4-(5-甲基-4-苯基三唑-1-基)苯酚 | 84292-46-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-(5-甲基-4-苯基三唑-1-基)苯酚
• 英文名称: 1-(4-Hydroxyphenyl)-4-phenyl-5-methyl-1,2,3-triazole
• 英文别名: 4-(5-methyl-4-phenyl-1H-1,2,3-triazol-1-yl)phenol；4-(5-methyl-4-phenyltriazol-1-yl)phenol
• CAS: 84292-46-6
• 化学式: C₁₅H₁₃N₃O
• 分子量: 251.288
• InChiKey: FBNCSVYGEFPMND-UHFFFAOYSA-N

物化性质

• 熔点：
  192-195 °C(Solv: N,N-dimethylformamide (68-12-2); water (7732-18-5))
• 沸点：
  460.9±47.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：
  50.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(5-甲基-4-苯基三唑-1-基)苯酚 在 sodium hydroxide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.67h， 生成 4-[4-(5-Methyl-4-phenyl-[1,2,3]triazol-1-yl)-phenoxy]-butyric acid
  参考文献：
  名称：

  da Settimo; Livi; Biagi, Farmaco, Edizione Scientifica, 1982, vol. 37, # 11, p. 728 - 739

  摘要：

  DOI：
• 作为产物：
  描述：

  1-叠氮基-4-甲氧基苯 在 三溴化硼 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 4-(5-甲基-4-苯基三唑-1-基)苯酚
  参考文献：
  名称：

  General role of the amino and methylsulfamoyl groups in selective cyclooxygenase(COX)-1 inhibition by 1,4-diaryl-1,2,3-triazoles and validation of a predictive pharmacometric PLS model

  摘要：

  A novel set of 1,4-diary1-1,2,3-triazoles were projected as a tool to study the effect of both the heteroaromatic triazole as a core ring and a variety of chemical groups with different electronic features, size and shape on the catalytic activity of the two COX isoenzymes. The new triazoles were synthesized in fair to good yields and then evaluated for their inhibitory activity towards COXs arachidonic acid conversion catalysis. Their COXs selectivity was also measured. A predictive pharmacometric Volsurf plus model, experimentally confirmed by the percentage (%) of COXs inhibition at the concentration of 50 mu M and IC50 values of the tested compounds, was built by using a number of isoxazoles of known COXs inhibitory activity as a training set. It was found that two compounds (4-(5-methyl-4-phenyl-1H-1,2,3-triazol-1-yl)benzenamine (18) and 4-[1-(4-methoxyphenyl)-5-methyl-1H-1,2,3-triazole-4-yl]benzenamine (19)) bearing an amino group (NH2) are potent and selective COX-1 inhibitors (IC50 = 15 and 3 mu M, respectively) and that the presence of a methylsulfamoyl group (SO2CH3) is not a rule to have a Coxib. In fact, 4-(4-methoxyphenyl)-5-methyl-1-[4-(methylsulfonyl)phenyl]-1H-1,2,3-triazole (23) has COX-1 IC50 = 23 mu M and was found inactive towards COX-2. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.049

文献信息

• Ester, amide and ether derivatives of 1-(<i>p</i>-phenyl-substituted)-1,2,3-triazoles
  作者：Oreste Livi、Giuliana Biagi、Pier Luigi Ferrarini、Gianpaolo Primofiore、Claudio Mori

  DOI：10.1002/jhet.5570200660

  日期：1983.11

  This paper describes the preparation of three series of 1-phenyl-1,2,3-triazol derivatives with an ester, amide or ether group on the phenyl ring. These derivatives were obtained from 4-hydroxyphenyl- and 4-aminophenyltriazoles, previously synthesized by us, by means of a nucleophilic substitution reaction with acetic anhydride, acyl and alkyl halides. The largest part of compounds were tested in an

  本文描述了在苯环上带有酯，酰胺或醚基的三个系列的1-苯基-1,2,3-三唑衍生物的制备。这些衍生物是由我们先前合成的4-羟基苯基-和4-氨基苯基三唑通过与乙酸酐，酰基和烷基卤化物的亲核取代反应获得的。化合物的最大部分在农药，营养和动物健康筛查计划中进行了测试。
• 1,3‐Dipolar Cycloaddition of Alkanone Enolates with Azides in Deep Eutectic Solvents for the Metal‐Free Regioselective Synthesis of Densely Functionalized 1,2,3‐Triazoles
  作者：Luciana Cicco、Filippo Maria Perna、Aurelia Falcicchio、Angela Altomare、Francesco Messa、Antonio Salomone、Vito Capriati、Paola Vitale

  DOI：10.1002/ejoc.202200843

  日期：2022.9.27

  The 1,3-dipolar cycloaddition reaction between alkanone enolates and azides proceeds smoothly and regioselectively in eco-friendly eutectic mixtures to yield densely functionalized 1,2,3-triazoles. Pharmacologically active triazoles have also been targeted directly in DESs via telescoped, one-pot cycloaddition/reduction processes.

  烷酮烯醇化物和叠氮化物之间的 1,3-偶极环加成反应在生态友好的低共熔混合物中顺利且区域选择性地进行，以产生致密官能化的 1,2,3-三唑。具有药理活性的三唑也已通过伸缩式一锅环加成/还原过程直接靶向 DES。
• DA, SETTIMO, A.;LIVI, O.;BIAGI, G.;PRIMOFIORE, G.;MASONI, G., FARMACO. ED. SCI., 1982, 37, N 11, 728-739
  作者：DA, SETTIMO, A.、LIVI, O.、BIAGI, G.、PRIMOFIORE, G.、MASONI, G.

  DOI：——

  日期：——
• LIVI, O.;BIAGI, G.;FERRARINI, P. L.;PRIMOFIORE, G.;MORI, C., J. HETEROCYCL. CHEM., 1983, 20, N 6, 1729-1733
  作者：LIVI, O.、BIAGI, G.、FERRARINI, P. L.、PRIMOFIORE, G.、MORI, C.

  DOI：——

  日期：——