(S)-3-butoxy-1-(2-hydroxypropyl)-4,5-dimethylimidazolium bromide | 1172064-80-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (S)-3-butoxy-1-(2-hydroxypropyl)-4,5-dimethylimidazolium bromide
• 英文别名: (S)-1-butoxy-4,5-dimethyl-3-(2-hydroxypropyl)imidazolium bromide
• CAS: 1172064-80-0
• 化学式: Br*C₁₂H₂₃N₂O₂
• 分子量: 307.231
• InChiKey: JGUVRYSOKYKIPU-PPHPATTJSA-M

反应信息

• 作为反应物：
  描述：

  (S)-3-butoxy-1-(2-hydroxypropyl)-4,5-dimethylimidazolium bromide 在 氟硼酸钠 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以91%的产率得到(S)-1-butoxy-4,5-dimethyl-3-(2-hydroxypropyl)imidazolium tetrafluoroborate
  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：

  正溴丁烷 、 (αS)-α,4,5-trimethyl-1H-imidazole-1-ethanol 3-oxide 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (S)-3-butoxy-1-(2-hydroxypropyl)-4,5-dimethylimidazolium bromide
  参考文献：
  名称：

  2-未取代的咪唑 N-氧化物作为衍生自反式-1,2-二氨基环己烷和其他手性氨基化合物的手性 3-烷氧基咪唑-2-亚基的新型前体

  摘要：

  通过用 α,ω-二卤代烷基化试剂处理反式-1,2-二氨基环己烷的“去对称化”导致单-NH2 衍生物（“伯-叔二胺”）。与甲醛反应后，这些产物形成单体甲醛二亚胺。随后，甲醛二亚胺与 α-羟基亚氨基酮反应生成相应的 2-未取代咪唑 N-氧化物衍生物，在此用作原位生成手性咪唑-2-亚基的新底物。通过O-选择性苄基化，获得了新的手性咪唑鎓盐，在元素硫存在下用三乙胺处理将其去质子化。在这些条件下，中间体咪唑-2-亚基被元素硫捕获，以良好的产率产生相应的手性非烯醇化咪唑-2-硫酮。

  DOI：

  10.3390/molecules24234398