(1R,4S,5S)-4-Methoxy-4-octyl-3,6-dioxa-bicyclo[3.1.0]hexan-2-one | 152694-72-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,4S,5S)-4-Methoxy-4-octyl-3,6-dioxa-bicyclo[3.1.0]hexan-2-one
• 英文别名: (1R,4S,5S)-4-methoxy-4-octyl-3,6-dioxabicyclo[3.1.0]hexan-2-one
• CAS: 152694-72-9
• 化学式: C₁₃H₂₂O₄
• 分子量: 242.315
• InChiKey: IZCMWJKUOJZJIP-MDZLAQPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  48.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,4S,5S)-4-Methoxy-4-octyl-3,6-dioxa-bicyclo[3.1.0]hexan-2-one 在 氨 作用下， 以 乙醚 为溶剂， 反应 1.75h， 以99%的产率得到(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 sodium hypochlorite 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (1R,4S,5S)-4-Methoxy-4-octyl-3,6-dioxa-bicyclo[3.1.0]hexan-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