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  • 标题:Studies on Ethylenic Compounds. I. Synthesis of a New Isomer of Dihydroionone
  • 本地全文:下载
  • 作者:Takuichi Miki ; Yujiro Hara
  • 期刊名称:Chemical and Pharmaceutical Bulletin
  • 印刷版ISSN:0009-2363
  • 电子版ISSN:1347-5223
  • 出版年度:1956
  • 卷号:4
  • 期号:2
  • 页码:85-88
  • DOI:10.1248/cpb1953.4.85
  • 出版社:The Pharmaceutical Society of Japan
  • 摘要:The synthesis of β-ionone starting from 2, 6, 6-trimethylcyclohexanone (I) was investigated. Oxidation of 2, 6, 6-trimethyl-1-vinylcyclohexanol (III) with chromium trioxide or ozone unexpectedly afforded (I). 1-(1'-Hydroxy-2', 6', 6'-trimethylcyclohexyl)-but-1-yn-3-ol (VI) was reduced with sodium in liquid ammonia and the product was oxidized with manganese dioxide to trans-1-(1'-hydroxy-2', 6', 6'-trimethylcyclohexyl) but-1-en-3-one (IX). An attempt to prepare β-ionone by the dehydration of (IX) was unsuccessful. Treatment of (IX) with zinc-acetic acid yielded a new isomer of dihydroionone, 1-(2', 6', 6'-trimethylcyclohexylidene) butan-3-one (XIII).
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