啶增强的前催化剂制备稳定起始）复合物。在不同的C–C偶联反应（例如芳基溴化物与芳基硼酸的Suzuki-Miyaura反应，芳基溴化物与苯乙烯的Heck偶联反应以及Sonogashira反应）中研究了桥接的双金属NHC-Pd-PEPPSI配合物的催化性能。芳基溴化物与苯乙炔。通常，所有桥接的双金属NHC-Pd-PEPPSI配合物在C-C偶联反应中均表现出良好的催化活性。
• Cytotoxic effects of coumarin substituted benzimidazolium salts against human prostate and ovarian cancer cells
  作者：Mert Olgun Karataş、Suat Tekin、Bülent Alici、Süleyman Sandal

  DOI：10.1007/s12039-019-1647-0

  日期：2019.8

  derivatives have individual biological activities including anticancer. In this study, we aimed to synthesize coumarin-benzimidazole hybrids in order to investigate their anticancer properties. For this purpose, six 6-substituted-4-chloromethylene coumarin derivatives were synthesized. Sixteen coumarin substituted benzimidazolium chlorides were synthesized by the reaction of 4-chloromethylene coumarin and N-benzylbenzimidazole

  摘要香豆素和苯并咪唑衍生物具有包括抗癌在内的单独的生物活性。在这项研究中，我们旨在合成香豆素-苯并咪唑杂种以研究其抗癌特性。为此目的，合成了六个6-取代的-4-氯亚甲基香豆素衍生物。通过4-氯亚甲基香豆素与N-苄基苯并咪唑衍生物的反应合成了十六种香豆素取代的苯并咪唑氯化物。所有合成的化合物的特征在于NMR，IR光谱技术和元素分析。（^ 1} \ hbox H} \）和\（^ 13} \ hbox C} \）。通过[3-（4,5-二甲基噻唑）-2-基] -2,5-二苯基-2 H测试所有化合物的细胞毒性-对人前列腺（PC-3）和卵巢（A2780）癌细胞进行溴化四唑鎓（MTT）分析。所有化合物对两种癌细胞系均在\（100 \，\ upmu \ hbox M} \）处表现出明显的细胞毒性。而且，一些化合物在两种细胞系中都在\（1 \，\ upmu \ hbox M} \）处表现出显着的