(9ci)-5-氯-2-乙基-1H-苯并咪唑 | 34569-15-8

• 物质功能分类: 医药中间体 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: (9ci)-5-氯-2-乙基-1H-苯并咪唑
• 英文名称: 5-chloro-2-ethylbenzimidazole
• 英文别名: 5-chloro-2-ethyl-1H-benzo[d]imidazole；2-ethyl-5-chlorobenzimidazole；6-chloro-2-ethyl-1H-benzimidazole
• CAS: 34569-15-8
• 化学式: C₉H₉ClN₂
• mdl: MFCD00995436
• 分子量: 180.637
• InChiKey: AIXMQUWDZVRMJJ-UHFFFAOYSA-N

物化性质

• 熔点：
  168-170 °C
• 沸点：
  376.0±15.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  (9ci)-5-氯-2-乙基-1H-苯并咪唑 在 potassium carbonate 、 sodium iodide 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 5-chloro-2-ethyl-1-(4-phenoxybutyl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Identification of Phenoxyalkylbenzimidazoles with Antitubercular Activity

  摘要：

  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.

  DOI：

  10.1021/acs.jmedchem.5b00546
• 作为产物：
  描述：

  2-硝基-5-氯苯胺 在 tin(II) chloride dihdyrate 、 三氯氧磷 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 6.0h， 生成 (9ci)-5-氯-2-乙基-1H-苯并咪唑
  参考文献：
  名称：

  SnCl 2催化还原体系在室温下合成2,5-二取代苯并咪唑

  摘要：

  氯化亚锡二水合物在2-硝基-5-取代的苯胺席夫碱的还原环化反应中用作有效的催化剂，从而以优异的收率和良好的纯度生成稳定的2，5-二取代的苯并咪唑衍生物。它提供了一种在室温下在还原体系下合成2,5-二取代的苯并咪唑的新方法。

  DOI：

  10.1016/j.cclet.2013.10.014

文献信息

• Ag–TiO₂/Clay Composite Photocatalyst for the Oxidation–Cyclization of 1,2-Diamine Compounds with Propylene Glycol or Alcohols
  作者：Kaliyamoorthy Selvam、Mari Annadhasan、Rengasamy Velmurugan、Meenakshisundaram Swaminathan

  DOI：10.1246/bcsj.20090319

  日期：2010.7.15

  Silver-loaded TiO2 (Ag–TiO2) and acidic clay (K10 montmorillonite) composite photocatalyst has been successfully applied for the light-induced conversion of o-phenylenediamine (OPD) and its derivatives to substituted benzimidazoles with various alcohols in acetonitrile using UV-A and solar light. The influence of the various photocatalysts, solvents, and substituents on the yield and selectivity of the products has been investigated. The mechanism of photocatalysis is proposed. Loading silver on TiO2 enhances product yield and selectivity both in UV and solar light. In the presence of primary alcohols, 2-aminothiophenol forms only disulfide and hence Ag–TiO2/clay can be used as a green catalyst for the synthesis of disulfides.

  负载银的TiO2（Ag–TiO2）和酸性粘土（K10蒙脱石）复合光催化剂已成功应用于紫外A和太阳光诱导的邻苯二胺（OPD）及其衍生物与多种醇在乙腈中的光催化转化合成取代苯并咪唑。考察了不同光催化剂、溶剂和取代基对产物收率和选择性的影响。提出了光催化机理。在TiO2上负载银可以提高紫外和太阳光下产物的收率和选择性。在存在一级醇的情况下，2-氨基硫酚仅形成二硫化物，因此Ag–TiO2/粘土可用作合成二硫化物的绿色催化剂。
• An easy one-step photocatalytic synthesis of 1-aryl-2-alkylbenzimidazoles by platinum loaded TiO2 nanoparticles under UV and solar light
  作者：K. Selvam、M. Swaminathan

  DOI：10.1016/j.tetlet.2011.04.090

  日期：2011.6

  One-pot synthesis of disubstituted benzimidazoles from N-substituted 2-nitroanilines or 1,2-diamines with 3–12 nm-sized platinum particles loaded on the TiO2 using solar and UV-A light is described. 1-Aryl-2-alkylbenzimidazoles from 2-nitrodiphenylamines are formed by combined redox photocatalytic reaction, condensation and catalytic dehydrogenation on Pt-TiO2. In case of diamines, this reaction is

