CAS: 4652-27-1; 4-Methoxybut-3-En-2-One

该化合物是α-β-不饱和克酮,配有甲氧替代物,在有机合成中提供多功能性再活动.它的同质内聚体结构使它成为迈克尔添加,循环添加和其他核生殖反应的宝贵中间体.退出电的碳基和电饱和的甲氧基组增强了其在再生选择性变异中的效用.该化合物在合成三环,制药和精美化学品方面特别有用.它在受控条件下和明确界定的再活动特征下保持稳定,确保实验室和工业应用的一贯性能.适当的处理是因为它对光和湿度的潜在敏感性而值得注意的.

结构式图片

相似化合物

51731-17-0 14405-43-7 57155-06-3

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合成工艺路线路线简述

  • 合成目标产物 4-Methoxy-3-Buten-2-One 主要起始原料 1-Methoxy-1-Buten-3-Yne
  • (文献来源)合成步骤主要原料 1-Methoxy-1-Buten-3-Yne
4-Methoxycarbonyloxy-But-3-En-2-One置于magnesium(II) Perchlorate体系中,用 苯 作为反应溶剂,化学反应生成 4-甲氧基-3-丁烯-2-酮
参考文献:Shramova,Z.I.; Skoldinov,A.P.,Journal Of Organic Chemistry Ussr (English Translation),1965,Vol. 1,P. 1768-1772
标题:Shramova,Z.I.; Skoldinov,A.P.,Journal Of Organic Chemistry Ussr (English Translation),1965,Vol. 1,P. 1768-1772

海关参考信息

专利信息


专利号:US-5097051-A
优先权日:1989-02-10
标题 :Cyclic triketone compounds and trimethylsilyloxy butadiene compounds and their use in the preparation of daunomycinone derivatives
发明人:SCHEEREN JOHAN W; DEBIE JOANNES F M; DEVOS DIRK
权利人:PHARMACHEMIE BV
摘要:The invention provides novel cyclic triketone compounds of the formulae wherein S is H, alkyl or alkoxy and R* is a group of the formule wherein R<1> is methyl and R2 is an alkyl group containing at least 2 carbon atoms, or R<1> is an alkyl group having 1-4 carbon atoms and R<2> is an aryl group, a hetero aryl group, a -CH2OR min , a -CH2N @@ group, a -CH2SR sec group or a -CH2CH=CH2 group, wherein R min and R sec are alkyl groups having 1-4 carbon atoms. These compounds can be used for preparing daunomycinone and derivatives thereof. Daunomycinone is used for preparing daunomycin and adriamycin. By introducing chirality at C-1 of ring A in the preparation of said novel compounds by using a novel diene of formula (1) in a Diels-Alder reaction for said preparation, the chirality of C-3 is established in the subsequent reaction with LiC IDENTICAL CSi(CH3)3 in the synthesis of daunomycinone and derivatives thereof. This last reaction leads to the desired compound wherein OH at C-3 and OR at C-1 are in the cis-position with respect to each other.

专利号:US-5183913-A
优先权日:1989-02-10
标 题 :Cyclic triketone compounds and trimethylsilyoxy butadiene compounds and their use in the preparation of daunomycinone derivatives
发明人:SCHEEREN JOHAN W; MARTINUS DE BIE JOANNES F; DE VOS DIRK
权利人:PHARMACHEMIE BV
摘要:The invention provides novel cyclic triketone compounds of the formulae (2) (3) wherein S is H, alkyl or alkoxy and R* is a group of the formule wherein R1 is methyl and R2 is an alkyl group containing at least 2 carbon atoms or R1 is an alkyl group having 1-4 carbon atoms and R2 is an aryl group, a hetero aryl group, a -CH2OR' group, a -CH2N (1) This last reaction leads to the desired compound wherein OH at C-3 and OR at C-1 are in the cis-position with respect to each other.

