4-(3,5-difluorophenyl)-1H-1,2,3-triazole | 1239962-25-4

• 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-(3,5-difluorophenyl)-1H-1,2,3-triazole
• 英文别名: 4-(3,5-difluorophenyl)-2H-triazole
• CAS: 1239962-25-4
• 化学式: C₈H₅F₂N₃
• 分子量: 181.145
• InChiKey: LRIMZNGRNOWNOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(3,5-difluorophenyl)-1H-1,2,3-triazole 、 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以5%的产率得到(2-benzylpiperidin-1-yl)(4-(3,5-difluorophenyl)-1H-1,2,3-triazol-1-yl)methanone
  参考文献：
  名称：

  Development and Optimization of Piperidyl-1,2,3-Triazole Ureas as Selective Chemical Probes of Endocannabinoid Biosynthesis

  摘要：

  We have previously shown that 1,2,3-triazole ureas (1,2,3-TUs) act as versatile class of irreversible serine hydrolase inhibitors that can be tuned to create selective probes for diverse members of this large enzyme class, including diacylglycerol lipase-beta (DAGL beta), a principal biosynthetic enzyme for the endocannabinoid 2-arachidonoylglycerol (2-AG). Here, we provide a detailed account of the discovery, synthesis, and structure-activity relationship (SAR) of (2-substituted)-piperidyl-1,2,3-TUs that selectively inactivate DAGL beta in living systems. Key to success was the use of activity-based protein profiling (ABPP) with broad-spectrum and tailored activity-based probes to guide our medicinal chemistry efforts. We also describe an expanded repertoire of DAGL-tailored activity-based probes that includes biotinylated and alkyne agents for enzyme enrichment coupled with mass spectrometry-based proteomics and assessment of proteome-wide selectivity. Our findings highlight the broad utility of 1,2,3-TUs for serine hydrolase inhibitor development and their application to create selective probes of endocannabinoid biosynthetic pathways.

  DOI：

  10.1021/jm400898x
• 作为产物：
  描述：

  1-乙炔基-3,5-二氟苯 在 叠氮基三甲基硅烷 作用下， 以82%的产率得到4-(3,5-difluorophenyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Catalyst-Free Regioselective N² Arylation of 1,2,3-Triazoles Using Diaryl Iodonium Salts

  摘要：

  The widespread application of 1,2,3-triazoles in pharmaceuticals has resulted in substantial interest toward developing efficient postmodification methods. Whereas there are many postmodification methods available to obtain N-1-substituted 1,2,3-triazoles, developing a selective and convenient protocol to synthesize N-2-aryl-1,2,3-triazoles has been challenging. We report a catalyst-free and regioselective method to access N-2-aryl-1,2,3-triazoles in good to excellent yields (66-97%). This scalable postmodification protocol is effective for a wide range of substrates.

  DOI：

  10.1021/acs.orglett.9b02140

文献信息

• Direct Synthesis of 4-Aryl-1,2,3-triazoles via I₂-Promoted Cyclization under Metal- and Azide-Free Conditions
  作者：Chun Huang、Xiao Geng、Peng Zhao、You Zhou、Xiao-Xiao Yu、Li-Sheng Wang、Yan-Dong Wu、An-Xin Wu

  DOI：10.1021/acs.joc.1c01702

  日期：2021.10.1

  We herein report an iodine-mediated formal [2 + 2 + 1] cyclization of methyl ketones, p-toluenesulfonyl hydrazines, and 1-aminopyridinium iodide for preparation of 4-aryl-NH-1,2,3-triazoles under metal- and azide-free conditions. Notably, this is achieved using p-toluenesulfonyl hydrazines and 1-aminopyridinium iodide as azide surrogates, providing a novel route toNH-1,2,3-triazoles. Furthermore, this

  本文我们报告碘介导的正式[2 + 2 + 1]甲基酮，环化p甲苯磺酰肼，和1-氨基吡啶碘化物用于制备4-芳基- NH下金属-1,2,3-三唑和无叠氮化物条件。值得注意的是，这是使用对甲苯磺酰肼和碘化 1-氨基吡啶鎓作为叠氮化物替代物实现的，为NH -1,2,3-三唑提供了一条新途径。此外，这种方法提供了对吲哚胺 2,3-双加氧酶 (IDO) 的强效抑制剂的快速且实用的途径。
• Catalyst and solvent free microwave-assisted synthesis of substituted 1,2,3-triazoles
  作者：Sahar Roshandel、Suresh C. Suri、Jacob C. Marcischak、Golam Rasul、G. K. Surya Prakash

  DOI：10.1039/c8gc01516c

  日期：——

  report a microwave-assisted catalyst and solvent free synthesis of 1,2,3-triazoles through the cycloaddition of trimethylsilylazide and acetylenes. Utilization of a thermally stable azide source, elimination of a metal catalyst, solvent or any additives, and a convenient isolation procedure result in an overall greener approach to access 1,2,3-triazoles on a practical scale with good to excellent yields

  我们报告了通过三甲基甲硅烷基叠氮化物和乙炔的环加成反应的微波辅助催化剂和1,2,3-三唑的无溶剂合成。利用热稳定的叠氮化物源，消除金属催化剂，溶剂或任何添加剂以及方便的分离程序，可以从整体上以更绿色的方式实际获得1,2,3-三唑，并具有良好或优异的收率（55）。 –99％）。
• Synthesis of 10β-Substituted Triazolyl Artemisinins and Their Growth Inhibitory Activity against Various Cancer Cells
  作者：Seok-Joon Lee

  DOI：10.5012/bkcs.2011.32.2.737

  日期：2011.2.20
• Acid-catalyzed synthesis of 10-substituted triazolyl artemisinins and their growth inhibitory activity against various cancer cells
  作者：Sangtae Oh、Woon-Seob Shin、Jungyeob Ham、Seokjoon Lee

  DOI：10.1016/j.bmcl.2010.05.074

  日期：2010.7

  A diastereomeric and regioisomeric library of 10-substituted triazolyl artemisinin compounds (6a-6h, 7a-7h, and 8a-8h) with a potent growth inhibitory activities against various cancer cell lines was established. These compounds were synthesized by a reaction with dihydroartemisinin (2) and various substituted triazoles (5a-5h) in methylene chloride using a BF(3)Et(2)O catalyst. Most of the compounds exhibited a strong potency in the submicromolar range, and, in particular, 6f, 7f, and 8f, which have a pentylphenyltriazole moiety, proved to be promising candidates for preclinical trials. (C) 2010 Elsevier Ltd. All rights reserved.