4,6,4'-Trimethylangelicin, TMA
4,6,9-三甲基-2H-呋喃并[2,3-H]色满-2-酮Chemical Name: 4,6,9-Trimethyl-2H-furo[2,3-h]-1-benzopyran-2-one; 4-Hydroxy-beta,3,7-trimethyl-5-benzofuranacrylic acid delta-lactone
CAS No. 90370-29-9
项目整合开发状态: Biological Testing
项目研究机构: Farmochimica (Originator)
合成路线:4,6-Dimethyl-7-acetylumbelliforone (4,6-dimethyl-7-acetoxycoumarin) (I) is submitted to the Fries' rearrangement,obtaining the 4,6-dimethyl-8-acetylumbelliferone (II); the latter (II) is condensed with ethylbromoacetate (A) and the resulting ethyl [(4,6-dimethyl-8-acetyl-7-coumarinyl)oxy]acetate (III) is hydrolyzed by refluxing with 5% KOH aqueous methanolic solution; from this solution,acidified with HCl,the [(4,6-dimethyl-8-acetyl-7-coumarinyl)oxy]acetic acid (IV) is extracted with EtOAc and purified by crystallization (EtOAc / n-hexane).Cyclization of (IV),carried out by refluxing in Ac2O in the presence of anhydrous natrium acetate,is accompanied by an almost complete decarboxylation of (V),yielding 4,6,4'-trimethylangelicin (TMA).
📌 参考资料/链接：
参考文献标题:4,6,4'-Trimethylangelicin
文献作者:Bordin,F.; Dall'Acqua,F.; Cristofolini,M.; Guiotto,A.
参考来源:Drugs Fut 1985,10(4),307
📄 详细内容
合成路线:4,6-Dimethyl-7-acetylumbelliforone (4,6-dimethyl-7-acetoxycoumarin) (I) is submitted to the Fries' rearrangement,obtaining the 4,6-dimethyl-8-acetylumbelliferone (II); the latter (II) is condensed with ethylbromoacetate (A) and the resulting ethyl [(4,6-dimethyl-8-acetyl-7-coumarinyl)oxy]acetate (III) is hydrolyzed by refluxing with 5% KOH aqueous methanolic solution; from this solution,acidified with HCl,the [(4,6-dimethyl-8-acetyl-7-coumarinyl)oxy]acetic acid (IV) is extracted with EtOAc and purified by crystallization (EtOAc / n-hexane).Cyclization of (IV),carried out by refluxing in Ac2O in the presence of anhydrous natrium acetate,is accompanied by an almost complete decarboxylation of (V),yielding 4,6,4'-trimethylangelicin (TMA).
参考文献标题:6-Methylangelicins: A new series of potential photochemotherapheutic agents for the treatment of psoriasis
文献作者:Guiotto,A.; Rodighiero,P.; Manzini,P.; Pastorini,G.; Bordin,F.; Baccichetti,F.; Carlassare,F.; Vedaldi,D.; Dall'Acqua,F.; Tamaro,M.; et al.
参考来源:J Med Chem 1984,27(8),959
产品链接: CAS No. 90370-29-9››