2-(p-tolyl)-1,3,4-thiadiazole | 1366397-88-7

• 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-(p-tolyl)-1,3,4-thiadiazole
• 英文别名: 2-(4-Methylphenyl)-1,3,4-thiadiazole
• CAS: 1366397-88-7
• 化学式: C₉H₈N₂S
• 分子量: 176.242
• InChiKey: WNBUANLMQNFDKH-UHFFFAOYSA-N

物化性质

• 熔点：
  40-43 °C
• 沸点：
  295.4±33.0 °C(predicted)
• 密度：
  1.199±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-碘吲哚 、 2-(p-tolyl)-1,3,4-thiadiazole 在 copper(l) iodide 、 palladium diacetate 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以38%的产率得到2-(1H-Indol-5-yl)-5-p-tolyl-1,3,4-thiadiazole
  参考文献：
  名称：

  Pd/Cu-Catalyzed C–H Arylation of 1,3,4-Thiadiazoles with (Hetero)aryl Iodides, Bromides, and Triflates

  摘要：

  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.

  DOI：

  10.1021/jo301401q
• 作为产物：
  描述：

  N'-formyl-4-methylbenzohydrazide 在 劳森试剂 作用下， 生成 2-(p-tolyl)-1,3,4-thiadiazole
  参考文献：
  名称：

  2-芳基-1,3,4-噻二唑的多核磁共振研究

  摘要：

  记录了芳基取代的 1,3,4-噻二唑的 1H、13C 和 15N 光谱。获得的结果与哈米特系数相关。将实验结果与 DFT 计算的化学位移进行比较。将所得结果与 1,3,4-恶二唑和 1,3,4-硒二唑的结果进行比较。版权所有 © 2012 John Wiley & Sons, Ltd.

  DOI：

  10.1002/mrc.3850

文献信息

• [EN] BIARYL SUBSTITUTED AZABICYCLIC ALKANE DERIVATIVES AS NICOTINIC ACETYLCHOLINE RECEPTOR ACTIVITY MODULATORS<br/>[FR] DÉRIVÉS D'ALCANE AZABICYCLIQUE À SUBSTITUTION BIARYLE EN TANT QUE MODULATEURS DE L'ACTIVITÉ DU RÉCEPTEUR NICOTINIQUE DE L'ACÉTYLCHOLINE
  申请人：ABBOTT LAB

  公开号：WO2009067579A1

  公开（公告）日：2009-05-28

  The invention relates to biaryl substituted azabicyclic alkane derivatives, compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions.

  这项发明涉及取代的双芳基氮杂环戊烷衍生物，包括这种化合物的组合物，以及使用这种化合物和组合物治疗疾病和疾病的方法。
• LINCOSAMIDE DERIVATIVES AND ANTIMICROBIAL AGENTS COMPRISING THE SAME AS ACTIVE INGREDIENT
  申请人：Umemura Eijirou

  公开号：US20100184746A1

  公开（公告）日：2010-07-22

  An objective of the present invention is to provide compounds of formula (I) or their pharmacologically acceptable salts or solvates wherein A represents aryl while R 1 represents a five- or six-membered monocyclic heterocyclic group, or A represents a four- to six-membered monocyclic heterocyclic group while R 1 represents aryl or a five- or six-membered monocyclic heterocyclic group; R 2 represents a hydrogen atom or C 1-6 alkyl; R 3 represents C 1-6 alkyl or C 3-6 cycloalkyl-C 1-4 alkyl; R 4 , R 5 , and R 6 represent a hydrogen atom; R 7 represents C 1-6 alkyl; and m is 1 to 3. The compounds are novel lincosamide derivatives that have a potent activity against resistant Streptococcus pneumoniae . Further, the compounds are usable as antimicrobial agents and are useful for preventing or treating bacterial infectious diseases.

  本发明的目标是提供式（I）的化合物或其药理学上可接受的盐或溶剂，其中A代表芳基，而R1代表五元或六元单环杂环基，或A代表四至六元单环杂环基，而R1代表芳基或五元或六元单环杂环基；R2代表氢原子或C1-6烷基；R3代表C1-6烷基或C3-6环烷基-C1-4烷基；R4、R5和R6代表氢原子；R7代表C1-6烷基；m为1至3。这些化合物是新型的林可霉素衍生物，对耐药性肺炎链球菌具有强效活性。此外，这些化合物可用作抗微生物剂，对预防或治疗细菌感染性疾病有用。
• Direct Heteroarylation of Tautomerizable Heterocycles into Unsymmetrical and Symmetrical Biheterocycles via Pd/Cu-Catalyzed Phosphonium Coupling
  作者：Abhishek Sharma、Dipak Vachhani、Erik Van der Eycken

  DOI：10.1021/ol300455e

  日期：2012.4.6

  The direct cross-coupling of tautomerizable heterocycles with various unfunctionalized heteroarenes has been achieved through PyBroP-mediated and Pd/Cu-catalyzed sequential C-OH/C-H activation. The methodology allows a facile entry into novel diazine-azole biheterocyclic frameworks. Moreover, an unprecedented Pd-catalyzed phosphonium homocoupling of tautomerizable heterocycles was also developed to afford a direct synthetic route to symmetrical 1,2-, 1,3-, and 1,4-bidiazine units.
• A KHSO4 promoted tandem synthesis of 1,3,4-thiadiazoles from thiohydrazides and DMF derivatives
  作者：Zongjie Gan、Binghua Tian、Jianyong Yuan、Dongzhi Ran、Lin Zhang、Gang Dong、Tao Pan、Yixin Zeng、Yu Yu

  DOI：10.1016/j.tetlet.2020.152195

  日期：2020.7

  An efficient, simple and environmentally benign method for the construction of 1,3,4-thiadiazole skeletons via the tandem coupling and cyclization of thiohydrazides with DMF derivatives in the presence of KHSO4 has been reported. This method reveals good reactivity and functional group tolerance, and a broad series of 1,3,4-thiadiazoles were obtained in moderate to good yields. (C) 2020 Elsevier Ltd. All rights reserved.
• BIARYL SUBSTITUTED AZABICYCLIC ALKANE DERIVATIVES AS NICOTINIC ACETYLCHOLINE RECEPTOR ACTIVITY MODULATORS
  申请人：Abbott Laboratories

  公开号：EP2231657A1

  公开（公告）日：2010-09-29