1-ethyl-3-methylimidazolium (S)-2-pyrrolidinecarboxylic acid salt

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-ethyl-3-methylimidazolium (S)-2-pyrrolidinecarboxylic acid salt
• 英文别名: 1-ethyl-3-methylimidazol-3-ium (S)-pyrrolidine-2-carboxylate；1-ethyl-3-methylimidazolium L-proline salt；1-ethyl-3-methylimidazol-3-ium L-prolinate；[C₂mim][L-Pro]；[C2mim][Pro]；[EMIM][Pro]；1-Ethyl-3-methyl-1H-imidazol-3-ium L-prolinate；1-ethyl-3-methylimidazol-3-ium;(2S)-pyrrolidine-2-carboxylate
• 化学式: C₅H₈NO₂*C₆H₁₁N₂
• 分子量: 225.291
• InChiKey: MDQLULFJEJPGQQ-VWMHFEHESA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.18
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  61
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-甲氧基苯基)甲亚胺 、 1-ethyl-3-methylimidazolium (S)-2-pyrrolidinecarboxylic acid salt 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 (1S,4S)-2-(4-methoxyphenyl)-2-azabicyclo[2.2.2]octan-5-one 、 (1R,4R)-2-(4-methoxyphenyl)-2-azabicyclo[2.2.2]octan-5-one 、 6-(4-methoxyphenyl)-6-aza-bicyclo[2.2.2]octan-3-one
  参考文献：
  名称：

  手性2-吡咯烷羧酸离子液体催化的直接不对称氮杂Diels-Alder反应

  摘要：

  已开发出[EMIm] [Pro]作为单锅直接不对称氮杂Diels-Alder反应的有效催化剂的用途。已经研究了一组环状的α，β-不饱和酮，产率高达93％，dr大于99/1，ee大于99％。此外，该催化体系可以循环使用六次，而催化活性没有任何重大损失。

  DOI：

  10.1016/j.catcom.2009.12.021
• 作为产物：
  描述：

  1-乙基-3-甲基溴化咪唑 在 amberlite IRA 400 OH 作用下， 以 水 为溶剂， 反应 12.0h， 生成 1-ethyl-3-methylimidazolium (S)-2-pyrrolidinecarboxylic acid salt
  参考文献：
  名称：

  Ionic amino acids: Application as organocatalysts in the aza-Michael reaction

  摘要：

  The ethyl methyl imidazolium salts of amino acids, [emiml[AA], have been used as catalysts in the aza-Michael reaction. Furthermore, when chiral amino acids were used, a stereoselective reaction was achieved. The mechanism of the transformation was verified by the detection of a key intermediate by electrospray ionization mass spectroscopy (ESI-MS). (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2012.11.012
• 作为试剂：
  描述：

  对硝基苯甲醛 、 环己酮 在 1-ethyl-3-methylimidazolium (S)-2-pyrrolidinecarboxylic acid salt 作用下， 反应 6.5h， 生成 (2S,1'R)-2-[1'-hydroxy-1'-(4-nitrophenyl)methyl]cyclohexan-1-one 、 2-[hydroxy(4-nitrophenyl)methyl]cyclohexan-1-one
  参考文献：
  名称：

  手性阴离子改性离子液体催化绿色高效的不对称羟醛反应

  摘要：

  源自 L-脯氨酸的手性阴离子改性离子液体被证明是一种绿色且高效的不对称有机催化剂，可用于室温下 [BMIm]BF 4 中的直接不对称醛醇反应。相应的醛醇产物具有中等至良好的分离产率（高达 99%）、抗非对映选择性（高达 97:3）和出色的对映选择性（高达 99% ee）。催化剂和溶剂 ([BMIm]BF 4 ) 最多可循环使用四次，但活性略有降低。

  DOI：

  10.1002/ejoc.201000304

文献信息

• Amino Acid Ionic Liquids as Chiral Ligands in Ligand-Exchange Chiral Separations
  作者：Qian Liu、Kangkang Wu、Fei Tang、Lihua Yao、Fei Yang、Zhou Nie、Shouzhuo Yao

  DOI：10.1002/chem.200900982

  日期：2009.9.28

  Recently, amino acid ionic liquids (AAILs) have attracted much research interest. In this paper, we present the first application of AAILs in chiral separation based on the chiral ligand exchange principle. By using 1‐alkyl‐3‐methylimidazolium L‐proline (L‐Pro) as a chiral ligand coordinated with copper(II), four pairs of underivatized amino acid enantiomers—dl‐phenylalanine (dl‐Phe), dl‐histidine

