发明授权
US5492887A 8-exo-formyl-2,6-exo-tricyclo(5.2.1.02,6)decane, method of preparing it
and use of the same
失效
8-外 - 甲酰基-2,6-二 - 三环(5.2.1.02,6)癸烷,其制备方法及其用途
- 专利标题: 8-exo-formyl-2,6-exo-tricyclo(5.2.1.02,6)decane, method of preparing it and use of the same
- 专利标题(中): 8-外 - 甲酰基-2,6-二 - 三环(5.2.1.02,6)癸烷,其制备方法及其用途
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申请号: US960431申请日: 1992-12-11
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公开(公告)号: US5492887A公开(公告)日: 1996-02-20
- 发明人: Ernst-Joachim Brunke , Claus-Hermann Kappey , Bernd Holscher , Hartmut Struwe
- 申请人: Ernst-Joachim Brunke , Claus-Hermann Kappey , Bernd Holscher , Hartmut Struwe
- 申请人地址: DEX Holzminden
- 专利权人: Dragoco Gerberding & Co. GmbH
- 当前专利权人: Dragoco Gerberding & Co. GmbH
- 当前专利权人地址: DEX Holzminden
- 优先权: DEX4112093.0 19910412
- 主分类号: A61K8/00
- IPC分类号: A61K8/00 ; A61Q13/00 ; B01J23/44 ; C07B61/00 ; C07C45/62 ; C07C45/67 ; C07C47/347 ; C11B9/00 ; C11D3/50 ; A61K7/46
摘要:
It was found that 8-exo-formyl-2,6-exo-tricyclo[5.2.1.0.sup.2,6 ]decane having the constitution and stereochemistry of formula (I) possesses particularly useful olfactory properties which are clearly superior to those of the 8-endo-epimer and which already have an effect if compound (I) is enriched with mixtures of 8-exo- and 8-endo-epimers. Compound (I) can therefore be advantageously used, in pure or enriched form, as a scent or as a component of perfume compositions. To prepare an enriched epimer mixture, a mixture obtained in a known manner (U.S. Pat. No. 3,270,061) and having an exo/endo ratio of 1.45:1 is brought into equilibrium by base catalysis, preferably by the action of alkali hydroxides in alcoholic solution, to give an exo/endo ratio of 5.25:1. Alternatively, the enriched epimer mixture can be prepared starting from 8-formyl-2,6-exo-tricyclo[5.2.1.0.sup.2,6 ]decene-3(4), catalytically hydrogenated for example with palladium coal and then optionally brought into equilibrium. Or 2,6-exo-tricyclo[5.2.1.0.sup.2,6 ]decene-8 can be hydroformylated and also optionally brought into equilibrium. The pure compound (I) is prepared by reducing preferably a mixture of 8-exo- and 8-endo-epimers obtained in the manner known per se to a mixture of the corresponding alcohols, from which the 8-exo-configured methylol is isolated by chromatography or distillation and oxidized to obtain the aldehyde (compound I) again.
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