合成路线:The synthesis of 3,4-bis(3'-methoxyphenyl)hexane (III) was accomplished in two different ways:1) Reductive coupling of the 3-methoxypropiophenone (I) using the TiCl4/Zn reaction -- introduced by Mukaiyama et al.-- yields preferably the cis-stilbene (II).Catalytic hydrogenation of this alkene using palladium on activated carbon results in the isomerically pure meso-3,4-bis(3'-methoxyphenyl)hexane (III).2) The reductive coupling of the 1-(3'-methoxyphenyl)-1-chloropropane (VI),obtained from 1-(3-methoxyphenyl)propanol (V) with dry HCl,according to Wilds and McCormack using COCl2 and ethylmagnesium bromide (A) yields mixture of the meso- and di-3,4-bis(3'-methoxyphenyl)hexanes (III).The meso-diastereomer (III) is separated by fractional crystallization from methanol.The ether cleavage of (III) to give 3,4-bis(3'-hydroxyphenyl)hexane is accomplished with BBr3.
参考文献标题:Metahexestrol
文献作者:Sch鰊enberger,H.; Engel,J.; Hartmann,R.W.
参考来源:Drugs Fut 1983,8(5),413
合成路线:The synthesis of 3,4-bis(3'-methoxyphenyl)hexane (III) was accomplished in two different ways:1) Reductive coupling of the 3-methoxypropiophenone (I) using the TiCl4/Zn reaction -- introduced by Mukaiyama et al.-- yields preferably the cis-stilbene (II).Catalytic hydrogenation of this alkene using palladium on activated carbon results in the isomerically pure meso-3,4-bis(3'-methoxyphenyl)hexane (III).2) The reductive coupling of the 1-(3'-methoxyphenyl)-1-chloropropane (VI),obtained from 1-(3-methoxyphenyl)propanol (V) with dry HCl,according to Wilds and McCormack using COCl2 and ethylmagnesium bromide (A) yields mixture of the meso- and di-3,4-bis(3'-methoxyphenyl)hexanes (III).The meso-diastereomer (III) is separated by fractional crystallization from methanol.The ether cleavage of (III) to give 3,4-bis(3'-hydroxyphenyl)hexane is accomplished with BBr3.
参考文献标题:Pentasubstituted quercetin analogues as selective inhibitors of particulate 3':5'-cyclic-AMP phosphodiesterase from rat brain
文献作者:Picq,M.; Prigent,A.F.; Nemoz,G.; Andre,A.C.; Pacheco,H.
参考来源:J Med Chem 1982,24(10),1192-97
合成路线:The synthesis of 3,4-bis(3'-methoxyphenyl)hexane (III) was accomplished in two different ways:1) Reductive coupling of the 3-methoxypropiophenone (I) using the TiCl4/Zn reaction -- introduced by Mukaiyama et al.-- yields preferably the cis-stilbene (II).Catalytic hydrogenation of this alkene using palladium on activated carbon results in the isomerically pure meso-3,4-bis(3'-methoxyphenyl)hexane (III).2) The reductive coupling of the 1-(3'-methoxyphenyl)-1-chloropropane (VI),obtained from 1-(3-methoxyphenyl)propanol (V) with dry HCl,according to Wilds and McCormack using COCl2 and ethylmagnesium bromide (A) yields mixture of the meso- and di-3,4-bis(3'-methoxyphenyl)hexanes (III).The meso-diastereomer (III) is separated by fractional crystallization from methanol.The ether cleavage of (III) to give 3,4-bis(3'-hydroxyphenyl)hexane is accomplished with BBr3.
参考文献标题:
文献作者:Resende,C.; Barros,L.; Mota,A.; Barros,M.A.; Veloso,T.; Mesquita-Guimaraes,J.; Cunha,A.P.
参考来源:J Cancer Res Clin Oncol 1982,103(Suppl.1),165-180
合成路线:The synthesis of 3,4-bis(3'-methoxyphenyl)hexane (III) was accomplished in two different ways:1) Reductive coupling of the 3-methoxypropiophenone (I) using the TiCl4/Zn reaction -- introduced by Mukaiyama et al.-- yields preferably the cis-stilbene (II).Catalytic hydrogenation of this alkene using palladium on activated carbon results in the isomerically pure meso-3,4-bis(3'-methoxyphenyl)hexane (III).2) The reductive coupling of the 1-(3'-methoxyphenyl)-1-chloropropane (VI),obtained from 1-(3-methoxyphenyl)propanol (V) with dry HCl,according to Wilds and McCormack using COCl2 and ethylmagnesium bromide (A) yields mixture of the meso- and di-3,4-bis(3'-methoxyphenyl)hexanes (III).The meso-diastereomer (III) is separated by fractional crystallization from methanol.The ether cleavage of (III) to give 3,4-bis(3'-hydroxyphenyl)hexane is accomplished with BBr3.
参考文献标题:
文献作者:El-Ashmawi,N.; Abdel-Samad,Z.; Sallam,F.; Nassar,S.; Gamae,M.
参考来源:Chem Lett 1973,16(Suppl.1),1041-44
合成路线:The synthesis of 3,4-bis(3'-methoxyphenyl)hexane (III) was accomplished in two different ways:1) Reductive coupling of the 3-methoxypropiophenone (I) using the TiCl4/Zn reaction -- introduced by Mukaiyama et al.-- yields preferably the cis-stilbene (II).Catalytic hydrogenation of this alkene using palladium on activated carbon results in the isomerically pure meso-3,4-bis(3'-methoxyphenyl)hexane (III).2) The reductive coupling of the 1-(3'-methoxyphenyl)-1-chloropropane (VI),obtained from 1-(3-methoxyphenyl)propanol (V) with dry HCl,according to Wilds and McCormack using COCl2 and ethylmagnesium bromide (A) yields mixture of the meso- and di-3,4-bis(3'-methoxyphenyl)hexanes (III).The meso-diastereomer (III) is separated by fractional crystallization from methanol.The ether cleavage of (III) to give 3,4-bis(3'-hydroxyphenyl)hexane is accomplished with BBr3.
参考文献标题:
文献作者:Hitova,M.; Kouzeva,V.
参考来源:J Org Chem 1949,14(Suppl.1),45-58
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