N-(4-phenoxybutyl)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: N-(4-phenoxybutyl)benzimidazole
• 英文别名: 1-(4-Phenoxybutyl)benzimidazole
• 化学式: C₁₇H₁₈N₂O
• mdl: MFCD04212615
• 分子量: 266.343
• InChiKey: HQRCBROAQIVXFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-phenoxybutyl)benzimidazole 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 生成 dibromo‐bis[1,3‐di(4‐phenoxybutyl)benzimidazol‐2‐ylidene]palladium(II)
  参考文献：
  名称：

  钯（II）-N-杂环碳配合物：呋喃与芳基卤化物直接C-H键丙烯酸化的高效催化剂

  摘要：

  本文包含了七个新的苯并咪唑鎓盐及其相应的通式为[PdX 2（NHC）2 ]的新钯（II）-NHC配合物的合成和表征，（NHC =  N杂环卡宾，X = Cl或Br ），以及它们在2-取代的呋喃衍生物与芳基溴化物和芳基氯化物的直接C-H键芳基化反应中的催化活性。在最佳条件下，这些钯（II）-NHC配合物对于2-取代的呋喃与（杂）芳基溴化物以及易于获得和廉价的芳基氯化物的直接C-H键芳基化反应均显示出良好的催化性能。通过使用1 mol％的钯（II）-NHC催化剂，C-H键芳基化可以选择性地产生C5-芳基化呋喃，且产率中等至高。

  DOI：

  10.1002/aoc.4399
• 作为产物：
  描述：

  苯并咪唑 、 4-苯氧基丁基溴 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以73%的产率得到N-(4-phenoxybutyl)benzimidazole
  参考文献：
  名称：

  钯（II）-N-杂环碳配合物：呋喃与芳基卤化物直接C-H键丙烯酸化的高效催化剂

  摘要：

  本文包含了七个新的苯并咪唑鎓盐及其相应的通式为[PdX 2（NHC）2 ]的新钯（II）-NHC配合物的合成和表征，（NHC =  N杂环卡宾，X = Cl或Br ），以及它们在2-取代的呋喃衍生物与芳基溴化物和芳基氯化物的直接C-H键芳基化反应中的催化活性。在最佳条件下，这些钯（II）-NHC配合物对于2-取代的呋喃与（杂）芳基溴化物以及易于获得和廉价的芳基氯化物的直接C-H键芳基化反应均显示出良好的催化性能。通过使用1 mol％的钯（II）-NHC催化剂，C-H键芳基化可以选择性地产生C5-芳基化呋喃，且产率中等至高。

  DOI：

  10.1002/aoc.4399

文献信息

• Synthesis of Quinoxaline-Linked Bis(Benzimidazolium) Salts and Their Catalytic Application in Palladium-Catalyzed Direct Arylation of Heteroarenes
  作者：Murat Kaloğlu、Mehmet Hanifi Şahan、Serpil Demir Düşünceli、İsmail Özdemir

  DOI：10.1007/s10562-021-03787-2

  日期：2022.7

  synthesized as bis-N-heterocyclic carbene (NHC) precursors. These bis(NHC) precursors were used as multidentate ligands for the construction of bi(hetero)aryls by palladium-catalyzed direct C-H activation process. The in situ prepared palladium complexes by mixtures of the Pd(OAc)2 and the bis(NHC) precursors were used as the catalyst for direct C-H activation of heteroarenes. These catalytic system exhibited

  摘要 在这项研究中，喹喔啉连接的双（苯并咪唑）盐被合成为双-N-杂环卡宾 (NHC) 前体。这些双 (NHC) 前体被用作多齿配体，用于通过钯催化的直接 CH 活化过程构建双 (杂) 芳基。通过Pd(OAc) 2和双(NHC)前体的混合物原位制备的钯配合物用作杂芳烃直接CH活化的催化剂。这些催化体系在具有多种（杂）芳基溴化物的五元杂芳烃的直接 CH 活化中表现出适度的催化活性。 图形摘要
• Half-sandwich ruthenium-carbene catalysts: Synthesis, characterization, and catalytic application in the N-alkylation of amines with alcohols
  作者：Murat Kaloğlu

