(S)-1-methyl-1-[(pyrrolidin-2-yl)methyl]pyrrolidin-1-ium methyl sulfate | 1416432-05-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 英文名称: (S)-1-methyl-1-[(pyrrolidin-2-yl)methyl]pyrrolidin-1-ium methyl sulfate
• CAS: 1416432-05-7
• 化学式: CH₃O₄S*C₁₀H₂₁N₂
• 分子量: 280.389
• InChiKey: OJGFLVWVIMIOII-PPHPATTJSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.07
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  78.46
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  (S)-(pyrrolidinemethyl)pyrrolidine 在 potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 20.0 ℃ 、400.01 kPa 条件下， 反应 0.83h， 生成 (S)-1-methyl-1-[(pyrrolidin-2-yl)methyl]pyrrolidin-1-ium methyl sulfate
  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

文献信息

• Basic chiral ionic liquids: A novel strategy for acid-free organocatalysis
  作者：Maria Vasiloiu、Daniel Rainer、Peter Gaertner、Christian Reichel、Christian Schröder、Katharina Bica

  DOI：10.1016/j.cattod.2012.07.002

  日期：2013.2

  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.