5,6-dimethyl-1-(2,4,6-trimethylbenzyl)-1H-benzo[d]imidazole | 637325-10-1

• 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: 5,6-dimethyl-1-(2,4,6-trimethylbenzyl)-1H-benzo[d]imidazole
• 英文别名: 5,6-Dimethyl-1-[(2,4,6-trimethylphenyl)methyl]-1H-benzimidazole；5,6-dimethyl-1-[(2,4,6-trimethylphenyl)methyl]benzimidazole
• CAS: 637325-10-1
• 化学式: C₁₉H₂₂N₂
• mdl: MFCD04330680
• 分子量: 278.397
• InChiKey: HLVSJZHTNXVFIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5,6-dimethyl-1-(2,4,6-trimethylbenzyl)-1H-benzo[d]imidazole 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 71.0h， 生成 (5,6-dimethyl-1,3-bis(2,4,6-trimethylbenzyl)-2,3-dihydro-1H-benzo[d]imidazole-2-yl)copper(II) chloride
  参考文献：
  名称：

  Copper-catalyzed azide–alkyne cycloaddition (CuAAC) under mild condition in water: Synthesis, catalytic application and biological activities

  摘要：

  A series of Cu-N-heterocyclic carbene (Cu-NHC) complexes, 3a-c, were synthesized and characterized by spectroscopic methods such as NMR, HRMS and elemental analysis. The performance of these (Cu-NHC) complexes, 3a-c showed excellent activity in 1,3-dipolar cycloaddition reactions between alkynes and azides to obtain 1,4-disubstituted triazoles 6a-d in 80%-91% isolated yields. All obtained complexes especially compounds 3a and 3c, presented significant inhibitory activity against the tested food-borne pathogens and clinical microorganisms. The compound 3a presents against S. aureus a MIC value of 4.8 mg/ml quite similar to that of ampicillin (4 mg/ml) used as standard. Compounds 3a and 3b, from a concentration of 0.5 mg/ml, present an identical scavenging activity to that of the two used controls butylated hydroxytoluene (BHT) and gallic acid (GA). Concerning acetylcholinesterase inhibition activity (AChEI), compound 6a presents an interesting AChEI activity with 68.3% of inhibition. (C) 2017 Published by Elsevier B.V.

  DOI：

  10.1016/j.jorganchem.2017.09.024
• 作为产物：
  描述：

  5,6-二甲基苯并咪唑 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 5,6-dimethyl-1-(2,4,6-trimethylbenzyl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  由 Pd(OAc)2 催化剂产生的高效原位 N-杂环卡宾钯(ii)，用于在惰性条件下芳基硼酸与 2-溴吡啶的羰基化 Suzuki 偶联反应，产生不对称芳基吡啶酮：合成、表征和细胞毒性活性†

  摘要：

  成功合成了N , N-取代的苯并咪唑盐，并通过1 H-NMR、 13 C { 1 H} NMR 和 IR 技术进行了表征，支持了所提出的结构。原位生成的催化剂可有效用于 2 溴吡啶与各种硼酸的羰基化交叉偶联反应。该反应在THF中、110℃、K 2 CO 3存在下、惰性条件下进行，生成不对称芳基吡啶酮。本工作中研究的所有N 、 N取代苯并咪唑盐2a-i和4a-i 均针对其针对人类癌细胞系（例如 MDA-MB-231、MCF-7 和 T47D）的细胞毒活性进行了筛选。 N 、 N-取代的苯并咪唑2e和2f表现出最大的细胞毒性作用，具有良好的细胞毒性活性，针对MDA-MB-231的IC 50值分别为4.45 μg mL -1 ，针对MCF7的IC 50 值分别为4.85 μg mL -1 。

