1-(benzo[d][1,3]dioxol-5-yl)-4-phenyl-1H-1,2,3-triazole | 1313994-65-8

• 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-(benzo[d][1,3]dioxol-5-yl)-4-phenyl-1H-1,2,3-triazole
• 英文别名: 1-(1,3-Benzodioxol-5-yl)-4-phenyltriazole；1-(1,3-benzodioxol-5-yl)-4-phenyltriazole
• CAS: 1313994-65-8
• 化学式: C₁₅H₁₁N₃O₂
• 分子量: 265.271
• InChiKey: IHPOVRUDEQLUNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  49.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯乙酮 在 过氧化苯甲酸叔丁酯 、 碘 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 12.0h， 生成 1-(benzo[d][1,3]dioxol-5-yl)-4-phenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  I₂/TBPB Mediated Oxidative Reaction of N-Tosylhydrazones with Anilines: Practical Construction of 1,4-Disubstituted 1,2,3-Triazoles under Metal-Free and Azide-Free Conditions

  摘要：

  An efficient I-2 (20 mol %)/TBPB mediated oxidative formal [4 + 1] cycloaddition of N-tosylhydrazones with anilines via C-N/N-N bond formation and S-N cleavage has been developed. This protocol represents a simple, general, and efficient approach for the construction of 1,2,3-triazoles under metal-free and azide-free conditions by utilizing a catalytic amount of I-2.

  DOI：

  10.1021/ol502431b

文献信息

• Magnetically Recoverable CuFe₂O₄Nanoparticles: Catalyzed Synthesis of Aryl Azides and 1,4-Diaryl-1,2,3-triazoles from Boronic Acids in Water
  作者：A. Suresh Kumar、M. Amarnath Reddy、M. Knorn、O. Reiser、B. Sreedhar

  DOI：10.1002/ejoc.201300343

  日期：2013.7

  Magnetically recoverable and reusable CuFe2O4 nanoparticles are shown to be highly efficient catalysts for the one-pot synthesis of biologically important 1,4-diaryl-1,2,3-triazoles starting from boronic acids, sodium azide, and acetylenes. The use of aqueous reaction medium at room temperature, the low cost and facile recovery of the catalyst by application of an external magnetic field, and consistently

  磁性可回收和可重复使用的 CuFe2O4 纳米颗粒被证明是一种高效的催化剂，用于从硼酸、叠氮化钠和乙炔开始一锅法合成生物学上重要的 1,4-二芳基-1,2,3-三唑。在室温下使用水性反应介质、通过施加外部磁场实现催化剂的低成本和容易回收，以及至少连续三个循环的持续高催化效率使该协议在操作上具有吸引力。
• Effect of temperature on triazole and bistriazole formation through copper-catalyzed alkyne–azide cycloaddition
  作者：Jaime González、Víctor M. Pérez、David O. Jiménez、Germán Lopez-Valdez、David Corona、Erick Cuevas-Yañez

  DOI：10.1016/j.tetlet.2011.05.002

  日期：2011.7

  Temperature is an important factor in the copper catalyzed alkyne azide cycloaddition under oxidative conditions. 1,2,3-Triazoles were obtained in high yields when several alkynes and azides were reacted at methanol reflux using catalytic amounts of both copper iodide and sodium hydroxide. On the other hand, bistriazoles were major products when reactions were performed at -35 degrees C using excess sodium hydroxide. (C) 2011 Elsevier Ltd. All rights reserved.
• I₂/TBPB Mediated Oxidative Reaction of <i>N</i>-Tosylhydrazones with Anilines: Practical Construction of 1,4-Disubstituted 1,2,3-Triazoles under Metal-Free and Azide-Free Conditions
  作者：Zhong-Jian Cai、Xin-Mou Lu、You Zi、Chao Yang、Ling-Jie Shen、Jian Li、Shun-Yi Wang、Shun-Jun Ji

  DOI：10.1021/ol502431b

  日期：2014.10.3

  An efficient I-2 (20 mol %)/TBPB mediated oxidative formal [4 + 1] cycloaddition of N-tosylhydrazones with anilines via C-N/N-N bond formation and S-N cleavage has been developed. This protocol represents a simple, general, and efficient approach for the construction of 1,2,3-triazoles under metal-free and azide-free conditions by utilizing a catalytic amount of I-2.