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公开(公告)号:US20220024846A1
公开(公告)日:2022-01-27
申请号:US17378936
申请日:2021-07-19
IPC分类号: C07C67/327
摘要: The present invention provides a process for preparing a compound of the following general formula (2): wherein R1 represents a monovalent hydrocarbon group having 1 to 10 carbon atoms, and R3 represents a hydrogen atom or a methyl group, the process comprising: subjecting a compound of the following general formula (1): wherein R1 and R2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 10 carbon atoms, R3 represents a hydrogen atom or a methyl group, and the wavy bond represents an E-configuration, a Z-configuration, or a mixture thereof, to a Dieckmann condensation in the presence of base to form the compound (2).
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公开(公告)号:US10882805B2
公开(公告)日:2021-01-05
申请号:US16722123
申请日:2019-12-20
发明人: Yuki Miyake , Takeshi Kinsho , Yusuke Nagae
IPC分类号: C07C29/143 , C07C51/487 , C07C51/56 , C07C45/45
摘要: The present invention provides a process for preparing 4-methyl-5-nonanone of the following formula (3): the process comprising at least a step of subjecting 2-methylpentanoic anhydride of the following formula (1) and an n-butyl nucleophilic reagent of the following general formula (2) in which M represents Li, MgZ1, or ZnZ1, wherein Z1 represents a halogen atom or an n-butyl group, to a nucleophilic substitution. reaction Coproduce 4-methyl-5-nonanone (3), as well as a process for preparing 4-methyl-5-nonanol of the following formula (5), the process comprising at least steps of preparing 4-methyl-5-nonanone; and subjecting the obtained 4-methyl-5-nonanone and a reducing agent to a reduction reaction to produce 4-methyl-5-nonanol (5).
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公开(公告)号:US10781194B2
公开(公告)日:2020-09-22
申请号:US16545887
申请日:2019-08-20
发明人: Miyoshi Yamashita , Yuki Miyake , Takeshi Kinsho
IPC分类号: C07D301/14
摘要: The object of the present invention is to provide an industrial and economical process for preparing (E2)-cis-6,7-epoxy-2-nonenal of the following formula (3): The present invention provides a process for preparing (E2)-cis-6,7-epoxy-2-nonenal (3), comprising at least steps of: subjecting (Z3,Z6)-3,6-nonadien-1-ol of the following formula (1) to oxidation: to form (E2,Z6)-2,6-nonadienal of the following formula (2); and epoxidizing the resulting (E2,Z6)-2,6-nonadienal to form the aforesaid (E2)-cis-6,7-epoxy-2-nonenal (3).
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公开(公告)号:US10781146B2
公开(公告)日:2020-09-22
申请号:US16533254
申请日:2019-08-06
发明人: Tomohiro Watanabe , Takeshi Kinsho , Yuki Miyake
IPC分类号: C07D301/03 , C07C1/32 , C07C41/01 , C07C41/20 , C07C43/15 , C07C45/42 , C07F1/00 , C07F1/02 , C07F1/04 , C07F3/02 , C07F7/08
摘要: The object of the present invention is to provide a process for preparing a 5-alken-1-yne compound efficiently at low costs and a process for preparing (2E,6Z)-2,6-nonadienal by making use of the aforesaid process for preparing the 5-alken-1-yne compound.There is provided a process for preparing a 5-alken-1-yne compound of the following formula (4): Y—Z—CR1═CR2—(CH2)2—C≡CH (4) in which Y in formula (4) represents a hydrogen atom or a hydroxyl group, the process comprising at least steps of: subjecting (i) an alkenylmagnesium halide compound prepared from a haloalkene compound of the following formula (1): Y—Z—CR1═CR2—(CH2)2—X1 (1) and (ii) an alkyne compound of the following formula (2): X2—C≡C—Si(R3)(R4)(R5) (2) to a coupling reaction to form a silane compound of the following formula (3): Y—Z—CR1═CR2—(CH2)2—C≡C—Si(R3)(R4)(R5) (3); and subjecting the silane compound (3) to a desilylation reaction to form the 5-alken-1-yne compound (4).
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公开(公告)号:US10737999B2
公开(公告)日:2020-08-11
申请号:US16388156
申请日:2019-04-18
发明人: Tomohiro Watanabe , Yuki Miyake , Takeshi Kinsho
IPC分类号: C07C67/03 , C07C17/263 , C07C29/124 , C07C21/04 , C07C33/02 , C07C69/587
摘要: A process to prepare (9E,11Z)-9,11-hexadecadienyl acetate with a good yield and high purity of the general formula (1): CH3—(CH2)3—CH═CH—CH═CH—(CH2)a—X.=The process includes a step of conducting a Wittig reaction between a haloalkenal of the general formula (2): OHC—CH═CH—(CH2)a—X, and a triarylphosphonium pentylide of the general formula (3): CH3—(CH2)3—CH−—P+Ar3, to obtain the 1-haloalkadiene, and the use of a (7E,9Z)-1-halo-7,9-tetradecadiene obtained by the process for a process of preparing (9E, 11Z)-9,11-hexadecadienyl acetate.