  DOI：

  10.1039/c8ra08897g

文献信息

• Anticancer, antimicrobial and antiparasitical activities of copper(I) complexes based on <i>N</i>-heterocyclic carbene (NHC) ligands bearing aryl substituents
  作者：Nedra Touj、Ibrahim S. Al Nasr、Waleed S. Koko、Tariq A. Khan、Ismail Özdemir、Sedat Yasar、Lamjed Mansour、Faisal Alresheedi、Naceur Hamdi

  DOI：10.1080/00958972.2020.1836359

  日期：2020.11.16

  Abstract New benzimidazolium salts were synthesized as N-heterocyclic carbene precursors. These NHC precursors were metallated with Cu2O and CuI in acetone and water under reflux to give novel copper(I) complexes. The structures of these benzimidazolium salts and copper(I) complexes were characterized on the basis of elemental analysis, 1H NMR, 13C NMR, IR and LC–MS spectroscopic techniques. The (NHC)Cu(I)

  摘要 合成了新的苯并咪唑鎓盐作为 N-杂环卡宾前体。这些 NHC 前体在丙酮和水中在回流下用 Cu2O 和 CuI 金属化，得到新的铜 (I) 配合物。这些苯并咪唑盐和铜 (I) 配合物的结构基于元素分析、1H NMR、13C NMR、IR 和 LC-MS 光谱技术进行表征。(NHC)Cu(I) 复合物 3-4 已针对 MCF7 和 MDA-MB-231 癌细胞、大肠杆菌、耐甲氧西林金黄色葡萄球菌 (MRSA) 和白色念珠菌微生物、利什曼原虫主要前鞭毛体和无鞭毛体、弓形虫寄生虫进行了测试并在体外对抗 Vero 细胞系。合成的铜NHC卡宾配合物4b(1,3-bis(2,3,4,5,6-pentamdthylbenzyl)-2, 3-二氢-1H-苯并[d]咪唑-2-基）氯化铜（I））对 MCF7 癌细胞最具活性（半数生长抑制浓度 (IC50) = 0.3 µg mL-1），以及对大肠杆菌（抑制区
• Rhodium(I) Complexes of New Ferrocenyl Benzimidazol‐2‐ylidene Ligands: The Importance of the Chelating Effect for Ketone Hydrosilylation Catalysis
  作者：Süleyman Gülcemal、Agnès Labande、Jean‐Claude Daran、Bekir Çetinkaya、Rinaldo Poli

  DOI：10.1002/ejic.200801163

  日期：2009.5

  bifunctional ligands, and related ferrocenyl 5,6-di-X-benzimidazol-2-ylidene iodide salts (X = H, 6a and Me, 6b), precursors of monodentate benzimidazol-2-ylidene ligands, have been prepared for the first time. Cationic rhodium(I) complexes 7a and 7b and neutral rhodium(I) complexes 8a and 8b have been obtained in good yields and have been fully characterised. Cationic rhodium(I) complexes 10a and 10b

  N-[(1-Phosphanylferrocen-1'-yl)methyl]-N'-[(2,4,6-trimethylphenyl)methyl]-5,6-di-X-苯并咪唑鎓四氟硼酸盐（X = H, 5a 和Me, 5b)，新膦-苯并咪唑-2-亚基双功能配体的前体，以及相关的二茂铁基 5,6-二-X-苯并咪唑-2-亚基碘化物盐（X = H, 6a 和 Me, 6b），首次制备了单齿苯并咪唑-2-亚基配体。阳离子铑(I)配合物7a和7b以及中性铑(I)配合物8a和8b已经以良好的产率获得并且已经被充分表征。阳离子铑(I)配合物10a和10b由8a和8b制备，用于与配合物7比较，但未分离。所有配合物对苯乙酮衍生物的催化氢化硅烷化均表现出良好的活性。活性远大于相关的咪唑-2-亚基系统，阳离子配合物比中性配合物活性高；对于更易溶解的复合物 7b，观察到最高的活性。事实证明，双齿配体的使用对于获得所需醇的良好选择性至关重要。（©
• Synthesis and use of mono- or bisxylyl linked bis(benzimidazolium) bromides as carbene precursors for C–C bond formation reactions
  作者：Hayati Türkmen、Serpil Denizaltı、Ismail Özdemir、Engin Çetinkaya、Bekir Çetinkaya

