4-allyl-5-(2-hydroxyphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione | 80570-90-7

• 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-allyl-5-(2-hydroxyphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
• 英文别名: 5-(o-hydroxyphenyl)-4-allyl-1,2,4-triazole-3-thione；2-(4-allyl-5-mercapto-4H-1,2,4-triazol-3-yl)phenol；3-(2-hydroxyphenyl)-4-prop-2-enyl-1H-1,2,4-triazole-5-thione
• CAS: 80570-90-7
• 化学式: C₁₁H₁₁N₃OS
• mdl: MFCD00519065
• 分子量: 233.294
• InChiKey: KZAQFAGWXZOUIA-UHFFFAOYSA-N

物化性质

• 熔点：
  158-159 °C
• 沸点：
  344.3±52.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  80
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-allyl-5-(2-hydroxyphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 在 tellurium oxide 、 氢溴酸 、 溶剂黄146 作用下， 反应 24.0h， 以50%的产率得到
  参考文献：
  名称：

  噻唑并[2,3-c][1,2,4]三唑的功能衍生物的合成及抗菌活性。

  摘要：

  背景：缩合三唑是一类众所周知的杂环化合物，具有广泛的生物活性。该研究致力于评估噻唑并[2,3-c][1,2,4]三唑类新功能衍生物的抗菌潜力。方法：有效、易于实施和低成本的生产途径报道了通过亲电分子内杂环化的标题化合物。研究了对革兰氏阳性菌和革兰氏阴性菌以及真菌的杀菌和杀真菌活性。讨论了官能团对被测噻唑并[2,3-c][1,2,4]三唑类生物活性的影响。结果：微生物学评价表明，6-[(trichlorotellanyl)methyl]-[1,3]噻唑并[2,3-c][1,2,4]三唑-3-胺氯化氢2a和3-(2-羟基苯基)-6-[(三氯-λ4-碲基)甲基]-5，

  DOI：

  10.2174/1570180819666220110145659
• 作为产物：
  描述：

  4-allyl-1-(2-hydroxybenzoyl)thiosemicarbazide 在 sodium hydroxide 作用下， 反应 4.0h， 以89.59%的产率得到4-allyl-5-(2-hydroxyphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
  参考文献：
  名称：

  Synthesis, Antibacterial and Antifungal Activity of 4-Substituted-5-Aryl-1,2,4-Triazoles

  摘要：

  合成了几种4-烯丙基/氨基-5-芳基-1,2,4-三唑并测试了它们对大肠杆菌、枯草芽孢杆菌、沙门氏菌、金黄色葡萄球菌、黑曲霉和白色念珠菌的抗菌和抗真菌效果。4-烯丙基-5-芳基-1,2,4-三唑通过适当的一取代-4-烯丙基缩氨基硫脲的氧化环合得到，而4-氨基-5-芳基-1,2,4-三唑通过适当取代的二硫代氨基甲酸钾盐与水合肼的环合反应得到。这些新合成的化合物通过IR、1H-NMR、13C-NMR和UV光谱数据以及元素分析进行了表征。

  DOI：

  10.3390/61000815

文献信息

• Synthesis, Antibacterial and Antifungal Activity of 4-Substituted-5-Aryl-1,2,4-Triazoles
  作者：Katica Colanceska-Ragenovic、Vesna Dimova、Vlado Kakurinov、Dora Molnar、Aleksandra Buzarovska

  DOI：10.3390/61000815

  日期：——

  A few 4-allyl/amino-5-aryl-1,2,4-triazoles were synthesized and tested for antibacterial and antifungal effects against Escherichia coli, Bacillus subtilis, Salmonella enteritidis, Staphylococcus aureus, Aspergillus niger and Candida albicans. 4-Allyl-5-aryl-1,2,4-triazoles were obtained by the oxidative cyclization of the appropriate 1-substituted-4-allylthiosemicarbazides and 4-amino-5-aryl-1,2,4-triazoles were obtained by cyclization of the potassium salts of appropriately substituted dithiocarbazinic acids with hydrazine hydrate. The new synthesized compounds were characterized using IR, 1H- NMR, 13C-NMR and UV spectral data together with elemental analysis.

