新产品编号:892757
Chemical Name: 5(R)-[2-(4-Methoxyphenyl)ethyl]-4(S)-methyl-3-methylenetetrahydrofuran-2-one
CAS No. 364335-55-7 (undefined stereoch.)
项目整合开发状态: Biological Testing
项目研究机构: CSIC (Originator), Industrial Farmac閡tica Cantabria (Originator), Universidad de Alcal?(Originator), Universidad del Bio-Bio (Originator), Universidad Palmas de Gran Canaria (Originator)
合成路线:4-Hydroxybenzaldehyde (I) was acetylated using Ac2O in pyridine.The resultant 4-(acetyloxy)benzaldehyde (II) was then subjected to a Wadsworth-Emmons condensation with trimethyl phosphonoacetate to afford methyl 4-(acetyloxy)cinnamate (III).After catalytic double bond hydrogenation,the resultant saturated ester (IV) was reduced by LiAlH4 to furnish 3-(4-hydroxyphenyl)-1-propanol (V) 朼lternatively (V) can be obtained by reduction with LiAlH4 of the propionic acid derivative (VI) (isolated from Asplenium onopteris)-.Methylation of the phenolic hydroxyl group of (V) with iodomethane and K2CO3 in acetone gave the methyl ether (VII).Then,oxidation of alcohol (VII) to 3-(4-methoxyphenyl)propanal (VIII) was accomplished by means of pyridinium chlorochromate.
合成路线:Condensation of acetaldehyde with methyl acrylate (VIII) under Bayliss-Hillmann conditions gave rise to the allylic alcohol (IX).Bromination of (IX) using N-bromosuccinimide and dimethyl sulfide proceeded with rearrangement to the allyl bromide (X).This was then coupled with aldehyde (VII) in the presence of metallic tin and catalytic amounts of HOAc to produce,after acid-catalyzed cyclization,the target methylene butyrolactone derivative.
📌 参考资料/链接：
参考文献标题:Derivs.of p-hydroxy phenyl propionic acid as antiproliferative agents
文献作者:Bermejo Barrera,J.; Hernandez Silva,M.; Alvarez de Mon,M.; Pivel Ranieri,J.P.(CSIC (Consejo Superior de Investigaciones Cient韋icas))
参考来源:ES 2160093; WO 0172733
📄 详细内容
合成路线:4-Hydroxybenzaldehyde (I) was acetylated using Ac2O in pyridine.The resultant 4-(acetyloxy)benzaldehyde (II) was then subjected to a Wadsworth-Emmons condensation with trimethyl phosphonoacetate to afford methyl 4-(acetyloxy)cinnamate (III).After catalytic double bond hydrogenation,the resultant saturated ester (IV) was reduced by LiAlH4 to furnish 3-(4-hydroxyphenyl)-1-propanol (V) 朼lternatively (V) can be obtained by reduction with LiAlH4 of the propionic acid derivative (VI) (isolated from Asplenium onopteris)-.Methylation of the phenolic hydroxyl group of (V) with iodomethane and K2CO3 in acetone gave the methyl ether (VII).Then,oxidation of alcohol (VII) to 3-(4-methoxyphenyl)propanal (VIII) was accomplished by means of pyridinium chlorochromate.
合成路线:Condensation of acetaldehyde with methyl acrylate (VIII) under Bayliss-Hillmann conditions gave rise to the allylic alcohol (IX).Bromination of (IX) using N-bromosuccinimide and dimethyl sulfide proceeded with rearrangement to the allyl bromide (X).This was then coupled with aldehyde (VII) in the presence of metallic tin and catalytic amounts of HOAc to produce,after acid-catalyzed cyclization,the target methylene butyrolactone derivative.
参考文献标题:Synthesis and antiproliferative activity of a new compound containing an alpha-methylene-gamma-lactone group
文献作者:Gonz醠ez,A.G.; Silva,M.H.; Padron,J.I.; Leon,F.; Reyes,E.; Alvarez-Mon,M.; Pivel,J.P.; Quintana,J.; Estevez,F.; Bermejo,J.
参考来源:J Med Chem 2002,45(12),2358