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    Process for preparing 5-acyl-2-(furfurylthio)dihydro-2,5-dialkyl-3-�2H!furanones
    1.
    发明授权
    Process for preparing 5-acyl-2-(furfurylthio)dihydro-2,5-dialkyl-3-�2H!furanones 失效
    制备5-亚氨基-2-（呋喃硫基）二氢-2,5-二烷基-3-（2H）呋喃酮的方法

    公开(公告)号：US4145354A

    公开(公告)日：1979-03-20

    申请号：US887637

    申请日：1978-03-17

    申请人： Braja D. Mookherjee ,  Donald A. Withycombe ,  Ira Katz ,  Alfred E. Goossens ,  Manfred H. Vock ,  William J. Evers ,  Joaquin F. Vinals ,  Jacob Kiwala

    发明人： Braja D. Mookherjee ,  Donald A. Withycombe ,  Ira Katz ,  Alfred E. Goossens ,  Manfred H. Vock ,  William J. Evers ,  Joaquin F. Vinals ,  Jacob Kiwala

    IPC分类号： A24B15/40 ,  C07D307/32 ,  C07D307/38 ,  C07D307/42 ,  C11B9/00 ,  C07D307/64

    CPC分类号： C07D307/32 ,  A24B15/406 ,  C07D307/38 ,  C07D307/42 ,  C11B9/0076

    摘要： Processes and compositions are described for the use in foodstuff, chewing gum, toothpaste and medicinal product flavor and aroma and tobacco flavor and aroma augmenting, modifying, enhancing and imparting compositions and as foodstuff, chewing gum, toothpaste, medicinal product and tobacco aroma and flavor imparting, augmenting, modifying and enhancing materials of one or more 5-acyl-2-(furfurylthio)dihydro-2,5-dialkyl-3-�2H!furanones having the generic structure: ##STR1## wherein R.sub.1 ', R.sub.2 ', R.sub.3 ' and R.sub.4 ' are each the same or different and each represents hydrogen or methyl produced according to the process of reacting one or more alpha, beta diketones containing from 4 up to 6 carbon atoms and having the generic structure: ##STR2## or one or more dimerization products thereof having the generic structure: ##STR3## wherein R.sub.1 ', R.sub.2 ', R.sub.3 ', R.sub.4 ', R.sub.5 ' and R.sub.6 ' are each the same or different and each represents hydrogen or methyl with furfuryl mercaptan having the structure: ##STR4## Addition of one or more 5-acyl-2-(furfurylthio)dihydro-2,5-dialkyl-3-�2H!furanones or "cis" or "trans" isomers thereof to consumable materials is indicated to produce: (A) In flavoring compositions for foodstuffs, chewing gums, toothpastes and medicinal products and in the foodstuffs, chewing gums, toothpastes, and medicinal products per se, coffee, roasted, cocoa-like, caramel-like, licorice and roasted almond aroma and flavor characteristics at levels of greater than or equal to 0.01 parts per million; and (B) In tobacco, flavoring compositions for tobacco, tobacco substitutes and flavoring compositions therefor, wheat, caramel/coffee aroma and taste characteristics prior to and on smoking and nutty/pyrazine-like flavor and aroma characteristics with roasted nut like nuances on smoking.

    Flavoring with 5-acyl-2-(furfurylthio)dihydro-2,5-dialkyl-3-[2H]furanones
    3.
    发明授权
    Flavoring with 5-acyl-2-(furfurylthio)dihydro-2,5-dialkyl-3-[2H]furanones 失效
    用5-亚氨基-2-（呋喃硫基）二氢-2H-二烷基-3-（2H）呋喃酮

    公开(公告)号：US4143173A

    公开(公告)日：1979-03-06

    申请号：US887632

    申请日：1978-03-17

    申请人： Braja D. Mookherjee ,  Donald A. Withycombe ,  Ira Katz ,  Alfred E. Goossens ,  Manfred H. Vock ,  William J. Evers ,  Joaquin F. Vinals ,  Jacob Kiwala