  合成了几种4-烯丙基/氨基-5-芳基-1,2,4-三唑并测试了它们对大肠杆菌、枯草芽孢杆菌、沙门氏菌、金黄色葡萄球菌、黑曲霉和白色念珠菌的抗菌和抗真菌效果。4-烯丙基-5-芳基-1,2,4-三唑通过适当的一取代-4-烯丙基缩氨基硫脲的氧化环合得到，而4-氨基-5-芳基-1,2,4-三唑通过适当取代的二硫代氨基甲酸钾盐与水合肼的环合反应得到。这些新合成的化合物通过IR、1H-NMR、13C-NMR和UV光谱数据以及元素分析进行了表征。
• Strzemecka, Leokadia, Polish Journal of Chemistry, 1983, vol. 57, # 4/5/6, p. 567 - 571
  作者：Strzemecka, Leokadia

  DOI：——

  日期：——
• BUDEANU, C.;IORGA, T.;RUSAN, M., REV. CHIM., RSR, 1983, 34, N 9, 791-794
  作者：BUDEANU, C.、IORGA, T.、RUSAN, M.

  DOI：——

  日期：——
• Molecular structure and vibrational bands and chemical shift assignments of 4-allyl-5-(2-hydroxyphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione by DFT and ab initio HF calculations
  作者：Tuncay Karakurt、Muharrem Dinçer、Ahmet Çetin、Memet Şekerci

  DOI：10.1016/j.saa.2010.05.006

  日期：2010.9

  The title molecule, 4-allyl-5-(2-hydroxyphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (C11H11N3OS), was synthesized and characterized by IR-NMR spectroscopy and single-crystal X-ray diffraction. The compound crystallizes in the monoclinic space group is P2(1)/c,a=9.0907(5)angstrom,b = 9.1288(7)angstrom, c= 13.6222(7)angstrom, alpha=90 degrees, beta=98.442(4), y=90 degrees and V=2683.7(6)angstrom(3),F(000)=488, D-x = 1.386 g/cm(3). In addition to the molecular geometry from X-ray experiment, the molecular geometry, vibrational frequencies, gauge including atomic orbital (GIAO) H-1 and C-13 chemical shift values of the title compound in the ground state have been calculated using the Hartree-Fock (HF) and density functional method (DFT/BLYP and DFT/B3LYP) with 6-31G(d) basis set. To determine conformational flexibility, molecular energy profile of the title compound was obtained by HF/6-31G(d) calculations with respect to selected degree of torsional freedom, which was varied from 180 degrees to +180 degrees in steps of 10 degrees. Besides, molecular electrostatic potential (MEP), frontier molecular orbitals (FMO), and several thermodynamic properties were performed by the HF and DRT methods. (c) 2010 Elsevier B.V. All rights reserved.
• Synthesis and Antimicrobial Activity of Functional Derivatives of thiazolo[ 2,3-c][1,2,4]triazoles
  作者：Mikhailo Slivka、Maksym Fizer、Ruslan Mariychuk、Marek Ostafin、Olexander Moyzesh、Galyna Koval、Oksana Holovko-Kamoshenkova、Ivan Rusyn、Vasyl Lendel

  DOI：10.2174/1570180819666220110145659

  日期：2022.9

  triazoles are a well-known class of heterocyclic compounds due to a wide range of biological activity. The study is dedicated to the evaluation of the antimicrobial potential of new functional derivatives of thiazolo[2,3-c][1,2,4]triazoles.Methods:Effective, easy-to-implement and low-cost routes to the production of title compounds via electrophilic intramolecular heterocyclization are reported. Bactericidal

  背景：缩合三唑是一类众所周知的杂环化合物，具有广泛的生物活性。该研究致力于评估噻唑并[2,3-c][1,2,4]三唑类新功能衍生物的抗菌潜力。方法：有效、易于实施和低成本的生产途径报道了通过亲电分子内杂环化的标题化合物。研究了对革兰氏阳性菌和革兰氏阴性菌以及真菌的杀菌和杀真菌活性。讨论了官能团对被测噻唑并[2,3-c][1,2,4]三唑类生物活性的影响。结果：微生物学评价表明，6-[(trichlorotellanyl)methyl]-[1,3]噻唑并[2,3-c][1,2,4]三唑-3-胺氯化氢2a和3-(2-羟基苯基)-6-[(三氯-λ4-碲基)甲基]-5，