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    8-exo-formyl-2,6-exo-tricyclo(5.2.1.02,6)decane, method of preparing it and use of the same
    3.
    发明授权
    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

    公开(公告)号：US5492887A

    公开(公告)日：1996-02-20

    申请号：US960431

    申请日：1992-12-11

    申请人： Ernst-Joachim Brunke ,  Claus-Hermann Kappey ,  Bernd Holscher ,  Hartmut Struwe

    发明人： Ernst-Joachim Brunke ,  Claus-Hermann Kappey ,  Bernd Holscher ,  Hartmut Struwe

    IPC分类号： A61K8/00 ,  A61Q13/00 ,  B01J23/44 ,  C07B61/00 ,  C07C45/62 ,  C07C45/67 ,  C07C47/347 ,  C11B9/00 ,  C11D3/50 ,  A61K7/46

    CPC分类号： C11B9/0042 ,  C07C47/347 ,  C11D3/50 ,  C07C2103/68

    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.

    摘要翻译： PCT No.PCT / DE92 / 00307 Sec。 371日期：1992年12月11日 102（e）日期1992年12月11日PCT提交1992年4月10日PCT公布。 WO92 / 18451 PCT出版物 日期为1992年10月26日。发现具有式（I）的构成和立体化学的8-外 - 甲酰基-2,6-二三环[5.2.1.0 2,6]癸烷具有特别有用的嗅觉性质 优于8-内差 - 差向异构体的那些，并且如果化合物（I）富含8-外消旋和8-内消旋异构体的混合物，其已经具有效果。 因此，化合物（I）可有利地以纯的或富集的形式用作香料或香料组合物的组分。 为了制备富集的差向异构体混合物，通过碱催化，优选通过碱金属氢氧化物在醇中的作用，以已知方式获得的混合物（美国专利3,270,061）并且具有1.45:1的外/内比 溶液，得到5.25:1的外/内比。 或者，可以从8-甲酰基-2,6-外三环[5.2.1.0 2,6]癸烯-3（4）开始制备富集的差向异构体混合物，催化氢化，例如用钯煤，然后任选地平衡。 或2,6-二三环[5.2.1.02,6]癸烯-8可以加氢甲酰化，也可任选地达到平衡。 纯化合物（I）通过将本身已知的方式获得的8-外消旋和8-内消旋异构体的混合物优选地还原为相应的醇的混合物，从其中分离出8-外型配位的羟甲基 通过色谱法或蒸馏法氧化得到醛（化合物I）。

    Process for preparing mono-oxomethyl substituted polyhydrodimethanonaphthalene derivatives
    5.
    发明授权
    Process for preparing mono-oxomethyl substituted polyhydrodimethanonaphthalene derivatives 失效

    公开(公告)号：US4460795A

    公开(公告)日：1984-07-17

    申请号：US478355

    申请日：1983-03-24

    申请人： Mark A. Sprecker ,  Marie R. Hanna ,  Richard J. Tokarzewski ,  Robert P. Belko ,  Hugh Watkins ,  Manfred H. Vock

    发明人： Mark A. Sprecker ,  Marie R. Hanna ,  Richard J. Tokarzewski ,  Robert P. Belko ,  Hugh Watkins ,  Manfred H. Vock

