3-methyl-1-(3-sulfopropyl)-imidazolium trifluoro acetate | 1247026-23-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-methyl-1-(3-sulfopropyl)-imidazolium trifluoro acetate
• 英文别名: 1-methyl-3-(3-sulfopropyl)imidazolium trifluoroacetate；1-Propylsulfonic-3-methylimidazolium trifluoroacetate；3-(3-methylimidazol-3-ium-1-yl)propane-1-sulfonic acid;2,2,2-trifluoroacetate
• CAS: 1247026-23-8
• 化学式: C₂F₃O₂*C₇H₁₃N₂O₃S
• 分子量: 318.274
• InChiKey: AYTWYJBDNDOBCT-UHFFFAOYSA-N

反应信息

• 作为产物：
  描述：

  3-(3-methyl-1H-imidazol-3-ium-1-yl)propane-1-sulfonate 、 三氟乙酸 以 水 为溶剂， 反应 5.0h， 生成 3-methyl-1-(3-sulfopropyl)-imidazolium trifluoro acetate
  参考文献：
  名称：

  布朗斯台德酸离子液体催化富电子芳烃与醛的烷基化弗里德尔-克拉夫茨

  摘要：

  三芳基甲烷（TRAM）和二芳基烷烃（DIAA）是有价值的中间体，在许多领域都有广泛的应用。通常从活化的芳基醛的酸催化的双芳基化获得TRAM。然而，该合成带来许多问题，例如苛​​刻的反应条件以及过量溶剂和/或有毒金属废物的处置。在这项研究中，设计并合成了一些功能化的离子液体，包括布朗斯台德酸性离子液体（BAIL）和传统离子液体。BAIL催化的Friedel-Crafts（FC）烷基化首次在该特定反应中应用。并且BAIL显示出充当催化剂和溶剂的双功能性质。研究表明，BAILs可在温和的反应条件下成功地用芳族或脂族醛催化富电子芳烃的F-C烷基化。此外，含有三氟甲基磺酸根阴离子的BAIL具有比其他BAIL和传统离子液体更高的活性。[HSO3- pmim] [OTf]在40°C下存在20 mol％的BAIL时得到最高的收率，从而得到相应的TRAMs衍生物。经过五个周期后，产率保持在93–97％左右。

  DOI：

  10.1016/j.apcata.2014.05.014
• 作为试剂：
  描述：

  吡咯 、 3-戊酮 在 3-methyl-1-(3-sulfopropyl)-imidazolium trifluoro acetate 、 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以80%的产率得到meso-octaethylporphyrinogen
  参考文献：
  名称：

  Efficient ZnCl2 assisted synthesis of calix[4]pyrroles catalysed by Brønsted acidic ionic liquids

  摘要：

  DOI：

  10.1016/j.tetlet.2014.10.020

文献信息

• Brønsted acidic ionic liquids for cellulose hydrolysis in an aqueous medium: structural effects on acidity and glucose yield
  作者：Shiori Suzuki、Yuko Takeoka、Masahiro Rikukawa、Masahiro Yoshizawa-Fujita

  DOI：10.1039/c8ra01950a

  日期：——

  The conversion of cellulose into valuable chemicals has attracted much attention, due to the concern about depletion of fossil fuels. The hydrolysis of cellulose is a key step in this conversion, for which Brønsted acidic ionic liquids (BAILs) have been considered promising acid catalysts. In this study, using BAILs with various structures, their acidic catalytic activity for cellulose hydrolysis assisted

  由于担心化石燃料的枯竭，将纤维素转化为有价值的化学品引起了很多关注。纤维素的水解是这种转化的关键步骤，为此，布朗斯台德酸性离子液体 (BAIL) 被认为是有前景的酸催化剂。在这项研究中，使用具有不同结构的BAILs，使用Hammett酸度函数（H 0）和理论计算评估了它们对微波辐照辅助纤维素水解的酸性催化活性。当BAIL水溶液的H 0值低于1.5时，葡萄糖产率超过10% 。在 1-(1-octyl-3-imidazolio)propane-3-sulfonate (Oimps)/硫酸 (H 2 SO 4 ) 中的最高葡萄糖产率约为 36%) 水溶液。咪唑鎓阳离子上的长烷基侧链增加了 BAIL 的疏水性，从而提高了葡萄糖产量。
• Mechanistic studies on counter-ionic effects of camphorsulfonate-based ionic liquids on kinetics, thermodynamics and stereoselectivity of β-amino carbonyl compounds
  作者：Sabahat Sardar、Erum Jabeen、Cecilia Devi Wilfred、Ahmad Sazali Hamzah、Jean-Marc Leveque

