2,4,5-tris(4-chlorophenyl)-1H-imidazole | 1498-38-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2,4,5-tris(4-chlorophenyl)-1H-imidazole
• 英文别名: 2,4,5-tris-(4-chloro-phenyl)-1H-imidazole；2,4,5-Tris-(4-chlor-phenyl)-1H-imidazol；2,4,5-Tris-<4-chlor-phenyl>-imidazol；Tris-2,4,5-(4-Chlor-phenyl)-imidazol；2,4,5-Tri(p-chlorophenyl)imidazole
• CAS: 1498-38-0
• 化学式: C₂₁H₁₃Cl₃N₂
• 分子量: 399.707
• InChiKey: SRSVFQOMBYOAET-UHFFFAOYSA-N

物化性质

• 熔点：
  268 °C
• 沸点：
  568.9±50.0 °C(Predicted)
• 密度：
  1.365±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-氯苯甲醇 在 bismuth(III) nitrate pentahydrate 、 六甲基二硅氮烷 作用下， 反应 5.5h， 以92%的产率得到2,4,5-tris(4-chlorophenyl)-1H-imidazole
  参考文献：
  名称：

  One-Pot Synthesis of 2,4,5-Triaryl-1H-imidazoles from Arylaldehydes, Benzyl Alcohols, or Benzyl Halides with Hexamethyldisilazane in Molten Tetrabutylammonium Bromide

  摘要：

  通过六甲基二硅氮烷与芳基醛、苄醇、苄基卤化物在作为廉价无毒溶剂的熔融四丁基溴化铵中的反应，开发出了一种简单高效的 2,4,5-三芳基-1H-咪唑衍生物的合成方法，产率从良好到极佳。这种方法的显著优点是操作过程简单、产品收率高、使用离子液体作为绿色溶剂以及试剂易得。

  DOI：

  10.1055/s-0030-1258393

文献信息

• Facile Method for One-Step Synthesis of 2,4,5-Triarylimidazoles Under Catalyst-Free, Solvent-Free, and Microwave-Irradiation Conditions
  作者：Jian-Feng Zhou、Gui-Xia Gong、Xiao-Jun Sun、Yu-Lan Zhu

  DOI：10.1080/00397910903043025

  日期：2010.3.19

  A green and efficient method for the synthesis of 2,4,5-triarylimidazoles by one-step condensation reaction of benzil, aromatic aldehyde, and ammonium acetate under catalyst-free, solvent-free, and microwave-irradiation conditions is reported. This method had many dramatic advantages, such as the short reaction time (3–5 min), good yields (80–99%), environmental friendliness, and convenient operation

  报道了一种在无催化剂、无溶剂和微波辐射条件下，通过苄基、芳香醛和乙酸铵一步缩合反应合成 2,4,5-三芳基咪唑的绿色高效方法。该方法具有反应时间短（3-5 分钟）、收率高（80-99%）、环境友好、操作方便等显着优点。
• Convenient One-Pot Synthesis of 2,4,5-Triaryl-1H-imidazoles from Arylaldehydes, Benzyl Alcohols, or Benzyl Halides with HMDS in the Presence of Molecular Iodine
  作者：Hojat Veisi、Ardashir Khazaei、Leila Heshmati、Saba Hemmati

  DOI：10.5012/bkcs.2012.33.4.1231

  日期：2012.4.20

  A one-pot efficient procedure for the synthesis of 2,4,5-triaryl-1H-imidazole derivatives in good to excellent yields by reaction between hexamethyldisilazane and arylaldehydes, benzyl alcohols, benzyl halides in the presence of molecular iodine has been developed. The remarkable advantages of this method are the simple workup procedure, high yields of products, and the availability of reagents.

  已经开发了一种通过六甲基二硅氮烷与芳基醛、苯甲醇、苄基卤在分子碘存在下反应以良好至优异产率合成 2,4,5-三芳基-1H-咪唑衍生物的一锅高效方法。该方法的显着优点是后处理程序简单，产品产量高，试剂可用。
• Efficient Synthesis of 2,4,5-Triaryl-1H-Imidazoles from Aromatic Aldehydes with HMDS Catalyzed by N-Bromosaccharin (NBSa)
  作者：Alireza Sedrpoushan、Zinab Joshani、Leila Fatollahi

  DOI：10.2174/15701786113106660091

  日期：2014.2

  A one-pot efficient procedure for the synthesis of 2, 4, 5-triaryl-1H-imidazole derivatives by the reactions of hexamethyldisilazane and arylaldehydes in the presence of N-bromosaccharin (NBSa) is studied. This new method offers several advantages, such as excellent yields, easy workup, short reaction times, and simple procedure.

  研究了一种在N-溴糖精(NBSa)存在下，通过六甲基二硅氮烷和芳香醛反应合成2,4,5-三芳基-1H-咪唑衍生物的一锅法高效合成工艺。这种新方法具有产率高、操作简单、反应时间短、工艺简便等优点。
• Photocatalytic coupling of amines to imidazoles using a Mo–ZnIn₂S₄ catalyst
  作者：Min Wang、Lihua Li、Jianmin Lu、Nengchao Luo、Xiaochen Zhang、Feng Wang

  DOI：10.1039/c7gc01728f

  日期：——

  we report a new route for the synthesis of substituted imidazoles via photocyclization of readily available amines at room temperature. The reaction is achieved by the visible-light-induced C–C/C–N bond coupling and subsequent dehydrogenation reaction over Mo–ZnIn2S4 as a heterogeneous photocatalyst. A wide range of amines were converted into the corresponding tri- and tetra-substituted imidazoles with

  取代的咪唑传统上是通过多种原料的共缩合反应合成的。在这里，我们报告了一种新的途径，用于在室温下通过光环化现成的胺来合成取代的咪唑。该反应是通过可见光诱导的C–C / C–N键偶联以及随后作为非均相光催化剂的Mo–ZnIn 2 S 4进行的脱氢反应来实现的。多种胺被转化为相应的三取代和四取代的咪唑，总收率高达96％。该新反应的简单性，高效性和温和条件的优点将使其能够用于合成转化中。
• Inhibition of the 5-lipoxygenase pathway
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0236628A1

  公开（公告）日：1987-09-16

  This invention relates to 4,5-diaryl-2-­(substituted)imidazoles or pharmaceutically acceptable salts thereof, for use in inhibiting the 5-lipoxygenase pathway of arachidonic acid metabolism, to methods for their preparation and to pharmaceutical compositions containing them.

  本发明涉及用于抑制花生四烯酸代谢的 5-脂氧合酶途径的 4,5-二芳基-2-（取代）咪唑或其药学上可接受的盐、其制备方法以及含有它们的药物组合物。

表征谱图