合成路线:The Friedel Kraft's acylation of 1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene (I) with acetyl chloride by means of AlCl3 in nitrobenzene gives 2-acetyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene (II),which is reduced with LiAlH4 in ether yielding 5,6,7,8-tetrahydro-alpha,5,5,8,8-pentamethylnaphthalene-2-methanol (III),The reaction of (III) with PBr3 in ether - hexane affords 2-(1-bromoethyl)-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene (IV),which by reaction with triphenylphosphine in hot xylene is converted into [1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)ethyl]triphenylphosphonium bromide (V).Finally,this compound is submitted to a Wittig condensation with ethyl 4-formylbenzoate (VI) in hot butylene oxide.
参考文献标题:RO-13-6298
文献作者:Blancafort,P.; Hopkins,S.J.; Serradell,M.N.; Castar,J.
参考来源:Drugs Fut 1983,8(5),432
合成路线:The Friedel Kraft's acylation of 1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene (I) with acetyl chloride by means of AlCl3 in nitrobenzene gives 2-acetyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene (II),which is reduced with LiAlH4 in ether yielding 5,6,7,8-tetrahydro-alpha,5,5,8,8-pentamethylnaphthalene-2-methanol (III),The reaction of (III) with PBr3 in ether - hexane affords 2-(1-bromoethyl)-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene (IV),which by reaction with triphenylphosphine in hot xylene is converted into [1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)ethyl]triphenylphosphonium bromide (V).Finally,this compound is submitted to a Wittig condensation with ethyl 4-formylbenzoate (VI) in hot butylene oxide.
参考文献标题:Arotinoids,a new class of highly active retinoids
文献作者:Mayer,H.; Loeliger,P.; Bollag,W.
参考来源:Eur J Med Chem - Chim Ther 1980,15(1),9-15
产品链接: CAS No. 71441-09-3››