2-(4-nitrophenyl)-5-phenyl-1,3,4-thiadiazole | 1456-68-4

• 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-nitrophenyl)-5-phenyl-1,3,4-thiadiazole
• 英文别名: 2-Phenyl-5-<4-nitro-phenyl>-1,3,4-thiadiazol；1,3,4-Thiadiazole,2-(4-nitrophenyl)-5-phenyl-
• CAS: 1456-68-4
• 化学式: C₁₄H₉N₃O₂S
• 分子量: 283.31
• InChiKey: NWFUWMNLVCEOJR-UHFFFAOYSA-N

物化性质

• 熔点：
  256-257 °C
• 沸点：
  481.7±47.0 °C(Predicted)
• 密度：
  1.363±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 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：
  99.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-Thiobenzoyl-N'-(p-nitrobenzyliden)-hydrazin 在 Eosin Y 、 氧气 作用下， 反应 18.0h， 生成 2-(4-nitrophenyl)-5-phenyl-1,3,4-thiadiazole
  参考文献：
  名称：

  Eosin Y Catalyzed Visible-light-promoted One –Pot Facile Synthesis of 1,3,4- Thiadiazole

  摘要：

  A novel one-pot visible light irradiated synthesis of 1,3,4-thiadiazole from aldehydes and thioacyl hydrazides have been reported in presence of eosin Y as an organophotoredox catalyst at room temperature under aerobic condition. This synthesis includes application of air and visible light as inexpensive, readily available, non-toxic and sustainable regents, which fulfils the basic principle of green chemistry.

  DOI：

  10.5562/cca2520

文献信息

• One-pot synthesis of 1,3,4-thiadiazoles using Vilsmeier reagent as a versatile cyclodehydration agent
  作者：Maaroof Zarei

  DOI：10.1016/j.tet.2017.02.042

  日期：2017.4

  A simple and efficient synthetic method for the one-pot synthesis of 1,3,4-thiadiazoles utilizing Vilsmeier reagent was developed. In this method carboxylic acids and hydrazine were converted to 1,3,4-thiadiazoles in the presence of Vilsmeier reagent and Lawesson's reagent. The influence of the thionation reagent, solvent, temperature and time, in this reaction was discussed. The developed methodology

  开发了一种简单有效的利用维尔斯迈尔试剂一锅法合成1,3,4-噻二唑的合成方法。在这种方法中，在Vilsmeier试剂和Lawesson试剂存在下，将羧酸和肼转化为1,3,4-噻二唑。讨论了该反应中硫磺化试剂，溶剂，温度和时间的影响。用于1,3,4-噻二唑合成的开发方法具有简单，环境反应条件，易于纯化以及产物收率良好至优异的优点。
• SYNTHESIS OF SUBSTITUTED 1,3,4-THIADIAZOLES USING LAWESSON'S REAGENT
  作者：B. Gierczyk、M. Zalas

  DOI：10.1080/00304940509354950

  日期：2005.6

  oxychloride or sulfuric acid have been used in such reactions. Another route for 1,3,4-thiadiazole ring synthesis, is via exchange of the oxygen atom in 1,3,4-oxadiazole to sulfur, using tetraphosphorus decasulfide or thiourea;I2 however in our experience, this method does not work in many cases. Lawesson has described the thionation of 1 ,2-diacylhydrazineswith 2,4bis(4-methoxypheny1)1,2,3,4-dithiadiphosphetane

  含硫化合物具有许多特殊和独特的性质，这使它们继续受到关注。由于其广泛的生物活性谱，1,3,4-噻二唑已被检查为潜在的抗菌剂，“抗病毒？镇痛剂：抗肿瘤剂：抗惊厥药、消炎药～、药物、杀虫剂和杀菌剂。其中一些形成热致液晶并具有有趣的电光特性。6 此外，噻二唑已被用作腐蚀和氧化抑制剂^,^染料或金属离子络合剂~。~ ~ J ~ J 这类化合物最常用的合成方法包括硫酰肼或其他底物与 SCNNCS 部分的环化和脱水。'2,6 通常在此类反应中使用磷酰氯或硫酸。1,3,4-噻二唑环合成的另一种途径是通过将 1,3,4-恶二唑中的氧原子交换为硫，使用十硫化四磷或硫脲；I2 但是根据我们的经验，这种方法在许多情况下不起作用案件。Lawesson 描述了 1 ,2-二酰基肼与 2,4 双(4-甲氧基苯基)1,2,3,4-二噻二膦（劳森试剂）的硫化作用，然后是自发环化和脱氢硫化，这是一种改进的噻二唑环形成方法。
• Eilingsfeld,H., Chemische Berichte, 1965, vol. 98, p. 1308 - 1321
  作者：Eilingsfeld,H.

  DOI：——

  日期：——
• Eosin Y Catalyzed Visible-light-promoted One –Pot Facile Synthesis of 1,3,4- Thiadiazole
  作者：Vishal Srivastava、Pravin K. Singh、Praveen P. Singh

  DOI：10.5562/cca2520

  日期：——

  A novel one-pot visible light irradiated synthesis of 1,3,4-thiadiazole from aldehydes and thioacyl hydrazides have been reported in presence of eosin Y as an organophotoredox catalyst at room temperature under aerobic condition. This synthesis includes application of air and visible light as inexpensive, readily available, non-toxic and sustainable regents, which fulfils the basic principle of green chemistry.