3-(2,4-dichloro-5-fluorophenyl)-4H-1,2,4-triazole-5-thiol | 306298-83-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(2,4-dichloro-5-fluorophenyl)-4H-1,2,4-triazole-5-thiol
• 英文别名: 5-(2,4-dichloro-5-fluorophenyl)-4H-1,2,4-triazole-3-thiol；5-(2,4-dichloro-5-fluorophenyl)-1,2-dihydro-1,2,4-triazole-3-thione
• CAS: 306298-83-9
• 化学式: C₈H₄Cl₂FN₃S
• 分子量: 264.11
• InChiKey: WRHWGAFPTYQAOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2,4-dichloro-5-fluorophenyl)-4H-1,2,4-triazole-5-thiol 、 α-bromo-(2,4-dichloro-5-fluoro)acetophenone 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 1-(2,4-dichloro-5-fluorophenyl)-2-[[5-(2,4-dichloro-5-fluorophenyl)-1H-1,2,4-triazol-3-yl]sulfanyl]ethanone
  参考文献：
  名称：

  Synthesis, analgesic, anti-inflammatory and antimicrobial studies of 2,4-dichloro-5-fluorophenyl containing thiazolotriazoles

  摘要：

  A series of 2,4-dichloro-5-fluorophenyl containing thiazolotriazoles (1) were synthesized starting from 3-(2,4-dichloro-5-fluorophenyl)-4H-1,2,4-triazole-3-thiol (5). The newly synthesized compounds were characterized by IR, H-1 NMR, mass and elemental analysis. Some of the synthesized compounds were tested for their anti-inflammatory, analgesic and antimicrobial activities. Compounds 8c, 8d and 8h exhibited excellent anti-inflammatory activity whereas compounds 8d, 8e and 8h showed excellent analgesic activity. Compounds 8a, 8c-e, and 8h exhibited good antibacterial activity and compounds 8c, 8e and 8h showed good antifungal activity. (c) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.04.022
• 作为产物：
  描述：

  2,4-二氯-5-氟苯酰氯 在 吡啶 、 氢氧化钾 作用下， 以 乙酸乙酯 为溶剂， 反应 5.0h， 生成 3-(2,4-dichloro-5-fluorophenyl)-4H-1,2,4-triazole-5-thiol
  参考文献：
  名称：

  Fluorine containing heterocyclic compounds: synthesis of 6-substituted-2-substituted-aryl-1,2,4-triazolo[5,1-b] 1,3,5-thiadiazin-7-one derivatives

  摘要：

  A group of heterocylic compounds of condensed triazole-thiadiazinone derivatives containing fluorine (ma-h) were obtained in good yields by the reactions of the corresponding 3-aryl-5-mercapto-1,2,4-triazole (IIa-d) with N-substituted-N-chloromethyl carbamoyl chloride (I) in the presence of potassium carbonate in N,N-dimethylformamide at room temperature. Cyclization of 3-(2,3,5-trifluoro-4-methoxyl)phenyl-5-mercapto-1,2,4-triazole (IIe) with I was difficult due to an intermolecular hydrogen bond of IIe. The structures of the compounds synthesized were confirmed by LR, MS, H-1 NMR and elemental analyses. Fungicidal and insecticidal activities of these compounds were also studied. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-1139(00)00287-6

文献信息

• Synthesis, antiinflammatory and antimicrobial activities of some 2,4-dichloro-5-fluorophenyl substituted arylidenetriazolothiazolidinones
  作者：Mari S. Karthikeyan、Bantwal S. Holla

  DOI：10.1007/s00706-007-0794-z

  日期：2008.6

  4-methylenedioxyphenyl, and 2,3,5-trichlorophenyl moiety showed excellent antiinflammatory activity. The antimicrobial screening studies revealed that compounds with 4-anisyl, 4-methylthiophenyl, 3,4-methylenedioxyphenyl, and 2,3,5-trichlorophenyl at position 5 of the arylidenetriazolothiazolidinone moiety showed excellent activity against all tested strains at 6.25 μg cm−3 concentrations.

  通过3-（2,4-二氯-5-氟苯基）-4 H -1,2,4-三唑-5-硫醇的一锅反应获得了一系列的2,4-二氯-5-氟苯基取代的芳基三唑并恶唑烷酮。 在乙酸酐，乙酸和乙酸钠存在下用取代的苯甲醛和一氯乙酸制得 新合成的化合物的结构经IR，1表征和确认1 H NMR，质谱和元素分析。带有4-甲基硫代苯基，3,4-亚甲基二氧苯基和2,3,5-三氯苯基部分的化合物显示出优异的抗炎活性。抗菌筛选研究表明，在芳基内氮杂唑并噻唑烷酮部分的5位上带有4-茴香基，4-甲硫基苯基，3,4-亚甲基二氧苯基和2,3,5-三氯苯基的化合物在6.25μgcm -3的条件下显示出对所有测试菌株的优异活性浓度。
• Fluorine containing heterocyclic compounds: synthesis of 6-substituted-2-substituted-aryl-1,2,4-triazolo[5,1-b] 1,3,5-thiadiazin-7-one derivatives
  作者：Suyou Liu、Xuhong Qian、Gonghua Song、Jing Chen、Weidong Chen

  DOI：10.1016/s0022-1139(00)00287-6

  日期：2000.7

  A group of heterocylic compounds of condensed triazole-thiadiazinone derivatives containing fluorine (ma-h) were obtained in good yields by the reactions of the corresponding 3-aryl-5-mercapto-1,2,4-triazole (IIa-d) with N-substituted-N-chloromethyl carbamoyl chloride (I) in the presence of potassium carbonate in N,N-dimethylformamide at room temperature. Cyclization of 3-(2,3,5-trifluoro-4-methoxyl)phenyl-5-mercapto-1,2,4-triazole (IIe) with I was difficult due to an intermolecular hydrogen bond of IIe. The structures of the compounds synthesized were confirmed by LR, MS, H-1 NMR and elemental analyses. Fungicidal and insecticidal activities of these compounds were also studied. (C) 2000 Elsevier Science S.A. All rights reserved.
• Synthesis, analgesic, anti-inflammatory and antimicrobial studies of 2,4-dichloro-5-fluorophenyl containing thiazolotriazoles
  作者：Mari Sithambaram Karthikeyan

  DOI：10.1016/j.ejmech.2008.04.022

  日期：2009.2

  A series of 2,4-dichloro-5-fluorophenyl containing thiazolotriazoles (1) were synthesized starting from 3-(2,4-dichloro-5-fluorophenyl)-4H-1,2,4-triazole-3-thiol (5). The newly synthesized compounds were characterized by IR, H-1 NMR, mass and elemental analysis. Some of the synthesized compounds were tested for their anti-inflammatory, analgesic and antimicrobial activities. Compounds 8c, 8d and 8h exhibited excellent anti-inflammatory activity whereas compounds 8d, 8e and 8h showed excellent analgesic activity. Compounds 8a, 8c-e, and 8h exhibited good antibacterial activity and compounds 8c, 8e and 8h showed good antifungal activity. (c) 2008 Elsevier Masson SAS. All rights reserved.