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公开(公告)号:US10736317B2
公开(公告)日:2020-08-11
申请号:US16223810
申请日:2018-12-18
发明人: Takeshi Kinsho , Tatsuya Fujii
摘要: A composition containing a substance having sex pheromone activity on San Jose scale (SJS) after finding the substance. More specifically, there are provided a composition having sex pheromone activity on SJS, the composition containing 3,7-dimethyl-7-octenyl propionate as a substance having sex pheromone activity on SJS; an attractant for SJS, the attractant containing the composition and a support for supporting the composition in such a manner as to allow the substance to be released; a mating disruptant for SJS, the disruptant containing the composition and a container for storing the composition in such a manner as to allow the substance to be released; and a method for attracting SJS or disrupting mating of SJS, the method including a step of installing the attractant or the mating disruptant for SJS in a field to release the substance from the attractant or the mating disruptant into the field.
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公开(公告)号:US20200062682A1
公开(公告)日:2020-02-27
申请号:US16545875
申请日:2019-08-20
发明人: Miyoshi Yamashita , Yuki Miyake , Takeshi Kinsho
IPC分类号: C07C45/29
摘要: The object of the present invention is to provide an industrial and economical process for preparing (E2,Z6)-2,6-nonadienal of the following formula (4): The present invention provides a process for preparing (E2,Z6)-2,6-nonadienal (4), comprising at least steps of: subjecting (Z3,Z6)-3,6-nonadien-1-ol of the following formula (1): to oxidation with a sulfoxide compound of the following formula (2): CH3(R′)S═O (2) in which R1 represents a monovalent hydrocarbon group having from 1 to 12 carbon atoms, in the presence of a sulfur trioxide complex and an amine compound of the following formula (3): N(R2)(R3)(R4) (3) in which R2, R3, and R4 each independently represent a monovalent hydrocarbon group having from 1 to 12 carbon atoms, or R3 and R4 may be bonded to each other to form a divalent hydrocarbon group having from 3 to 12 carbon atoms, R3-R4, to form the aforesaid (E2,Z6)-2,6-nonadienal (4).
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公开(公告)号:US10221123B1
公开(公告)日:2019-03-05
申请号:US16048943
申请日:2018-07-30
发明人: Yuki Miyake , Takeshi Kinsho , Yusuke Nagae
IPC分类号: C07C67/10 , C07C17/263 , C07C17/354
摘要: A high-yield process for preparing (4Z,7Z)-4,7-decadien-1-yl acetate, with reduced number of steps, without using a protecting group. A process for preparing (4Z,7Z)-4,7-decadien-1-yl acetate is provided, the process including at least the following steps: reducing a 10-halo-3,6-decadiyne of the general formula (1) to form a (3Z,6Z)-10-halo-3,6-decadiene of the general formula (2); and converting the (3Z,6Z)-10-halo-3,6-decadiene into (4Z,7Z)-4,7-decadien-1-yl acetate of the formula (4) having an acetoxy group in place of the halogen atom of the (3Z,6Z)-10-halo-3,6-decadiene.
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公开(公告)号:US10138191B2
公开(公告)日:2018-11-27
申请号:US15951765
申请日:2018-04-12
发明人: Yuki Miyake , Takeshi Kinsho , Tatsuya Fujii
IPC分类号: C07C45/42 , C07C41/52 , C07C21/00 , C07C17/263 , C07C21/04
摘要: Provided are a 1-halo-6,9-pentadecadiene useful as an intermediate having a skipped diene skeleton and a method for producing (7Z,10Z)-7,10-hexadecadienal. More specifically, provided are a method for producing (7Z,10Z)-7,10-hexadecadienal including steps of subjecting a Grignard reagent formed from a (6Z,9Z)-1-halo-6,9-pentadecadiene to a nucleophilic substitution reaction with an orthoformate ester to obtain a (7Z,10Z)-1,1-dialkoxy-7,10-hexadecadiene; and hydrolyzing the (7Z,10Z)-1,1-dialkoxy-7,10-hexadecadiene in the absence of an oxidation reaction to obtain the (7Z,10Z)-7,10-hexadecadienal; and the like.
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公开(公告)号:US10138179B2
公开(公告)日:2018-11-27
申请号:US15951607
申请日:2018-04-12
发明人: Naoki Ishibashi , Yuki Miyake , Yusuke Nagae , Takeshi Kinsho
摘要: Methods of producing a 2,4-dienal acetal compound and a 2,4-dienal compound useful as synthesis intermediates of a sex pheromone compound having a conjugated diene structure or a conjugated triene structure. More specifically, a method produces a 2,4-dienal acetal compound of Formula (2): R1CH═CH—CH═CH—CH(OR2)(OR3), including a step of subjecting a 2-enal acetal compound having a leaving group X at position C5 and being expressed by Formula (1): R1CHX—CH2—CH═CH—CH(OR2)(OR3) to an elimination reaction in the presence of a base to obtain the 2,4-dienal acetal compound (2); and a method for producing a 2,4-dienal compound of Formula (3): R1CH═CH—CH═CH—CHO, further including a step of deprotecting the 2,4-dienal acetal compound (2) to obtain the 2,4-dienal compound (3).
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