(S)-5-Methoxy-5-octyl-5H-furan-2-one | 152694-71-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-5-Methoxy-5-octyl-5H-furan-2-one
• CAS: 152694-71-8
• 化学式: C₁₃H₂₂O₃
• 分子量: 226.316
• InChiKey: CLNJHSVFNJXMKW-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  16.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-5-Methoxy-5-octyl-5H-furan-2-one 在 sodium hypochlorite 、 氨 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.75h， 生成 (2R,3S)-2,3-epoxy-4-oxo-dodecanamide
  参考文献：
  名称：

  Synthesis of optically active butenolides via chromium alkoxycarbene complexes: total synthesis of (+)-tetrahydrocerulenin and two butenolides from the marine sponge Plakortis lita

  摘要：

  Optically active butenolides were synthesized from the corresponding cyclobutanones, derived from the photolysis of chromium alkoxycarbene complexes and optically active ene-carbamates. The cyclobutanones were oxidized (Baeyer-Villiger) to the corresponding lactones, and subsequent base-induced elimination of the beta-oxazolidinone ring provided optically active butenolides efficiently. The butenolides were utilized in the syntheses of (+)-tetrahydrocerulenin and two marine natural products.

  DOI：

  10.1021/jo00076a044
• 作为产物：
  描述：

  (S)-3-((2S,3S)-2-Methoxy-2-octyl-5-oxo-tetrahydro-furan-3-yl)-4-phenyl-oxazolidin-2-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以90%的产率得到(S)-5-Methoxy-5-octyl-5H-furan-2-one
  参考文献：
  名称：

  Synthesis of optically active butenolides via chromium alkoxycarbene complexes: total synthesis of (+)-tetrahydrocerulenin and two butenolides from the marine sponge Plakortis lita

  摘要：

  Optically active butenolides were synthesized from the corresponding cyclobutanones, derived from the photolysis of chromium alkoxycarbene complexes and optically active ene-carbamates. The cyclobutanones were oxidized (Baeyer-Villiger) to the corresponding lactones, and subsequent base-induced elimination of the beta-oxazolidinone ring provided optically active butenolides efficiently. The butenolides were utilized in the syntheses of (+)-tetrahydrocerulenin and two marine natural products.

  DOI：

  10.1021/jo00076a044

文献信息

• Synthesis of optically active butenolides via chromium alkoxycarbene complexes: total synthesis of (+)-tetrahydrocerulenin and two butenolides from the marine sponge Plakortis lita
  作者：Michael Miller、Louis S. Hegedus

  DOI：10.1021/jo00076a044

  日期：1993.11

  Optically active butenolides were synthesized from the corresponding cyclobutanones, derived from the photolysis of chromium alkoxycarbene complexes and optically active ene-carbamates. The cyclobutanones were oxidized (Baeyer-Villiger) to the corresponding lactones, and subsequent base-induced elimination of the beta-oxazolidinone ring provided optically active butenolides efficiently. The butenolides were utilized in the syntheses of (+)-tetrahydrocerulenin and two marine natural products.