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1. 发明专利

JPS59112941A Preparation of 3-methyl-4-penten-1-ol derivative 失效
标题翻译： 3-甲基-4-丁烯-1-醇衍生物的制备
公开(公告)号：JPS59112941A
公开(公告)日：1984-06-29
申请号：JP22450082
申请日：1982-12-20
申请人： Kuraray Co Ltd
发明人： KANEHIRA KOUICHI , SHIONO MANZOU , FUJITA YOSHIJI , SUZUKI SHIGEAKI , OONISHI TAKASHI , NISHIDA TAKUJI
IPC分类号： C07C67/14 , C07C67/293 , C07C67/297 , C07C69/007 , C11B9/00
摘要： PURPOSE: To prepare the titled compound useful as a perfume component of perfumery, etc., economically, by reducing a specific alkene derivative corresponding to the objective compoud with metallic zinc, metallic tin and/or metallic magnesium in the presence of a proton donor solvent.
CONSTITUTION: The objective compound of formula II useful also as an adjuvant for modifying or promoting the aroma of other perfumery component or their intermediate, can be prepared easily from a raw material available easily and inexpensively, by reducing the alkene derivative of formula I (R is organic group; X is halogen) with at least one kind of metal selected from metallic zinc, metallic, metallic tin and metallic magnesium in the presence of a proton donor solvent preferably acetic acid or a mixture of acetic acid and hydrochloric acid. The starting compound of formula I can be prepared easily by reacting 4-methyl-5,6-dihydro-2H-pyran with the acid derivative of formula IIIin the presence of a Lewis acid.
COPYRIGHT: (C)1984,JPO&Japio
摘要翻译：目的：经济地制备用作香料香料成分的标题化合物，通过在质子供体溶剂存在下，通过还原与金属锌，金属锡和/或金属镁相对应的目标物质的特定烯烃衍生物。构成：通过将式I的烯烃衍生物（R（R））还原，可以容易地从廉价的原料制备用作改性或促进其它香料成分或其中间体香气的佐剂的目标化合物II 是有机基团; X是卤素）与至少一种选自金属锌，金属，金属锡和金属镁的金属在质子供体溶剂优选乙酸或乙酸和盐酸的混合物存在下反应。在路易斯酸存在下，可以通过使4-甲基-5,6-二氢-2H-吡喃与式III的酸衍生物反应来容易地制备式I的起始化合物。

2. 发明专利

JPS59112932A Preparation of 3-methyl-4-penten-1-ol 失效
标题翻译： 3-甲基-4-戊烯-1-醇的制备
公开(公告)号：JPS59112932A
公开(公告)日：1984-06-29
申请号：JP22265282
申请日：1982-12-17
申请人： Kuraray Co Ltd
发明人： KANEHIRA KOUICHI , SHIONO MANZOU , FUJITA YOSHIJI , SUZUKI SHIGEAKI , OONISHI TAKASHI , NISHIDA TAKUJI
IPC分类号： C07C29/132 , B01J27/00 , B01J27/08 , C07B61/00 , C07C27/00 , C07C33/025 , C07C67/00
CPC分类号： Y02P20/52
摘要： PURPOSE: To prepare the titled compound useful as a perfumery component of perfume, etc., easily, in high selectivity, by reducing easily and inexpensively available 4-methyl-5,6-dihydro-2H-pyran with metallic A1, and treating the product with a proton donor solvent.
CONSTITUTION: 4-Methyl-5,6-dihydro-2H-pyran of formula I is reduced with metallic A1 at 100W200°C for several hours to about 1 day in the presence of mercury halide such as HgCl
2 . In the above reaction, an alkyl halide such as CH
3 I and/ or a metalic halide such as ZnCl
2 which is a Lewis acid are added to the system to impove efficiency of the reaction. The obtained reaction product is treated with a proton donor solvent preferably water to effect the hydrolysis or solvolysis and obtain the objective compound of formula II.
USE: A perfumery component of perfume or an adjuvant to modify or promote the aroma of other perfumery component, and their synthetic intermediate.
COPYRIGHT: (C)1984,JPO&Japio
摘要翻译：目的：通过以金属A1还原易于且廉价的4-甲基-5,6-二氢-2H-吡喃的方式，以高选择性容易地制备可用作香料等香料成分的标题化合物，并处理产物与质子供体溶剂。构成：式I的4-甲基-5,6-二氢-2H-吡喃在金卤素如HgCl 2的存在下，在100-200℃下还原数小时至约1天。在上述反应中，将诸如CH 3 I的烷基卤化物和/或诸如路易斯酸的ZnCl 2等金属卤化物加入到体系中以消除反应的效率。所得反应产物用质子给体溶剂优选水处理以进行水解或溶剂解，得到目标式II的化合物。用途：用于改善或促进其他香料组分及其合成中间体香气的香料或佐剂的香料组分。

