dimethyl 3-methoxy-1-(methoxymethyl)-4-oxo-8-oxabicyclo[3.2.1]octa-2,6-diene-6,7-dicarboxylate | 1414861-07-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: dimethyl 3-methoxy-1-(methoxymethyl)-4-oxo-8-oxabicyclo[3.2.1]octa-2,6-diene-6,7-dicarboxylate
• CAS: 1414861-07-6
• 化学式: C₁₄H₁₆O₈
• 分子量: 312.276
• InChiKey: QYQBYPGNVVFEKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.47
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  dimethyl 3-methoxy-1-(methoxymethyl)-4-oxo-8-oxabicyclo[3.2.1]octa-2,6-diene-6,7-dicarboxylate 在 三氯化硼 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 1.2h， 以85%的产率得到dimethyl 5,7-dihydroxy-3-(methoxymethyl)-6-oxocyclohepta-2,4,7-triene-1,2-dicarboxylate
  参考文献：
  名称：

  An Oxidopyrylium Cyclization/Ring-Opening Route to Polysubstituted α-Hydroxytropolones

  摘要：

  alpha-Hydroxytropolones are a class of molecules with therapeutic potential against several human diseases. However, structure-activity relationship studies on these molecules have been limited due to a scarcity of efficient synthetic methods to access them. It is demonstrated herein that alpha-hydroxytropolones can be generated through a BCl3-mediated ring-opening/aromatization/demethylation process on 8-oxabicyclo[3.2.1]octenes. Used in conjunction with an improved method based on established oxidopyrylium dipolar cycloadditions, several polysubstituted alpha-hydroxytropolones can be accessed in three steps from readily available alpha-hydroxy-gamma-pyrones.

  DOI：

  10.1021/ol302892g
• 作为产物：
  描述：

  5-hydroxy-2-(methoxymethyl)-4H-pyran-4-one 在 N,N-二异丙苯胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.75h， 生成 dimethyl 3-methoxy-1-(methoxymethyl)-4-oxo-8-oxabicyclo[3.2.1]octa-2,6-diene-6,7-dicarboxylate
  参考文献：
  名称：

  An Oxidopyrylium Cyclization/Ring-Opening Route to Polysubstituted α-Hydroxytropolones

  摘要：

  alpha-Hydroxytropolones are a class of molecules with therapeutic potential against several human diseases. However, structure-activity relationship studies on these molecules have been limited due to a scarcity of efficient synthetic methods to access them. It is demonstrated herein that alpha-hydroxytropolones can be generated through a BCl3-mediated ring-opening/aromatization/demethylation process on 8-oxabicyclo[3.2.1]octenes. Used in conjunction with an improved method based on established oxidopyrylium dipolar cycloadditions, several polysubstituted alpha-hydroxytropolones can be accessed in three steps from readily available alpha-hydroxy-gamma-pyrones.

  DOI：

  10.1021/ol302892g