公开(公告)号：US08153826B2

公开(公告)日：2012-04-10

申请号：US12375680

申请日：2007-07-27

申请人： Takashi Aoki ,  Yoshiharu Ataka

发明人： Takashi Aoki ,  Yoshiharu Ataka

IPC分类号： C07D307/00

CPC分类号： C07D307/92

摘要： The present invention relates to industrially useful production processes in which (±)-3a,6,6,9a-tetramethyldecahydronaphtho[2,1-b]furan-2(1H)-ones and further (±)-3a,6,6,9a-tetramethyldo decahydronaphtho[2,1-b]furans are produced from raw materials which are readily available at low costs, through short steps and in a simple manner. The process for producing (±)-3a,6,6,9a-tetramethyldecahydronaphtho[2,1-b]furan-2(1H)-ones represented by the general formula (III): which includes the steps of cyclizing a homofarnesylic acid amide represented by the general formula (I): wherein R1 and R2 are each independently an alkyl group having 1 to 4 carbon atoms; and wavy lines each represents a carbon-to-carbon single bond having a cis or trans structure, and/or a monocyclohomofarnesylic acid amide represented by the general formula (II): wherein R1 and R2 and wavy lines are the same as defined above; and dotted lines represent that a carbon-to-carbon double bond is present at any of positions represented by the dotted lines, in the presence of an acid agent; and subjecting the cyclized product to hydrolysis.

摘要翻译： 本发明涉及工业上有用的生产方法，其中（±）-3a，6,6,9a-四甲基十氢萘并[2,1-b]呋喃-2（1H） - 酮和进一步（±）-3a，6,6 9a-四甲基十氢萘并[2,1-b]呋喃由原料以低成本容易获得，通过短步骤和简单的方式制备。 用于制备由通式（III）表示的（±）-3a，6,6,9a-四甲基十氢萘并[2,1-b]呋喃-2（1H）酮的方法：其包括以下步骤：使高丝氨酸 由通式（I）表示的酰胺：其中R 1和R 2各自独立地为具有1至4个碳原子的烷基; 并且波浪线各自表示具有顺式或反式结构的碳 - 碳单键和/或由通式（II）表示的单环洛夫糖酰胺：其中R1和R2和波浪线与上述定义相同; 虚线表示在酸剂的存在下，由虚线表示的任何位置存在碳 - 碳双键; 并使环化产物水解。

公开(公告)号：US20090270639A1

公开(公告)日：2009-10-29

申请号：US12375680

申请日：2007-07-27

申请人： Takashi Aoki ,  Yoshiharu Ataka

发明人： Takashi Aoki ,  Yoshiharu Ataka

IPC分类号： C07D307/33 ,  C07D307/92

CPC分类号： C07D307/92

摘要： The present invention relates to industrially useful production processes in which (±)-3a,6,6,9a-tetramethyldecahydronaphtho[2,1-b]furan-2(1H)-ones and further (±)-3a,6,6,9a-tetramethyldo decahydronaphtho[2,1-b]furans are produced from raw materials which are readily available at low costs, through short steps and in a simple manner. The process for producing (±)-3a,6,6,9a-tetramethyldecahydronaphtho[2,1-b]furan-2(1H)-ones represented by the general formula (III): which includes the steps of cyclizing a homofarnesylic acid amide represented by the general formula (I): wherein R1 and R2 are each independently an alkyl group having 1 to 4 carbon atoms; and wavy lines each represents a carbon-to-carbon single bond having a cis or trans structure, and/or a monocyclohomofarnesylic acid amide represented by the general formula (II): wherein R1 and R2 and wavy lines are the same as defined above; and dotted lines represent that a carbon-to-carbon double bond is present at any of positions represented by the dotted lines, in the presence of an acid agent; and subjecting the cyclized product to hydrolysis.