3. 发明专利

JPS59106433A Ether and its preparation 失效
标题翻译：以及其制备
公开(公告)号：JPS59106433A
公开(公告)日：1984-06-20
申请号：JP21730382
申请日：1982-12-10
申请人： Kuraray Co Ltd
发明人： SUZUKI SHIGEAKI , FUJITA YOSHIJI , SHIONO MANZOU , KANEHIRA KOUICHI , OONISHI TAKASHI , NISHIDA TAKUJI
IPC分类号： C07C69/025 , B01J31/22 , C07B61/00 , C07C41/00 , C07C41/22 , C07C43/17 , C07C43/178 , C07C67/00
CPC分类号： Y02P20/52
摘要： NEW MATERIAL:The ether of formula I [R
1 and R
2 are H or methyl and are different form each other; A is group of formula II or formula III (Z is halogen, lower acyloxy, or OH)].
EXAMPLE: 2-Chloro-3-methyl-3-butenyl prenyl ether.
USE: Synthetic intermediate of terpene.
PROCESS: The compound of formula I can be prepared by (1) reacting the ether of formula IV with the tert-butyl hypohalite of formula V (X' is halogen) or reacting the ether with hypochlorous acid in a binary system of an organic solvent (immiscible with water) and water, (2) reacting the resultant halogenated ether of formula VI (X
2 is X
1 or Cl) with an alkali metal salt of a lower aliphatic monocarboxylic acid in the presence of either (a) a 0-valent Pd complex, (b) an aprotic polar solvent, or (c) a ketone solvent, a trialkylamine and an alkali metal iodide according to the case, and if ncessary (3) hydrolyzing the obtained acyloxyether of formula VII and/or formula VIII and optionally reacting with a halogenation agent.
COPYRIGHT: (C)1984,JPO&Japio
摘要翻译：新材料：式I [R 1和R 2]的醚是H或甲基并且彼此不同; A是式II或式III的基团（Z是卤素，低级酰氧基或OH）]。实施例：2-氯-3-甲基-3-丁烯基异戊烯基醚。用途：萜烯的合成中间体。方法：式I化合物可以通过以下方法制备：（1）使式Ⅳ的醚与式Ⅴ的（Ⅴ'是卤素）的次卤酸叔丁酯反应，或者使醚与次氯酸在有机溶剂的二元体系中反应（与水不混溶）和水，（2）使得到的式VI的卤代醚（X 2为X 1或Cl）与低级脂族一元羧酸的碱金属盐在（a ）0价Pd络合物，（b）非质子极性溶剂或（c）根据情况的酮溶剂，三烷基胺和碱金属碘化物，并且如果得到（3）水解得到的式VII的酰氧基醚和 /或式VIII，并任选地与卤化剂反应。

4. 发明专利

JPS58192842A Polyprenyl compound 失效
标题翻译：聚丙烯化合物
公开(公告)号：JPS58192842A
公开(公告)日：1983-11-10
申请号：JP7416882
申请日：1982-04-30
申请人： Kuraray Co Ltd
发明人： SUZUKI SHIGEAKI , OONISHI TAKASHI , FUJITA YOSHIJI , NISHIDA TAKUJI , MORI FUMIO , TAKIGAWA TETSUO , MIZUNO MASAO
IPC分类号： C07C69/587 , A61K36/00 , C07C27/00 , C07C33/02 , C07C45/00 , C07C47/21 , C07C51/00 , C07C57/03 , C07C67/00
摘要： NEW MATERIAL:A polyprenyl compound expressed by formula I [formula II is the trans-type isoprene unit; formula III is the cis-type isoprene unit; n is an integer 11W19; Z is -CH
2 OH, -CHO or -CO
2 R (R is H or lower alkyl)].
USE: A raw material for medicines and cosmetics, particularly a synthetic intermediate for mammalian dolichol.
PROCESS: A polyprenyl halide expressed by formula IV (X is halogen) is present preferably in a solvent in the presence of a basic compound, e.g. n-butyl lithium, with a coordination compound, e.g. N,N, N',N'-tetramethylethylenediamine, and then isopentenyl alcohol expressed by formula V is reacted therewith at -70W +20°C to give the aimed compound expressed by formula I .
COPYRIGHT: (C)1983,JPO&Japio
摘要翻译：新材料：由式I表示的聚异戊二烯基化合物[式II为反式异戊二烯单元; 式III是顺式异戊二烯单元; n是整数11-19; Z是-CH 2 OH，-CHO或-CO 2 R（R是H或低级烷基）]。用途：用于药物和化妆品的原料，特别是哺乳动物多酚的合成中间体。方法：由式IV表示的聚异戊二烯基卤（X为卤素）优选存在于碱性化合物如正丁基锂，配位化合物，例如 N，N，N'，N'-四甲基乙二胺，然后将式V表示的异戊烯醇在-70〜+ 20℃下反应，得到式I表示的目标化合物。