专利号:US-4471139-A
优先权日:1982-05-24
标题 :Processes for making 3-methylthiophene-2-carboxaldehyde and intermediates therefor
发明人:ANDREWS GLENN C
权利人:PFIZER
摘要:Processes for preparing isomerically pure 3-methylthiophene-2-carboxaldehyde, an intermediate for synthesis of anthelmintic agents, by reaction of mercaptoacetaldehyde or the dimer, or a polymer thereof, or a dialkylacetal thereof in the presence of a base with (1) methyl vinyl ketone or an alpha- or beta-oxidized derivative of methyl vinyl ketone to form a 3-oxobutylmercaptoacetaldehyde or dialkyl acetal thereof, or an alpha- or beta-substituted derivative thereof which is then converted to 3-methylthiophene-2-carboxaldehyde via appropriate steps including, if necessary, treatment with acid, followed, if necessary, by enamine catalyzed cyclization and, in the case of using methyl vinyl ketone as reactant, a dehydrogenation step; or (2) 3-butyn-2-one to produce a mixture of isomeric 3-oxobut-1-enylmercaptoacetaldehyde or dialkyl acetals thereof which is cyclized to 3-methylthiophene-2-carboxaldehyde. n A further aspect of this invention is an improved process for making dialkyl acetals of 2-mercaptoacetaldehyde which comprises reacting an alkyl vinyl ether with sulfur chloride to produce a bis(2-chloro-2-alkoxy ethyl)disulfide which is then treated with an alcohol to afford a bis(2,2-dialkoxyethyl)disulfide which is reduced under alkaline conditions to 2-mercaptoethyl acetaldehyde alkali metal salt which can be alkylated to a thioether, a valuable intermediate.

专利号:US-9777013-B2
优先权日:2013-08-14
标题 :Derivatives of uncialamycin, methods of synthesis and their use as antitumor agents
发明人:NICOLAOU KYRIACOS C; LU MIN; MANDAL DEBASHIS; GANGWAR SANJEEV; CHOWDARI NAIDU S; POUDEL YAM B
权利人:UNIV RICE WILLIAM M; BRISTOL MYERS SQUIBB CO; SCRIPPS RESEARCH INST
摘要:In one aspect, the present disclosure provides new analogs of uncialamycin of formulae (I) and (II). The present disclosure also provides novel synthetic pathways to obtaining uncialamycin and analogs thereof. Additionally, the present disclosure also describes methods of use of uncialamycin and analogs thereof. In another aspect, the present disclosure provides antibody-drug conjugates comprising the compounds of formulae (I) and (II).

专利号:US-4476312-A
优先权日:1982-05-24
标 题:Processes for making 3-methylthiophene-2-carboxaldehyde and intermediates therefor
发明人:ANDREWS GLENN C
权利人:PFIZER
摘要:Processes for preparing isometrically pure 3-methylthiophene-2-carboxaldehyde, an intermediate for synthesis of anthelmintic agents, by reaction of mercaptoacetaldehyde or the dimer, or a polymer thereof, or a dialkylacetal thereof in the presence of a base with (1) methyl vinyl ketone or an alpha- or beta- oxidized derivative of methyl vinyl ketone to form a 3-oxobutylmercaptoacetaldehyde or dialkyl acetal thereof, or an alpha- or beta-substituted derivative thereof which is then converted to 3-methylthiophene-2-carboxaldehyde via appropriate steps including, if necessary, treatment with acid, followed, if necessary, by enamine catalyzed cyclization and, in the case of using methyl vinyl ketone as reactant, a dehydrogenation step; or (2) 3-butyn-2-one to produce a mixture of isomeric 3-oxobut-1-enylmercaptoacetaldehyde or dialkyl acetals thereof which is cyclized to 3-methylthiophene-2-carboxaldehyde. n A further aspect of this invention is an improved process for making dialkyl acetals of 2-mercaptoacetaldehyde which comprises reacting an alkyl vinyl ether with sulfur chloride to produce a bis(2-chloro-2-alkoxy ethyl)disulfide which is then treated with an alcohol to afford a bis(2,2-dialkoxyethyl)disulfide which is reduced under alkaline conditions to 2-mercaptoethyl acetaldehyde alkali metal salt which can be alkylated to a thioether, a valuable intermediate.

专利号:CN-116925023-A
优先权日:2023-07-18
标题 :Improved synthesis of 2-perfluoroalkyl-4H-pyran-4-one derivatives
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合成参考文献


参考文献:10.1055/s-2006-958958
摘要:Langer P, Feist H. One-Pot Synthesis of Functionalized Carbacycles by Formal [3+3] Cyclizations of 1,3-Bis(silyl enol ethers) with 1,3-Dielectrophiles. Synthesis. 2007 Feb;2007(3):327–47. doi: 10.1055/s-2006-958958.
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