摘要翻译： 本发明涉及工业上有用的生产方法，其中（±）-3a，6,6,9a-四甲基十氢萘并[2,1-b]呋喃-2（1H） - 酮和进一步（±）-3a，6,6 9a-四甲基十氢萘并[2,1-b]呋喃由原料以低成本容易获得，通过短步骤和简单的方式制备。 用于制备由通式（III）表示的（±）-3a，6,6,9a-四甲基十氢萘并[2,1-b]呋喃-2（1H）酮的方法：其包括以下步骤：使高丝氨酸 由通式（I）表示的酰胺：其中R 1和R 2各自独立地为具有1至4个碳原子的烷基; 并且波浪线各自表示具有顺式或反式结构的碳 - 碳单键和/或由通式（II）表示的单环洛夫糖酰胺：其中R1和R2和波浪线与上述定义相同; 虚线表示在酸剂的存在下，由虚线表示的任何位置存在碳 - 碳双键; 并使环化产物水解。

公开(公告)号：US20110034722A1

公开(公告)日：2011-02-10

申请号：US12937443

申请日：2009-04-02

申请人： Makiko Muroi ,  Atsushi Nagasawa ,  Kunshi Matsumoto ,  Mariko Kagaya ,  Hirotsugu Nishimura ,  Yoshiharu Ataka

发明人： Makiko Muroi ,  Atsushi Nagasawa ,  Kunshi Matsumoto ,  Mariko Kagaya ,  Hirotsugu Nishimura ,  Yoshiharu Ataka

IPC分类号： C07C69/716 ,  C07C45/61

CPC分类号： C07C51/00 ,  C07C45/66 ,  C07C67/347 ,  C07C2601/08 ,  C07C49/597 ,  C07C69/716

摘要： The present invention relates to [1] a process for producing a 2-alkyl-2-cycloalken-1-one represented by the following general formula (2), which includes the step of subjecting a 2-(1-hydroxyalkyl)cycloalkan-1-one to dehydration and isomerization in the co-existence of an acid and a platinum group metal catalyst, and [2] a process for producing an alkyl(3-oxo-alkylcycloalkyl)acetate which is useful as a perfume material, using the 2-alkyl-2-cycloalken-1-one: wherein n is an integer of 1 or 2; and R1 and R2 are each independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms with the proviso that R1 and R2 may form a ring through a carbon atom adjacent thereto.

摘要翻译： 本发明涉及[1]由以下通式（2）表示的2-烷基-2-环烯烃-1-酮的制备方法，其包括使2-（1-羟基烷基）环烷烃-1-酮 1-酮在酸和铂族金属催化剂的共存下脱水和异构化，[2]制备可用作香料的烷基（3-氧代 - 烷基环烷基）乙酸酯的方法，使用 2-烷基-2-环烯烃-1-酮：其中n为1或2的整数; 并且R 1和R 2各自独立地为氢原子或具有1至8个碳原子的烷基，条件是R 1和R 2可以通过与其相邻的碳原子形成环。

公开(公告)号：US20050004210A1

公开(公告)日：2005-01-06

申请号：US10878389

申请日：2004-06-29

申请人： Akira Umada ,  Yoshiharu Ataka ,  Shigeyoshi Tanaka ,  Kazuki Naito ,  Koji Mine

发明人： Akira Umada ,  Yoshiharu Ataka ,  Shigeyoshi Tanaka ,  Kazuki Naito ,  Koji Mine

IPC分类号： C07D309/08 ,  C07D309/18 ,  A61K31/35 ,  C07

CPC分类号： C07D309/18 ,  C07D309/08

摘要： The invention relates to a process for producing a mixture of a pyran represented by the formula (II) and a hydroxypyran represented by the formula (III) by reacting aldehyde (I) with isoprenol. wherein R1 represents an alkyl or alkenyl group having 1 to 12 carbon atoms, an optionally alkyl- or alkoxy-substituted aryl group having 6 to 12 carbon atoms in total, or the like. Further, the hydroxypyran compound in the resulting mixture is subjected to dehydration reaction in the presence of an acid to produce a pyran compound represented by the formula (II).

摘要翻译： 本发明涉及通过使醛（I）与异戊二烯醇反应来制备由式（II）表示的吡喃与式（III）表示的羟基吡喃的混合物的方法。 其中R 1表示具有1至12个碳原子的烷基或烯基，任选烷基或烷氧基取代的总共具有6至12个碳原子的芳基等。 此外，将所得混合物中的羟基吡喃化合物在酸的存在下进行脱水反应，得到式（II）表示的吡喃化合物。

