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    • 93. 发明授权
    • Isosolanone and solanone intermediates and organoleptic uses
    • Isosolanone和solanone中间体和感官用途
    • US4560499A
    • 1985-12-24
    • US609349
    • 1984-06-22
    • John B. HallJames M. SandersJames N. Siano
    • John B. HallJames M. SandersJames N. Siano
    • A24B15/32C07C29/40C07C33/02C07C45/54C07C45/67C07C45/75C07C49/203C11D3/50C11B9/00
    • C11D3/50A24B15/32C07C29/40C07C33/02C07C45/54C07C45/67C07C45/75C07C49/203C07C67/03
    • Described is a novel genus of compounds defined according to the structure: ##STR1## wherein Z represents hydrogen, MgX and the moiety having the structure: ##STR2## and X represents chloro, bromo or iodo; as well as the novel compounds defined according to the structures: ##STR3## and mixtures of same shown according to the structure: ##STR4## wherein the wavy lines indicate both cis and trans juxtaposition of the hydrogen and methallyl moieties about the carbon-carbon double bond; uses of same as intermediates in a process for producing isosolanone which is a mixture of compounds having the structures: ##STR5## or shown by the single structure: ##STR6## and solanone which is a mixture of compounds having the structures: ##STR7## or shown by the structure: ##STR8## wherein the wavy lines are indicative of a cis or trans juxtaposition of the hydrogen or 2-propenyl moieties about the double bond; and organoleptic uses of the compounds having the structures: ##STR9##
    • 描述了根据以下结构定义的化合物的新颖属性:其中Z表示氢,MgX和具有以下结构的部分:其中X表示氯,溴或碘; 以及根据以下结构定义的新颖化合物:根据以下结构显示的相同的结构:其中波浪线表示氢和甲代烯丙基部分在碳 - 碳双键上的顺式和反式并置 键; 在作为制备具有以下结构的化合物的混合物的方法中使用与中间体的相同的化合物:具有以下结构的化合物:或者由单一结构显示:作为化合物的混合物,其具有以下结构:或 由以下结构示出:其中波浪线表示在双键上的氢或2-丙烯基部分的顺式或反式并置; 和具有以下结构的化合物的感官用途:
    • 94. 发明授权
    • Process for the production of isosolanone and solanone, intermediates
useful in said process and organoleptic uses of said intermediates
    • 用于生产异溶胶酮和溶胶酮的方法,可用于所述方法的中间体和所述中间体的感官用途
    • US4609754A
    • 1986-09-02
    • US609348
    • 1984-06-22
    • John B. HallJames M. SandersJames N. Siano
    • John B. HallJames M. SandersJames N. Siano
    • A24B15/32C07C29/40C07C33/02C07C45/54C07C45/67C07C45/75C07C49/203C11D3/50C07C69/72
    • C11D3/50A24B15/32C07C29/40C07C33/02C07C45/54C07C45/67C07C45/676C07C45/75C07C49/203C07C67/03C07C69/72
    • Described is a novel genus of compounds defined according to the structure: ##STR1## wherein Z represents hydrogen, MgX and the moiety having the structure: ##STR2## and X represents chlor, bromo, or iodo; as well as 5-isopropyl-8-methyl-5,8-nonadien-2-one; uses of same as intermediates in a process for producing isosolanone and solanone; and organoleptic uses of 5-isopropyl-8-methyl-5,8-nonadien-2-one and 2,6-dimethyl-5-methylene-1-hepten-4-ol.The novel process of our invention involved the steps of:(i) formation of the compound having the structure: ##STR3## by means of reacting 3-methyl-2-methylenebutanal with the compound having the structure: ##STR4## (ii) acid hydrolysis of the resulting compound in order to form 2,6-dimethyl-5-methylene-1-heptene-4-ol;(iii) reaction of 2,6-dimethyl-5-methylene-1-hepten-4-ol with methyl aceto acetate in order to form 2,6-dimethyl-5-methylene-1-hepten-4-yl aceto acetate or, directly, 5-isopropyl-8-methyl-5,8-nonadiene-2-one;(iv) reacting 2,6-dimethyl-5-methylene-1-hepten-4-yl aceto acetate in the presence of an appropriate catalyst to form the 5-isopropyl-8-methyl-5,8-nonadiene-2-one; and(v) isomerizing the 5-isopropyl-8-methyl-5,8-nonadien-2-one in order to form a mixture of solanone and the isosolanone or 5-isopropyl-8-methyl-5,8-nonadiene-2-one.
    • 描述了根据以下结构定义的化合物的新颖属性:其中Z表示氢,MgX和具有以下结构的部分:< IMAGE> X表示氯,溴或碘; 以及5-异丙基-8-甲基-5,8-壬二烯-2-酮; 在制备异山芋酮和solanone的方法中使用与中间体相同的物质; 和5-异丙基-8-甲基-5,8-壬二烯-2-酮和2,6-二甲基-5-亚甲基-1-庚烯-4-醇的感官用途。 本发明的新方法涉及以下步骤:(i)通过使3-甲基-2-亚甲基丁醛与具有以下结构的化合物反应形成具有以下结构的化合物:(ⅱ)酸 水解所得化合物以形成2,6-二甲基-5-亚甲基-1-庚烯-4-醇; (iii)2,6-二甲基-5-亚甲基-1-庚烯-4-醇与乙酰乙酸甲酯的反应,以形成2,6-二甲基-5-亚甲基-1-庚烯-4-基乙酸乙酯或 直接得到5-异丙基-8-甲基-5,8-壬二烯-2-酮; (iv)使2,6-二甲基-5-亚甲基-1-庚烯-4-基乙酸乙酯在合适的催化剂存在下反应,形成5-异丙基-8-甲基-5,8-壬二烯-2-酮 ; 和(v)异构化5-异丙基-8-甲基-5,8-壬二烯-2-酮,以形成Solone和二异丙基酮或5-异丙基-8-甲基-5,8-壬二烯-2-酮的混合物 -一。