1-butyl-3-[[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]methyl]-pyridinium bromide | 1431629-17-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-butyl-3-[[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]methyl]-pyridinium bromide
• 英文别名: (S)-1-[(pyridin-3-yl)methyl]pyrrolidine-2-methanol；[(2S)-1-(pyridin-3-ylmethyl)pyrrolidin-2-yl]methanol
• CAS: 1431629-17-2
• 化学式: C₁₁H₁₆N₂O
• 分子量: 192.261
• InChiKey: IOKGXVKPPOVVNL-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  36.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-butyl-3-[[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]methyl]-pyridinium bromide 以 水 为溶剂， 反应 24.25h， 生成 1-butyl-3-[[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]methyl]pyridinium bis(trifluoromethanesulfonyl)imide
  参考文献：
  名称：

  配位手性离子液体†

  摘要：

  从市售的氨基醇开始开发了具有氨基醇结构基序的新型配位手性离子液体的实用合成方法。这些基本的手性离子液体可以成功地用作醛的不对称烷基化的催化剂，并具有高达91％ee的高对映选择性。

  DOI：

  10.1039/c3ob41635f
• 作为产物：
  描述：

  3-吡啶甲醛 、 L-脯氨醇 在 sodium tetrahydroborate 作用下， 以 乙腈 、 甲醇 为溶剂， 反应 14.0h， 以93%的产率得到1-butyl-3-[[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]methyl]-pyridinium bromide
  参考文献：
  名称：

  Design, synthesis, and application of novel chiral ONN ligands for asymmetric alkylation

  摘要：

  Starting from easily available chiral pool amino alcohols, a set of novel chiral ONN ligands was synthesized and their catalytic potential was examined in asymmetric alkylation. Ligands with a secondary central NH group and N-methylated ONN ligands were successfully applied as catalysts in the addition of diethyl zinc to various aromatic aldehydes, yielding secondary alcohols in excellent yields of up to 99 % ee.

  DOI：

  10.1007/s00706-012-0900-8

文献信息

• Design, synthesis, and application of novel chiral ONN ligands for asymmetric alkylation
  作者：Katharina Bica、Sonja Leder、Kurt Mereiter、Peter Gaertner

  DOI：10.1007/s00706-012-0900-8

  日期：2013.4

  Starting from easily available chiral pool amino alcohols, a set of novel chiral ONN ligands was synthesized and their catalytic potential was examined in asymmetric alkylation. Ligands with a secondary central NH group and N-methylated ONN ligands were successfully applied as catalysts in the addition of diethyl zinc to various aromatic aldehydes, yielding secondary alcohols in excellent yields of up to 99 % ee.
• Coordinating chiral ionic liquids
  作者：Maria Vasiloiu、Sonja Leder、Peter Gaertner、Kurt Mereiter、Katharina Bica

  DOI：10.1039/c3ob41635f

  日期：——

  A practical synthesis of novel coordinating chiral ionic liquids with an amino alcohol structural motif was developed starting from commercially available amino alcohols. These basic chiral ionic liquids could be successfully applied as catalysts in the asymmetric alkylation of aldehydes and gave high enantioselectivities of up to 91% ee.

  从市售的氨基醇开始开发了具有氨基醇结构基序的新型配位手性离子液体的实用合成方法。这些基本的手性离子液体可以成功地用作醛的不对称烷基化的催化剂，并具有高达91％ee的高对映选择性。