  描述了使用太阳光和UV-A光由N-取代的2-硝基苯胺或1,2-二胺与负载在TiO 2上的3–12 nm大小的铂颗粒一锅合成二取代的苯并咪唑。通过在Pt-TiO 2上进行氧化还原光催化反应，缩合反应和催化脱氢反应，由2-硝基二苯胺形成1-芳基-2-烷基苯并咪唑类化合物。在二胺的情况下，该反应通过Pt-TiO 2辅助的醇的光催化氧化和铂纳米颗粒表面上的中间体的催化脱氢而进行。在这两种情况下，产物的形成都是通过在Pt-TiO 2上进行串联光催化和催化反应来实现的。
• Building Heterocyclic Systems with RC(OR)2+ Carbocations in Recyclable Brønsted Acidic Ionic Liquids: Facile Synthesis of 1-Substituted 1H-1,2,3,4-Tetrazoles, Benzazoles and Other Ring Systems with CH(OEt)3 and EtC(OEt)3 in [EtNH3][NO3] and [PMIM(SO3H)][O
  作者：Gopalakrishnan Aridoss、Kenneth K. Laali

  DOI：10.1002/ejoc.201100128

  日期：2011.5

  IL-1/CH(OEt) 3 . The latter was also formed from 2-aminobenzoic acid in IL-1/CH(OEt) 3 . Mechanistic implications are addressed. The reported protocols enable rapid assembly of a host of heterocyclic systems in high yields with the added advantage of recycling and reuse of the ILs.

  1-芳基/烷基-1H-1,2,3,4-四唑可以通过与TMSN 3 和CH(OEt) 3 反应，使用容易获得的、可回收的、布朗斯台德酸性从相应的胺在一锅反应中方便地合成离子液体 [EtNH 3] -[NO 3 ] IL-1 和 [PMIM(SO 3 H)][OTf] IL-2 在温和条件下以高收率。基于对比反应，虽然两种 IL 都是极好的促进剂，但使用 IL-2 可以在更短的反应时间和更高的产率下完成反应。在提供的 24 个实施例中，除了 2-氨基苯甲酸与 IL-2 形成四唑和 IL-1 形成 2-乙基喹唑啉-4(3H)-one 外，通过两种 IL 获得了相同的产物。通过从反应中排除 TMS-N 3，原位形成的 CH(OEt) 2 + 和 Et-C(OEt) 2 +（通过它们相应的原酸酯）在超声处理下与带有各种取代基的邻苯二胺、邻氨基苯硫酚和邻氨基苯酚反应，形成一系列广泛的苯并咪唑（苯并咪唑
• A Highly Effective Sulfamic Acid/Methanol Catalytic System for the Synthesis of Benzimidazole Derivatives at Room Temperature
  作者：Zhan-Hui Zhang、Tong-Shuang Li、Jian-Jiong Li

  DOI：10.1007/s00706-006-0566-1

  日期：2007.1

  Sulfamic acid/methanol was found to be an efficient catalytic system for the synthesis of benzimidazole compounds through the condensation of o -phenylenediamine with orthoester in high yields at room temperature.

  发现氨基磺酸/甲醇是通过 邻 苯二胺与原酸酯在室温下高收率缩合来合成苯并咪唑化合物的有效催化体系 。
• Synthesis of 2-substituted benzimidazoles by iodine-mediated condensation of orthoesters with 1,2-phenylenediamines
  作者：Zhan-Hui Zhang、Jian-Jiong Li、Yuan-Zhe Gao、Yu-Heng Liu

  DOI：10.1002/jhet.5570440642

  日期：2007.11

  Iodine was found to be an efficient catalyst for the synthesis of 2-substituted benzimidazoles by the condensation of orthoesters and 1,2-phenylenediamines in good to excellent yields under mild reaction conditions.

  发现碘是在温和的反应条件下，通过原酸酯和1,2-苯二胺的缩合反应，可以高效合成2-取代的苯并咪唑的有效催化剂。