2-ethyl-1,3-dimethylimidazolium methyl carbonate | 1551375-54-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-ethyl-1,3-dimethylimidazolium methyl carbonate
• CAS: 1551375-54-2
• 化学式: C₂H₃O₃*C₇H₁₃N₂
• 分子量: 200.238
• InChiKey: HQXVMOJSSIHPSL-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.61
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  58.17
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-ethyl-1,3-dimethylimidazolium methyl carbonate 以 甲苯 为溶剂， 反应 8.0h， 生成 2-ethyl-1,3-dimethylimidazolium-4-carboxylate
  参考文献：
  名称：

  Reactivity of 1,3-dimethylimidazolium-2-carboxylate with dimethylcarbonate at high temperature: Unexpected 2-ethyl-functionalisation of the imidazolium moiety and employment of the NHC-CO2/dimethylcarbonate system in a base promoted reaction

  摘要：

  The reaction of 1,3-dimethylimidazolium-2-carboxylate and dimethylcarbonate (DMC) at high temperature yielded the new compounds 2-ethyl-1,3-dimethylimidazolium methyl carbonate salt and 2-ethyl-1,3-dimethylimidazolium-4-carboxylate zwitterion which were obtained as a mixture in approximately 4:1 molar ratio. The compounds were also isolated in pure form through alternative synthetic procedures and characterized by ESI-HRMS, H-1, C-13 NMR and FTIR spectroscopy. The 1,3-dimethylimidazolium-2-carboxylate/dimethylcarbonate system was employed in the synthesis of 1,7-heptanedioic acid dimethyl ester from cyclohexanone and DMC. The target compound was obtained in 49% yield and 66% selectivity. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.catcom.2013.11.013
• 作为产物：
  描述：

  2-乙基咪唑 、 碳酸二甲酯 反应 144.0h， 以7%的产率得到2-ethyl-1,3-dimethylimidazolium methyl carbonate
  参考文献：
  名称：

  Reactivity of 1,3-dimethylimidazolium-2-carboxylate with dimethylcarbonate at high temperature: Unexpected 2-ethyl-functionalisation of the imidazolium moiety and employment of the NHC-CO2/dimethylcarbonate system in a base promoted reaction

  摘要：

  The reaction of 1,3-dimethylimidazolium-2-carboxylate and dimethylcarbonate (DMC) at high temperature yielded the new compounds 2-ethyl-1,3-dimethylimidazolium methyl carbonate salt and 2-ethyl-1,3-dimethylimidazolium-4-carboxylate zwitterion which were obtained as a mixture in approximately 4:1 molar ratio. The compounds were also isolated in pure form through alternative synthetic procedures and characterized by ESI-HRMS, H-1, C-13 NMR and FTIR spectroscopy. The 1,3-dimethylimidazolium-2-carboxylate/dimethylcarbonate system was employed in the synthesis of 1,7-heptanedioic acid dimethyl ester from cyclohexanone and DMC. The target compound was obtained in 49% yield and 66% selectivity. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.catcom.2013.11.013
• 作为试剂：
  描述：

  环己酮 、 碳酸二甲酯 在 2-ethyl-1,3-dimethylimidazolium methyl carbonate 作用下， 反应 9.0h， 以37%的产率得到庚二酸二甲酯
  参考文献：
  名称：

  Reactivity of 1,3-dimethylimidazolium-2-carboxylate with dimethylcarbonate at high temperature: Unexpected 2-ethyl-functionalisation of the imidazolium moiety and employment of the NHC-CO2/dimethylcarbonate system in a base promoted reaction

  摘要：

  The reaction of 1,3-dimethylimidazolium-2-carboxylate and dimethylcarbonate (DMC) at high temperature yielded the new compounds 2-ethyl-1,3-dimethylimidazolium methyl carbonate salt and 2-ethyl-1,3-dimethylimidazolium-4-carboxylate zwitterion which were obtained as a mixture in approximately 4:1 molar ratio. The compounds were also isolated in pure form through alternative synthetic procedures and characterized by ESI-HRMS, H-1, C-13 NMR and FTIR spectroscopy. The 1,3-dimethylimidazolium-2-carboxylate/dimethylcarbonate system was employed in the synthesis of 1,7-heptanedioic acid dimethyl ester from cyclohexanone and DMC. The target compound was obtained in 49% yield and 66% selectivity. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.catcom.2013.11.013