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    • 1. 发明授权
    • Synthesis of triconjugated dienones and intermediates used in said
process
    • 在所述方法中使用的三氯联二烯酮和中间体的合成
    • US4560791A
    • 1985-12-24
    • US551480
    • 1983-11-14
    • William J. EversGilbert StorkBraja D. MookherjeeHoward H. Heinsohn, Jr.
    • William J. EversGilbert StorkBraja D. MookherjeeHoward H. Heinsohn, Jr.
    • C07C45/67C07C49/203C07C69/157C11B9/00C11D3/50
    • C11D3/50C07C45/673C07C45/676C07C49/203C07C67/293C07C67/297C07C69/63C11B9/0015C11B9/0061
    • 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 dehydroacyloxylating 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 akali metal carbonate and dimethylformamide solvent.
    • 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; 然后将具有以下结构的化合物脱氢酰化氧化:为了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存在下进行脱氢甲酰氧基化步骤。
    • 2. 发明授权
    • Synthesis of triconjugated dienones and novel intermediates used in said
process
    • 三氯联二烯酮的合成和所述方法中使用的新型中间体
    • US4467820A
    • 1984-08-28
    • US551551
    • 1983-11-14
    • William J. EversGilbert StorkBraja D. MookherjeeHoward H. Heinsohn, Jr.
    • William J. EversGilbert StorkBraja D. MookherjeeHoward H. Heinsohn, Jr.
    • C07C45/67C07C49/203C11B9/00C11D3/50A24B3/12
    • C11D3/50C07C45/673C07C45/676C07C49/203C07C67/293C07C67/297C11B9/0015C11B9/0061
    • 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## 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 dehydroacyloxylating 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.
    • 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碳 - 碳双键中的一个或两个上的“Cis”或“反式”并置,该方法涉及具有 结构:具有以下结构的取代或未取代的异戊二烯基酯:其中R 3在氯化铝催化剂和二氯甲烷溶剂的存在下代表C 1 -C 5烷基,以形成根据 结构: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型化合物:其中虚线之一代表 碳 - 碳双键,虚线中的另一个代表碳 - 碳单键; 然后将具有以下结构的化合物脱氢酰化氧化:为了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氧基化步骤。
    • 3. 发明授权
    • Synthesis of triconjugated dienones and novel intermediates used in said
process
    • 三氯联二烯酮的合成和所述方法中使用的新型中间体
    • US4560802A
    • 1985-12-24
    • US620086
    • 1984-06-13
    • William J. EversGilbert StorkBraja D. MookherjeeHoward H. Heinsohn, Jr.
    • William J. EversGilbert StorkBraja D. MookherjeeHoward H. Heinsohn, Jr.
    • C07C45/67C07C49/203C11B9/00C11D3/50C07C45/65
    • C11D3/50C07C45/673C07C45/676C07C49/203C07C67/293C07C67/297C11B9/0015C11B9/0061
    • 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.
    • 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。
    • 4. 发明授权
    • Synthesis of triconjugated dienones and novel intermediates used in said
process
    • 三氯联二烯酮的合成和所述方法中使用的新型中间体
    • US4623749A
    • 1986-11-18
    • US620163
    • 1984-08-17
    • William J. EversGilbert StorkBraja D. MookherjeeHoward H. Heinsohn, Jr.
    • William J. EversGilbert StorkBraja D. MookherjeeHoward H. Heinsohn, Jr.
    • C07C45/67C07C49/203C07C69/145C07C69/157C11B9/00C11D3/50
    • C11D3/50C07C45/673C07C45/676C07C49/203C07C67/293C11B9/0015C11B9/0061
    • 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 with a substituted or unsubstituted prenyl ester having the structure: ##STR2## 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 a halogen-ester intermediate defined according to the structure: ##STR3## then dehydrohalogenating said halogen-ester intermediate using an alkali metal carbonate and a dimethylformamide solvent in order to form a ketoester having the structure: ##STR4## 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 dehydroacyloxylating the ketoester in the presence of an alkali metal carbonate and dimethylformamide solvent in order to form the triconjugated dienone.