  DOI：10.1016/j.ica.2019.119163

  日期：2019.12

  the synthesis and characterization of new half-sandwich ruthenium complexes containing oxygen functionalised N-aryl and N-alkyl benzimidazol-2-ylidene ligands have been reported. All ruthenium complexes were tested as catalysts for a wide range of substrates in the N-alkylation of secondary cyclic amines such as pyrrolidine and piperidine, and 4-methylaniline which was a primary aromatic amine with

  摘要在这项研究中，已经报道了含有氧官能化的N-芳基和N-烷基苯并咪唑-2-亚烷基配体的新型半三明治钌络合物的合成和表征。所有的钌络合物都被用作催化剂，用于仲环胺（例如吡咯烷和哌啶）和4-甲基苯胺（它是通过醇借入醇与醇形成的芳香族伯胺）的N-烷基化反应中用于多种底物的催化剂。在无溶剂条件下，在120℃，16 h的条件下，以1 mol％的催化剂负载量进行催化反应。所有钌配合物均显示出优异的催化活性，并且选择性地获得了N-烷基化产物。
• Synthesis, characterization, crystal structure, Hirshfeld surface analysis, and theoretical study on a <i>N</i>-heterocyclic carbene salt and two NHC–palladium complexes
  作者：Namık Özdemir、Murat Kaloğlu、Nazan Kaloğlu、Nevin Gürbüz、İsmail Özdemir

  DOI：10.1080/24701556.2021.1897140

  日期：——

  N-ethylphthalimide functionalized 1,3-dialkylbenzimidazolium salt has been synthesized and characterized by elemental analysis, FTIR, 1H NMR, and 13C NMR spectroscopy. Crystal structures of the salt and two palladium complexes were determined by single-crystal X-ray diffraction studies. Theoretical calculations were obtained by density functional theory (DFT) methods at the HSEh1PBE/SDD level of theory. Structural

  摘要 合成了一种N-乙基邻苯二甲酰亚胺官能化的 1,3-二烷基苯并咪唑鎓盐，并通过元素分析、FTIR、1 H NMR 和13对其进行了表征。C 核磁共振波谱。通过单晶 X 射线衍射研究确定了盐和两种钯配合物的晶体结构。理论计算是通过 HSEh1PBE/SDD 理论水平的密度泛函理论 (DFT) 方法获得的。化合物的结构参数可以通过 DFT 计算很好地表示。还通过基于 Hirshfeld 表面分析的二维指纹图研究了化合物中的非共价相互作用。确定前沿分子轨道（HOMO-LUMO）及其能隙以探索分子的稳定性。大的 HOMO-LUMO 能隙表明化合物在其电子转移中的高动力学稳定性。
• Identification of Phenoxyalkylbenzimidazoles with Antitubercular Activity
  作者：N. Susantha Chandrasekera、Torey Alling、Mai A. Bailey、Megan Files、Julie V. Early、Juliane Ollinger、Yulia Ovechkina、Thierry Masquelin、Prashant V. Desai、Jeffrey W. Cramer、Philip A. Hipskind、Joshua O. Odingo、Tanya Parish

  DOI：10.1021/acs.jmedchem.5b00546

  日期：2015.9.24

  We conducted an evaluation of the phenoxyalkylbenzimidazole series based on the exemplar 2-ethyl-1-(3-phenoxypropyl)-1H-benzo[d]imidazole for its antitubercular activity. Four segments of the molecule were examined systematically to define a structure activity relationship with respect to biological activity. Compounds had submicromolar activity against Mycobacterium tuberculosis; the most potent compound had a minimum inhibitory concentration (MIC) of 52 nM and was not cytotoxic against eukaryotic cells (selectivity index = 523). Compounds were selective for M. tuberculosis over other bacterial species, including the closely related Mycobacterium smegmatis. Compounds had a bacteriostatic effect against aerobically grown, replicating M. tuberculosis, but were bactericidal against nonreplicating bacteria. Representative compounds had moderate to high permeability in MDCK cells, but were rapidly metabolized in rodents and human liver microsomes, suggesting the possibility of rapid in vivo hepatic clearance mediated by oxidative metabolism. These results indicate that the readily synthesized phenoxyalkylbenzimidazoles are a promising class of potent and selective antitubercular agents, if the metabolic liability can be solved.