1-(R)-1-pyrrolidin-2-ylmethyl-1H-pyridin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-(R)-1-pyrrolidin-2-ylmethyl-1H-pyridin-2-one
• 英文别名: 1-[[(2R)-pyrrolidin-2-yl]methyl]pyridin-2-one
• 化学式: C₁₀H₁₄N₂O
• 分子量: 178.234
• InChiKey: OMQIFLOHFZCQNH-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  Boc-D-脯氨醇 在 盐酸 、 caesium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 73.75h， 生成 1-(R)-1-pyrrolidin-2-ylmethyl-1H-pyridin-2-one
  参考文献：
  名称：

  Solvent free, fast and asymmetric Michael additions of ketones to nitroolefins using chiral pyrrolidine–pyridone conjugate bases as organocatalysts

  摘要：

  New chiral organocatalysts are envisaged based on a pyrrolidine-pyridone conjugate and synthesized from commercially available proline employing standard protocols. These catalysts were found to be useful for asymmetric Michael additions of ketones to nitroolefins to afford the desired products in very good yields (up to 98%) with excellent diastereo- and enantioselectivities (>97:3 syn/anti and up to 98% ee) in very short reaction time compared with the existing reports. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.03.002
• 作为试剂：
  描述：

  β-硝基苯乙烯 、 环己酮 在 1-(R)-1-pyrrolidin-2-ylmethyl-1H-pyridin-2-one 、 三氟乙酸 作用下， 以 neat (no solvent) 为溶剂， 反应 3.17h， 以91%的产率得到(R)-2-((S)-2-nitro-1-phenylethyl)-cyclohexanone
  参考文献：
  名称：

  Solvent free, fast and asymmetric Michael additions of ketones to nitroolefins using chiral pyrrolidine–pyridone conjugate bases as organocatalysts

  摘要：

  New chiral organocatalysts are envisaged based on a pyrrolidine-pyridone conjugate and synthesized from commercially available proline employing standard protocols. These catalysts were found to be useful for asymmetric Michael additions of ketones to nitroolefins to afford the desired products in very good yields (up to 98%) with excellent diastereo- and enantioselectivities (>97:3 syn/anti and up to 98% ee) in very short reaction time compared with the existing reports. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.03.002

文献信息

• Solvent free, fast and asymmetric Michael additions of ketones to nitroolefins using chiral pyrrolidine–pyridone conjugate bases as organocatalysts
  作者：Chandan K. Mahato、Mrinalkanti Kundu、Animesh Pramanik

  DOI：10.1016/j.tetasy.2017.03.002

  日期：2017.4

  New chiral organocatalysts are envisaged based on a pyrrolidine-pyridone conjugate and synthesized from commercially available proline employing standard protocols. These catalysts were found to be useful for asymmetric Michael additions of ketones to nitroolefins to afford the desired products in very good yields (up to 98%) with excellent diastereo- and enantioselectivities (>97:3 syn/anti and up to 98% ee) in very short reaction time compared with the existing reports. (C) 2017 Elsevier Ltd. All rights reserved.