    • 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,该方法涉及酰卤与 具有以下结构的取代或未取代的异戊二烯基酯:其中R 3在氯化铝催化剂和二氯甲烷溶剂的存在下代表C 1 -C 5烷基,以形成根据以下结构定义的卤素 - 酯中间体: 然后使用碱金属碳酸盐和二甲基甲酰胺溶剂将所述卤代酯中间体脱卤化氢,以形成具有以下结构的酮酯: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; 然后在碱金属碳酸盐和二甲基甲酰胺溶剂的存在下,使酮酯脱羟基酰化,以形成三羟甲基封端的二烯酮。
    • 7. 发明授权
    • 2,6,6-Trimethyl-.alpha.-(iso)propenyl-1-cyclohexene-1-methanols and
-1,3-cyclohexadiene-1-methanols and organoleptic uses thereof
    • 2,6,6-三甲基-α-(异)丙烯-1-环己烯-1-甲醇和1,3-环己二烯-1-甲醇及其感官用途
    • US4278098A
    • 1981-07-14
    • US119858
    • 1980-02-08
    • Richard A. WilsonWilliam L. SchreiberBraja D. MookherjeeJacob KiwalaJoaquin F. VinalsManfred H. VockGilbert StorkFrederick L. Schmitt
    • Richard A. WilsonWilliam L. SchreiberBraja D. MookherjeeJacob KiwalaJoaquin F. VinalsManfred H. VockGilbert StorkFrederick L. Schmitt
    • A24B15/30A24B15/34C07C29/09C07C29/40C07C29/68C07C33/14C11B9/00A24B3/12A24B15/36
    • C11B9/0034A24B15/34C07C29/09C07C29/40C07C29/68C07C33/14C07C403/08C07B2200/09C07C2101/16
    • Processes and compositions are described for use in foodstuff, chewing gum, toothpaste and medicinal product flavor and aroma, smoking tobacco flavor and aroma and perfume and perfumed article aroma augmenting, enhancing and imparting compositions; and as foodstuff, chewing gum, toothpaste, medicinal product, smoking tobacco, perfume and perfumed article aroma and/or flavor imparting materials of 2,6,6-trimethyl-.alpha.-(iso)propenyl-1-cyclohexene-1-methanol and -1,3-cyclohexadiene-1-methanol derivatives or one or more of their geometric or stereoisomers as defined by the generic structure: ##STR1## wherein one of R.sub.1, R.sub.2 or R.sub.3 is methyl and the other two of R.sub.1, R.sub.2 and R.sub.3 represents hydrogen; the dashed line is a carbon-carbon double bond or a carbon-carbon single bond; with the proviso that when R.sub.1 is hydrogen, the dashed line is a carbon-carbon double bond.Addition of one or more of the 2,6,6-trimethyl-.alpha.-(iso)propenyl-1-cyclohexene-1-methanols or -1,3-cyclohexadiene-1-methanols of our invention to consumable materials is indicated to produce:A. In foodstuffs, chewing gums, toothpastes and medicinal products, sweet, camphoraceous, damascenone, raspberry-like, raspberry juice-like, rosey, woody/ionone-like, oriental, tobacco-like, tea-like, grape-like, fruity and ionone-like aromas and flavor notes;B. In perfumes, colognes and perfumed articles, leathery, hay, woody, mustard, minty, spicey (clove) and pulegone-like aromas and hay/tobacco and honey ionone-like topnotes with safronal-like nuances; andC. In tobaccos and tobacco flavors, a sweet-musty, hay-tobacco-like, fruity-raspberry, ionone-like aroma prior to smoking and a fruity tobacco-like, Virginia tobacco-like aroma on smoking both in the main stream and in the side stream.
    • 描述了用于食品,口香糖,牙膏和药用产品风味和香气,吸烟烟草风味和香气以及香料和香料制品香气增强,增强和赋予组合物的方法和组合物; 以及2,6,6-三甲基-α-(异)丙烯基-1-环己烯-1-甲醇的食品,口香糖,牙膏,药用产品,吸烟烟草,香料和香料制品香气和/或调味材料,以及 -1,3-环己二烯-1-甲醇衍生物或其一般结构定义的其几何或立体异构体中的一种或多种:其中R 1,R 2或R 3中的一个为甲基,R 1,R 2和R 3中的另外两个为 表示氢; 虚线是碳 - 碳双键或碳 - 碳单键; 条件是当R1是氢时,虚线是碳 - 碳双键。 将本发明的一种或多种2,6,6-三甲基-α-(异)丙烯-1-环己烯-1-甲醇或-1,3-环己二烯-1-甲醇添加到消耗材料中被指示产生 :A.在食品,口香糖,牙膏和药用产品中,甜,樟脑,大马士革,覆盆子样,覆盆子汁,玫瑰,木/紫罗兰酮样,东方,烟草状,茶状,葡萄状 ,水果和紫罗兰酮样香气和风味香气; B.香水,古龙水和香水制品,革质,干草,木质,芥末,小茴香,香料(丁香)和香菇样香气和干草/烟草和蜂蜜类似紫罗兰酮的顶峰,具有丰富的细微差别; 在烟草和烟草香料中,在吸烟之前是一种甜味,干草烟样,果香 - 覆盆子,类胡萝卜素的香气,并且在主流中吸烟时具有类似烟草般的弗吉尼亚烟草样香气 并在旁边的流。