5. 发明专利

JPS59157046A Preparation of delta, epsilon-unsaturated ketone 失效
标题翻译：三苯乙酸不饱和酮的制备
公开(公告)号：JPS59157046A
公开(公告)日：1984-09-06
申请号：JP3330383
申请日：1983-02-28
申请人： Kuraray Co Ltd
发明人： OONISHI TAKASHI , FUJITA YOSHIJI , NISHIDA TAKUJI
IPC分类号： C07C45/00 , C07C45/51 , C07C49/20 , C07C49/76 , C07C67/00
摘要： PURPOSE: To obtain the titled compound useful as an intermediate for preparing perfume, cosmetic base, etc. easily in high yield, by using a specific sulfur- containing homoallyl alcohol as a raw material, oxidizing it to give a sulfoxide, reacting it under heating.
CONSTITUTION: An allyl Grignard reagent shown by the formula I (R
1 WR
3 are H, alkyl, cycloalkyl, alkenyl, or aryl; X is Cl, Br, or I) is reacted with α-thioketone shown by the formula II [R
5 is alkyl, or aryl; R
6 is R
5 , or group shown by the formula III (R
7 is H, or alkyl; R
8 =R
5 )] to give a sulfur-containing homoallyl alcohol shown by the formula IV in high yield. The alcohol is oxidized with an oxidizing agent such as preferably m-perchlorobenzoic acid, etc. at -30W50°C to give a sulfoxide, which is reacted under heating at 100W600°C in a liquid phase or gaseous phase to give a δ, ε-unsaturated ketone shown by the formula V(R
4 is as shown for R
6 when R
6 of the formula II is R
5 , or group shown by the formula VI when R
6 is group shown by the formula III).
USE: An intermediate for preparing drugs, agricultural chemicals, etc.
COPYRIGHT: (C)1984,JPO&Japio
摘要翻译：目的：通过使用特定的含硫高聚烯丙醇作为原料，可以容易地获得用作制备香料，化妆品基质等的中间体的标题化合物，将其氧化得到亚砜，在加热下反应。构成：式I所示的烯丙基格氏试剂（R 1 -R 3是H，烷基，环烷基，烯基或芳基; X是Cl，Br或I）与α-硫酮反应，式II [R 5]是烷基或芳基; R 6是R 5，或由式III表示的基团（R 7是H，或烷基; R 8 = R 5）]，得到由下式表示的含硫高密度醇配方四，产量高。醇在-30-50℃下用氧化剂如优选的全氯苯甲酸等进行氧化，得到亚砜，其在100-600℃的加热下在液相或气相中反应得到式V所示的δ，ε-不饱和酮（R 4如式R 6的R 6为R 5时，R 6如R 6所示）或式VI所示的基团 R 6是式III）所示的基团。用途：制备药物，农药等的中间体