    发明人： Braja D. Mookherjee ,  Donald A. Withycombe ,  Ira Katz ,  Alfred E. Goossens ,  Manfred H. Vock ,  William J. Evers ,  Joaquin F. Vinals ,  Jacob Kiwala

    IPC分类号： A24B15/40 ,  C07D307/32 ,  C07D307/38 ,  C07D307/42 ,  C11B9/00 ,  A23L1/234

    CPC分类号： C07D307/32 ,  A24B15/406 ,  C07D307/38 ,  C07D307/42 ,  C11B9/0076

    摘要： Processes and compositions are described for the use in foodstuff, chewing gum, toothpaste and medicinal product flavor and aroma and tobacco flavor and aroma augmenting, modifying, enhancing and imparting compositions and as foodstuff, chewing gum, toothpaste, medicinal product and tobacco aroma and flavor imparting, augmenting, modifying and enhancing materials of one or more 5-acyl-2-(furfurylthio)dihydro-2,5-dialkyl-3-[2H]furanones having the generic structure: ##STR1## wherein R.sub.1 ', R.sub.2 ', R.sub.3 ' and R.sub.4 ' are each the same or different and each represents hydrogen or methyl produced according to the process of reacting one or more alpha, beta diketones containing from 4 up to 6 carbon atoms and having the generic structure: ##STR2## or one or more dimerization products thereof having the generic structure: ##STR3## wherein R.sub.1 ', R.sub.2 ', R.sub.3 ', R.sub.4 ', R.sub.5 ' and R.sub.6 ' are each the same or different and each represents hydrogen or methyl with furfuryl mercaptan having the structure: ##STR4## Addition of one or more 5-acyl-2-(furfurylthio)dihydro-2,5-dialkyl-3-[2H]furanones or "cis" or "trans" isomers thereof to consumable materials is indicated to produce:(A) In flavoring compositions for foodstuffs, chewing gums, toothpastes and medicinal products and in the foodstuffs, chewing gums, toothpastes and medicinal products per se, coffee, roasted, cocoa-like, caramel-like, licorice and roasted almond aroma and flavor characteritics at levels of greater than or equal to 0.01 parts per million; and(B) In tobacco, flavoring compositions for tobacco, tobacco substitutes and flavoring compositions therefor, wheat, caramel/coffee aroma and taste characteristics prior to and on smoking and nutty/pyrazine-like flavor and aroma characteristics with roasted nut like nuances on smoking.

    Process for preparing 2-acyl-5-substituted thiatetrahydrofuran-4-ones
    4.
    发明授权
    Process for preparing 2-acyl-5-substituted thiatetrahydrofuran-4-ones 失效
    2-酰基-5-取代的四氢呋喃-4-酮的制备方法

    公开(公告)号：US4138413A

    公开(公告)日：1979-02-06

    申请号：US887631

    申请日：1978-03-17

    申请人： Braja D. Mookherjee ,  William J. Evers ,  Alfred E. Goossens

    发明人： Braja D. Mookherjee ,  William J. Evers ,  Alfred E. Goossens

    IPC分类号： A24B15/40 ,  C07D307/32 ,  C07D307/64 ,  C11B9/00

    CPC分类号： C07D307/32 ,  A24B15/406 ,  C07D307/64 ,  C11B9/0076

    摘要： Described are 2-acyl-5-substituted thiatetrahydrofuran-4-ones having the generic structure: ##STR1## wherein R.sub.1, R.sub.2, R.sub.1 ' and R.sub.2 ' are the same or different and each represents hydrogen or methyl and wherein R.sub.3 represents one of C.sub.1 -C.sub.9 alkyl, benzyl, phenyl, substituted or unsubstituted allyl having the structure: ##STR2## substituted or unsubstituted 3-furyl having the structure: ##STR3## (wherein R.sub.4 and R.sub.8 are the same or different and each represents hydrogen or methyl) hydroxy alkyl, oxoalkyl, hydroxycycloalkyl or oxocycloalkyl having the structure: ##STR4## (wherein R.sub.5 and R.sub.6, taken separately, represent hydrogen or C.sub.1 -C.sub.3 alkyl or R.sub.5 and R.sub.6, taken together, complete a cycloalkyl group and wherein Q is one of the moieties: ##STR5## prepared according to the process of dimerizing one or more alpha, beta-alkane dione(s) to form one or more alpha, beta-alkane dione dimer(s) having the structure: ##STR6## and reacting the said alkane dione dimer(s) in acidic medium and in the presence of a solvent with a mercaptan, having the structure:R.sub.3 SHthe 2-acyl-5-substituted thiatetrahydrofuran-4-ones of our invention have organoleptic properties which make them useful for augmenting or enhancing the aroma or flavor of foodstuffs, tobaccos and the aroma of perfumes and perfumed articles.

