1H-苯并咪唑,5-氯-6-(2,3-二氯苯氧基)-2-(三氟甲基)- | 145771-00-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1H-苯并咪唑,5-氯-6-(2,3-二氯苯氧基)-2-(三氟甲基)-
• 英文名称: 5-chloro-6-(2,3-dichlorophenoxy)-2-trifluoromethyl-1H-benzimidazole
• 英文别名: 6-chloro-5-(2,3-dichlorophenoxy)-2-(trifluoromethyl)-1H-benzimidazole
• CAS: 145771-00-2
• 化学式: C₁₄H₆Cl₃F₃N₂O
• 分子量: 381.569
• InChiKey: YECZAJWJKFBTCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-chloro-6-(2,3-dichlorophenoxy)-2H-benzimidazole-2-spirocyclohexane 在 盐酸 、 sodium dithionite 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 生成 1H-苯并咪唑,5-氯-6-(2,3-二氯苯氧基)-2-(三氟甲基)-
  参考文献：
  名称：

  2H-benzimidazoles (isobenzimidazoles). Part 7. A new route to triclabendazole [5-chloro-6-(2,3-dichlorophenoxy)-2-methylthio-1H-benzimidazole] and congeneric benzimidazoles

  摘要：

  A new synthesis of the selective anthelmintic agent triclabendazole 7 from the readily available 5,6-dichloro-2H-benzimidazole-2-spirocyclohexane 2 by simple steps is described. Analogous benzimidazoles difficult to prepare by conventional methods are similarly obtained. Triclabendazole can exist as a low-melting metastable solid (m.p. 85-90-degrees-C) convertible by heating or recrystallisation from ethanol into its stable form (m.p. 1 76-1 78-degrees-C).

  DOI：

  10.1039/p19920003129

文献信息

• Synthesis and biological activity of 2-(trifluoromethyl)-1H-benzimidazole derivatives against some protozoa and Trichinella spiralis
  作者：Francisco Hernández-Luis、Alicia Hernández-Campos、Rafael Castillo、Gabriel Navarrete-Vázquez、Olivia Soria-Arteche、Manuel Hernández-Hernández、Lilián Yépez-Mulia

  DOI：10.1016/j.ejmech.2010.03.050

  日期：2010.7

  mexicana, and they showed nanomolar activities against the first three protozoa tested. The compounds were also tested in vitro and in vivo against the nematode Trichinella spiralis. Compounds 1b, 1c and 1e had the most desirable in vitro antiparasitic profile against all parasites studied. In the in vivo model against T. spiralis, compounds 1b and 1e showed good activity against the adult phase at 75 mg/Kg

  通过取代的1,2-苯二胺和三氟乙酸的Phillips缩合反应，合成了一系列2-（三氟甲基）-1 H-苯并咪唑衍生物（1a – 1i）。对合成的化合物进行了体外抗多种原生动物寄生虫的评估：肠道贾第虫，溶血性变形杆菌，阴道毛滴虫和墨西哥利什曼原虫，它们显示出对前三个原生动物的纳摩尔活性。该化合物还进行了体外和体内针对线虫旋毛虫的测试。化合物1b，1c和1e对所有研究的寄生虫具有最理想的体外抗寄生虫特性。在针对螺旋旋毛虫的体内模型中，化合物1b和1e以75 mg / Kg的浓度对成年期表现出良好的活性。但是，针对肌肉幼虫阶段，仅化合物1f表现出体内抗寄生虫功效。
• 2H-benzimidazoles (isobenzimidazoles). Part 7. A new route to triclabendazole [5-chloro-6-(2,3-dichlorophenoxy)-2-methylthio-1H-benzimidazole] and congeneric benzimidazoles
  作者：Brian Iddon、Peter Kutschy、Andrew G. Robinson、Hans Suschitzky、Walter Kramer、Franz A. Neugebauer

  DOI：10.1039/p19920003129

  日期：——

  A new synthesis of the selective anthelmintic agent triclabendazole 7 from the readily available 5,6-dichloro-2H-benzimidazole-2-spirocyclohexane 2 by simple steps is described. Analogous benzimidazoles difficult to prepare by conventional methods are similarly obtained. Triclabendazole can exist as a low-melting metastable solid (m.p. 85-90-degrees-C) convertible by heating or recrystallisation from ethanol into its stable form (m.p. 1 76-1 78-degrees-C).