3-[4-(hydroxymethyl)-1,2,3-triazol-1-yl]propan-1-ol | 887908-60-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-[4-(hydroxymethyl)-1,2,3-triazol-1-yl]propan-1-ol
• 英文别名: 3-[4-(hydroxymethyl)-1H-1,2,3-triazole-1-yl]propan-1-ol；3-[4-(hydroxymethyl)triazol-1-yl]propan-1-ol；4-hydroxymethyl-1-(3-hydroxypropyl)-1,2,3-triazole；3-[4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl]propan-1-ol
• CAS: 887908-60-3
• 化学式: C₆H₁₁N₃O₂
• 分子量: 157.172
• InChiKey: XROZELKTFLMHSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  71.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[4-(hydroxymethyl)-1,2,3-triazol-1-yl]propan-1-ol 、 碘甲烷 以 乙腈 为溶剂， 反应 24.0h， 以83%的产率得到4-(hydroxymethyl)-1-(3-hydroxypropyl)-3-methyl-1H-1,2,3-triazole-3-ium iodide
  参考文献：
  名称：

  Synthesis of 1,2,3-Triazolium-Based Ionic Liquid and Preliminary Pretreatment to Enhance Hydrolysis of Sugarcane Bagasse

  摘要：

  Ionic liquids (ILs) are salts which are liquid at low temperatures, typically with melting points under 100 degrees C. In recent years, the properties of many ILs have been extensively studied and have been considered as green solvents capable of replacing traditional organic solvents. Herein, ILs derived from triazole have been synthesized, thus solubility in different solvents increases with the dielectric constant of the considered solvents. Three novel 1,2,3-triazolium-based were used for the pretreatment of sugarcane bagasse. The effect of this pretreatment on lignocellulosic biomass was analyzed by scanning electron microscopy, showing an increase in the exposure surface of the bagasse samples as structural changes in the fiber.

  DOI：

  10.5935/0103-5053.20140198
• 作为产物：
  描述：

  3-叠氮基丙醇 、 2-丙炔-1-醇 在 Amberlyst A-21*CuI 作用下， 以 乙腈 为溶剂， 以70%的产率得到3-[4-(hydroxymethyl)-1,2,3-triazol-1-yl]propan-1-ol
  参考文献：
  名称：

  在自动化方案中用于[3 + 2] Huisgen环加成的可重复使用的聚合物负载型催化剂。

  摘要：

  [反应：见正文]由碘化亚铜（I）和Amberlyst A-21制备了用于聚合物在惠斯根[3 + 2]环上进行叠氮化物与炔烃环加成反应的催化剂。然后将该催化剂用于自动合成1,4-二取代的1,2,3-三唑，以高收率获得这些产物。该催化剂显示出良好的活性，稳定性和再循环能力。

  DOI：

  10.1021/ol060283l

文献信息

• “Flash” Solvent-free Synthesis of Triazoles Using a Supported Catalyst
  作者：Ibtissem Jlalia、Faouzi Meganem、Jean Herscovici、Christian Girard

  DOI：10.3390/molecules14010528

  日期：——

  A solvent-free synthesis of 1,4-disubstituted-1,2,3-triazoles using neat azides and alkynes and a copper(I) polymer supported catalyst (Amberlyst) A21*CuI) is presented herein. As it provides the products in high yields and purities within minutes, this method thus being characterized as a "flash" synthesis, and was exemplified through the synthesis of a 24-compound library on a small scale.

  本文介绍了使用纯叠氮化物和炔烃以及铜 (I) 聚合物负载催化剂 (Amberlyst) A21*CuI) 的无溶剂合成 1,4-二取代-1,2,3-三唑。由于它在几分钟内以高产率和纯度提供产品，因此该方法被称为“快速”合成，并通过小规模合成 24 化合物库来举例说明。
• Highly active, thermo-responsive polymeric catalytic system for reuse in aqueous and organic CuAAC reactions
  作者：Sofie Wallyn、Mieke Lammens、Rachel K. O'reilly、Filip Du Prez

  DOI：10.1002/pola.24723

  日期：2011.7.1

  point temperature of the catalyst system. The polymer catalyst system could be regenerated via extraction by making use of its lower critical solution temperature (LCST)‐behavior, and then reused for further copper(I) catalyzed azide‐alkyne cycloaddition (CuAAC) reactions. While a reduced catalytic activity is observed as a result of copper leaching in aqueous click reactions, the recycling experiments

  将三（苄基三唑基甲基）胺（TBTA）固定在苯乙烯单体上，然后与N-异丙基丙烯酰胺（NIPAM）共聚，以提供催化活性的热响应共聚物，用于铜辅助点击化学。P（TBTA- co- NIPAM）共聚物的合成方法是每条链掺入2至10个配体单元，分子量可调节（28-148 kDa）。组合11 H NMR光谱法，尺寸排阻色谱法（SEC）和元素分析法（EA）证实了这些聚合物的合成受控，并可以量化TBTA-官能化单体的掺入程度。装载溴化铜（I）后，将此均相催化剂体系添加到水/乙酸乙酯两相体系中。使用这种双相系统，水点击反应可以在室温下进行，而有机点击化学可以在催化剂体系的浊点温度以上进行。可以通过利用较低的临界溶液温度（LCST）行为通过萃取来再生聚合物催化剂体系，然后再用于进一步的铜（I）催化的叠氮化物-炔烃环加成（CuAAC）反应。尽管由于水点击反应中铜的浸出而导致催化活性降低，但有机相中的再循环实验表
• An ‘in-water’ halogen-ion compatible “click” catalyst for cucurbituril guest ligation
  作者：Hao Chen、Shengzhen Hou、Yebang Tan

  DOI：10.1080/10610278.2016.1142089

  日期：2016.10.2

  Most of the cucurbituril (CB) guests are water soluble cationic compounds with halogen counter-ions. Here, an in-water' halogen-ion compatible copper catalysed azide-alkyne cycloaddition (CuAAC) catalyst, tris[1-(3-hyroxypropyl)-1H-1,2,3-triazol-4-yl]methanolCuCl (THPTMCuCl), was designed for CB guest ligation. The catalyst demonstrates not only high catalytic activity, but also compatibility to cationic substrates, halogen-ions and free amino groups. A CB[8]-based star pseudo[5]rotaxane and a CB[7]-based main-chain alternative polypseudorotaxane were constructed using THPTMCuCl, which further verified its applicability for the construction of CB-based supramolecular architectures.
• Rapid aqueous ‘click chemistry’ using Cu(I)-loaded dendrimers as macromolecular catalysts
  作者：Eli Moore、Steven J. McInnes、Andrew Vogt、Nicolas H. Voelcker

  DOI：10.1016/j.tetlet.2011.02.090

  日期：2011.5

  Here, we investigate the catalytic activity of various copper (Cu)-loaded poly(amido amine) (PAMAM) dendrimers towards the Cu(I)-catalysed azide-alkyne cycloaddition (CuAAC). Reactivity is tested on a model reaction between azido propanol and propargyl alcohol in aqueous solution. We observe significantly faster conversion using PAMAM dendrimers as macromolecular Cu(I) ligands compared to traditional small molecular ligand systems, and demonstrate that the macromolecular catalyst can be removed by ultrafiltration. (C) 2011 Elsevier Ltd. All rights reserved.