5-(3-氟苯基)-1,3,4-噻二唑-2-硫醇 | 276254-76-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-(3-氟苯基)-1,3,4-噻二唑-2-硫醇
• 英文名称: 5-(3-Fluoro-phenyl)-[1,3,4]thiadiazole-2-thiol
• 英文别名: 5-(3-Fluorophenyl)-1,3,4-thiadiazole-2-thiol；5-(3-fluorophenyl)-3H-1,3,4-thiadiazole-2-thione
• CAS: 276254-76-3
• 化学式: C₈H₅FN₂S₂
• 分子量: 212.272
• InChiKey: KMUGZQUJQXAZQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 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：
  81.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(3-氟苯基)-1,3,4-噻二唑-2-硫醇 在 sodium hydroxide 、 双氧水 作用下， 以 乙醇 、 水 、 溶剂黄146 为溶剂， 生成 2-(3-Fluorophenyl)-5-methylsulfonyl-1,3,4-thiadiazole
  参考文献：
  名称：

  Synthesis and Anticonvulsant Activity of 5-Aryl-1,3,4-thiadiazole Derivatives

  摘要：

  DOI：

  10.1211/146080800128735430
• 作为产物：
  描述：

  间氟苯甲酸 在 硫酸 、 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 5-(3-氟苯基)-1,3,4-噻二唑-2-硫醇
  参考文献：
  名称：

  Development of Novel (+)-Nootkatone Thioethers Containing 1,3,4-Oxadiazole/Thiadiazole Moieties as Insecticide Candidates against Three Species of Insect Pests

  摘要：

  DOI：

  10.1021/acs.jafc.1c05853

文献信息

• Efficient copper-catalyzed C–S cross-coupling of heterocyclic thiols with aryl iodides
  作者：Liang-Feng Niu、Yan Cai、Chao Liang、Xin-Ping Hui、Peng-Fei Xu

  DOI：10.1016/j.tet.2011.02.064

  日期：2011.4

  A copper-catalyzed cross-coupling of heterocyclic thiols with aryl iodides is reported. The reaction was carried out in the presence of CuI (5 mol %), 1,10-phenanthroline (10 mol %) and K2CO3 (1.3 equiv) in DMF at 120 °C. A variety of heterocyclic sulfides were prepared in high selectivities and yields.

  据报道，铜催化的杂环硫醇与芳基碘化物的交叉偶联。反应在120℃下在CuI（5mol％），1，10-菲咯啉（10mol％）和K 2 CO 3（1.3当量）的存在下在DMF中进行。以高选择性和高产率制备了各种杂环硫化物。
• Synthesis, antifungal activity and 3D-QSAR study of novel nopol-based 1,3,4-thiadiazole–thioether compounds
  作者：Xiu Wang、Wen-Gui Duan、Gui-Shan Lin、Ming Chen、Fu-Hou Lei

  DOI：10.1007/s11164-021-04510-x

  日期：2021.10

  A series of novel nopol derivatives containing 1,3,4-thiadiazole–thioether moiety were synthesized from β-pinene, which is a natural, abundant and renewable biomass resource. Their structures were characterized by FT-IR, 1H NMR, 13C NMR, ESI–MS and elemental analysis. In vitro antifungal activity of the target compounds was preliminarily evaluated against eight tested plant pathogens, including Fusarium oxysporum f. sp. cucumerinum, Cercospora arachidicola, Physalospora piricola, Alternaria solani, Gibberella zeae, Rhizoeotnia solani, Bipolaris maydis and Colleterichum orbicalare. The bioassay results revealed that, at the concentration of 50 μg/mL, all the target compounds showed certain inhibition activity against the eight tested fungi. Compounds 5f (R = m–OCH3), 5i (R = m–F) and 5r (R = m–I) had excellent inhibition rates of 77.8%, 88.9% and 77.8%, respectively, against P. piricola, showing much better antifungal activity than that of the positive control chlorothalonil. Meanwhile, compound 5 m (R = p–Cl) displayed antifungal activity of 80.7% against R. solani. Furthermore, the analysis of three-dimensional quantitative structure–activity relationship (3D-QSAR) was performed for the relationship between the structures of the target compounds and their antifungal activity against P. piricola by CoMFA method. A reasonable CoMFA model (n = 6; q2 = 0.597; r2 = 0.985) was established.

  一系列包含1,3,4-噻二唑-硫醚基团的新型nopol衍生物是从β-松油烯合成的，这是一种天然、丰富且可再生的生物质资源。其结构通过FT-IR、1H NMR、13C NMR、ESI-MS和元素分析进行了表征。针对八种植物病原菌的体外抗真菌活性进行了初步评估，包括黄瓜纹枯病菌（Fusarium oxysporum f. sp. cucumerinum）、落花生斑点病菌（Cercospora arachidicola）、梨果病病菌（Physalospora piricola）、马铃薯晚疫病病菌（Alternaria solani）、玉米镰刀菌（Gibberella zeae）、水稻稻瘟病菌（Rhizoctonia solani）、玉米大斑病菌（Bipolaris maydis）和圆孢纹枯病菌（Colletotrichum orbicalare）。生物测定结果显示，在50 μg/mL的浓度下，所有目标化合物对这八种测试真菌均表现出一定的抑制活性。化合物5f（R = m-OCH3）、5i（R = m-F）和5r（R = m-I）对P. piricola的抑制率分别为77.8%、88.9%和77.8%，表现出比阳性对照氯硝噻啶更优越的抗真菌活性。同时，化合物5m（R = p-Cl）对R. solani表现出80.7%的抗真菌活性。此外，通过CoMFA方法对目标化合物的结构与其对P. piricola的抗真菌活性之间的关系进行了三维定量构效关系（3D-QSAR）分析，建立了合理的CoMFA模型（n = 6; q2 = 0.597; r2 = 0.985）。
• Facile synthesis of novel fluorinated thieno[2,3-d]pyrimidine derivatives containing 1,3,4-thiadiazole
  作者：Xin Jian Song、Zheng Chao Duan、Yu Shao、Xing Gao Dong

  DOI：10.1016/j.cclet.2012.02.007

  日期：2012.5

  Abstract A series of novel fluorinated thieno[2,3-d]pyrimidine derivatives incorporating 1,3,4-thiadiazole were synthesized by a facile microwave-assisted procedure, including the cyclization of 2-aminothiophene-3-carbonitrile with trifluoroacetic acid, chlorination and nucleophilic substitution reaction. This protocol offered such advantages as mild reaction conditions, short reaction time, simple

  摘要通过简便的微波辅助方法，包括2-氨基噻吩-3-甲腈与三氟乙酸的环化反应，氯化反应，合成了一系列新的含1,3,4-噻二唑的氟化噻吩并[2,3-d]嘧啶衍生物。和亲核取代反应。该方案具有反应条件温和，反应时间短，纯化简单，收率高等优点。产物的结构通过1 H NMR，MS，元素分析和X射线衍射进行表征。
• US6080772A
  申请人：——

  公开号：US6080772A

  公开（公告）日：2000-06-27
• Development of Novel (+)-Nootkatone Thioethers Containing 1,3,4-Oxadiazole/Thiadiazole Moieties as Insecticide Candidates against Three Species of Insect Pests
  作者：Ruige Yang、Meiyue Han、Jiangping Fan、Wanqing Cheng、Nannan Ma、Xiaoting Yan、Yong Guo

  DOI：10.1021/acs.jafc.1c05853

  日期：2021.12.29