N-methoxyethyl-N-methylimidazolium bis(trifluoromethanesulfonyl)amide | 178631-01-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-methoxyethyl-N-methylimidazolium bis(trifluoromethanesulfonyl)amide
• 英文别名: 1-(1-methoxyethyl)-3-methylimidazoliumbis(trifluoromethylsulfonyl)amide；1-methoxyethyl-3-methylimidazolium bis(fluorosulfonyl)imide；1-(2-methoxyethyl)-3-methylimidazolium bis(trifluoromethylsulfonyl)imide；{[(COC₂)mim]N(SO₂CF₃)₂}；1-methyl-3-(2-methoxyethyl)imidazolium bistriflicimide；1-methyl-3-methoxyethylimidazolium bistriflicimide；[(C1OC2)C1im][NTf2]；[Moemim][Tf2N]；NSC747123；1-Methoxyethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide；bis(trifluoromethylsulfonyl)azanide;1-(2-methoxyethyl)-3-methylimidazol-3-ium
• CAS: 178631-01-1
• 化学式: C₂F₆NO₄S₂*C₇H₁₃N₂O
• 分子量: 421.342
• InChiKey: QTWXKUATXFJTAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.02
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  palladium dichloride 、 N-methoxyethyl-N-methylimidazolium bis(trifluoromethanesulfonyl)amide 以 乙腈 为溶剂， 以99%的产率得到[1-(1-methoxyethyl)-3-methylimidazolium]PdCl4
  参考文献：
  名称：

  Suzuki Coupling Reactions in Ether-Functionalized Ionic Liquids: The Importance of Weakly Interacting Cations

  摘要：

  Imidazolium- and pyridinium-based ionic liquids with ether/polyether substituents have been evaluated as solvents for palladiurn-catalyzed Suzuki C-C coupling reactions. In general, reactions proceed more efficiently in these solvents compared to other ionic liquids, which is believed to be due to better stabilization of the palladium catalyst, involving weak interactions with the ether groups. The position and the number of oxygen atoms in the ether side chain strongly influence the outcome of the coupling reactions in the imidazolium-based ionic liquids, whereas for the pyridinium-based liquids no influence is observed. Carbene derivatives, generated from the imidazolium-based ionic liquids, are believed to play a role by terminating the catalytic cycle, and representative species have been isolated and characterized from stoichiometric reactions.

  DOI：

  10.1021/om800355g
• 作为产物：
  描述：

  bis(trifluoromethane)sulfonimide lithium 、 1-(2-methoxyethyl)-3-methylimidazolium chloride 以 丙酮 为溶剂， 反应 24.0h， 以88.9%的产率得到N-methoxyethyl-N-methylimidazolium bis(trifluoromethanesulfonyl)amide
  参考文献：
  名称：

  Equimolar Carbon Dioxide Absorption by Ether Functionalized Imidazolium Ionic Liquids

  摘要：

  一系列基于咪唑鎓阳离子的离子液体$[C_3Omim]$[X]，其中烷基侧链上具有醚功能团，已经合成并通过多种技术如$^1H$、$^{13}C$核磁共振波谱、MS-ESI、FTIR光谱和元素分析确认了其结构。更具体地，通过改变相同阳离子下的阴离子进行了影响研究。在常压下（0-1.6 bar）和30°C及$50^{\circ}C$下评估了离子液体对$CO_2$的吸收能力。具有醚功能化的离子液体显示出显著高的$CO_2$吸收能力。一般而言，随着压力增加，离子液体的$CO_2$吸收能力增加，而随着温度升高则降低。获得的结果显示，吸收能力在$30^{\circ}C$下达到约0.9摩尔$CO_2$每摩尔离子液体。通过FTIR光谱和$^{13}C$核磁共振波谱研究了与$CO_2$相互作用的最可能机制，结果表明$CO_2$在醚功能化离子液体中的吸收是一个化学过程。$CO_2$吸收结果和详细研究指出1:1机制的主导性，其中$CO_2$与一个离子液体反应形成氨基甲酸。对于不同阴离子的离子液体，$CO_2$吸收能力遵循以下趋势：$BF_4$ < DCA < $PF_6$ < TfO < $Tf_2N$。此外，合成的离子液体具有选择性、热稳定性和长寿命操作，可以在$70^{\circ}C$或真空下回收并重复使用。