  DOI：10.1016/j.jorganchem.2007.11.015

  日期：2008.2

  Two benzimidazolium moieties linked by one or two xylyls (m- and p-) have been synthesized, characterized and then they were used for Heck coupling reactions as in situ formed catalysts. Mono bridged salts are more efficient as compared to bisbridged salts. In addition, mono bridged salts were converted to Rh–NHC complexes which were tested as catalysts for the arylation of aldehydes.

  已经合成，表征了两个由一个或两个二甲苯基（m-和p-）连接的苯并咪唑部分，然后将它们作为原位形成的催化剂用于Heck偶联反应。与双桥盐相比，单桥盐更有效。此外，单桥盐被转化为Rh-NHC络合物，经测试可作为醛芳基化的催化剂。
• New palladium(II)-<i>N</i>-heterocyclic carbene complexes containing benzimidazole-2-ylidene ligand derived from menthol: synthesis, characterization and catalytic activities
  作者：Rafet Kılınçarslan、M. Emin Günay、Rukiye Fırıncı、Serpil Denizaltı、Bekir Çetinkaya

  DOI：10.1002/aoc.3427

  日期：2016.5

  A new series of sterically hindered ligands containing (1R,2S,4R)‐(+)‐menthoxymethyl group attached to benzimidazole‐based N‐heterocyclic carbene (NHC), palladium–bis‐NHC complexes and (κ2‐C,N)‐palladacyclic NHC complexes have been synthesized and characterized using appropriate spectroscopic techniques. Catalytic performance of the palladium complexes has been investigated for allylic alkylation,

  一系列新的空间位阻的配体包含（1 - [R，2小号，4 - [R ）- （+） -薄荷氧基团连接的苯并咪唑为基础，以ñ -杂环卡宾（NHC），钯-双- NHC络合物和（κ 2 - Ç，N）-四环环NHC复合物已经合成，并使用适当的光谱技术进行了表征。已经研究了钯配合物的催化性能，用于烯丙基烷基化，Suzuki和Heck碳-碳偶联反应。这些配合物可以平稳地催化碳-碳键的形成反应。版权所有©2016 John Wiley＆Sons，Ltd.
• Heterogenization of homogeneous NHC-Pd-pyridine catalysts and investigation of their catalytic activities in Suzuki-Miyaura coupling reactions
  作者：Cihangir Boztepe、Asim Künkül、Sedat Yaşar、Nevin Gürbüz

  DOI：10.1016/j.jorganchem.2018.07.004

  日期：2018.10

  NHC-Pd-pyridine complexes was conducted by using NMR, FT-IR while the structural characterization of crosslinked polymeric catalyst systems was made by using FT-IR, SEM, SEM-EDX, TEM and TGA analysis techniques. The synthesized polymer-based NHC-Pd-pyridine catalysts showed good catalytic activity for Suzuki reaction of aryl bromides with phenylboronic acid in aqueous media. They exhibited good stability and

  通过将NHC-Pd-吡啶配合物与丙烯酰胺（AAm）和2-丙烯酰胺基-2-甲基丙烷磺酸（AMPS）进行自由基聚合，可以制备出包括催化活性NHC-Pd-吡啶配合物在内的新一代新型环保型聚合物非均相催化剂。 N，N'-亚甲基双丙烯酰胺（MBA）交联剂存在下的单体。NHC-Pd-吡啶配合物的结构表征是通过NMR，FT-IR进行的，而交联的聚合物催化剂体系的结构表征是通过FT-IR，SEM，SEM-EDX，TEM和TGA分析技术进行的。合成的聚合物基NHC-Pd-吡啶催化剂在水性介质中对芳基溴化物与苯基硼酸的Suzuki反应表现出良好的催化活性。