(S)-N-(hex-1-en-3-yl)but-3-enamide | 1163716-27-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-N-(hex-1-en-3-yl)but-3-enamide
• CAS: 1163716-27-5
• 化学式: C₁₀H₁₇NO
• 分子量: 167.251
• InChiKey: PGRKFMKPOGFINL-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.03
• 重原子数：
  12.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  乙烯基乙酸 、 (S)-3-hex-1-enylamine 在 N,N'-二环己基碳二亚胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 以2.6 g的产率得到(S)-N-(hex-1-en-3-yl)but-3-enamide
  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