trimethyl (E)-1-(3-bromo-2-oxo-2H-pyran-6-yl)hex-4-ene-1,1,5-tricarboxylate | 1004750-51-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: trimethyl (E)-1-(3-bromo-2-oxo-2H-pyran-6-yl)hex-4-ene-1,1,5-tricarboxylate
• 英文别名: trimethyl (E)-1-(5-bromo-6-oxopyran-2-yl)hept-5-ene-1,1,6-tricarboxylate
• CAS: 1004750-51-9
• 化学式: C₁₈H₂₁BrO₈
• 分子量: 445.264
• InChiKey: DXHKPYNZGQEPQJ-YRNVUSSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  trimethyl (E)-1-(3-bromo-2-oxo-2H-pyran-6-yl)hex-4-ene-1,1,5-tricarboxylate 以 苯 为溶剂， 反应 72.0h， 以76%的产率得到trimethyl (1R,6S,7R,8R)-8-bromo-7-methyl-9-oxo-10-oxatricyclo[6.2.2.01,6]dodec-11-ene-2,2,7-tricarboxylate
  参考文献：
  名称：

  Progress toward the Synthesis of the Basiliolides and Transtaganolides:  An Intramolecular Pyrone Diels−Alder Entry into a Novel Class of Natural Products

  摘要：

  Efforts directed toward the synthesis of a basiliolide/transtaganolide model system are disclosed. A highly endo-selective intramolecular pyrone Diels-Alder (IMPDA) cycloaddition rapidly constructs the tricyclic core of the basiliolides and transtaganolides.

  DOI：

  10.1021/ol702501s
• 作为产物：
  描述：

  methyl (E)-6-iodo-2-methylhex-2-enoate 、 dimethyl 2-(3-bromo-2-oxo-2H-pyran-6-yl)propane-1,3-dioate 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以58%的产率得到trimethyl (E)-1-(3-bromo-2-oxo-2H-pyran-6-yl)hex-4-ene-1,1,5-tricarboxylate
  参考文献：
  名称：

  Progress toward the Synthesis of the Basiliolides and Transtaganolides:  An Intramolecular Pyrone Diels−Alder Entry into a Novel Class of Natural Products

  摘要：

  Efforts directed toward the synthesis of a basiliolide/transtaganolide model system are disclosed. A highly endo-selective intramolecular pyrone Diels-Alder (IMPDA) cycloaddition rapidly constructs the tricyclic core of the basiliolides and transtaganolides.

  DOI：

  10.1021/ol702501s