4-benzylidenamino-5-phenyl-4H-1,2,4-triazole-3-thiol | 22706-12-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-benzylidenamino-5-phenyl-4H-1,2,4-triazole-3-thiol
• 英文别名: 4-(benzylideneamino)-5-phenyl-4H-1,2,4-triazole-3-thiol；4-(benzylideneamino)-3-phenyl-1H-1,2,4-triazole-5-thione
• CAS: 22706-12-3
• 化学式: C₁₅H₁₂N₄S
• 分子量: 280.353
• InChiKey: DFCISOWMWAKUDC-UHFFFAOYSA-N

物化性质

• 熔点：
  180 °C
• 沸点：
  408.9±28.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-benzylidenamino-5-phenyl-4H-1,2,4-triazole-3-thiol 在 三乙胺 作用下， 以 乙醇 为溶剂， 230.0 ℃ 、6.67 Pa 条件下， 反应 1.25h， 生成 3,6-diphenyl-7-ethoxycarbonyl-1H-pyrazolo[5,1-c][1,2,4]triazole
  参考文献：
  名称：

  二氢噻二嗪和二氢噻二唑的立体选择性合成及其热解脱硫环的收缩

  摘要：

  分子内碱催化的C–C键形成导致反式-6,7-dihydro-5 H- [1,2,4]三唑[3,4- b ] [1,3,4]噻二嗪，反式的排他立体选择性合成-7,8-二氢-6- ħ - [1,2,4]三嗪并[3,4- b ] [1,3,4]噻二嗪-4-酮，和反式-3,4-二氢2 ħ - [1,3,4] thiadiazino [2,3 - b ] quinazolin-10-one。反式-6,7-二氢-5- ħ - [1,2,4]三唑并[3,4- b ] [1,3,4]噻二嗪在CDCl慢慢异构化3和更迅速地在DMSO- d 6为相应的顺式立体异构体。另一个反式-6,7-二氢-[1,3,4]噻二嗪在DMSO- d 6中也异构化为相应的顺式立体异构体。这些杂环缩合的二氢噻二嗪热解转化为其相应的吡唑并[5,1- b ] [1,2,4]三唑，吡唑并[5,1- c ] [1,2,4]三嗪-4-酮和吡唑并[描述了通过脱硫环收缩的4，3

  DOI：

  10.1016/j.tet.2011.06.034
• 作为产物：
  描述：

  potassium 3-benzoyldithiocarbazinate 在 hydrazine hydrate 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 4.17h， 生成 4-benzylidenamino-5-phenyl-4H-1,2,4-triazole-3-thiol
  参考文献：
  名称：

  Antibacterial, antioxidant and anthelmintic studies of inclusion complexes of some 4-arylidenamino-5-phenyl-4H-1,2,4-triazole-3-thiols

  摘要：

  A series of 4-arylidenamino-5-phenyl-4H-1,2,4-triazole-3-thiols have been synthesised and their inclusion complexes have been prepared with -cyclodextrin. The compounds and their inclusion complexes have been characterised by studying their physical and spectral properties. The thermodynamic stability constant and free energy of activation have been determined to know the stability of inclusion complexes. Finally, the compounds and their inclusion complexes are screened for antibacterial, antioxidant and anthelmintic activities. It is found that inclusion complexes of the newly synthesised compounds have appreciable stability and inclusion complex formation increases the antibacterial, antioxidant and anthelmintic activities significantly as compared to naked compound.

  DOI：

  10.1080/10610278.2015.1075533

文献信息

• Studies on Absorption and Emission Characteristics of Inclusion Complexes of Some 4-Arylidenamino-5-phenyl-4H-1, 2, 4-triazole-3-thiols
  作者：Sunakar Panda、Sashikanta Nayak

  DOI：10.1007/s10895-015-1728-5

  日期：2016.3

  The inclusion complexes of a series of 4-arylidenamino-5-phenyl-4H-1, 2, 4-triazole-3-thiols have been prepared with β-cyclodextrin. The compounds and their inclusion complexes have been characterized by studying their physical and spectral properties. The thermodynamic stability constant and free energy of activation have been determined to know the stability of inclusion complexes and type of host-guest

