2-(4-fluorophenyl)-5-phenyl-1,3,4-thiadiazole | 1620385-48-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-fluorophenyl)-5-phenyl-1,3,4-thiadiazole
• CAS: 1620385-48-9
• 化学式: C₁₄H₉FN₂S
• 分子量: 256.303
• InChiKey: OFWXTIXWDHRPFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对氟苯甲醛 在 N-氯代丁二酰亚胺 、 一水合肼 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 60.0h， 生成 2-(4-fluorophenyl)-5-phenyl-1,3,4-thiadiazole
  参考文献：
  名称：

  Structural studies of 2,5-disubstituted 1,3,4-thiadiazole derivatives from dithioesters under the mild condition: Studies on antioxidant, antimicrobial activities, and molecular docking

  摘要：

  A series of 2,5-disubstituted 1,3,4-thiadiazole was synthesized and evaluated for their antioxidant and molecular docking studies. These molecules were efficiently synthesized under mild and inexpensive starting material. Construction of these molecules developed using substituted aldehydes and substituted dithioesters in presence of NCS (N-Chorosuccinimide). The compounds 4a, 4b, 4c, 4f, and 4k showed good antibacterial and antioxidant activity among which, 4k possess excellent antibacterial and antioxidant activity. The results of antioxidant activity studies revealed that compound 4k manifested profound antioxidant potential. The molecular docking study was performed with respective newly synthesized compounds to ascertain the binding mode of 4k with respect to the critical proteins involved in biosynthesis and metabolic pathways.

  DOI：

  10.1080/00397911.2020.1745843

文献信息

• C–H arylation of azaheterocycles: a direct ligand-free and Cu-catalyzed approach using diaryliodonium salts
  作者：Dalip Kumar、Meenakshi Pilania、V. Arun、Savita Pooniya

  DOI：10.1039/c4ob01061b

  日期：——

  An efficient and high yielding Cu-catalyzed direct C–H arylation of azaheterocycles including oxadiazoles, thiadiazoles, benzoxazoles and benzothiazoles has been achieved by employing easily accessible diaryliodonium salts.

  通过使用易于获得的二芳基碘盐，成功实现了一种高效且高产率的铜催化的直接C-H键芳基化反应，其中包括嘧啶、噻二唑、苯并噁唑和苯并噻唑等氮杂环化合物的合成。
• An efficient one-pot synthesis of 2,5-disubstituted-1,3,4-thiadiazoles from aldehydes and hydrazides using Lawesson’s reagent
  作者：Inseok Ko、Soojin Park、Goeun Lee、Hakwon Kim

  DOI：10.24820/ark.5550190.p010.871

  日期：——

  important and prevalent scaffold in the development of novel leads in medicinal chemistry for a variety of therapeutic targets. A two-step, onepot synthesis of 2,5-disubstituted-1,3,4-thiadiazole derivatives from aryl hydrazides and aryl aldehydes using Lawesson’s reagent is described, yielding 2,5-disubstituted-1,3,4-thiadiazoles in moderate-to-high yields. Based on preliminary biological experiments

  五元杂环系统，如噻二唑，仍然是开发各种治疗靶点的药物化学新线索的重要和普遍的支架。描述了使用 Lawesson 试剂从芳基酰肼和芳基醛两步一锅合成 2,5-二取代-1,3,4-噻二唑衍生物，在温和条件下生成 2,5-二取代-1,3,4-噻二唑- 高收益。根据初步的生物学实验，一些新合成的噻二唑显示出抗氧化活性。
• Novel Approach for the Synthesis of 2, 5-disubstituted 1, 3, 4-thiadiazoles from Benzothiohydrazides and Ethylbenzimidate
  作者：Shobha S、Kemparajegowda、Swamy Savvemala Girimanchanaika、Hassan A. Swarup、Kempegowda Mantelingu

  DOI：10.2174/1570178620666230602085830

  日期：2023.9.7

  In the current study, a simple and reliable technique for the synthesis of 2,5-disubstituted 1,3,4-thiadiazoles from ethylbenzimidate and benzothiohydrazides were devised. This protocol goes via a base-mediated nucleophilic addition elimination process, followed by intramolecular rearrangement. Our method utilizes commonly accessible and non-toxic substrates and a simple workup procedure to produce

  在目前的研究中，设计了一种简单可靠的技术，用于从苯甲亚胺酸乙酯和苯并硫代酰肼合成2,5-二取代1,3,4-噻二唑。该方案经过碱基介导的亲核加成消除过程，然后进行分子内重排。我们的方法利用常用且无毒的底物和简单的后处理程序，以高收率（70-91%）生产具有多种取代基的 2,5-二苯基 1,3,4-噻二唑衍生物。我们提出了一种简单的合成 1, 3, 4-噻二唑的方法，使用苯甲亚胺乙酯和苯并硫代酰肼，在 Et3N 存在下，在 DMSO 溶剂中作为经济实惠且易于获得的起始材料，在环境条件下生成衍生物。