N-(4-methoxybenzyl)benzimidazole | 46885-71-6

• 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: N-(4-methoxybenzyl)benzimidazole
• 英文别名: 1-(4-methoxybenzyl)-1H-benzo[d]imidazole；1-[(4-methoxyphenyl)methyl]-1H-1,3-benzodiazole；1-[(4-methoxyphenyl)methyl]benzimidazole
• CAS: 46885-71-6
• 化学式: C₁₅H₁₄N₂O
• mdl: MFCD08163104
• 分子量: 238.289
• InChiKey: RRMGDBMJFCPAPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.133
• 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-methoxybenzyl)benzimidazole 在 palladium diacetate 、 copper (I) acetate 、 copper(II) acetate monohydrate 、 cesium pivalate 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以54%的产率得到3-methoxy-11H-isoindolo[2,1-a]benzimidazole
  参考文献：
  名称：

  Intramolecular arylation of benzimidazoles via Pd(II)/Cu(I) catalyzed cross-dehydrogenative coupling

  摘要：

  Electron poor benzimidazole substrates were arylated via an intramolecular cross-dehydrogenative coupling (CDC) reaction. These CDC reactions were catalyzed by a Pd(II)/Cu(I) catalyst system, capable of producing moderate yields on a large library of substrates. The substrate scope consisted of tethered arene-benzimidazoles that upon coupling, produced a fused polycyclic motif. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.01.103
• 作为产物：
  描述：

  2-溴苯胺 在 palladium diacetate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 potassium hydroxide 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 N-(4-methoxybenzyl)benzimidazole
  参考文献：
  名称：

  通过 Pd 催化的 C-N 键形成和环化方便合成 N-1-烷基苯并咪唑

  摘要：

  摘要 N -1-烷基-2-未取代的苯并咪唑通过甲酰亚胺与苄胺的分子间偶联直接合成；合成由 Pd(OAc) 2在一锅中催化，产生中等至良好的产率。由相应的苯胺和N,N-二甲基甲酰胺二甲基乙缩醛的反应可以很容易地以高产率制备具有各种取代基的芳族甲脒作为原料。

  DOI：

  10.1080/00397911.2021.1939056

文献信息

• Bergman cycloaromatization of imidazole-fused enediynes: the remarkable effect of N-aryl substitution
  作者：Zhengrong Zhao、Yunshan Peng、N.Kent Dalley、John F Cannon、Matt A Peterson

  DOI：10.1016/j.tetlet.2004.02.152

  日期：2004.4

  A series of N-aryl substituted `imidazole-fused' (Z) 3-ene-1,5-diynes was prepared and kinetic parameters for their Bergman cycloaromatization reactivities were determined. N-Arylation enhanced rates relative to N-alkyl derivatives by up to sevenfold (ANOVA p<0.0001). The greatest enhancement was exhibited by the N-phenyl derivative (sevenfold at 145 °C).

  制备了一系列的N-芳基取代的“咪唑稠合的”（Z）3-烯-1,5-二炔，并确定了其Bergman环芳化反应活性的动力学参数。N-芳基化相对于N-烷基衍生物的速率提高了七倍（ANOVA p <0.0001）。N-苯基衍生物表现出最大的增强作用（在145°C时为七倍）。
• Benzimidazolium sulfonate ligand precursors and application in ruthenium-catalyzed aromatic amine alkylation with alcohols
  作者：Nazan Kaloglu、Ismail Özdemir、Nevin Gürbüz、Mathieu Achard、Christian Bruneau

  DOI：10.1016/j.catcom.2015.10.028

  日期：2016.1

  New benzimidazolium sulfonate salts have been prepared and fully characterized. They have been associated in situ with [RuCl2(p-cymene)]2 to generate efficient catalytic systems operating at 120 °C under neat conditions in the presence of potassium tert-butylate for selective N-alkylation of primary aromatic amines into secondary amines.

