E-0712
Chemical Name: 4-(3,7,11,15-Tetramethyl-1-oxo-6,10,14-hexadecatrienyl)morpholine; 4-(3,7,11,15-Tetramethyl-6,10,14-hexadecatrienoyl)morpholine
CAS No. 80016-56-4 (E,E-isomer)
项目整合开发状态: Biological Testing
项目研究机构: Eisai (Originator)
合成路线:The condensation of ethyl cyanoacetate (I) with farnesylacetone (II) by means of acetic acid ammonium acetate in refluxing benzene gives ethyl 2-cyano-3,7,11,15-tetramethyl-6,10,14-hexadecatrienoate (III),which is decarbo-xylated with NaOH in propylene glycol at room temperature yielding 3,7,11,15-tetramethyl-6,10,14-hexadecatrienonitrile (IV).The hydrolysis of (IV) with KOH in propylene glycol water at 130 C affords 3,7,11,15-tetramethyl-6,10,14-hexa-decatrienoic acid (V),which is finally condensed with morpholine (VI) by means of ethyl chlorocarbonate (VII) and triethylamine in THF.
📌 参考资料/链接：
参考文献标题:Polyprenylcarboxylic acid amides useful for treating liver dysfunction
文献作者:Yamatsu,I.; et al.(Eisai Co.,Ltd.)
参考来源:BE 0884754; DE 3030462; FR 2463122; FR 2497802; GB 2058782; JP 8126852; JP 8132442; US 4456603
📄 详细内容
合成路线:The condensation of ethyl cyanoacetate (I) with farnesylacetone (II) by means of acetic acid ammonium acetate in refluxing benzene gives ethyl 2-cyano-3,7,11,15-tetramethyl-6,10,14-hexadecatrienoate (III),which is decarbo-xylated with NaOH in propylene glycol at room temperature yielding 3,7,11,15-tetramethyl-6,10,14-hexadecatrienonitrile (IV).The hydrolysis of (IV) with KOH in propylene glycol water at 130 C affords 3,7,11,15-tetramethyl-6,10,14-hexa-decatrienoic acid (V),which is finally condensed with morpholine (VI) by means of ethyl chlorocarbonate (VII) and triethylamine in THF.
参考文献标题:E-0712
文献作者:Serradell,M.N.; Castar,J.
参考来源:Drugs Fut 1985,10(5),387