2-(4-fluorophenyl)-5-(p-tolyl)-1,3,4-thiadiazole | 1401253-93-7

• 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-(p-tolyl)-1,3,4-thiadiazole
• 英文别名: 2-(4-Fluorophenyl)-5-(4-methylphenyl)-1,3,4-thiadiazole；2-(4-fluorophenyl)-5-(4-methylphenyl)-1,3,4-thiadiazole
• CAS: 1401253-93-7
• 化学式: C₁₅H₁₁FN₂S
• 分子量: 270.33
• InChiKey: OKYIGGQRAPJUCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 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：
  54
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对甲基苯甲醛 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-(p-tolyl)-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

• Sulfuric acid-mediated synthesis of 2,5-disubstituted 1,3,4-thiadiazole via intramolecular cyclization reaction from dithioesters: An approach to crystal structure prediction, DFT studies and Hirshfeld surface analysis
  作者：Kemparajegowda、Hassan A. Swarup、S. Chandrasekhar、B.K. Jayanna、Karthik Kumara、N.K. Lokanath、Sridhar B. Thimmaiah、Kempegowda Mantelingu

  DOI：10.1016/j.molstruc.2021.131970

  日期：2022.3

  the use of organic solvents. An efficient and facile synthesis of 2, 5-disubstituted 1, 3, 4-thiadiazoles via intramolecular cyclization from dithioesters and benzoic acid in presence of H2SO4 has been developed using dithioesters. The synthesized compound was characterized and confirmed by NMR analysis and single-crystal X-ray diffraction studies. The geometry (bond lengths and bond angles), and molecular

  迫切需要发现新方法，通过原子经济和环境友好的反应，最大限度地减少有机溶剂的使用，从而使多种功能化的分子可用。在 H 2 SO 4存在下，通过二硫酯和苯甲酸的分子内环化反应高效、简便地合成 2, 5-二取代的 1, 3, 4-噻二唑已使用二硫酯开发。合成的化合物通过核磁共振分析和单晶 X 射线衍射研究进行表征和确认。几何形状（键长和键角）和分子性质是通过密度泛函理论 (DFT) 在 B3LYP/6-31G 理论水平估计的，没有对称约束。使用优化的结构绘制前沿分子轨道（HOMO 和 LUMO），阐明了化合物的电荷转移协作和化学稳定性。发现了良好的相关系数 (R 2= 0.9629 和 0.9176,) 在实验键长和键角与理论值之间。Hirshfeld 表面 (HS) 分析表明，5h 化合物的氧和氮原子可能充当 H 键受体，预计某些 H 键接触会在分子的 HS 上显示为红点。
• 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。
• Thiadiazoles or oxadiazoles possessing one alkyl, alkenyl or alkynyl tail and a 4-fluorophenyl or 4-cyanophenyl group
  申请人：Citizen Finedevice Co., Ltd.

  公开号：US10577338B2

  公开（公告）日：2020-03-03

  New classes of thiadiazole and oxadiazole compounds for use in LC mixtures are disclosed. In an embodiment, the new classes of thiadiazoles and oxadiazoles comprise at least one phenyl ring attached to the heterocyclic ring, where no alkyl, alkenyl or alkynyl tails are attached to the phenyl ring, but one alkyl, alkenyl or alkynyl tail is attached to the other end of the molecule, and a fluoro or cyano group appears in the para position of the phenyl ring. These compounds are disclosed as being effective at inducing smectic A phases in liquid crystal mixtures, particularly in liquid crystal mixtures also possessing a smectic C phase, more particularly in materials possessing a chiral smectic C (ferroelectric) phase.

  本发明公开了用于低浓度混合物的新型噻二唑和噁二唑化合物。在一个实施方案中，新类别的噻二唑和噁二唑包括至少一个连接到杂环上的苯基环，其中苯基环上没有连接烷基、烯基或炔基尾部，但分子的另一端连接了一个烷基、烯基或炔基尾部，苯基环的对位出现了一个氟或氰基。这些化合物可以有效地诱导液晶混合物中的 Smectic A 相，特别是在同时具有 Smectic C 相的液晶混合物中，尤其是在具有手性 Smectic C（铁电）相的材料中。
• Pd/Cu-Catalyzed C–H Arylation of 1,3,4-Thiadiazoles with (Hetero)aryl Iodides, Bromides, and Triflates
  作者：Dipak D. Vachhani、Abhishek Sharma、Erik Van der Eycken

  DOI：10.1021/jo301401q

  日期：2012.10.5

  The direct C-H arylation of 1,3,4-thiadiazoles with a wide range of (hetero)aryl iodides, bromides, and triflates is described using a Pd/Cu-catalyzed protocol. The methodology is compatible with substrates possessing electron-donating or electron-withdrawing substituents and also tolerates sterically hindered aryl halides. The utility of the developed protocol is demonstrated by a one-pot C-H arylation-Suzuki coupling sequence.
• 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
  作者：Kemparaje Gowda、Hassan A. Swarup、Sandhya C. Nagarakere、Shobith Rangappa、Rangappa S. Kanchugarkoppal、Mantelingu Kempegowda

  DOI：10.1080/00397911.2020.1745843

  日期：2020.5.18

  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.