5,6-benzo-2,3-diethoxy-4-oxo-2-hepten-7-olide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奥昔康唑
• 英文名称: 5,6-benzo-2,3-diethoxy-4-oxo-2-hepten-7-olide
• 英文别名: (4Z)-4,5-diethoxy-1H-2-benzoxocine-3,6-dione
• 化学式: C₁₅H₁₆O₅
• 分子量: 276.289
• InChiKey: CEHPVIKGPCZAEX-YPKPFQOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  方酸二乙酯 在 正丁基锂 、 四甲基乙二胺 、 碘苯二乙酸 作用下， 以 甲醇 、 正己烷 、 正戊烷 为溶剂， 反应 13.5h， 生成 5,6-benzo-2,3-diethoxy-4-oxo-2-hepten-7-olide
  参考文献：
  名称：

  PhI(OAc)₂-Promoted Rearrangement of the Hydroxyl Group:  Ring Expansion of 4-Hydroxy-2-cyclobutenone to 2(5H)-Furanone in Comparison with Ring Cleavage of the α-Hydroxycycloalkanone to the ω-Formyl Ester

  摘要：

  Reaction of 4-hydroxy-2-cyclobutenones with PhI(OAc)(2) in 1,2-dichloroethane at reflux temperature gave rise to 5-acetoxy-2(5H)-furanones as a rearranged product, formation of which is explained by ring cleavage of the once formed hypervalent iodine intermediate and following recyclization of the resulting acyl cation with a carbonyl oxygen. Likewise, 5-methoxy-2(5H)-furanones were obtained in better yields by using methanol as both a solvent and a nucleophile. Extension of this reaction to simple 2-hydroxycycloalkanones resulted in ring cleavage to methyl omega-formylalkanoates under milder conditions. In this case, the mechanism is explained by known glycol cleavage with PhI(OAc)(2).

  DOI：

  10.1021/jo990704v