1-(4-chlorophenyl)-5-methyl-4-phenyl-1H-1,2,3-triazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-chlorophenyl)-5-methyl-4-phenyl-1H-1,2,3-triazole
• 英文别名: 1-(4-Chlorophenyl)-5-methyl-4-phenyltriazole；1-(4-chlorophenyl)-5-methyl-4-phenyltriazole
• 化学式: C₁₅H₁₂ClN₃
• 分子量: 269.733
• InChiKey: DVHSNAOUDHDLPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 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：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对氯苯胺 在 盐酸 、 sodium azide 、 potassium tert-butylate 、 sodium nitrite 作用下， 以 水 、 叔丁醇 为溶剂， 反应 7.0h， 生成 1-(4-chlorophenyl)-5-methyl-4-phenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  烷酮烯醇化物与叠氮化物在深共晶溶剂中的 1,3-偶极环加成用于密集官能化 1,2,3-三唑的无金属区域选择性合成

  摘要：

  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。

  DOI：

  10.1002/ejoc.202200843

文献信息

• An Enolate-Mediated Organocatalytic Azide-Ketone [3+2]-Cycloaddition Reaction: Regioselective High-Yielding Synthesis of Fully Decorated 1,2,3-Triazoles
  作者：Adluri B. Shashank、S. Karthik、R. Madhavachary、Dhevalapally B. Ramachary

  DOI：10.1002/chem.201405501

  日期：2014.12.15

  An enolate‐mediated organocatalytic azide–ketone [3+2]‐cycloaddition (OrgAKC) reaction of a variety of enolizable arylacetones and deoxybenzoins with aryl azides was developed for the synthesis of fully decorated 1,4‐diaryl‐5‐methyl(alkyl)‐1,2,3‐triazoles in excellent yields with high regioselectivity at 25 °C for 0.5–6 h. This reaction has an excellent outcome with reference to reaction rate, yield

  烯醇介导的有机催化叠氮化物-酮[3 + 2]-环加成（OrgAKC）反应由多种可烯醇化的丙酮和脱氧安息香素与叠氮化物开发，用于合成完全装饰的1,4-二芳基-5-甲基（烷基） ‐1,2,3-三唑在25°C下保持0.5–6 h时具有极高的选择性，并具有较高的区域选择性。该反应在反应速率，产率，区域选择性，操作简便性以及底物和催化剂的可用性方面具有优异的结果。该反应比以前已知的金属介导反应更具优势。
• 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
  作者：Maria Grazia Perrone、Paola Vitale、Andrea Panella、Cosimo G. Fortuna、Antonio Scilimati

  DOI：10.1016/j.ejmech.2015.02.049

  日期：2015.4

  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.
• 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。