(S)-6-propyl-1,6-dihydropyridin-2(3H)-one | 1163716-30-0

• 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: (S)-6-propyl-1,6-dihydropyridin-2(3H)-one
• 英文别名: (2S)-2-propyl-2,5-dihydro-1H-pyridin-6-one
• CAS: 1163716-30-0
• 化学式: C₈H₁₃NO
• 分子量: 139.197
• InChiKey: WHRTUXJQEZAQGH-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-6-propyl-1,6-dihydropyridin-2(3H)-one 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 以87%的产率得到(S)-6-propylpiperidin-2-one
  参考文献：
  名称：

  Asymmetric Synthesis of Unsaturated Monocyclic and Bicyclic Nitrogen Heterocycles

  摘要：

  Hydrolysis of scalemic trichloroacetamides Cl3CCONHCH(R)CHCH2 and allylation, or acylation with but-3-enoic acid, followed by ring-closing metathesis resulted in the formation of unsaturated pyrrolidine and piperidine building blocks. These were employed in the synthesis of (S)-coniine (R = Pr) and a formal synthesis of (+)-anisomycin (R = p-MeOC5H4). Extension of this methodology with R = CH2CHCH2 employing two ring-closing metatheses resulted in the synthesis of unsaturated quinolizidinone and indolizidinone frameworks.

  DOI：

  10.1021/ol900880w
• 作为产物：
  描述：

  (S)-N-(hex-1-en-3-yl)but-3-enamide 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以70%的产率得到(S)-6-propyl-1,6-dihydropyridin-2(3H)-one
  参考文献：
  名称：

  Asymmetric Synthesis of Unsaturated Monocyclic and Bicyclic Nitrogen Heterocycles

  摘要：

  Hydrolysis of scalemic trichloroacetamides Cl3CCONHCH(R)CHCH2 and allylation, or acylation with but-3-enoic acid, followed by ring-closing metathesis resulted in the formation of unsaturated pyrrolidine and piperidine building blocks. These were employed in the synthesis of (S)-coniine (R = Pr) and a formal synthesis of (+)-anisomycin (R = p-MeOC5H4). Extension of this methodology with R = CH2CHCH2 employing two ring-closing metatheses resulted in the synthesis of unsaturated quinolizidinone and indolizidinone frameworks.

  DOI：

  10.1021/ol900880w

文献信息

• Asymmetric Synthesis of Unsaturated Monocyclic and Bicyclic Nitrogen Heterocycles
  作者：Hiroshi Nomura、Christopher J. Richards

  DOI：10.1021/ol900880w

  日期：2009.7.2

  Hydrolysis of scalemic trichloroacetamides Cl3CCONHCH(R)CHCH2 and allylation, or acylation with but-3-enoic acid, followed by ring-closing metathesis resulted in the formation of unsaturated pyrrolidine and piperidine building blocks. These were employed in the synthesis of (S)-coniine (R = Pr) and a formal synthesis of (+)-anisomycin (R = p-MeOC5H4). Extension of this methodology with R = CH2CHCH2 employing two ring-closing metatheses resulted in the synthesis of unsaturated quinolizidinone and indolizidinone frameworks.