    IPC分类号： A24B15/34 ,  C07C47/347 ,  C07C47/445 ,  C07C93/16

    CPC分类号： A24B15/345 ,  C07C47/347 ,  C07C47/445

    摘要： Described are mono-oxomethyl substituted polyhydrodimethanonaphthalene derivatives having the generic structure: ##STR1## wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond; wherein R.sub.1, R.sub.1 ', R.sub.1 ", R.sub.1 "', R.sub.1 "", R.sub.3, R.sub.5, R.sub.5 ', R.sub.5 ", R.sub.5 "', R.sub.5 "" and R.sub.6 represent hydrogen or methyl with the provisos:(i) at least four of R.sub.1, R.sub.1 ', R.sub.1 ", R.sub.1 "' and R.sub.1 "" are hydrogen; and (ii) at least four of R.sub.5, R.sub.5 ', R.sub.5 ", R.sub.5 "' and R.sub.5 "" represent hydrogen;and wherein Z represents one of the moieties:(i) carboxaldehyde having the structure: ##STR2## (ii) alkylene dioxy or dialkoxy methyl having the structure: ##STR3## (iii) hydroxy methyl having the structure: ##STR4## (iv) acetoxymethyl having the structure: ##STR5## and wherein R.sub.7 and R.sub.8 taken separately represent C.sub.1 -C.sub.4 lower alkyl or R.sub.7 and R.sub.8 taken together represent C.sub.2 -C.sub.4 alkylene; wherein the line represented by:[++++]is either (i) a carbon-carbon single bond when R.sub.7 and R.sub.8 taken together are C.sub.2 -C.sub.4 alkylene or (ii) no bond at all when R.sub.7 and R.sub.8 taken separately represent C.sub.1 -C.sub.4 lower alkyl. Also described are processes for preparing such mono-oxomethyl substituted polyhydrodimethanonaphthalene derivatives, and processes for using the above defined mono-oxomethyl substituted polyhydrodimethanonaphthalene derivatives for their organoleptic properties and compositions containing said mono-oxomethyl substituted polyhydrodimethanonaphthalene derivatives including perfumes, perfumed articles (such as solid or liquid anionic, cationic, nonionic or zwitterionic detergents, perfumed polymers, fabric softeners and cosmetic powders), foodstuffs, chewing gums, toothpastes, medicinal products, chewing tobaccos, smoking tobaccos and smoking tobacco articles.

    Methyl substituted norbornane carboxaldehydes, organoleptic uses thereof and process for preparing same
    9.
    发明授权
    Methyl substituted norbornane carboxaldehydes, organoleptic uses thereof and process for preparing same 失效
    甲基取代的降冰片烷甲醛，其感官用途及其制备方法

    公开(公告)号：US4335152A

    公开(公告)日：1982-06-15

    申请号：US220646

    申请日：1980-12-29

    申请人： Philip T. Klemarczyk ,  James M. Sanders ,  Manfred H. Vock ,  Joaquin F. Vinals ,  Frederick L. Schmitt ,  Edward J. Granda

    发明人： Philip T. Klemarczyk ,  James M. Sanders ,  Manfred H. Vock ,  Joaquin F. Vinals ,  Frederick L. Schmitt ,  Edward J. Granda

    IPC分类号： C07C45/69 ,  C07C47/347 ,  C11B9/00 ,  A23L2/26

    CPC分类号： C11B9/0046 ,  C07C45/69 ,  C07C47/347

    摘要： Described are methyl-substituted norbornane carboxaldehyde having the generic structure: ##STR1## wherein the dashed line is a carbon-carbon single bond, or a carbon-carbon double bond, and R.sub.1 R.sub.2 and R.sub.3 each represent methyl or hydrogen with the proviso that (i) R.sub.1 is hydrogen when R.sub.3 is methyl and (ii) R.sub.1 is methyl when R.sub.3 is hydrogen.Also described are processes and compositions for augmenting or enhancing the flavor and/or aroma of consumable materials including foodstuffs, chewing gums, medicinal products, toothpastes, chewing tobaccos, perfumes, colognes and perfumed articles such as solid or liquid anionic, cationic, nonionic or zwitterionic detergents or fabric softeners or fabric softener articles using as the essential ingredient at least one of the methyl substituted norbornane carboxaldehydes of our invention.

    摘要翻译： 描述了具有以下通用结构的甲基取代的降冰片烷甲醛：其中虚线是碳 - 碳单键或碳 - 碳双键，R1R2和R3各自表示甲基或氢，条件是（ i）当R3为甲基时，R 1为氢，（ii）当R 3为氢时，R 1为甲基。 还描述了用于增强或增强消耗材料的风味和/或香气的方法和组合物，包括食品，口香糖，药用产品，牙膏，咀嚼烟草，香水，古龙水和香料制品，例如固体或液体阴离子，阳离子，非离子或非离子的 使用本发明的至少一种甲基取代的降冰片烷甲醛作为必需成分的两性离子洗涤剂或织物柔软剂或织物柔软剂制品。