6-acetyl-3-methoxy-5-methyl-8-oxabicyclo[3.2.1]octa-3,6-dien-2-one | 1414861-09-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 6-acetyl-3-methoxy-5-methyl-8-oxabicyclo[3.2.1]octa-3,6-dien-2-one
• 英文别名: 6-Acetyl-3-methoxy-5-methyl-8-oxabicyclo[3.2.1]octa-3,6-dien-2-one
• CAS: 1414861-09-8
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: MHKWQNZQEXOESE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-acetyl-3-methoxy-5-methyl-8-oxabicyclo[3.2.1]octa-3,6-dien-2-one 在 三氯化硼 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 1.2h， 以95%的产率得到4-acetyl-2,7-dihydroxy-5-methylcyclohepta-2,4,6-trienone
  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：

  别麦芽酚 在 N,N-二异丙苯胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 4.25h， 生成 6-acetyl-3-methoxy-5-methyl-8-oxabicyclo[3.2.1]octa-3,6-dien-2-one
  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

• [EN] COMPOSITIONS AND METHODS FOR INHIBITING INFLUENZA RNA POLYMERASE PA ENDONUCLEASE<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR INHIBER L'ENDONUCLÉASE DE LA PA DE L'ARN POLYMÉRASE DE LA GRIPPE
  申请人：UNIV CALIFORNIA

  公开号：WO2017156194A1

  公开（公告）日：2017-09-14

  There are provided inter alia metalloenzyme inhibitors, such as inhibitors of influenza A RNA dependent RNA polymerase PA subunit endonuclease, and methods of synthesis and use of the same.

  其中提供了金属酶抑制剂，例如流感A病毒RNA依赖性RNA聚合酶PA亚基内切酶的抑制剂，以及其合成和使用方法。
• Compositions and methods for inhibiting influenza RNA polymerase PA endonuclease
  申请人：The Regents of the University of California

  公开号：US10889556B2

  公开（公告）日：2021-01-12

  There are provided inter alia metalloenzyme inhibitors, such as inhibitors of influenza A RNA dependent RNA polymerase PA subunit endonuclease, and methods of synthesis and use of the same.

  除其他外，还提供了金属酶抑制剂，例如甲型流感 RNA 依赖性 RNA 聚合酶 PA 亚基内切酶抑制剂，以及合成和使用这些抑制剂的方法。
• COMPOSITIONS AND METHODS FOR INHIBITING INFLUENZA RNA POLYMERASE PA ENDONUCLEASE
  申请人：The Regents of the University of California

  公开号：US20190106398A1

  公开（公告）日：2019-04-11

  There are provided inter alia metalloenzyme inhibitors, such as inhibitors of influenza A RNA dependent RNA polymerase PA subunit endonuclease, and methods of synthesis and use of the same.
• 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.