  DOI：

  10.5012/bkcs.2012.33.7.2325
• 作为试剂：
  描述：

  乙烷,三氯氟- 在 氧气 、 dioxide titanium 、 N-methoxyethyl-N-methylimidazolium bis(trifluoromethanesulfonyl)amide 作用下， 100.0 ℃ 、500.01 kPa 条件下， 生成 4-硝基甲苯 、 二(4-甲基苯基)二氮烯 、 (4-甲基苯基)-(4-甲基苯基)亚氨基氧化铵
  参考文献：
  名称：

  Ionic liquid effect: selective aniline oxidative coupling to azoxybenzene by TiO₂

  摘要：

  TiO2促进苯胺通过氧化催化偶联反应生成偶氮化合物。在离子液体中，高选择性地形成偶氮苯，而在甲苯中几乎专一性地生成偶氮苯。

  DOI：

  10.1039/c4cy01257g

文献信息

• The first Cu(i)-mediated nucleophilic trifluoromethylation reactions using (trifluoromethyl)trimethylsilane in ionic liquids
  作者：Jinwi Kim、Jean'ne M. Shreeve

  DOI：10.1039/b412480b

  日期：——

  The new ionic liquids (5a-8a) were used as reaction media for nucleophilic trifluoromethylation reactions of trifluoromethyl(trimethyl)silane with (1) aryl, allyl, benzyl, and alkyl halides in Cu(I)-mediated C-C bond formation reactions, and (2) carbonyl functionalities catalyzed with Ph3P or CsF. In addition, conversion of benzyl bromide as a model compound to benzyl fluoride was examined in using

  新的离子液体（5a-8a）用作三氟甲基（三甲基）硅烷与（1）芳基，烯丙基，苄基和烷基卤化物在Cu（I）介导的CC键形成反应中的亲核三氟甲基化反应的反应介质，以及（2）用Ph3P或CsF催化的羰基官能团。另外，使用6a CsF作为氟化试剂，检查了作为模型化合物的苄基溴向苄基氟的转化。基于吗啉鎓的离子液体（6a）是一种有效的溶剂体系，可与有机溶剂媲美，并且优于在这项工作中制备的其他新离子液体以及[bmim] + [PF6]-。N-甲基恶唑烷（1），N-甲基吗啉（2），N-甲基咪唑（3）或N-甲基三唑（4）与2-（2-乙氧基乙氧基）乙基溴（BrCH2CH2OCH2CH2OCH2CH3，）或2-溴乙基甲基醚（BrCH2CH2OCH3，10）在75或105摄氏度下得到N-（2-乙氧基乙氧基）乙基或N-甲氧基乙基取代的恶唑烷鎓，吗啉鎓，咪唑鎓和三唑鎓季铵盐（1a-4a，1b -4b）与LiN（SO2C
• Distinct influence of the anion and ether group on the polarity of ammonium and imidazolium ionic liquids
  作者：Shiguo Zhang、Zhengjian Chen、Xiujuan Qi、Youquan Deng

  DOI：10.1039/c2nj20965a

  日期：——

  The polarity of ionic liquids (ILs), usually denoted as ET(30) by the solvatochromic probe Reichardt’s dye, is one of the most fundamental properties that remarkably affect the solvation and chemical reaction in ILs. It was generally accepted that the ET(30) of ILs was dominated by the nature of the cation. However, in this work, it was found that the common ammonium-based ILs showed strongly anion-dependent ET(30). For example, the ET(30) value for [N1124][DCA] and [N1124][NTf2] is 49.0 and 59.0 kcal mol−1, respectively, while the corresponding imidazolium ILs bearing the same anions possess nearly identical ET(30), the ET(30) value for [BMIm][DCA] and [BMIm][NTf2] is 51.4 and 51.6 kcal mol−1, respectively. Moreover, introduction of an ether group was found to increase the ET(30) of imidazolium ILs while having no obvious effect on that of ammonium-based ILs. The Kamlet–Taft parameters and density functional theory (DFT) calculations indicated that the distinct result is related to different stabilization of the ground state of Reichardt's dye 30. In imidazolium ILs, the main interactions between ILs and zwitterionic dye involve both coulombic interaction (between the cation and the phenolate oxygen atom) and H-bonding interaction (between the acidic hydrogen on imidazolium ring and the phenolate oxygen atom). However, with the ammonium ILs lack of active hydrogen, the dye is only stabilized by the coulombic interaction between the cation and the phenolate oxygen atom. Interestingly, in both imidazolium and ammonium-based ILs, the spiropyran–merocyanine equilibrium exhibit obvious anion-dependent photochromism, solvatochromism, and thermal relaxation.

