3-methyl-1-((1S)-1-phenylethyl)-1H-imidazol-3-ium bis(trifluoromethanesulfonyl)imide | 1253119-40-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 3-methyl-1-((1S)-1-phenylethyl)-1H-imidazol-3-ium bis(trifluoromethanesulfonyl)imide
• CAS: 1253119-40-2
• 化学式: C₂F₆NO₄S₂*C₁₂H₁₅N₂
• 分子量: 467.413
• InChiKey: MKZBFZZDSCKKAM-MERQFXBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  91.19
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  3-methyl-1-(1-phenylethyl)-1H-imidazolium iodide 、 bis(trifluoromethane)sulfonimide lithium 以 水 为溶剂， 以79%的产率得到3-methyl-1-((1S)-1-phenylethyl)-1H-imidazol-3-ium bis(trifluoromethanesulfonyl)imide
  参考文献：
  名称：

  Synthesis of novel room temperature chiral ionic liquids: application as reaction media for the heck arylation of aza-endocyclic acrylates

  摘要：

  New achiral and chiral RTILs were prepared using novel and/or optimized synthetic routes. These new series of imidazolinium, imidazolium, pyridinium and nicotine-derived ionic liquids were fully characterized including differential scanning calorimetry (DSC) analysis. The performance of these achiral and chiral room temperature ionic liquids (RTILs) was demonstrated by means of the Heck arylation of endocyclic acrylates employing arenediazonium salts and aryl iodides. The Heck arylations performed in the presence of these ionic entities, either as a solvent or as an additive, were effective leading to complete conversion of the substrate and good to excellent yield of the Heck adduct. In spite of the good performances, no asymmetric induction was observed in any of the cases studied. Two new diastereoisomeric NHC-palladium complexes were prepared in good yields from a chiral imidazolium salt and their structure characterized by X-ray diffraction. Overall, the Heck arylations employing arenediazonium tetrafluoroborates in RTILs were more effective than the traditional protocols employing aryl iodides in terms of reactivity and yields.

  DOI：

  10.1590/s0103-50532010000500009