    摘要翻译： 描述了具有以下通用结构的2-酰基-5-取代的硫代四氢呋喃-4-酮：其中R 1，R 2，R 1'和R 2'相同或不同，各自表示氢或甲基，并且其中R 3表示C1 -C9烷基，苄基，苯基，具有以下结构的取代或未取代的烯丙基：具有以下结构的取代或未取代的3-呋喃基：其中R 4和R 8相同或不同，各自表示氢或甲基）羟基 烷基，氧代烷基，羟基环烷基或氧代环烷基，其结构为：其中R 5和R 6分别代表氢或C 1 -C 3烷基或R 5和R 6一起形成环烷基，其中Q是部分之一 ：根据使一种或多种α，β-烷烃二酮二聚形成一种或多种具有以下结构的α，β-烷烃二酮二聚体的方法制备：＆lt; IMAGE＆gt;并使所述烷烃 二酸二聚体在酸性介质中并在溶剂存在下进行 具有硫醇，具有以下结构：

    Synthesis of triconjugated dienones and novel intermediates used in said process
    8.
    发明授权
    Synthesis of triconjugated dienones and novel intermediates used in said process 失效
    三氯联二烯酮的合成和所述方法中使用的新型中间体

    公开(公告)号：US4560802A

    公开(公告)日：1985-12-24

    申请号：US620086

    申请日：1984-06-13

    申请人： William J. Evers ,  Gilbert Stork ,  Braja D. Mookherjee ,  Howard H. Heinsohn, Jr.

    发明人： William J. Evers ,  Gilbert Stork ,  Braja D. Mookherjee ,  Howard H. Heinsohn, Jr.

    IPC分类号： C07C45/67 ,  C07C49/203 ,  C11B9/00 ,  C11D3/50 ,  C07C45/65

    CPC分类号： C11D3/50 ,  C07C45/673 ,  C07C45/676 ,  C07C49/203 ,  C07C67/293 ,  C07C67/297 ,  C11B9/0015 ,  C11B9/0061

    摘要： Described is a process for preparing triconjugated dienones defined according to the structure: ##STR1## wherein R.sub.1 represents C.sub.1 -C.sub.8 alkyl, phenyl or phenyl methyl and wherein R.sub.2 represents hydrogen or C.sub.1 -C.sub.5 lower alkyl; and wherein the wavy lines are indicative of a "cis" or a "trans" juxtaposition of the R.sub.2, methyl, acyl or vinyl moieties about one or both of the carbon-carbon double bonds which process involves the reaction of an acyl halide having the structure: ##STR2## (wherein X represents chloro) with a substituted or unsubstituted prenyl ester having the structure: ##STR3## wherein R.sub.3 represents C.sub.1 -C.sub.5 alkyl in the presence of an aluminum chloride catalyst and a methylene dichloride solvent in order to form the novel intermediate genus defined according to the structure: ##STR4## then dehydrohalogenating the compound defined according to the structure: ##STR5## using an alkali metal carbonate and a dimethylformamide solvent in order to form the novel compound genus having the structure: ##STR6## wherein one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represents a carbon-carbon single bond; and then dehydrocyloxylating the compound having the structure: ##STR7## in order to form the compound having the structure: ##STR8## the dehydroacyloxylation step taking place in the presence of an alkali metal carbonate and dimethylformamide solvent.