  离子液体（ILs）的极性通常用溶剂色谱探针Reichardt染料的ET(30)表示，这是影响ILs中溶剂化和化学反应的重要基本属性之一。一般认为，ILs的ET(30)主要由阳离子的性质主导。然而，在这项研究中发现，常见的基于铵的ILs表现出明显依赖阴离子的ET(30)。例如，[N1124][DCA]和[N1124][NTf2]的ET(30)值分别为49.0和59.0 kcal mol−1，而对应的带有相同阴离子的咪唑鎓ILs的ET(30)几乎相同，[BMIm][DCA]和[BMIm][NTf2]的ET(30)值分别为51.4和51.6 kcal mol−1。此外，引入醚基团被发现可以提高咪唑鎓ILs的ET(30)，而对铵基ILs则没有明显影响。Kamlet–Taft参数和密度泛函理论（DFT）计算表明，结果的差异与Reichardt染料30基态的不同稳定性有关。在咪唑鎓ILs中，ILs与具有二氨离子的染料之间的主要相互作用包括库仑相互作用（阳离子与酚氧原子之间）和氢键相互作用（咪唑环上的酸性氢与酚氧原子之间）。然而，由于铵ILs缺乏活性氢，染料只能通过阳离子与酚氧原子之间的库仑相互作用来稳定。有趣的是，在咪唑鎓和铵基ILs中，spiropyran-merocyanine平衡表现出明显的阴离子依赖性光致变色、溶剂色谱效应和热弛豫现象。
• 一种离子液体增塑剂及制备方法和应用
  申请人：郑州中科新兴产业技术研究院

  公开号：CN114436968A

  公开（公告）日：2022-05-06

  本发明提出了一种离子液体增塑剂及制备方法和应用，用以解决增塑剂容易从产品中迁移的技术问题，所述离子液体由阴阳离子组成，该离子液体增塑剂的制备方法包括如下步骤：将咪唑或三唑前体、卤化物RX和溶剂A加入反应容器中，搅拌反应，反应结束后分液，洗涤、萃取得到有机相，去除溶剂获得离子液体Ⅰ；将步骤（1）得到的离子液体Ⅰ、无机盐和溶剂B加入到反应容器中进行反应，反应后得到沉淀，洗涤、去除溶剂，干燥得到离子液体增塑剂；本发明得到的离子液体作为聚氨酯和环氧树脂的增塑剂，固化后的产品具有较好的耐热性和耐迁移性能，能在保持拉伸强度小幅度增长的前提下，明显增加产品的断裂伸长率，增加产品的韧性、降低脆性。
• Arylation of Sensitive 1-(Pyrrolidin-1-yl)-diazen-1-ium-diolate in Ionic Liquids
  作者：Carlos A. Velázquez、Geoffrey M. Lynn、Vineet Kumar、Larry K. Keefer、Sanjay V. Malhotra

  DOI：10.1080/00397910903074079

  日期：2010.4.12

  The purpose of this research was to investigate the stability and reactivity of 1-(pyrrolidin-1-yl)diazen-1-ium-1,2-diolate (PYRRO/NO) in dimethylformamide (DMF, as the reference solvent) and compare them to those obtained using different ionic liquids. The results of our experiments showed that PYRRO/NO is more stable (based on reactivity) in ionic liquid [EMIM][Ms] (with reaction yields up to 52%) than in DMF, that substitution products can be separated directly and quantitatively from the ionic liquid using a single flash-column separation, and that the ionic liquids can also be recovered and reused in a second iteration of the same reaction to achieve similar yields.
• Expanding the polarity range of ionic liquids
  作者：Sergei V. Dzyuba、Richard A. Bartsch

  DOI：10.1016/s0040-4039(02)00858-4

  日期：2002.5

  The polarity of several [X-mim]NTf2 ionic liquids. as measured with solvatochromic dyes. Reichardt's dye and Nile Red, may be varied over a wide range by attachment of functional group-containing substituents (X) to the imidazolium cation. (C) 2002 Elsevier Science Ltd. All rights reserved.