公开(公告)号：US08816136B2

公开(公告)日：2014-08-26

申请号：US13381504

申请日：2010-06-30

申请人： Mitsuharu Kitamura ,  Shinji Kotachi ,  Shinya Nagasawa ,  Yoshiharu Ataka

发明人： Mitsuharu Kitamura ,  Shinji Kotachi ,  Shinya Nagasawa ,  Yoshiharu Ataka

IPC分类号： C07C31/13

CPC分类号： C07C29/149 ,  C07C51/58 ,  C07C67/14 ,  C07C2601/14 ,  C07C31/1355 ,  C07C69/75 ,  C07C61/08

摘要： Disclosed is a method for producing an alicyclic alcohol represented by general formula (III) which is useful as a starting material for a flavor mixture or the like at low cost in high yield. The alicyclic alcohol represented by general formula (III) is produced by preparing a cyclohexanecarbonyl compound represented by general formula (II) through the carbonylation of an unsaturated hydrocarbon represented by general formula (I) (preferably a compound obtained through the partial reduction of a diene compound) using carbon monoxide in the presence of HF, and thereafter reducing the cyclohexanecarbonyl compound. In formulae (I), (II), and (III), R1 represents an alkyl group having 1 to 4 carbon atoms, R2 represents an alkyl group having 1 to 4 carbon atoms, R3 represents an OH group, fluorine, or an OR4 group, and R4 represents an alkyl group having 1 to 4 carbon atoms.

摘要翻译： 公开了以低成本，高收率地用作风味剂混合物等的起始原料的由通式（III）表示的脂环族醇的制造方法。 由通式（III）表示的脂环醇通过通过通式（I）表示的不饱和烃的羰基化（优选通过二烯的部分还原获得的化合物）制备通式（II）表示的环己烷羰基化合物 化合物），在HF存在下使用一氧化碳，然后还原环己烷羰基化合物。 在式（I），（II）和（III）中，R 1表示具有1至4个碳原子的烷基，R 2表示具有1至4个碳原子的烷基，R 3表示OH基，氟或OR 4 并且R 4表示具有1至4个碳原子的烷基。

公开(公告)号：US08378147B2

公开(公告)日：2013-02-19

申请号：US12988164

申请日：2009-04-02

申请人： Kunshi Matsumoto ,  Atsushi Nagasawa ,  Yoshiharu Ataka

发明人： Kunshi Matsumoto ,  Atsushi Nagasawa ,  Yoshiharu Ataka

IPC分类号： C07C45/67 ,  B01J21/18

CPC分类号： C07C45/67 ,  B01J21/18 ,  B01J23/42 ,  B01J23/44 ,  B01J37/18 ,  C07C2601/10

摘要： The present invention relates to a process for producing a 2-alkyl-2-cycloalken-1-one represented by the following general formula (2), including the step of reacting a 2-alkylidene cycloalkanone in the presence of a palladium and/or platinum catalyst which is treated in the following steps (a) and (b); and a method for activating the palladium and/or platinum catalyst including the following steps (a) and (b): Step (a): activating the palladium and/or platinum catalyst in an atmosphere containing a hydrogen gas; and Step (b): replacing the hydrogen gas being present as the atmosphere for the catalyst in the step (a), with an inert gas to remove the hydrogen gas out of the reaction system, wherein m is 0 to 3; n is 1 or 2; R1 and R2 are each independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms; and R3 is an alkyl group having 1 to 5 carbon atoms. In accordance with the present invention, the 2-alkyl-2-cycloalken-1-one can be produced with a high purity and a high productivity.

摘要翻译： 本发明涉及一种由以下通式（2）表示的2-烷基-2-环烯烃-1-酮的制备方法，包括使2-亚烷基环烷酮在钯和/或 铂催化剂，其在以下步骤（a）和（b）中处理; 以及包括以下步骤（a）和（b）活化钯和/或铂催化剂的方法：步骤（a）：在包含氢气的气氛中活化钯和/或铂催化剂; 和步骤（b）：用惰性气体代替在步骤（a）中作为催化剂的气氛存在的氢气，以将氢气从反应体系中除去，其中m为0-3; n为1或2; R 1和R 2各自独立地为氢原子或具有1至8个碳原子的烷基; R3为碳原子数为1〜5的烷基。 根据本发明，可以以高纯度和高生产率制备2-烷基-2-环烯烃-1-酮。

