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公开(公告)号：US11097999B2
公开(公告)日：2021-08-24
申请号：US17010236
申请日：2020-09-02
发明人： Yuki Miyake , Naoki Ishibashi , Takeshi Kinsho
摘要： A process for preparing 4-penten-2-ynal of the following formula (2): CH2═CHC≡CCHO (2) the process comprising a step of hydrolyzing a 5,5-dialkoxy-1-penten-3-yne compound of the following general formula (1): CH2═CHC≡CCH(OR1)(OR2) (1) wherein R1 and R2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, preferably 1 to 8, more preferably 1 to 4, or R1 and R2 may be bonded to each other to form a divalent hydrocarbon group, R1-R2, having from 2 to 10 carbon atoms, to obtain 4-penten-2-ynal (2).
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52.发明申请公开(公告)号：US20210198172A1
公开(公告)日：2021-07-01
申请号：US17128306
申请日：2020-12-21
发明人： Yuki Miyake , Miyoshi Yamashita , Takeshi Kinsho , Akihiro Baba
摘要： The present invention provides a process for preparing an alkoxymethyl alkynyl ether compound having a terminal triple bond of the following formula (4): H—C≡C(CH2)aOCH2OCH2R (4), wherein R represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, and “a” represents an integer of 1 to 10, the method comprising subjecting an alkynol compound having a terminal triple bond of the following formula (1): H—C≡C(CH2)aOH (1), wherein “a” is as defined above, to an alkoxymethylation with a halomethyl alkyl ether compound of the following formula (3): RCH2OCH2X (3), wherein X represents a halogen atom, and R is as defined above, in the presence of a dialkylaniline compound of the following formula (2): [CH3(CH2)b][CH3(CH2)c]NC6H5 (2), wherein b and c represent, independently of each other, an integer of 0 to 9, to form the alkoxymethyl alkynyl ether compound (4) having a terminal triple bond.
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公开(公告)号：US20210009489A1
公开(公告)日：2021-01-14
申请号：US16922679
申请日：2020-07-07
发明人： Yuki Miyake , Takeshi Kinsho , Ryo Komatsu
IPC分类号： C07C17/275 , A01N29/02
摘要： The present invention provides a process for preparing an 11-halo-3-undecene compound (7) in which X1 represents a halogen atom, the process comprising a step of subjecting a nucleophilic reagent, 3-hexenyl compound (5): in which M2 represents Li or MgZ2, wherein Z2 represents a halogen atom or a 3-hexenyl group, to a coupling reaction with a 1-halo-5-halopentane compound (6) in which X3 and X4 may be same with or different from each other and represent a halogen atom, to produce the 11-halo-3-undecene compound (7). The present invention also provides a process for preparing a 9-dodecenal compound (4): the process comprising a step of subjecting a nucleophilic reagent, 8-undecenyl compound (1) in which M1 represents Li or MgZ1, wherein Z1 represents a halogen atom or an 8-undecenyl group, and an orthoformic ester compound (2) in which R may be same with or different from each other and represents an alkyl group having 1 to 6 carbon atoms, to a nucleophilic substitution reaction to produce a 1,1-dialkoxy-9-dodecene compound (3) in which R are as defined above; and hydrolyzing the 1,1-dialkoxy-9-dodecene compound (3) thus obtained to produce the 9-dodecenal compound (4).
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公开(公告)号：US10730817B2
公开(公告)日：2020-08-04
申请号：US16545875
申请日：2019-08-20
发明人： Miyoshi Yamashita , Yuki Miyake , Takeshi Kinsho
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(R1)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：US20200062725A1
公开(公告)日：2020-02-27
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：US09822050B2
公开(公告)日：2017-11-21
申请号：US15447817
申请日：2017-03-02
IPC分类号： C07C45/00 , C07C43/303 , C07C41/54
CPC分类号： C07C43/303 , C07B2200/09 , C07C41/50 , C07C41/54 , C07C45/00 , C07C45/515 , C07C45/59 , C07D317/12 , C07C47/21
摘要： Provided are a terminal conjugated trienal acetal compound useful as an intermediate for producing a terminal conjugated trienal compound, and a method for producing a terminal conjugated trienal compound through deprotection of the terminal conjugated trienal acetal compound. More specifically, provided are a terminal conjugated trienal acetal compound represented by General Formula (1); a method for producing a (Z,E)-terminal conjugated trienal acetal compound, the method comprising the step of: reacting a phosphonium salt represented by General Formula (7) with (E)-2,4-pentadienal through Wittig reaction to obtain a (Z,E)-terminal conjugated trienal acetal compound represented by General Formula (3); and a method for producing a terminal conjugated trienal compound, the method comprising the step of: deprotecting the terminal conjugated trienal acetal compound represented by General Formula (1) to obtain a terminal conjugated trienal compound represented by General Formula (2).