    摘要翻译： 描述了根据以下结构定义的三结合双酮的方法：其中R 1表示C 1 -C 8烷基，苯基或苯基甲基，并且其中R 2表示氢或C 1 -C 5低级烷基; 并且其中波浪线表示R2，甲基，酰基或乙烯基部分在一个或两个碳 - 碳双键上的“顺式”或“反式”并置，该方法涉及具有 结构：其中X表示氯，具有以下结构的取代或未取代的异戊二烯基酯：其中R 3表示C 1 -C 5烷基，在氯化铝催化剂和二氯甲烷溶剂的存在下，形成 根据以下结构定义的新型中间体：然后使用碱金属碳酸盐和二甲基甲酰胺溶剂将根据结构定义的化合物脱卤化氢，以形成具有以下结构的新颖化合物：其中 虚线中的一条代表碳 - 碳双键，另一条虚线表示碳 - 碳单键; 然后脱氢甲基化具有以下结构的化合物：以形成具有以下结构的化合物：在碱金属碳酸盐和二甲基甲酰胺溶剂的存在下进行脱氢甲酰化步骤。

    1,2,3,3,5,6-Hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol, process for producing same, intermediates useful in said process and organoleptic uses of same
    9.
    发明授权
    1,2,3,3,5,6-Hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol, process for producing same, intermediates useful in said process and organoleptic uses of same 失效
    1,2,3,3,5,6-六甲基 - 双环[2.2.2]辛-5-烯-2-醇，其制备方法，可用于所述方法的中间体和其相同的感官用途

    公开(公告)号：US4549972A

    公开(公告)日：1985-10-29

    申请号：US671406

    申请日：1984-11-14

    申请人： William J. Evers ,  Braja D. Mookherjee ,  Anton Van Ouwerkerk ,  Augustinus G. Van Loveren

    发明人： William J. Evers ,  Braja D. Mookherjee ,  Anton Van Ouwerkerk ,  Augustinus G. Van Loveren

    IPC分类号： C07C29/40 ,  C07C35/31 ,  C07C45/62 ,  C07C45/67 ,  C07C45/69 ,  C11B9/00 ,  C11D3/50 ,  C07C35/22 ,  C11D9/44

    CPC分类号： C11D3/50 ,  C07C29/40 ,  C07C35/31 ,  C07C45/62 ,  C07C45/673 ,  C07C45/69 ,  C11B9/0046 ,  C07C2102/44

    摘要： Described is 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol as a mixture of isomers and in its isomeric forms having the structures: ##STR1## and the uses thereof in augmenting or enhancing the aroma of perfume compositions, perfumed articles, and colognes. Also described is a novel process for preparing 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol by first reacting the compound having the structure: ##STR2## with the compound having the structure: ##STR3## in order to produce the ketone defined according to the structure: ##STR4## which is hydrogenated to form the compound having the structure: ##STR5## and further hydrogenated to form the ketone having the structure: ##STR6## This ketone is reacted with CH.sub.3 M wherein M represents Li or MgX and wherein X is chloro, bromo or iodo to form the organometallic intermediate defined according to the structures: ##STR7## These compounds are then hydrolyzed with dilute acid to form the organoleptically useful 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol isomers of our invention defined according to the structures: ##STR8##

    摘要翻译： 描述为1,2,3,3,5,6-六甲基 - 双环[2.2.2]辛-5-烯-2-醇作为异构体的混合物，其异构体具有以下结构：和 其用于增强或增强香料组合物，香料制品和古龙水的香气。 还描述了制备1,2,3,3,5,6-六甲基 - 双环[2.2.2]辛-5-烯-2-醇的新方法，首先使具有以下结构的化合物：＆lt; IMAGE＆gt; 具有以下结构的化合物：为了制备根据以下结构定义的酮：将其氢化形成具有以下结构的化合物：进一步氢化以形成具有以下结构的酮： 图像>该酮与CH 3 M反应，其中M表示Li或MgX，并且其中X是氯，溴或碘，以形成根据以下结构定义的有机金属中间体：然后将这些化合物用稀酸水解以形成感官有用的 本发明的1,2,3,3,5,6-六甲基 - 双环[2.2.2]辛-5-烯-2-醇异构体根据以下结构定义：