1-(4-methoxybenzyl)-5-phenyl-1H-1,2,3-triazole | 126800-12-2

• 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-methoxybenzyl)-5-phenyl-1H-1,2,3-triazole
• 英文别名: 1-[(4-Methoxyphenyl)methyl]-5-phenyltriazole
• CAS: 126800-12-2
• 化学式: C₁₆H₁₅N₃O
• 分子量: 265.315
• InChiKey: UPKJBWYIPSNBOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-甲氧基氯苄 在 sodium azide 、 二(三苯基膦)环戊二烯基氯化钌(II) 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 14.0h， 生成 1-(4-methoxybenzyl)-5-phenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Designing 2-aminoimidazole alkaloids analogs with anti-biofilm activities: Structure–activities relationships of polysubstituted triazoles

  摘要：

  In order to discover novel probes that may help in the investigation and the control of bacterial biofilms, we have designed a library of triazole-based analogs of 2-aminoimidazole marine alkaloids: naamine A and isonaamine A. Twenty-two compounds were screened for their biofilm inhibitory activity against two strains of Gram-negative bacteria. Four compounds were shown to act as non-toxic inhibitors of biofilm development without effect on bacterial growth even at high concentrations (100 mu M). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.050

文献信息

• A general metal-free route towards the synthesis of 1,2,3-triazoles from readily available primary amines and ketones
  作者：Joice Thomas、Sampad Jana、Jubi John、Sandra Liekens、Wim Dehaen

  DOI：10.1039/c5cc08347h

  日期：——

  An unprecedented approach that enables the direct and selective preparation of 1,5-disubstituted 1,2,3-triazoles from abundantly available building blocks such as primary amines, enolizable ketones and 4-nitrophenyl azide as a renewable...

  一种前所未有的方法，可以从伯胺，可烯醇化的酮和4-硝基苯叠氮化物等可再生原料中大量获得，直接和选择性地制备1,5-二取代1,2,3-三唑。
• Multi-component reaction for the preparation of 1,5-disubstituted 1,2,3-triazoles by in-situ generation of azides and nickel-catalyzed azide-alkyne cycloaddition
  作者：Virgyl Camberlein、Nicolas Kraupner、Nour Bou Karroum、Emmanuelle Lipka、Rebecca Deprez-Poulain、Benoit Deprez、Damien Bosc

  DOI：10.1016/j.tetlet.2021.153131

  日期：2021.6

  An efficient one-pot procedure combining bromide conversion into azide followed by NiAAC for the preparation of 1,5-disubstituted 1,2,3-triazoles has been developed. This procedure prevents the use of isolated azides, which are insufficiently commercially available and could be potentially unstable and difficult to handle. Moreover, this one-pot method tolerates a broad range of functional moieties

  已经开发了一种高效的一锅法，将溴化物转化为叠氮化物，然后是 NiAAC，用于制备 1,5-二取代 1,2,3-三唑。该程序防止使用分离的叠氮化物，这些叠氮化物在商业上供应不足，并且可能不稳定且难以处理。此外，这种一锅法可以耐受广泛的功能部分，包括酯、氨基甲酸酯或醇。多种 1,5-二取代的 1,2,3-三唑可以从官能化的芳基和烷基炔烃和溴化物中获得，产率和区域选择性适中至极好。该过程将能够合成功能化的 1,5-二取代 1,2,3-三唑文库，特别有助于多种应用，如药物化学和化学生物学目的。
• Abu-Orabi, Sultan T.; Atfah, M. Adnan; Jibril, Ibrahim, Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 1461 - 1468
  作者：Abu-Orabi, Sultan T.、Atfah, M. Adnan、Jibril, Ibrahim、Mari'i, Fakhri M.、Ali, Amer Al-Sheikh

  DOI：——

  日期：——
• A tunable route to oxidative and eliminative [3+2] cycloadditions of organic azides with nitroolefins: CuO nanoparticles catalyzed synthesis of 1,2,3-triazoles under solvent-free condition
  作者：D. Gangaprasad、J. Paul Raj、T. Kiranmye、R. Sasikala、K. Karthikeyan、S. Kutti Rani、J. Elangovan

  DOI：10.1016/j.tetlet.2016.06.004

  日期：2016.7

  A regioselective and tunable synthesis of 1,5-disubstituted 1,2,3-triazloles from oxidative and eliminative [3+2] cycloadditions of nitroolefins and organic azides under solvent-free condition in the presence and absence of commercially available CuO nanoparticle catalyst is described. In the presence of the catalyst under solvent-free condition, nitro group is retained in the product while it gets eliminated in the absence of the catalyst. (C) 2016 Elsevier Ltd. All rights reserved.
• ABU-ORABI, SULTAN T.;ATFAH, M. ADNAN;JIBRIL, IBRAHIM;MARII, FAKHRI M.;ALI+, J. HETEROCYCL. CHEM., 26,(1989) N, C. 1461-1468
  作者：ABU-ORABI, SULTAN T.、ATFAH, M. ADNAN、JIBRIL, IBRAHIM、MARII, FAKHRI M.、ALI+

  DOI：——

  日期：——