1-(3-nitrobenzyl)-2-(3-nitrophenyl)-1H-benzimidazole | 29878-50-0

• 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-nitrobenzyl)-2-(3-nitrophenyl)-1H-benzimidazole
• 英文别名: 1-(3-nitrobenzyl)-2-(3-nitrophenyl)-1H-benzo[d]imidazole；1-(3-nitrobenzyl)-2-(3-nitrophenyl)-1H-1,3-benzimidazole；1-Nitroben-zyl-2-nitrophenyl benzimidazole；2-(3-nitrophenyl)-1-[(3-nitrophenyl)methyl]benzimidazole
• CAS: 29878-50-0
• 化学式: C₂₀H₁₄N₄O₄
• 分子量: 374.356
• InChiKey: OSMPAFWJPRRTKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(3-nitrobenzyl)-2-(3-nitrophenyl)-1H-benzimidazole 在 ammonium sulfide 作用下， 生成 3-[1-(3-amino-benzyl)-1H-benzimidazol-2-yl]-aniline
  参考文献：
  名称：

  Pinnow; Wiskott, Chemische Berichte, 1899, vol. 32, p. 900

  摘要：

  DOI：
• 作为产物：
  描述：

  N¹,N²-bis(3-nitrobenzylidene)phenylene diamine 在 对甲苯磺酸 作用下， 以 neat (no solvent) 为溶剂， 以93%的产率得到1-(3-nitrobenzyl)-2-(3-nitrophenyl)-1H-benzimidazole
  参考文献：
  名称：

  Facile Synthesis of 1,2-Disubstituted Benzimidazoles Usingp-Toluenesulfonic Acid through Grinding Method

  摘要：

  An efficient synthetic method for the highly selective synthesis of pharmacologically active 1,2-disubstituted benzimidazole derivatives fromo-phenylenediamine and various aromatic aldehydes catalyzed byp-toluenesulfonic acid through grinding under solvent-free condition is described. The reaction requires the catalyst only during the conversion of intermediateN,N '-dibenzylidene-o-phenylenediamine into the desired product. The products were obtained within a short time with good yields by using only a mortar and pestle, which makes the proposed method convenient and cost-effective.

  DOI：

  10.1134/s1070428020090201

文献信息

• Synthesis of functionalized benzimidazoles and quinoxalines catalyzed by sodium hexafluorophosphate bound Amberlite resin in aqueous medium
  作者：Pranab Ghosh、Amitava Mandal

  DOI：10.1016/j.tetlet.2012.09.045

  日期：2012.11

  for the selective synthesis of 1,2-disubstituted benzimidazoles and quinoxalines in water–methanol (1:1) mixture with the aid of resin bound hexafluorophosphate ion as catalyst is reported. The method is also effective for the incorporation of quinoxaline nucleus at the A ring of pentacyclic triterpenoid, friedelin. A plausible mechanism for the formation of disubstituted benzimidazole has also been suggested

  报道了一种非常简单，环保和通用的方法，该方法可通过树脂结合的六氟磷酸根离子作为催化剂，在水-甲醇（1：1）混合物中选择性合成1,2-二取代的苯并咪唑和喹喔啉。该方法对于在五环三萜类化合物Friedelin的A环上引入喹喔啉核也是有效的。还已经提出了形成二取代的苯并咪唑的合理机理。
• Chitosan-supported Fe3O4 nanoparticles: a magnetically recyclable heterogeneous nanocatalyst for the syntheses of multifunctional benzimidazoles and benzodiazepines
  作者：Ali Maleki、Nakisa Ghamari、Maryam Kamalzare

  DOI：10.1039/c3ra47366j

  日期：——

  An environmentally benign and clean biopolymer-based heterogeneous nanocatalyst was prepared and its properties and morphology were characterized using scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDX) and X-ray diffraction (XRD). Then, its catalytic activity was investigated in two important organic reactions. In these reactions, efficient and selective syntheses of 1,2-disubstituted benzimidazole and 1,5-benzodiazepine derivatives were carried out using 1,2-diamines and aldehydes or ketones in the presence of a catalytic amount of magnetically recoverable chitosan-supported iron oxide nanoparticles (Fe3O4/chitosan), as a biodegradable nanocomposite, in ethanol at ambient temperature in high yields. The Fe3O4/chitosan nanocatalyst can be recovered easily and reused without any significant loss of the catalytic activity.