6. 发明专利

JPS58201745A Trimethylcyclohexene derivative and perfume composition containing the same 失效
标题翻译：含三聚氰胺的衍生物和香料组合物
公开(公告)号：JPS58201745A
公开(公告)日：1983-11-24
申请号：JP8365382
申请日：1982-05-17
申请人： Kuraray Co Ltd
发明人： OONISHI TAKASHI , SUZUKI SHIGEAKI , FUJITA YOSHIJI , NISHIDA TAKUJI
IPC分类号： C07C45/61 , A61K8/35 , A61Q13/00 , C07C45/00 , C07C49/573 , C07C67/00 , C11B9/00
摘要： NEW MATERIAL:A compound of formula I (R is lower alkyl).
EXAMPLE: 1-(3-Hydroxybutyryl)-2,4,4-trimethyl-2-cyclohexene.
USE: A perfume composition for flavoring cosmetic products, cleaning agents or detergents.
PROCESS: A compound of formula IV is reacted with an alkyl Grignard reagent, e.g. ethylmagnesium chloride, in a solvent, e.g. diethyl ether or tetrahydrofuran (THF), at -20W+35°C to give an organometallic compound of formula II, which is then reacted with an aldehyde of formula III in a solvent, e.g. benzene, at -10W+15°C to afford a compound of formula V. The resultant compound of formula V is then hydrolyzed in a weak acid, e.g. dilute hydrochloric acid, to give the aimed compound of formula I . A perfume composition containing 0.005W95wt% compound of formula I is obtained.
COPYRIGHT: (C)1983,JPO&Japio
摘要翻译：新材料：式Ⅰ化合物（R为低级烷基）。实施例：1-（3-羟基丁酰基）-2,4,4-三甲基-2-环己烯。用途：用于调味化妆品，清洁剂或洗涤剂的香料组合物。方法：式Ⅳ化合物与烷基格氏试剂反应，乙基氯化镁，在溶剂中，例如乙醚或四氢呋喃（THF）中，在-20- + 35℃下，得到式II的有机金属化合物，然后将其与式III的醛在溶剂如苯，在-10- + 15℃下，得到式V的化合物。然后将所得到的式Ⅴ化合物在弱酸例如水中水解。稀盐酸，得到目标化合物Ⅰ。得到含有0.005-95wt％式I化合物的香料组合物。

7. 发明专利

JPS59106434A Preparation of citral or isolavandulyl aldehyde 失效
标题翻译： CITRAL或异黄酮醛的制备
公开(公告)号：JPS59106434A
公开(公告)日：1984-06-20
申请号：JP1906783
申请日：1983-02-07
申请人： Kuraray Co Ltd
发明人： SUZUKI SHIGEAKI , FUJITA YOSHIJI , SHIONO MANZOU , KANEHIRA KOUICHI , OONISHI TAKASHI , NISHIDA TAKUJI
IPC分类号： C07C45/00 , B01J31/00 , B01J31/22 , C07B61/00 , C07C45/51 , C07C47/21 , C07C67/00
CPC分类号： Y02P20/52
摘要： PURPOSE: To prepare the titled compound useful as perfume, etc., by using a novel ether obtained economically from prenyl halide, prenol, etc., and heating the ether in the presence of a 0-valent Pd complex and if necessary an alkali metal salt of an aliphatic monocarboxylic acid.
CONSTITUTION: Citral or isolavandulyl aldehyde can be prepared by the thermal reaction of the novel ether of formula I [R
1 and R
2 are H or methyl; A is group of formula II (Z is halogen or acyloxy) or formula III] in the presence of a 0- valent Pd complex [e.g. Pd[P(C
6 H
5 )
3 ]
4 , etc.], if necessary in the copresence of an alkali metal salt of a lower aliphatic monocarboxylic acid (e.g. lithium acetate) at about 100W200°C. The compound of formula VI (X
2 is X
1 or Cl) which is one of the starting compounds of formula I can be obtained e.g. by reacting the ether of formula IV with the tert-butyl hypohalite of formula V (X
1 is halogen).
COPYRIGHT: (C)1984,JPO&Japio
摘要翻译：目的：通过使用从异戊基卤，异戊醇等经济地获得的新型醚，并在0价Pd络合物的存在下加热醚，并根据需要制备可用作香料等的标题化合物，并且如果需要，可以使用碱金属脂肪族单羧酸的盐。组分：柠檬醛或异山梨醛可以通过式I的新型醚的热反应制备[R 1和R 2是H或甲基; 在0价Pd络合物的存在下，A是式II的基团（Z是卤素或酰氧基）或式III]。 Pd [P（C 6 H 5）3] 4等]，如果需要，在约100-200℃下，低级脂族一元羧酸（例如乙酸锂）的碱金属盐的共存。作为式I的起始化合物之一的式VI化合物（X 2是X 1或Cl）可以例如获得。通过使式IV的醚与式V的叔丁基次卤酸盐（X 1是卤素）反应。

