dimethyl 3-methoxy-1-methyl-4-oxo-8-oxabicyclo[3.2.1]octa-2,6-diene-6,7-dicarboxylate | 141996-31-8

• 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-methyl-4-oxo-8-oxabicyclo[3.2.1]octa-2,6-diene-6,7-dicarboxylate
• 英文别名: Dimethyl 3-methoxy-1-methyl-4-oxo-8-oxabicyclo[3.2.1]octa-2,6-diene-6,7-dicarboxylate
• CAS: 141996-31-8
• 化学式: C₁₃H₁₄O₇
• 分子量: 282.25
• InChiKey: PMVBHXXNRVQDMF-UHFFFAOYSA-N

物化性质

• 沸点：
  419.9±45.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dimethyl 3-methoxy-1-methyl-4-oxo-8-oxabicyclo[3.2.1]octa-2,6-diene-6,7-dicarboxylate 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以33%的产率得到dimethyl 7-hydroxy-5-methoxy-3-methyl-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-4-methoxy-2-methylpyrylium trifluoromethanesulfonate 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 0.08h， 生成 dimethyl 3-methoxy-1-methyl-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

文献信息

• Preparation and cycloadditions of a 4-methoxy-3-oxidopyrylium ylid: a reagent for the synthesis of highly substituted seven-membered rings and tetrahydrofurans
  作者：Paul A. Wender、Jose L. Mascareñas

  DOI：10.1016/0040-4039(92)88154-w

  日期：1992.4

  The preparation of 4-methoxy-6-methyl-3-oxidopyrylium ylid from α-deoxykojic acid and its cycloaddition behavior as a 5 carbon dipole or carbonyl ylid with various dipolarophiles is described.

  描述了由α-脱氧曲酸制备4-甲氧基-6-甲基-3-氧代氧化吡啶基吡啶及其与各种双极性亲核剂一起作为5碳偶极或羰基吡啶的环加成行为。
• An Oxidopyrylium Cyclization/Ring-Opening Route to Polysubstituted α-Hydroxytropolones
  作者：Christine Meck、Noushad Mohd、Ryan P. Murelli

  DOI：10.1021/ol302892g

  日期：2012.12.7

  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.