  制备了一种环境友好且清洁的生物聚合物基异质纳米催化剂，并通过扫描电子显微镜（SEM）、能量色散X射线光谱（EDX）和X射线衍射（XRD）对其性质和形态进行了表征。随后，研究了其在两种重要有机反应中的催化活性。在这些反应中，使用1,2-二胺和醛或酮在催化量的可磁回收壳聚糖支持铁氧化物纳米颗粒（Fe3O4/壳聚糖）的存在下，在室温下的乙醇中高效且选择性地合成了1,2-取代的苯并咪唑和1,5-苯并二氮杂卓衍生物。Fe3O4/壳聚糖纳米催化剂可以轻松回收并重复使用，且没有显著的催化活性损失。
• ZrO₂-β-cyclodextrin catalyzed synthesis of 2,4,5-trisubstituted imidazoles and 1,2-disubstituted benzimidazoles under solvent free conditions and evaluation of their antibacterial study
  作者：Yarabhally R. Girish、Kothanahally S. Sharath Kumar、Kuntebommanahalli N. Thimmaiah、Kanchugarakoppal S. Rangappa、Sheena Shashikanth

  DOI：10.1039/c5ra13891d

  日期：——

  A series of 2,4,5-trisubstituted imidazoles and 1,2-disubstituted benzimidazoles catalyzed by ZrO₂-supported-β-cyclodextrin (ZrO₂-β-CD) under solvent free conditions have been synthesized and characterized by spectral methods.

  通过ZrO₂支持的β-环糊精（ZrO₂-β-CD）催化的一系列2,4,5-三取代咪唑和1,2-二取代苯并咪唑在无溶剂条件下合成，并通过光谱方法进行了表征。
• Tosic Acid-on-Silica Gel: A Cheap and Eco-friendly Catalyst for a Convenient One-pot Synthesis of Substituted Benzimidazoles
  作者：Manas Chakrabarty、Ratna Mukherjee、Sulakshana Karmakar、Yoshihiro Harigaya

  DOI：10.1007/s00706-007-0714-2

  日期：2007.12

  2-Substituted and 1,2-disubstited benzimidazoles were prepared efficiently from o -phenylenediamines and aryl aldehydes using p -toluenesulphonic acid (5 mol%)-on-silica gel as a cheap and environmentally benign catalyst.

  使用 对 甲苯磺酸（5摩尔％）作为廉价廉价的环境友好型催化剂，由 邻 苯二胺和芳基醛 高效制备2-取代和1,2-二取代的苯并咪唑 。
• Efficient Synthesis of 2-Aryl-1-arylmethyl-1<i>H</i>-benzimidazoles in Ball Mill without Solvent
  作者：Meihong Jin、Guowei Song、Zhenjiang Li、Feng Zhou、Bo Fan、Pingkai Ouyang

  DOI：10.1002/jhet.1113

  日期：2014.11

  2‐Aryl‐1‐arylmethyl‐1H‐benzimidazoles were prepared in excellent yields by the condensation of o‐phenylenediamine with aldehydes under mechanically activated solvent‐free conditions in ball mill using FeCl3·6H2O as the catalyst.

  通过在球磨机中使用FeCl 3 ·6H 2 O作为催化剂，在机械活化的无溶剂条件下，邻苯二胺与醛的缩合，可以制备出高收率的2-芳基-1-芳基甲基-1 H-苯并咪唑。