5-氯-2-(三氟甲基)苯并咪唑 | 656-49-5

• 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: 5-氯-2-(三氟甲基)苯并咪唑
• 中文别名: 2-(4-氯苄基)-2,5-二氮杂双环[2.2.1]庚烷
• 英文名称: 6-chloro-2-(trifluoromethyl)-1H-benzimidazole
• 英文别名: 6-chloro-2-(trifluoromethyl)-1H-1,3-benzodiazole；6-chloro-2-(trifluoromethyl)-1H-benzo[d]imidazole；5-chloro-2-(trifluoromethyl)-1H-benzimidazole；5-Chloro-2-(trifluoromethyl)benzimidazole
• CAS: 656-49-5
• 化学式: C₈H₄ClF₃N₂
• mdl: MFCD00808236
• 分子量: 220.581
• InChiKey: OQKQEDXERMELRT-UHFFFAOYSA-N

物化性质

• 熔点：
  203 °C
• 沸点：
  301.0±42.0 °C(Predicted)
• 密度：
  1.569±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5-氯-2-(三氟甲基)苯并咪唑 在 溴 作用下， 以 水 为溶剂， 反应 24.0h， 以82%的产率得到4,6,7-Tribromo-5-chloro-2-trifluoromethylbenzimidazole0
  参考文献：
  名称：

  Polyhalogenobenzimidazoles: synthesis and Their inhibitory activity against casein kinases

  摘要：

  A series of novel polyhalogenated benzimidazoles have been prepared by exhaustive bromination of a variety of 2-substituted benzimidazoles. The efficacy of both new compounds and a number of their previously described cognates as inhibitors of casein kinases CK1, CK2 and G-CK was investigated. The type of N-1 alkyl substituent as well as introduction of a polyfluoroalkyl moiety at position 2 did not markedly influence the inhibitory efficacy toward CK2 of the respective 4,5,6,7-tetra-bromobenzimidazole derivatives which conversely were almost ineffective toward CK1 and G-CK. However, 4,5,6,7-tetra-bromobenzimidazoles substituted at position 2 with either chlorine, bromine or sulfur atom, while manifesting a still considerable inhibitory activity against CK2 (IC50 in the 0.49-0.93 muM range) proved to be potentially powerful inhibitors also against CK1 (IC50 in the 18.4-2.2 muM range). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00403-6
• 作为产物：
  描述：

  2-硝基-5-氯苯胺 在 镍 氢气 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 5-氯-2-(三氟甲基)苯并咪唑
  参考文献：
  名称：

  Synthesis and antiparasitic activity of 2-(Trifluoromethyl)benzimidazole derivatives

  摘要：

  2-(Trifluoromethyl)benzimidazole derivatives substituted at the 1-, 5-, and 6-positions have been synthesized and in vitro tested against the protozoa Giardia lamblia, Entamoeba histolytica, and the helminth Trichinella spiralis. Results indicate that all the compounds tested are more active as antiprotozoal agents than Albendazole and Metronidazole. One compound (20) was as active as Albendazole against T. spiralis. These compounds were also tested for their effect on tubulin polymerization and none inhibited tubulin polymerization. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00619-3

文献信息

• 大黄素唑醇化合物及其制备方法和应用
  申请人：西南大学

  公开号：CN112209881B

  公开（公告）日：2022-08-26

  本发明涉及大黄素唑醇化合物及其制备方法和应用，属于化学合成技术领域。大黄素唑醇化合物如通式I‑VII所示，该类化合物对革兰阳性菌、革兰阴性菌和真菌中的一种或多种具有一定抑制活性，可以用于制备抗细菌和/或抗真菌药物，从而为临床抗微生物治疗提供更多高效、安全的候选药物，有助于解决日趋严重的耐药性、顽固的致病性微生物以及新出现的有害微生物等临床治疗问题。其制备原料简单，廉价易得，合成路线短，对抗感染方面的应用具有重要意义。
• Synthesis and antiprotozoal activity of some 2-(trifluoromethyl)-1H-benzimidazole bioisosteres
  作者：G NAVARRETEVAZQUEZ、M ROJANOVILCHIS、L YEPEZMULIA、V MELENDEZ、L GERENA、A HERNANDEZCAMPOS、R CASTILLO、F HERNANDEZLUIS