  已经制备并充分表征了新的苯并咪唑磺酸盐。它们已与[RuCl 2（p- cymene）] 2原位缔合，以产生有效的催化体系，在叔丁酸钾存在下于纯条件下在120°C的条件下运行，用于将伯芳族胺选择性N-烷基化为仲胺。 。
• N-heterocyclic carbene based ruthenium complexes for selective β-C(sp3)-H functionalization of N-fused saturated cyclic amines
  作者：Nazan Kaloğlu

  DOI：10.1016/j.tet.2018.12.049

  日期：2019.4

  Herein, a series of new ruthenium(II) complexes with the general molecular formula [RuCl2(arene)(NHC)], (arene = η6-p-cymene, NHC = N-heterocyclic carbene) were synthesized from in situ prepared silver(I)-NHCs by the transmetallation method. These complexes were fully characterized by analytical and spectral methods. Ruthenium(II) complexes were tested as promising catalyst for selective β-C(sp3)-H

  在本文中，与一般分子式将[RuCl了一系列新的钌（II）络合物2（芳烃）（NHC）]，（芳烃=  η 6 - p -cymene，NHC = Ñ -杂环卡宾）从合成原位制备通过过渡金属化法制备银（I）-NHC。这些配合物已通过分析和光谱方法进行了全面表征。钌（II）配合物被测试为在外部酸性添加剂存在下通过氢转移将N-甲基哌啶与各种醛选择性进行β-C（sp 3）-H官能化的有前途的催化剂。这些环保的交叉脱氢偶联剂可以生产C（3）-烷基化的N-不带烯胺的-甲基哌啶衍生物，仅二氧化碳和水为良性副产物。
• Decarboxylative C_sp³–N Bond Formation by Electrochemical Oxidation of Amino Acids
  作者：Xiaoqing Shao、Yue Zheng、Lifang Tian、Inmaculada Martín-Torres、Antonio M. Echavarren、Yahui Wang

  DOI：10.1021/acs.orglett.9b03696

  日期：2019.11.15

  Decarboxylative Csp3–N coupling reactions have been developed through electrochemical oxidation of amino acids. The reaction proceeds via anodic oxidative decarboxylation of carboxylic acids to form stabilized carbocations, which are trapped by azoles or amides to construct C–N bonds. This method avoids the preactivation of carboxylic acids and the use of expensive transition-metals and external chemical

  通过氨基酸的电化学氧化已经开发出脱羧的C sp 3 –N偶联反应。反应通过羧酸的阳极氧化脱羧反应进行，以形成稳定的碳正离子，这些碳正离子被唑或酰胺捕获，从而构建了C–N键。该方法避免了羧酸的预活化以及避免使用昂贵的过渡金属和外部化学氧化剂。
• The first used half sandwich ruthenium(II) complexes bearing benzimidazole moiety for N-alkylation of amines with alcohols
  作者：Serpil Demir、Feyzullah Coşkun、İsmail Özdemir

  DOI：10.1016/j.jorganchem.2014.01.007

  日期：2014.4

  Half sandwich ruthenium(II) complexes were synthesized from [RuCl2(η6-p-cymene)]2 and N-substituted benzimidazole. All new compounds were characterized by elemental analysis, 1H NMR, 13C NMR, and IR spectroscopy. Aminoarenes were readily converted into secondary amines by the reaction at 150 °C with benzyl alcohol and in the presence of a catalytic amount of novel ruthenium complexes. All of [RuCl

  半夹心钌（II）配合物合成自将[RuCl 2（η 6 - p -cymene）] 2和N-取代苯并咪唑。所有新化合物均通过元素分析，1 H NMR，13 C NMR和IR光谱进行了表征。通过在150°C下与苄醇反应，并在催化量的新型钌配合物存在下，氨基芳烃很容易转化为仲胺。所有的合成将[RuCl 2（η 6 - p -cymene）（ñ -取代的苯并咪唑）]配合物的最有效的催化剂Ñ借用氢方法进行烷基化反应。