合成路线:The condensation of diethyl 2-acetylglutarate (I) with 5-(1,1-dimethylheptyl)resorcinol (II) by means of POCl3 gives ethyl 7-(1,1-dimethylheptyl)-5-hydroxy-4-methyl-2-oxo-2H-1-benzopyran-3-propionate (III),which is cyclized by means of NaH in DMSO yielding 3-(1,1-dimethylheptyl)-7,10-dihydro-1-hydroxy-6H-dibenzo[b,d]pyran-6,9-(8H)-dione (IV).The ketalization of (IV) with ethylene glycol (A) and p-toluenesulfonic acid affords the ketal (V),which by a Grignard reaction with methylmagnesium iodide in refluxing ether is converted into dl-3-(1,1-dimethylheptyl)-6,6a,7,8-tetrahydro-1-hydroxy-6,6-dimethyl-9H-dibenzo[b,d]pyran-9-one (VI).Finally,this compound is reduced with Li in liquid ammonia.
参考文献标题:Hexahydro-dibenzo[b,d]pyran-9-ones as analgesic drugs
文献作者:Archer,R.A.
参考来源:US 3944673
合成路线:The condensation of diethyl 2-acetylglutarate (I) with 5-(1,1-dimethylheptyl)resorcinol (II) by means of POCl3 gives ethyl 7-(1,1-dimethylheptyl)-5-hydroxy-4-methyl-2-oxo-2H-1-benzopyran-3-propionate (III),which is cyclized by means of NaH in DMSO yielding 3-(1,1-dimethylheptyl)-7,10-dihydro-1-hydroxy-6H-dibenzo[b,d]pyran-6,9-(8H)-dione (IV).The ketalization of (IV) with ethylene glycol (A) and p-toluenesulfonic acid affords the ketal (V),which by a Grignard reaction with methylmagnesium iodide in refluxing ether is converted into dl-3-(1,1-dimethylheptyl)-6,6a,7,8-tetrahydro-1-hydroxy-6,6-dimethyl-9H-dibenzo[b,d]pyran-9-one (VI).Finally,this compound is reduced with Li in liquid ammonia.
参考文献标题:Dihydroxyhexahydrodibenzo[b,d]pyrans
文献作者:Archer,R.A.
参考来源:DE 2451934; ES 431674; FR 2249664; GB 1487637; JP 50071678; US 3968125
合成路线:The condensation of diethyl 2-acetylglutarate (I) with 5-(1,1-dimethylheptyl)resorcinol (II) by means of POCl3 gives ethyl 7-(1,1-dimethylheptyl)-5-hydroxy-4-methyl-2-oxo-2H-1-benzopyran-3-propionate (III),which is cyclized by means of NaH in DMSO yielding 3-(1,1-dimethylheptyl)-7,10-dihydro-1-hydroxy-6H-dibenzo[b,d]pyran-6,9-(8H)-dione (IV).The ketalization of (IV) with ethylene glycol (A) and p-toluenesulfonic acid affords the ketal (V),which by a Grignard reaction with methylmagnesium iodide in refluxing ether is converted into dl-3-(1,1-dimethylheptyl)-6,6a,7,8-tetrahydro-1-hydroxy-6,6-dimethyl-9H-dibenzo[b,d]pyran-9-one (VI).Finally,this compound is reduced with Li in liquid ammonia.
参考文献标题:Hexahydro-dibenzo[b,d]pyran-9-ones as an anti-anxiety drug
文献作者:Archer,R.A.
参考来源:DE 2451932; ES 431675; FR 2249663; GB 1487636; JP 50082073; NL 7414437; US 3928598
合成路线:The condensation of diethyl 2-acetylglutarate (I) with 5-(1,1-dimethylheptyl)resorcinol (II) by means of POCl3 gives ethyl 7-(1,1-dimethylheptyl)-5-hydroxy-4-methyl-2-oxo-2H-1-benzopyran-3-propionate (III),which is cyclized by means of NaH in DMSO yielding 3-(1,1-dimethylheptyl)-7,10-dihydro-1-hydroxy-6H-dibenzo[b,d]pyran-6,9-(8H)-dione (IV).The ketalization of (IV) with ethylene glycol (A) and p-toluenesulfonic acid affords the ketal (V),which by a Grignard reaction with methylmagnesium iodide in refluxing ether is converted into dl-3-(1,1-dimethylheptyl)-6,6a,7,8-tetrahydro-1-hydroxy-6,6-dimethyl-9H-dibenzo[b,d]pyran-9-one (VI).Finally,this compound is reduced with Li in liquid ammonia.
参考文献标题:Hexahydro-dibenzo[b,d]pyran-9-ones as psychotropic,particularly anti-depressant drugs
文献作者:Archer,R.A.
参考来源:US 3953603
产品链接: CAS No. 51022-71-0››