Synthesis of exaltone anddl-muscone based on 1,5,9-cyclododecatriene
作者:
H. Nozaki,
H. Yamamoto,
T. Mori,
期刊:
Canadian Journal of Chemistry
(NRC Available online 1969)
卷期:
Volume 47,
issue 7
页码: 1107-1112
ISSN:0008-4042
年代: 1969
DOI:10.1139/v69-179
出版商: NRC Research Press
数据来源: NRC
摘要:
Bicyclo[9•4•1]hexadecan-16-one is prepared from cyclododecanoneviafour steps: ethoxycarbonylation, condensation with 1,4-dibromobutane, saponification, and decarboxylation. Photolysis of the bicyclic ketone yields a ketene which is trapped with methanol to afford methyl cyclopentadecanecarboxylate or alternatively oxidized to exaltone directly. The ester is also converted into exaltoneviafive steps.dl-Muscone is prepared by applying the same scheme to cyclotridecanone with 14-methylbicyclo-[10•3•1]hexadecan-16-one as the key intermediate.
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