  用β-环糊精制备了一系列4-芳基氨基-5-苯基-4H-1、2、4-三唑-3-硫醇的包合物。通过研究它们的物理和光谱特性，可以对化合物及其包合物进行表征。确定了热力学稳定性常数和活化自由能，以了解包合物的稳定性和主体-客体关系的类型。最后，对化合物（4-芳基氨基-5-苯基-4H-1、2，4-三唑-3-硫醇）及其包合物的吸收，激发和发射光谱进行了测定。发现包合物的形成引起新合成的化合物的吸收和荧光特性（激发和发射光谱）都发生急剧变化。
• Synthesis, characterization, antimicrobial, and MOE evaluation of nano 1,2,4‐triazole‐based Schiff base ligand with some d‐block metal ions
  作者：Nessma F. Mahmoud、Ashraf A. Abbas、Gehad G. Mohamed

  DOI：10.1002/aoc.6219

  日期：2021.6

  bidentate manner with the metal ions through the azomethine N and thiol S. The thiol group coordinated to the metal ions without proton displacement as confirmed from the 1H NMR spectra. The conductivity data showed the electrolytic nature of the Fe (III) and Cu (II) complexes while the Zn (II) complex was nonelectrolyte. All metal complexes had octahedral structure as depicted by spectral and elemental

  三种新的4-（亚苄基氨基）-5-苯基-4H-1,2,4-三唑-3-硫醇配体（L）和三种过渡金属离子的金属配合物：Fe（III），Cu（II）和Zn （II）被合成并表征。衍生自4-氨基-5-苯基-1,2,4-三唑-3-硫醇和苯甲醛的配体以1：1的摩尔比合成。通过元素分析，电导率测量，热分析，FT-IR和1 H-NMR光谱对所有螯合物进行表征。红外光谱表明，席夫碱配体通过偶氮甲碱N和硫醇S与金属离子以中性双齿配位。如11 H NMR谱。电导率数据显示Fe（III）和Cu（II）配合物的电解性质，而Zn（II）配合物为非电解质。如光谱和元素分析所示，所有金属络合物均具有八面体结构。配合物在35°C开始分解，并以四到五个步骤分解。扫描电子显微镜（SEM）分析证实了纳米结构中金属配合物的存在。已经筛选了1,2,4-三唑希夫碱配体（L）及其过渡金属配合物的抗菌（革兰氏阳性菌）：枯草芽孢杆菌和金黄色葡
• Sireesha, Aliya B.; Reddy, Ch. Venkata Ramana; Devi, Ch. Sarala, Journal of the Indian Chemical Society, 2008, vol. 85, # 9, p. 926 - 929
  作者：Sireesha, Aliya B.、Reddy, Ch. Venkata Ramana、Devi, Ch. Sarala

  DOI：——

  日期：——
• Nayak, Sashikanta; Panda, Sunakar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2016, vol. 55B, # 9, p. 1144 - 1150
  作者：Nayak, Sashikanta、Panda, Sunakar

  DOI：——

  日期：——
• Efficient synthesis and antimicrobial activity of some novel S-β-d-glucosides of 5-aryl-1,2,4-triazole-3-thiones derivatives
  作者：Dan Ji、JunRui Lu、BoWei Lu、ChunWei Xin、JiangBei Mu、JianFa Li、ChunYong Peng、XiuRong Bao

  DOI：10.1016/j.bmcl.2013.02.038

  日期：2013.4

  A series of 3-S-beta-D-glucosides-4-arylideneamino-5-aryl-1,2,4-triazoles were rationally designed and synthesized according to the principle of superposition of bioactive substructures by the combination of 1,2,4-triazole, Schiff base and glucosides. The structures of the target compounds have been characterized by H-1 NMR, C-13 NMR, IR, MS and HRMS. All the newly synthesized compounds have been evaluated for their antimicrobial activities in vitro against Staphylococcus aureus (ATCC 6538), Escherichia coli (ATCC 8099) as well as Monilia albican (ATCC 10231). The bioactive assay showed that most of the tested compounds displayed variable inhibitory effects on the growth of the Gram-positive bacterial strain (Staphylococcus aureus), Gram-negative bacterial strains (Escherichia coli) and fungal strains (Monilia albican). All the target compounds exhibited better antifungal activity than antibacterial activity. Especially, compounds 6b, 6c, 6f, 6j, 6k and 6l showed excellent activity against fungus Monilia albican with MIC values of 16 mu g/mL. (C) 2013 Elsevier Ltd. All rights reserved.