  DOI：10.1016/j.molliq.2020.114370

  日期：2020.12

  Catalysis is important in various applications of organic chemistry and its output product control for stereoselective compounds is outrageous. Establishment of experimental facts of stereoselective compounds from catalysis and their validation using theoretical evidences is the key to understand various mechanisms of optically active compounds. A family of new ionic liquids (ILs) with various imidazolium

  催化作用在有机化学的各种应用中很重要，其对立体选择化合物的输出产物控制非常苛刻。通过催化作用建立立体选择性化合物的实验事实，并使用理论证据对其进行验证，是理解旋光化合物各种机理的关键。已经合成了具有各种咪唑鎓阳离子和樟脑磺酸根阴离子作为对环境有益的液态盐的一系列新型离子液体（IL），并将其用于催化β-氨基羰基化合物。使用IL作为均相催化剂形成产物，具有优异的产物收率和非对映选择性。根据反应动力学和产物收率，研究了抗衡离子，IL的哈米特酸度和粘度以及溶剂和温度的影响。密度泛函理论（DFT）用于研究反应机理的热力学研究。DFT计算预测，催化机理涉及IL的两个抗衡离子。此外，有证据表明，合成途径需要较低的活化能，而反途径产生热力学稳定的产物。这项研究探索了使用IL作为潜在的均相催化剂生产立体选择性物质的新途径。
• Hydration of alkynes using Brönsted acidic ionic liquids in the absence of Nobel metal catalyst/H2SO4
  作者：Rajkumar Kore、T.J. Dhilip Kumar、Rajendra Srivastava

  DOI：10.1016/j.molcata.2012.04.010

  日期：2012.8

  In this study, a variety of imidazole based sulfonic acid group functionalized Bronsted acidic ionic liquids (BAILs) were synthesized. BAILs have been successfully developed as task specific ionic liquids for hydration of alkynes under mild conditions to give high yields of ketones as a selective product. Acidity of BAILs was determined using volumetric titration and UV-visible spectroscopic methods. The Hammett acidity order and acid value of BAILS correlate well with the activity order observed for most of the BAILs in the hydration reaction of phenylacetylene. Theoretical studies demonstrate that hydrogen bonding plays a key role in tuning the acidity of BAILs. Density function theory calculations are also able to explain the difference in activity observed in these BAILS. The activity of ionic liquids was theoretically studied by computing the activation energy for the hydration reaction. Recycling experiments suggest that these novel BAILS can be reused without significant loss in activity. BAILS are simple and easy to prepare and exhibit excellent activity toward the hydration of a variety of alkynes to ketones. Moreover, the reaction involving BAILS does not involve heavy metal catalysts or H2SO4. Novel BAILs offer several attractive features such as sustainable synthetic route, low cost, moisture stability, high yields, and recyclability. (c) 2012 Elsevier B.V. All rights reserved.
• Wu, Xiaodan; Han, Xiaoxiang; Zhou, Lingxiao, Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 2012, vol. 51, # 6, p. 791 - 799
  作者：Wu, Xiaodan、Han, Xiaoxiang、Zhou, Lingxiao、Li, Ang

  DOI：——

  日期：——
• A simple, eco-friendly, and recyclable bi-functional acidic ionic liquid catalysts for Beckmann rearrangement
  作者：Rajkumar Kore、Rajendra Srivastava

  DOI：10.1016/j.molcata.2013.04.021

  日期：2013.9

  A library of ionic liquids was prepared by varying the cations and anions. Bi-functional acidic ionic liquids were prepared by the direct combination of ionic liquids and ZnCl2. Ionic liquids were investigated in the Beckmann rearrangements. A simple, eco-friendly, and recyclable bi-functional acidic ionic liquid based protocol for Beckmann rearrangement is developed, which is based on the fine tuning of the Bronsted and the Lewis acidity of ionic liquids. (C) 2013 Elsevier B.V. All rights reserved.