(3R,3aS,6S,7S,7aS)-3-Dimethylaminomethyl-7-isopropenyl-6-methyl-6-vinyl-hexahydro-benzofuran-2-one | 68510-44-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3R,3aS,6S,7S,7aS)-3-Dimethylaminomethyl-7-isopropenyl-6-methyl-6-vinyl-hexahydro-benzofuran-2-one
• CAS: 68510-44-1
• 化学式: C₁₇H₂₇NO₂
• 分子量: 277.407
• InChiKey: FBXAKWYDYSJQLO-KSXIZUIISA-N

反应信息

• 作为反应物：
  描述：

  (3R,3aS,6S,7S,7aS)-3-Dimethylaminomethyl-7-isopropenyl-6-methyl-6-vinyl-hexahydro-benzofuran-2-one 在 碘甲烷 、 碳酸氢钠 作用下， 以85 %的产率得到1H-咪唑-5-甲酰胺,4-羟基-1-[(4-硝基苯基)甲基]-
  参考文献：
  名称：

  Microwave-Assisted Rearrangement of Costunolide Catalyzed by Palladium(II)

  摘要：

  The structure of costunolide was modified before conducting the Cope rearrangement under thermal conditions. This modification was undertaken to block the highly reactive Michael acceptor α-methylene-γ-lactone, thus preventing side reactions at high temperatures. In this work, the reaction was performed under heating or microwave irradiation using costunolide, not its modified version. Rates of Cope reactions catalyzed by palladium(II) assisted by microwave were substantially enhanced. The rearrangements of costunolide to elemanolide, eudesmanolides, and germacranolide were catalyzed by palladium acetate, bis(benzonitrile)palladium dichloride, and a mixture of both organometallics. Rates of microwave promoted rearrangements of costunolide were six times faster than the reactions assisted by heating. The best success rate for elemanolide (7) was obtained using a mixture of Pd(OAc)2 and (NCPh)2PdCl2. In this case, compound 7 was obtained in a yield of 34%, while the other sesquiterpene lactones were formed only in trace amounts. The reaction products were isolated using semi-preparative high performance liquid chromatography and further purified through sequential analytical high performance liquid chromatography. Bioactivity profiles that used etiolated wheat coleoptiles were conducted for compounds 6, 7, and 9. The tested compounds presented very high phytotoxicity, with inhibition up to 97%.

  DOI：

  10.21577/0103-5053.20240038
• 作为产物：
  描述：

  二甲胺 、 木香烃内酯 以 甲醇 为溶剂， 以67 %的产率得到(3R,3aS,6S,7S,7aS)-3-Dimethylaminomethyl-7-isopropenyl-6-methyl-6-vinyl-hexahydro-benzofuran-2-one
  参考文献：
  名称：

  Microwave-Assisted Rearrangement of Costunolide Catalyzed by Palladium(II)

  摘要：

  The structure of costunolide was modified before conducting the Cope rearrangement under thermal conditions. This modification was undertaken to block the highly reactive Michael acceptor α-methylene-γ-lactone, thus preventing side reactions at high temperatures. In this work, the reaction was performed under heating or microwave irradiation using costunolide, not its modified version. Rates of Cope reactions catalyzed by palladium(II) assisted by microwave were substantially enhanced. The rearrangements of costunolide to elemanolide, eudesmanolides, and germacranolide were catalyzed by palladium acetate, bis(benzonitrile)palladium dichloride, and a mixture of both organometallics. Rates of microwave promoted rearrangements of costunolide were six times faster than the reactions assisted by heating. The best success rate for elemanolide (7) was obtained using a mixture of Pd(OAc)2 and (NCPh)2PdCl2. In this case, compound 7 was obtained in a yield of 34%, while the other sesquiterpene lactones were formed only in trace amounts. The reaction products were isolated using semi-preparative high performance liquid chromatography and further purified through sequential analytical high performance liquid chromatography. Bioactivity profiles that used etiolated wheat coleoptiles were conducted for compounds 6, 7, and 9. The tested compounds presented very high phytotoxicity, with inhibition up to 97%.

  DOI：

  10.21577/0103-5053.20240038