  最近，氨基酸离子液体（AAIL）引起了很多研究兴趣。在本文中，我们提出了基于手性配体交换原理的AILs在手性分离中的首次应用。通过使用1-烷基-3-甲基咪唑大号-脯氨酸（大号-Pro）与铜（II）配位的手性配体，4双未衍生化的氨基酸的enantiomers- DL -苯丙氨酸（DL -Phe），DL组氨酸（DL -His），dl-色氨酸（dl- Trp）和dl-酪氨酸（dl-Tyr）-已成功通过HPLC和毛细管电泳（CE）这两种主要的手性分离技术成功分离，其对映体选择性高于常规使用的氨基酸配体（HPLC的分离度（R s）= 3.26–10.81；R s = 1.34–4.27力量）。有趣的是，增加AAIL阳离子的烷基链长度显着提高了对映选择性。可以推断，烷基甲基咪唑鎓阳离子和L- Pro在固定相的表面或毛细管的内表面形成离子对。因此，带有L ‐Pro的三元铜络合物附着在载体表面上，从而引起
• 2-Pyrrolidinecarboxylic Acid Ionic Liquid as a Highly Efficient Organocatalyst for the Asymmetric One-Pot Mannich Reaction
  作者：Xin Zheng、Yun-Bo Qian、Yongmei Wang

  DOI：10.1002/ejoc.200901088

  日期：2010.1

  A novel one-pot three-component asymmetric Mannich reaction using [EMIm][Pro] (1) as a catalyst has been developed. By employing this new reaction system, a variety of optically active β-amino carbonyl compounds were synthesized in up to 99 % yield with up to >99 dr and >99 % ee. The reaction conditions have been optimized and the mechanism for the asymmetric induction is discussed.

  已经开发了一种使用 [EMIm][Pro] (1) 作为催化剂的新型一锅三组分不对称曼尼希反应。通过采用这种新的反应系统，合成了多种光学活性 β-氨基羰基化合物，产率高达 99%，高达 >99 dr 和 >99% ee。优化了反应条件并讨论了不对称诱导的机制。
• Density, Viscosity, and Refractive Index of Ionic Liquid Mixtures Containing Cyano and Amino Acid-Based Anions
  作者：Andreia S. L. Gouveia、Liliana C. Tomé、Isabel M. Marrucho

  DOI：10.1021/acs.jced.5b00242

  日期：2016.1.14

  In this work, mixtures of five ionic liquids (ILs) based on a common cation, 1-ethyl-3-methylimidazolium ([C(2)mim](+)), and amino acid anions, namely glycinate ([Gly](-)), l-alaninate ([l-Ala](-)), taurinate ([Tau](-)), L-serinate ([L-Ser](-)), and L-prolinate ([L-Pro](-)) with 1-ethyl-3-methylimidazolium tricyanomethane, [C(2)mim][C(CN)(3)], were prepared. The thermophysical properties, namely density, viscosity, and refractive index, of the neat ILs and their mixtures were measured in the temperature range of T = (293.15 up to 353.15) K. The thermal expansion coefficients were calculated for the neat ILs and were considered to be independent of temperature in the working temperature range. Overall, experimental density, viscosity, and refractive index data of the neat AAILs were in a good agreement with those reported in literature. A dramatic decrease in the viscosity was observed for the IL mixtures as the [C(2)mim][C(CN)(3)] content increased. The obtained results indicate that mixing [C(2)mim][C(CN)(3)] with amino acid-based ILs is a potential mean to further increase flexibility and the fine-tune capacity of the physical and chemical properties of amino acid-based ILs.
• Synthesis and Thermophysical Properties of Low Viscosity Amino Acid-Based Ionic Liquids
  作者：Nawshad Muhammad、Zakaria B. Man、Mohamad Azmi Bustam、M. I. Abdul Mutalib、Cecilia D. Wilfred、Sikander Rafiq

  DOI：10.1021/je2002368

  日期：2011.7.14

  Nowadays ionic liquids are in the focus of scientific interest owing to their attractive properties. In this context, a series of amino acid-based ionic liquids (AAILs; EmimGly, EmimAla, EmimPro, and EmimSer) were synthesized and characterized by NMR and elemental analysis. Thermophysical properties such as density and viscosity were measured in the temperature range of T = (293.15 to 353.15) K and refractive index in the temperature range of T = (293.15 to 333.15) K. The thermal expansion coefficient values were calculated from the acquired experimental density values for T = (293.15 to 363.15) K. A thermogravimetric analyzer (TGA) was used to investigate the thermal degradation behavior of synthesized ionic liquids.
• Ionic amino acids: Application as organocatalysts in the aza-Michael reaction
  作者：Naoki Morimoto、Yasuo Takeuchi、Yuta Nishina

  DOI：10.1016/j.molcata.2012.11.012

  日期：2013.3

  The ethyl methyl imidazolium salts of amino acids, [emiml[AA], have been used as catalysts in the aza-Michael reaction. Furthermore, when chiral amino acids were used, a stereoselective reaction was achieved. The mechanism of the transformation was verified by the detection of a key intermediate by electrospray ionization mass spectroscopy (ESI-MS). (C) 2012 Elsevier B.V. All rights reserved.