1-ethyl-3-methylimidazolium-2-carboxylate | 1017847-51-6

• 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-ethyl-3-methylimidazolium-2-carboxylate
• 英文别名: 1-Ethyl-3-methylimidazol-3-ium-2-carboxylate
• CAS: 1017847-51-6
• 化学式: C₇H₁₀N₂O₂
• 分子量: 154.169
• InChiKey: AACQANZPAVCEIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  48.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-ethyl-3-methylimidazolium-2-carboxylate 在 水 作用下， 以 氘代甲醇 为溶剂， 生成 1-乙基-3-甲基咪唑鎓碳酸氢盐
  参考文献：
  名称：

  A Solventless Route to 1-Ethyl-3-methylimidazolium Fluoride Hydrofluoride, [C₂mim][F]·xHF

  摘要：

  The ionic liquid 1-ethyl-3-methylimidazolium fluoride hydrofluoride, [C(2)mim] [F].xHF, has been synthesized through a new, solventless route that excludes halogen metathesis. The byproducts are salts, alcohols, and carbon dioxide.

  DOI：

  10.1021/jo800578b
• 作为产物：
  描述：

  1-乙基-3-甲基溴化咪唑 在 potassium tert-butylate 、 potassium hydride 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 生成 1-ethyl-3-methylimidazolium-2-carboxylate
  参考文献：
  名称：

  N-杂环烯烃-二氧化碳和-二氧化硫加合物：结构和有趣的反应模式

  摘要：

  根据溶液中甲醇的含量，已发现N杂环卡宾（NHC）和N杂环烯烃（NHO）的CO 2加合物与相应的碳酸甲酯盐[EMIm] [OCO 2 ]完全可逆平衡。Me]和[EMMIm] [OCO 2 Me]。已经研究了代表性的1-乙基-3-甲基-NHO-CO 2加合物4的反应模式，并将其与相应的NHC-CO 2两性离子进行了比较：4用HX质子化生成咪唑鎓盐[NHO-CO 2 H ] [X]，它在亲核催化剂的存在下脱羧成[EMMIm] [X]。NHO–CO 2两性离子4可以作为对CH酸（如乙腈）的有效羧化剂。形成的[EMMIm]氰基乙酸盐和[EMMIm] 2氰基丙二酸盐是与NHO活化的CO 2的第一个C-C键形成羧化反应的例证。游离的NHO与碳酸二甲酯的反应选择性地产生了甲氧基羰基化的NHO，这是合成功能化IL [NHO-CO 2 Me] [X]的理想前体。合成了第一个NHO-SO 2加合物并对其结构进行

  DOI：

  10.1002/chem.201602973
• 作为试剂：
  描述：

  苯甲酸乙酯 、 C.I.酸性橙108 在 1-ethyl-3-methylimidazolium-2-carboxylate 作用下， 反应 3.0h， 以99%的产率得到N-(2-hydroxyethyl)-benzamide
  参考文献：
  名称：

  Imidazol(in)ium-2-carboxylates as Latent, Thermally Activated Organocatalysts for Transesterification Reactions

  摘要：

  1,3-Disubstituted imidazol(in)ium-2-carboxylates (ImCO(2)) were used as precatalysts for transesterification reactions of unactivatcd ethyl benzoate with monohydric alcohols, dihydric alcohols, and amino alcohols. Highly active N-heterocyclic carbenes (NHCs) are usually not used directly as catalysts because of their air and moisture sensitivity. Here they were liberated in situ by thermal decarboxylation of ImCO(2) at designated temperatures. The results showed that the yield of the reactions reached up to 95% within 3 h using only 0.5 mol% catalyst. No active enol esters, molecular sieves, or a 20-fold excess of alcohol were used to drive the reaction to completion. It was proved that unsaturated imidazolium-2-carboxylates have a better activity than saturated species in this type of reaction. Different types of substituting groups of ImCO(2) exhibited varied transesterification activity.

  DOI：

  10.1016/s1872-2067(11)60353-7

文献信息

• Amidate compound, catalyst for polyurethane production, and method for producing polyurethane resin
  申请人：KOEI CHEMICAL COMPANY, LIMITED

  公开号：US10689478B2

  公开（公告）日：2020-06-23

  Provided is an amidate compound represented by the formula (1): wherein A is a substituted or unsubstituted hydrocarbon group, n is an integer of 1 or more, and D is a nitrogen-containing organic group represented by the formula (2): wherein R1, R2, and R3 are the same or different, and are each a hydrocarbon group that may contain a heteroatom; some or all of R1, R2, and R3 may be bonded together to form a ring structure; X is a nitrogen atom, an oxygen atom, or a sulfur atom; and a is 0 or 1, wherein a is 1 when X is a nitrogen atom, and a is 0 when X is an oxygen atom or a sulfur atom.

