| 933069-74-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• CAS: 933069-74-0
• 化学式: C₄H₆N₂*C₁₀H₁₆O₄S
• 分子量: 314.406
• InChiKey: RFLRZBUTOGRFFD-YUWZRIFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.69
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  89.26
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  、 丁烯酮 以 乙醇 为溶剂， 反应 72.0h， 以95%的产率得到[N-(3'-oxobutyl)-N-methylimidazolium][(1R)-camphor-10-sulfonate]
  参考文献：
  名称：

  咪唑樟脑磺酸盐离子液体中的手性转移通过离子配对效应

  摘要：

  Abstractmagnified imageThe paper describes our studies on ion pair interactions in ionic liquids (IL) using an asymmetric hydrogenation reaction as probe. Three different ionic liquids carrying prochiral keto‐functionalized cations were hydrogenated in the presence of their chiral, enantiomerically pure counter‐ion using an achiral heterogeneous ruthenium catalyst. For the hydrogenation of N‐(3′‐oxobutyl)‐N‐methylimidazolium camphorsulfonate (2), N‐(3′‐oxobutyl)imidazolium camphorsulfonate (4) and N‐(5′‐oxohexyl)‐N‐methylimidazolium camphorsulfonate (6) we found a strong dependency of the enantiomeric excess (ee in the cation) on the polarity of the solvent, the concentration of the IL and the structure of the IL. The highest ee values of up to 94% were found for the hydrogenation of 2 in ethanol. Interestingly, we observed that the ee (and consequently the strength of ion pair interaction) had a pronounced maximum for a certain concentration of the IL in the solvent depending on the nature of the solvent and on the substrate. Remarkably, the concentration leading to the maximum ee could be rationalized by independent determination of the degree of dissociation which was obtained by a combination of diffusion‐ordered NMR spectroscopy and conductivity measurements.

  DOI：

  10.1002/adsc.200800569
• 作为产物：
  描述：

  N-甲基咪唑 、 左旋樟脑磺酸 以 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  咪唑樟脑磺酸盐离子液体中的手性转移通过离子配对效应

  摘要：

  Abstractmagnified imageThe paper describes our studies on ion pair interactions in ionic liquids (IL) using an asymmetric hydrogenation reaction as probe. Three different ionic liquids carrying prochiral keto‐functionalized cations were hydrogenated in the presence of their chiral, enantiomerically pure counter‐ion using an achiral heterogeneous ruthenium catalyst. For the hydrogenation of N‐(3′‐oxobutyl)‐N‐methylimidazolium camphorsulfonate (2), N‐(3′‐oxobutyl)imidazolium camphorsulfonate (4) and N‐(5′‐oxohexyl)‐N‐methylimidazolium camphorsulfonate (6) we found a strong dependency of the enantiomeric excess (ee in the cation) on the polarity of the solvent, the concentration of the IL and the structure of the IL. The highest ee values of up to 94% were found for the hydrogenation of 2 in ethanol. Interestingly, we observed that the ee (and consequently the strength of ion pair interaction) had a pronounced maximum for a certain concentration of the IL in the solvent depending on the nature of the solvent and on the substrate. Remarkably, the concentration leading to the maximum ee could be rationalized by independent determination of the degree of dissociation which was obtained by a combination of diffusion‐ordered NMR spectroscopy and conductivity measurements.

  DOI：

  10.1002/adsc.200800569