  DOI：10.1016/j.ejmech.2005.09.001

  日期：2006.1

  against both species, which make them significantly more potent than either standard. Compound 4 [2,5(6)-bis(trifluoromethyl)-1H-benzimidazole], was 14 times more active than albendazole against T. vaginalis. This compound (4) also showed moderate antimalarial activity against W2 and D6 strains of Plasmodium falciparum (5.98 and 6.12 microM, respectively). Studying further structure activity relationships

  使用短合成路线制备了一系列具有各种5-和6-位生物等位取代基（-Cl，-F，-CF3，-CN），即1-7的2-（三氟甲基）-1H-苯并咪唑衍生物。与阿苯达唑和甲硝唑相比，每种类似物均在体外针对原虫贾第鞭毛虫和阴道毛滴虫进行了测试。几种类似物对这两个物种的IC50值均小于1 microM，这使其比任何一种标准都具有更高的效力。化合物4 [2,5（6）-双（三氟甲基）-1H-苯并咪唑]的活性比阿苯达唑高14倍。该化合物（4）对恶性疟原虫的W2和D6菌株也显示出中等的抗疟活性（分别为5.98和6.12 microM）。
• Fe(OTf) 3 -catalyzed practical synthesis of 2-trifluoromethylarylimidazoles from o -arylenediamines and hexafluoroacetylacetone
  作者：Yanmei Zhou、Guanshuo Shen、Yuebo Sui、Haifeng Zhou

  DOI：10.1016/j.tetlet.2016.06.086

  日期：2016.7

  An iron-catalyzed practical synthesis of 2-trifluoromethylarylimidazoles through condensation of o-arylenediamines and hexafluoroacetylacetone followed by intramolecular addition and C–C bond cleavage in one-pot has been developed. A series of title compounds were obtained with up to 99% yield. This method is quite practical and suitable for scalable preparation due to simple experimental procedure

  已经开发出铁催化的实际合成方法，即通过邻芳基二胺和六氟乙酰丙酮的缩合，然后分子内加成和一锅中C–C键的裂解，合成2-三氟甲基芳基咪唑。获得了一系列标题化合物，产率高达99％。由于简单的实验程序和容易获得的试剂，该方法非常实用并且适合于可扩展的制备。
• Nouvelle voie de synthèse des 2-trifluorométhylarylimidazoles sur montmorillonite K10 en ‘milieu sec’ sous micro-onde
  作者：Khalid Bougrin、André Loupy、Alain Petit、Boujemâa Daou、Mohamed Soufiaoui

  DOI：10.1016/s0040-4020(00)00992-3

  日期：2001.1

  Cyclocondensation of N-(carbotrifluoromethyl)-ortho-arylenediamines leads to a series of 2-trifluoromethylarylimidazoles with good yields on montmorillonite K10 in ‘dry media’ under microwave irradiation within 2 min in a domestic oven. By conventional heating in the same conditions, no reaction is observed.

  的环化缩合ñ - （carbotrifluoromethyl） -邻-arylenediamines导致对蒙脱土K10在“干媒体”在2分钟内在家用烤箱一系列2-trifluoromethylarylimidazoles具有良好产率微波辐射下。在相同条件下通过常规加热，未观察到反应。
• Synthesis of 2-trifluoromethyl benzimidazoles, benzoxazoles, and benzothiazoles <i>via</i> condensation of diamines or amino(thio)phenols with CF₃CN
  作者：Bo Lin、Yunfei Yao、Minze Wu、Lu Qin、Shouxiong Chen、Yi You、Zhiqiang Weng

  DOI：10.1039/d3ob00517h

  日期：——

  method is developed for the synthesis of 2-trifluoromethyl benzimidazoles, benzoxazoles, and benzothiazoles in good to excellent yields by the condensation of diamines or amino(thio)phenols with in situ generated CF3CN. Additionally, the synthetic utility of the 2-trifluoromethyl benzimidazole and benzoxazole products is demonstrated via gram scale synthesis. The mechanistic study suggests that the reaction

  通过二胺或氨基（硫代）酚与原位生成的 CF 3 CN 的缩合，开发了一种新的有效方法，以良好至极好的收率合成 2-三氟甲基苯并咪唑、苯并恶唑和苯并噻唑。此外，通过克级合成证明了 2-三氟甲基苯并咪唑和苯并恶唑产品的合成效用。机理研究表明，该反应通过三氟乙腈与二胺衍生物的氨基进行亲核加成反应，形成亚胺中间体，然后进行分子内环化。