(S)-1-dodecyl-1-[(pyrrolidin-2-yl)methyl]pyrrolidin-1-ium bis(trifluoromethylsulfonyl)imide | 1416432-15-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (S)-1-dodecyl-1-[(pyrrolidin-2-yl)methyl]pyrrolidin-1-ium bis(trifluoromethylsulfonyl)imide
• CAS: 1416432-15-9
• 化学式: C₂F₆NO₄S₂*C₂₁H₄₃N₂
• 分子量: 603.735
• InChiKey: QIMLWTPXZPHKAX-BOXHHOBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.33
• 重原子数：
  38.0
• 可旋转键数：
  15.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  94.41
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  benzyl (S)-2-[(pyrrolidin-1-yl)methyl]pyrrolidine-1-carboxylate 、 溴代十二烷 、 bis(trifluoromethane)sulfonimide lithium 在 5%-palladium/activated carbon 、 氢气 作用下， 以 水 、 甲醇 为溶剂， 80.0 ℃ 、400.01 kPa 条件下， 反应 49.0h， 以92%的产率得到(S)-1-dodecyl-1-[(pyrrolidin-2-yl)methyl]pyrrolidin-1-ium bis(trifluoromethylsulfonyl)imide
  参考文献：
  名称：

  Basic chiral ionic liquids: A novel strategy for acid-free organocatalysis

  摘要：

  We present design, synthesis and application of basic chiral ionic liquids based on commercially available (S)-proline. This new set of chiral ionic liquids was specifically designed to replace trifluoroacetic acid in enamine-based organocatalysis for asymmetric C-C bond formation. Based on their permanent charge, these chiral ionic liquids could be applied as organocatalysts in asymmetric aldol reaction of 4-nitrobenzaldehyde and acetone, and good yields and selectivities up to 80%ee could be obtained without additional acid. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cattod.2012.07.002
• 作为试剂：
  描述：

  对硝基苯甲醛 在 (S)-1-dodecyl-1-[(pyrrolidin-2-yl)methyl]pyrrolidin-1-ium bis(trifluoromethylsulfonyl)imide 作用下， 反应 48.0h， 生成 (4R)-4-hydroxy-4-(4-nitrophenyl)-butan-2-one 、 (4S)-4-hydroxy-4-(4-nitrophenyl)-butan-2-one
  参考文献：
  名称：

  Basic chiral ionic liquids: A novel strategy for acid-free organocatalysis

  摘要：

  We present design, synthesis and application of basic chiral ionic liquids based on commercially available (S)-proline. This new set of chiral ionic liquids was specifically designed to replace trifluoroacetic acid in enamine-based organocatalysis for asymmetric C-C bond formation. Based on their permanent charge, these chiral ionic liquids could be applied as organocatalysts in asymmetric aldol reaction of 4-nitrobenzaldehyde and acetone, and good yields and selectivities up to 80%ee could be obtained without additional acid. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cattod.2012.07.002