(S)-N-allyl-3-(1-ethoxy)ethoxy-4-hydroxybutyramide | 186429-05-0

• 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-allyl-3-(1-ethoxy)ethoxy-4-hydroxybutyramide
• 英文别名: (3S)-3-(1-ethoxyethoxy)-4-hydroxy-N-prop-2-enylbutanamide
• CAS: 186429-05-0
• 化学式: C₁₁H₂₁NO₄
• 分子量: 231.292
• InChiKey: QMIIVTCEUPUOAC-AXDSSHIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-N-allyl-3-(1-ethoxy)ethoxy-4-hydroxybutyramide 在 rhodium(III) chloride 、 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 5.0h， 生成 (4S)-4-(1-乙氧基乙氧基)-2-吡咯烷酮
  参考文献：
  名称：

  Efficient Syntheses of (S)-4-Hydroxy-2-pyrrolidinone Derivatives

  摘要：

  Efficient syntheses of (S)-4-hydroxy-2-pyrrolidinone ((S)-2) and (R)-4-acetylthio-2-pyrrolidinone (5), which are key intermediates of oral carbapenem CS-834, were studied. The most efficient route to (S)-2 from (S)-3-hydroxybutyrolactone (8) was accomplished in high yield via (S)-N-allyl-3-(1-ethoxy)ethoxy-4-hydroxybutyramide (14).

  DOI：

  10.3987/com-99-8689
• 作为产物：
  描述：

  丙烯胺 、 (3S)-3-(1-乙氧基乙氧基)-gamma-丁内酯 反应 4.0h， 以92%的产率得到(S)-N-allyl-3-(1-ethoxy)ethoxy-4-hydroxybutyramide
  参考文献：
  名称：

  Efficient Syntheses of (S)-4-Hydroxy-2-pyrrolidinone Derivatives

  摘要：

  Efficient syntheses of (S)-4-hydroxy-2-pyrrolidinone ((S)-2) and (R)-4-acetylthio-2-pyrrolidinone (5), which are key intermediates of oral carbapenem CS-834, were studied. The most efficient route to (S)-2 from (S)-3-hydroxybutyrolactone (8) was accomplished in high yield via (S)-N-allyl-3-(1-ethoxy)ethoxy-4-hydroxybutyramide (14).

  DOI：

  10.3987/com-99-8689

文献信息

• Efficient Syntheses of (S)-4-Hydroxy-2-pyrrolidinone Derivatives
  作者：Osamu Kanno、Masao Miyauchi、Isao Kawamoto

  DOI：10.3987/com-99-8689

  日期：——

  Efficient syntheses of (S)-4-hydroxy-2-pyrrolidinone ((S)-2) and (R)-4-acetylthio-2-pyrrolidinone (5), which are key intermediates of oral carbapenem CS-834, were studied. The most efficient route to (S)-2 from (S)-3-hydroxybutyrolactone (8) was accomplished in high yield via (S)-N-allyl-3-(1-ethoxy)ethoxy-4-hydroxybutyramide (14).