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公开(公告)号：US20170079267A1
公开(公告)日：2017-03-23
申请号：US15259500
申请日：2016-09-08
CPC分类号： A01N35/02 , A01N27/00 , A01N2300/00
摘要： Provided are a novel sex pheromone composition of peach fruit moth which is expected to be used in emergence forecast, mass trapping and mating disruption and has higher attractiveness than that of conventional sex pheromone compositions; and a sex attractant, a mating disruptant and a control method comprising the novel sex pheromone composition as an active ingredient. Specifically provided are a novel sex pheromone composition of peach fruit moth comprising (Z)-7-tricosene and (Z)-13-eicosen-10-one, a sex attractant and a mating disruptant comprising this sex pheromone composition, and a method for controlling peach fruit moth using this sex pheromone composition.
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58.发明授权公开(公告)号：US09126920B2
公开(公告)日：2015-09-08
申请号：US14527239
申请日：2014-10-29
发明人： Takeshi Kinsho , Naoki Ishibashi , Miyoshi Yamashita , Yuki Miyake , Akihiro Baba , Yusuke Nagae
IPC分类号： C07C67/08 , C07C51/353 , C07C51/09
CPC分类号： C07C51/353 , A01N49/00 , C07C29/147 , C07C51/09 , C07C67/14 , C07C67/333 , C07C69/587 , C07C33/02 , C07C57/03 , C07C69/24
摘要： Provided is a simple and efficient method for producing 2-isopropylidene-5-methyl-4-hexenyl butyrate. More specifically, provided is a method for producing 2-isopropylidene-5-methyl-4-hexenyl butyrate, the method including the steps of: isomerizing 2-isopropenyl-5-methyl-4-hexenoic acid ester (1) into 2-isopropylidene-5-methyl-4-hexenoic acid ester (2), reducing thus formed 2-isopropylidene-5-methyl-4-hexenoic acid ester (2) into 2-isopropylidene-5-methyl-4-hexenol (3), and butyrylating thus formed 2-isopropylidene-5-methyl-4-hexenol (3) into 2-isopropylidene-5-methyl-4-hexenyl butyrate (4), wherein R represents a C1-10 hydrocarbon group.
摘要翻译： 提供了生产2-异亚丙基-5-甲基-4-己烯基丁酸酯的简单有效的方法。 更具体地说，提供了2-异亚丙基-5-甲基-4-己烯基丁酸酯的制造方法，其特征在于，将2-异丙烯基-5-甲基-4-己烯酸酯（1）异构化成2-异丙叉 -5-甲基-4-己烯酸酯（2），将由此形成的2-异亚丙基-5-甲基-4-己烯酸酯（2）还原成2-异亚丙基-5-甲基-4-己烯醇（3），和 将由此形成的2-异亚丙基-5-甲基-4-己烯醇（3）丁酰化成2-异丙叉-5-甲基-4-己烯基丁酸酯（4），其中R表示C1-10烃基。
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59.发明申请公开(公告)号：US20140275657A1
公开(公告)日：2014-09-18
申请号：US14189373
申请日：2014-02-25
IPC分类号： C07C17/07
摘要： Provided is a method for producing a chlorohydrocarbon having conjugated double bonds by stereoselectively chlorinating an alcohol having conjugated double bonds. More specifically, provided is a method for producing a chlorohydrocarbon having conjugated double bonds, the method including a step of chlorinating an alcohol having conjugated double bonds with a chlorinating agent in a solvent in the presence of a base and in the absence of metal salt for chlorination of the alcohol, and the alcohol being represented by the formula (1): RCH═CHCH═CH—Z—OH (1) wherein R represents a hydrogen atom or a linear, branched or cyclic C1-17 monovalent hydrocarbon group which may have at least one double bond or at least one triple bond; and Z represents a linear, branched or cyclic C1-17 divalent hydrocarbon group which may have at least one double bond or at least one triple bond.
摘要翻译： 提供通过立体选择性氯化具有共轭双键的醇来制备具有共轭双键的氯代烃的方法。 更具体地说，提供了具有共轭双键的氯代烃的制造方法，其特征在于，在碱的存在下，在不存在金属盐的情况下，在溶剂中，用氯化剂将具有共轭双键的醇氯化， 醇的卤化，由式（1）表示的醇：RCH = CHCH = CH-Z-OH（1）其中R表示氢原子或直链，支链或环状的C 1-17单价烃基，其可以 具有至少一个双键或至少一个三键; Z表示可以具有至少一个双键或至少一个三键的直链，支链或环状的C1-17二价烃基。
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