公开(公告)号：US09056820B2

公开(公告)日：2015-06-16

申请号：US13977274

申请日：2011-12-27

申请人： Mitsuharu Kitamura ,  Yoshiharu Ataka ,  Kazuyuki Fukuda

发明人： Mitsuharu Kitamura ,  Yoshiharu Ataka ,  Kazuyuki Fukuda

IPC分类号： C07C31/135 ,  C11B9/00 ,  C07C29/147 ,  C07C53/44 ,  C07C35/08 ,  C07C29/149 ,  C07C51/58 ,  C07C67/14

CPC分类号： C07C35/08 ,  C07C29/149 ,  C07C31/1355 ,  C07C51/58 ,  C07C67/14 ,  C07C2601/14 ,  C11B9/0034 ,  C07C61/08 ,  C07C69/75

摘要： Provided is an alicyclic alcohol compound which can be used as a raw material for a compound perfume, and which has excellent floral-green-like aromas which are crisp and fresh; also provided are a manufacturing method for the same, and a perfume composition which contains the alicyclic alcohol compound. An alicyclic alcohol compound having a specified structure represented by chemical formula (1) has excellent floral-green-like aromas which are crisp and fresh; and a method for manufacturing the alicyclic alcohol compound represented by chemical formula (1) by reacting, in the presence of hydrogen fluoride, 1-isopropyl-4-methylcyclohexene and carbon monoxide, reacting the resulting 4-isopropyl-1-methylcyclohexane carboxylic acid fluoride with alcohol, and, after having acquired a cyclohexane carbonyl compound, reducing the cyclohexane carbonyl compound.

摘要翻译： 提供可用作复合香料的原料的脂环族醇化合物，其具有优良的鲜绿色的花绿色香气， 还提供了其制备方法和含有脂环族醇化合物的香料组合物。 由化学式（1）表示的具有特定结构的脂环族醇化合物具有优异的花绿色香气，其清爽新鲜; 以及在氟化氢，1-异丙基-4-甲基环己烯和一氧化碳的存在下使化学式（1）表示的脂环族醇化合物的制造方法，使得到的4-异丙基-1-甲基环己烷羧酸氟化物 与醇反应后，在获得环己烷羰基化合物后，还原环己烷羰基化合物。

公开(公告)号：US20130345477A1

公开(公告)日：2013-12-26

申请号：US13977221

申请日：2011-12-27

申请人： Mitsuharu Kitamura ,  Yoshiharu Ataka ,  Kazuyuki Fukuda

发明人： Mitsuharu Kitamura ,  Yoshiharu Ataka ,  Kazuyuki Fukuda

IPC分类号： C07C31/135 ,  C07C29/147

CPC分类号： C07C31/1355 ,  C07C29/147 ,  C07C29/149 ,  C07C31/135 ,  C07C53/44 ,  C07C2601/14 ,  C11B9/0034

摘要： Provided is an alicyclic alcohol compound which can be used as a raw material for a compound perfume, and which has excellent floral-green-like aromas which are crisp and fresh; also provided are a manufacturing method for the same, and a perfume composition which contains the alicyclic alcohol compound. An alicyclic alcohol compound having a specified structure represented by chemical formula (1) has excellent floral-green-like aromas which are crisp and fresh; and a method for manufacturing the alicyclic alcohol compound represented by chemical formula (1) by reacting, in the presence of hydrogen fluoride, 4-isopropyl-1-methylcyclohexene and carbon monoxide, isomerising the resulting 4-isopropyl-1-methylcyclohexane carboxylic acid fluoride, thus making 2-methyl-2-(4-methylcyclohexyl)-propionyl fluoride, reacting with alcohol and acquiring a cyclohexane carbonyl compound, and then reducing the cyclohexane carbonyl compound.