  提供的是由式（1）表示的酰胺化合物：其中A是取代或未取代的碳氢基团，n是大于或等于1的整数，D是由式（2）表示的含氮有机基团：其中R1、R2和R3相同或不同，均为可能含有杂原子的碳氢基团；R1、R2和R3中的一些或全部可能结合在一起形成环结构；X是氮原子、氧原子或硫原子；a为0或1，当X为氮原子时，a为1，当X为氧原子或硫原子时，a为0。
• Synthesis of rhodium N-heterocyclic carbene complexes and their catalytic activity in the hydrosilylation of alkenes in ionic liquid medium
  作者：Jiayun Li、Jiajian Peng、Ying Bai、Guoqiao Lai、Xiaonian Li

  DOI：10.1016/j.jorganchem.2010.11.017

  日期：2011.5

  Rhodium complexes bearing N-heterocyclic carbene (NHC) ligands were prepared from bis(η4-1,5-cyclooctadiene) dichlorodirhodium and 1-alkyl-3-methylimidazolium-2-carboxylate, and the catalytic properties of rhodium complexes prepared in the hydrosilylation of alkenes in ionic liquid media were investigated. It was found that both the catalytic activity and selectivity of the rhodium complexes bearing

  铑络合物轴承ñ -杂环卡宾（NHC）配体从双制备（η 4 -1,5-环辛二烯）dichlorodirhodium和1-烷基-3-甲基咪唑-2-羧酸乙酯，和铑配合物的催化性能在氢化硅烷化制备的研究了离子液体介质中烯烃的结构。已经发现，带有NHC配体的铑配合物的催化活性和选择性都受到咪唑鎓阳离子附着的替代物的影响。此外，在离子液体BMimPF 6中带有NHC配体的铑配合物可以重复使用而不会明显降低催化活性和选择性。
• Sterically controlling 2-carboxylated imidazolium salts for one-step efficient hydration of epoxides into 1,2-diols
  作者：Qian Su、Xin Tan、Xiaoqian Yao、Ting Ying、Li Dong、Mengqian Fu、Weiguo Cheng、Suojiang Zhang

  DOI：10.1039/d1gc00788b

  日期：——

  the disadvantages of excessive water and many byproducts in the conventional process of epoxide hydration into 1,2-diols, 2-carboxylated imidazolium salts were first adopted as efficient catalysts for one-step hydration of epoxides into 1,2-diols. By regulating the cation chain lengths, different steric structures of 2-carboxylated imidazolium salts with chain lengths from C1 to C4 were prepared. The

  为了克服在环氧水合成1,2-二醇的常规方法中过量的水和许多副产物的缺点，首先采用2-羧基化的咪唑鎓盐作为有效的催化剂，将环氧化合物一步水合为1,2-二醇。通过调节阳离子链的长度，制备了链长为C1至C4的2-羧化咪唑鎓盐的不同空间结构。具有最短取代基链（DMIC）的盐表现出更好的热稳定性和水合催化性能，在120°C，0.5 h，仅5倍的条件下可实现近100％的环氧乙烷（EO）转化率和100％的乙二醇（EG）选择性。 H 2的摩尔比O到EO。XPS分析和DFT计算都进一步证实并解释了这种趋势。与较长链的其它盐相比，DMIC有CO的更强的相互作用2 -阴离子和咪唑鎓阳离子，表现出较低的倾向，以释放CO 2 -和形成HO-CO 2 - ，其可进行亲核攻击，环氧化物的协同激活开环与咪唑阳离子。强巨大空间位动态结构的开环过渡态减慢副反应，和阳离子和阴离子稳定过渡态咪唑-EG-HO-CO 2 -，这两者
• Esterification of carboxylate-based ionic liquids with alkyl halides
  作者：Bin Zhao、Lasse Greiner、Walter Leitner

  DOI：10.1039/c0cc04798h

  日期：——

  A facile reaction of 1-ethyl-3-methylimidazolium acetate ([EMIm]Ac) with dichloromethane at room temperature was observed with esters among the products. This esterification can be exploited for mild solvent-free esterification with a range of other carboxylate-based ionic liquids and alkyl halides.

  观察到1-乙基-3-甲基咪唑铵醋酸盐（[EMIm]Ac）与二氯甲烷在室温下发生的简单反应中产生了酯类产品。这种酯化反应可以用于与多种其他基于羧酸盐的离子液体和烷基卤化物进行温和的无溶剂酯化。
• Demonstration of Chemisorption of Carbon Dioxide in 1,3-Dialkylimidazolium Acetate Ionic Liquids
  作者：Gabriela Gurau、Héctor Rodríguez、Steven P. Kelley、Peter Janiczek、Roland S. Kalb、Robin D. Rogers

  DOI：10.1002/anie.201105198

  日期：2011.12.9

  Real chemistry: Spectroscopic and crystallographic analyses confirm the chemical reaction of CO2 with carbene present in 1,3‐dialkylimidazolium acetate ionic liquids and the supporting role of the acetate ion. When CO2 was bubbled through [C2mim][OAc], formation of the corresponding imidazolium carboxylate, [C2mim+‐COO−], could be observed.

  实际化学：光谱和晶体学分析证实了乙酸1，3-二烷基咪唑鎓离子液体中存在的卡宾与CO 2的化学反应以及乙酸根离子的支持作用。当CO 2通过[C鼓泡2个MIM] [OAC]，在形成对应的咪唑鎓羧酸盐的，[C 2 MIM + -COO - ]，可以观察到。