methyl (R)-2-(4,5-dimethyl-1H-imidazol-1-yl)propanoate | 1172064-65-1

• 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: methyl (R)-2-(4,5-dimethyl-1H-imidazol-1-yl)propanoate
• 英文别名: methyl (2R)-2-(4,5-dimethylimidazol-1-yl)propanoate
• CAS: 1172064-65-1
• 化学式: C₉H₁₄N₂O₂
• 分子量: 182.222
• InChiKey: BPPLTCNYDVHUKT-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  正溴丁烷 、 methyl (R)-2-(4,5-dimethyl-1H-imidazol-1-yl)propanoate 以 二氯甲烷 为溶剂， 反应 48.0h， 以44%的产率得到(R)-1-butyl-3-[1-(methoxycarbonyl)ethyl]-4,5-dimethylimidazolium bromide
  参考文献：
  名称：

  Exploration of 4,5-dimethyl-1H-imidazole N-oxide derivatives in the synthesis of new achiral and chiral ionic liquids

  摘要：

  New 1-alkoxy-3-alkyl-4,5-dimethylimidazolium bromides were synthesized by alkylation of the corresponding 1-alkylimidazole 3-oxides, which were conveniently prepared via condensation of alpha-(hydroxyimino)ketones, primary aliphatic amines, and formaldehyde. By using enantiomerically pure chiral amines, optically active imidazolium Salts were obtained. Treatment with sodium tetrafluoroborate in acetone yielded the corresponding imidazolium tetrafluoroborates. All these compounds, with only one exception, were obtained as oils, which are considered as potential ionic liquids and 'chiral ionic liquids'. The reduction of the chiral or non-chiral 1-alkylimidazole 3-oxides with Raney-Ni, followed by alkylation with alkyl bromides and subsequent ion exchange to tetra fluoroborates, gave the corresponding 1,3-dialkylimidazolium salts, most of them showing properties of ionic liquids. The alkylation of 1-butyl-4,5-dimethylimidazole 3-oxide and the corresponding imidazole, respectively, with 1,3-dibromopropane led to the first bis-imidazolium dibromides and bis-tetrafluoroborates. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.053
• 作为产物：
  描述：

  methyl (R)-2-(4,5-dimethyl-3-oxido-1H-imidazol-1-yl)propanoate 在 镍 作用下， 以 乙醇 为溶剂， 以65%的产率得到methyl (R)-2-(4,5-dimethyl-1H-imidazol-1-yl)propanoate
  参考文献：
  名称：

  Exploration of 4,5-dimethyl-1H-imidazole N-oxide derivatives in the synthesis of new achiral and chiral ionic liquids

  摘要：

  New 1-alkoxy-3-alkyl-4,5-dimethylimidazolium bromides were synthesized by alkylation of the corresponding 1-alkylimidazole 3-oxides, which were conveniently prepared via condensation of alpha-(hydroxyimino)ketones, primary aliphatic amines, and formaldehyde. By using enantiomerically pure chiral amines, optically active imidazolium Salts were obtained. Treatment with sodium tetrafluoroborate in acetone yielded the corresponding imidazolium tetrafluoroborates. All these compounds, with only one exception, were obtained as oils, which are considered as potential ionic liquids and 'chiral ionic liquids'. The reduction of the chiral or non-chiral 1-alkylimidazole 3-oxides with Raney-Ni, followed by alkylation with alkyl bromides and subsequent ion exchange to tetra fluoroborates, gave the corresponding 1,3-dialkylimidazolium salts, most of them showing properties of ionic liquids. The alkylation of 1-butyl-4,5-dimethylimidazole 3-oxide and the corresponding imidazole, respectively, with 1,3-dibromopropane led to the first bis-imidazolium dibromides and bis-tetrafluoroborates. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.053

文献信息

• Exploration of 4,5-dimethyl-1H-imidazole N-oxide derivatives in the synthesis of new achiral and chiral ionic liquids
  作者：Grzegorz Mlostoń、Jarosław Romański、Marcin Jasiński、Heinz Heimgartner

  DOI：10.1016/j.tetasy.2009.02.053

  日期：2009.5

  New 1-alkoxy-3-alkyl-4,5-dimethylimidazolium bromides were synthesized by alkylation of the corresponding 1-alkylimidazole 3-oxides, which were conveniently prepared via condensation of alpha-(hydroxyimino)ketones, primary aliphatic amines, and formaldehyde. By using enantiomerically pure chiral amines, optically active imidazolium Salts were obtained. Treatment with sodium tetrafluoroborate in acetone yielded the corresponding imidazolium tetrafluoroborates. All these compounds, with only one exception, were obtained as oils, which are considered as potential ionic liquids and 'chiral ionic liquids'. The reduction of the chiral or non-chiral 1-alkylimidazole 3-oxides with Raney-Ni, followed by alkylation with alkyl bromides and subsequent ion exchange to tetra fluoroborates, gave the corresponding 1,3-dialkylimidazolium salts, most of them showing properties of ionic liquids. The alkylation of 1-butyl-4,5-dimethylimidazole 3-oxide and the corresponding imidazole, respectively, with 1,3-dibromopropane led to the first bis-imidazolium dibromides and bis-tetrafluoroborates. (c) 2009 Elsevier Ltd. All rights reserved.