摘要翻译： 提供可用作复合香料的原料的脂环族醇化合物，其具有优良的鲜绿色的花绿色香气， 还提供了其制备方法和含有脂环族醇化合物的香料组合物。 由化学式（1）表示的具有特定结构的脂环族醇化合物具有优异的花绿色香气，其清爽新鲜; 以及通过在氟化氢，4-异丙基-1-甲基环己烯和一氧化碳的存在下，使得到的4-异丙基-1-甲基环己烷羧酸氟化物异构化来制造由化学式（1）表示的脂环族醇化合物的方法 ，由此制备2-甲基-2-（4-甲基环己基） - 丙酰氟，与醇反应并获得环己烷羰基化合物，然后还原环己烷羰基化合物。

公开(公告)号：US20050101799A1

公开(公告)日：2005-05-12

申请号：US10942880

申请日：2004-09-17

申请人： Mitsuharu Kitamura ,  Takashi Kojima ,  Yoshiharu Ataka ,  Tomoaki Kubota ,  Kinji Kato ,  Kazuyuki Fukuda

发明人： Mitsuharu Kitamura ,  Takashi Kojima ,  Yoshiharu Ataka ,  Tomoaki Kubota ,  Kinji Kato ,  Kazuyuki Fukuda

IPC分类号： C07C51/58 ,  C07C61/135 ,  C07C67/14 ,  C07C67/60 ,  C07C69/74

CPC分类号： C07C67/60 ,  C07B2200/09 ,  C07C51/58 ,  C07C67/14 ,  C07C2603/68 ,  C07C61/135 ,  C07C69/753

摘要： An object of the present invention is to provide a process for producing high purity tricyclo[5.2.1.02,6]decane-2-carboxylic acid ester which has a small content of an unsaturated compound and which has an excellent fragrance and is useful as a perfume or a perfume component. In a process for producing tricyclo[5.2.1.02,6]decane-2-carboxylic acid ester by reacting tricyclo[5.2.1.02,6]deca-3-ene with carbon monoxide and alcohol in the presence of HF, carried out separately are (a) a step in which tricyclo[5.2.1.02,6]deca-3-ene is reacted with carbon monoxide to produce acyl fluoride and (b) a step in which acyl fluoride obtained in the step described above is reacted with alcohol to produce an ester, whereby tricyclo[5.2.1.02,6]decane-2-carboxylic acid ester having a small content of an unsaturated compound can be obtained at a high yield. Also, the reaction conditions at the step (a) described above are selected or a step for carrying out isomerization reaction of tricyclo[5.2.1.02,6] decane-2-carboxylic fluoride obtained at the step (a) is interposed between the step (a) and the step (b), whereby capable of being efficiently produced is tricyclo[5.2.1.02,6]decane-2-carboxylic acid ester having a structural ratio of 1.0 or more in exo-tricyclo[5.2.1.02,6]decane-endo-2-carboxylic acid ester/endo-tricyclo[5.2.1.02,6]decane-exo-2-carboxylic acid ester. Further, the crude product of tricyclo[5.2.1.02,6]decane-2-carboxylic acid ester thus obtained is subjected to contact treatment with specific glycol in the presence of an acid catalyst and then distilled, whereby high purity tricyclo[5.2.1.02,6]decane-2-carboxylic acid ester which is reduced in impurity aldehyde and which is excellent in a fragrance can industrially advantageously be produced.

公开(公告)号：US08367874B2

公开(公告)日：2013-02-05

申请号：US12810609

申请日：2008-12-22

申请人： Junko Ueda ,  Yoshiharu Ataka

发明人： Junko Ueda ,  Yoshiharu Ataka

IPC分类号： C07C45/64

CPC分类号： C07C45/72 ,  C07C49/493

摘要： The present invention relates to a process for producing a 2-(1-hydroxyalkyl)cycloalkanone which includes the steps of (i) continuously mixing a cycloalkanone and an alkyl aldehyde in the water and a base catalyst to form a reaction system and allow both the compounds to react with each other; (ii) continuously withdrawing a reaction mixture produced in the step (i) out of the reaction system while allowing the step (i) to proceed; and (iii) adding an additional amount of water containing the base catalyst to the reaction system to maintain a constant concentration of the base catalyst and/or a constant amount of water in the reaction system while allowing the step (ii) to proceed.

摘要翻译： 本发明涉及一种2-（1-羟基烷基）环烷酮的制备方法，其包括以下步骤：（i）在水中连续混合环烷酮和烷基醛和碱催化剂以形成反应体系， 化合物相互反应; （ii）在允许步骤（i）进行的同时，将步骤（i）中产生的反应混合物从反应体系中连续取出; 和（iii）向所述反应体系中加入额外量的含有所述碱催化剂的水以在所述步骤（ii）进行的同时维持所述反应体系中所述碱催化剂和/或恒定量的水的恒定浓度。