8. 发明专利

JPS59175451A Production of dienol derivative 失效
标题翻译：二烯衍生物的生产
公开(公告)号：JPS59175451A
公开(公告)日：1984-10-04
申请号：JP5116383
申请日：1983-03-25
申请人： Kuraray Co Ltd
发明人： SUZUKI SHIGEAKI , FUJITA YOSHIJI , SHIONO MANZOU , KANEHIRA KOUICHI , OONISHI TAKASHI , NISHIDA TAKUJI
IPC分类号： C07C69/025 , B01J31/12 , B01J31/24 , C07B61/00 , C07C67/28 , C07C67/293 , C07C69/145
CPC分类号： Y02P20/52
摘要： PURPOSE: An easily and inexpensively available alkene derivative is used as a starting compound and heated in the presence of a palladium or nickel catalyst to enable high-yield production of the titled compound used as a synthetic intermediate of a smell component for perfume.
CONSTITUTION: An alkene derivative of formula I (R is lower alkyl; Q is halogen, RCOO- group) is heated in the presence of a palladium catalyst, preferably a combination of Pd[P(C
6 H
5 )
3 ]
4 or Pd(OCOCH
3 )
2 with triphenyl phosphine or a nickel catalyst, preferably Ni(CO)
2 [P(C
6 H
5 )
3 ]
2 , when necessary, in the coexistence of an alkali metal salt of lower aliphatic carboxylic acid, a carbonate or bicarbonate alkali metal salt, preferably NaOCOCH
3 or Na
2 CO
3 , to give the compound of formula II (one of X or Y is H, the other incorporate Z to form a single bond).
COPYRIGHT: (C)1984,JPO&Japio
摘要翻译：目的：使用容易且廉价的烯烃衍生物作为起始化合物，并在钯或镍催化剂的存在下加热，以使得能够高产量地制备用作香料气味组分的合成中间体的标题化合物。组成：在钯催化剂，优选Pd [P（C 6 H 5）3] 4或Pd（OCOCH 3））的存在下加热式I的烯烃衍生物（R是低级烷基; Q是卤素，RCOO-基） 2与三苯基膦或镍催化剂，优选为Ni（CO）2 [P（C 6 H 5）3] 2，如果需要，在低级脂族羧酸的碱金属盐，碳酸盐或碳酸氢盐碱金属盐的共存下，优选 NaOCOCH 3或Na 2 CO 3，得到式II化合物（X或Y之一为H，另一个结合Z形成单键）。

9. 发明专利

JPS5910538A Preparation of propargyl type alcohol 失效
标题翻译：丙烷类型醇的制备
公开(公告)号：JPS5910538A
公开(公告)日：1984-01-20
申请号：JP11880482
申请日：1982-07-07
申请人： Kuraray Co Ltd
发明人： OONISHI TAKASHI , FUJITA YOSHIJI , NISHIDA TAKUJI
IPC分类号： C07C29/40 , C07C27/00 , C07C33/048 , C07C33/05 , C07C33/28 , C07C67/00
摘要： PURPOSE: To obtain the titled various compounds useful as a perfume, or an intermediate for other perfumes, medicines or agricultural chemicals without the limitation on the structure, by reacting an allyl Grignard reagent with ethynyl ketone.
CONSTITUTION: A compound of formula I (R
1 and R
2 are H, alkyl, cycloalkyl, alkenyl or aryl or together with the carbon atom to which they are linked form a ring; R
3 is H or lower alkyl; X is Cl, Br or I) is reacted with ethynyl ketone of formula II (R
4 is alkyl, cycloalkyl, alkenyl or aryl, etc.) at -10W+30°C to give the aimed compound of formula III. Infinitely various propargly type compounds can be easily obtained without the following limitation of the conventional method when the (iso)mesityl oxide is used as a raw material: The (iso) mesityl oxide has the methyl groups at the 3- and 5-positions of the basic skeleton and one hydrocarbon group at the 4-position thereof.
COPYRIGHT: (C)1984,JPO&Japio
摘要翻译：目的：通过使烯丙基格氏试剂与乙炔基酮反应，得到可用作香料或其它香料，药物或农药的标题化合物，不受结构限制。构成：式I化合物（R 1和R 2）是H，烷基，环烷基，链烯基或芳基，或与它们所连接的碳原子一起形成环; R 3是H或更低烷基; X是Cl，Br或I）与式II的乙炔基酮（R 4是烷基，环烷基，烯基或芳基等）在-10- + 30℃反应，得到目标化合物公式三。当使用（异）平均三氧化物作为原料时，无需常规方法的以下限制，可以容易地获得各种各样的各种各样的炔属化合物：（异）平均三氧化物在3-和5-位的甲基基本骨架和其4位上的一个烃基。

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