有机合成技巧课件.ppt

1、 有机合成技巧有机合成技巧常见几种类型的TM之分析方法1单官能团CH3CH3CH3OEtA:CH3CH3CH3OEtCH3C+CH3CH3+O-CH2CH3CH3CH3CH3Br+Na OEtCH3CH3CH3O-+CH2+CH3CH3CH3CH3OK+BrEtababCH3N HC H3C H3CH3N HC H3C H3FG ICH3N HC H3C H3OCH3C lO+NH2C H3C H3CH3C lONH2C H3C H3+CH3N HC H3C H3O1 LiA lH42 H3O+TMCH3NHCH3CH3FGICH3NCH3CH3CH3NH2+OCH3CH3disa.s.OCH

2、3CH3CH3NH2+CH3NCH3CH3H2NiTMH5C6CH3a.H5C6CH3H5C6CH3disH5C6CHP(C6H5)3+OCH3a.H5C6CH3FGAH5C6CH3OdisC6H6+CH3ClOConclusion:醚：R-O-R1disR-ONa+R1XRCR2O HR1d isR2CR1O H+R M g XR1R2R3R4d isP(C6H5)3R1R2+OR3R4RCOOHd isR M g X+C O2RCH2COOHd isCH2(COOC2H5)2+R B rRCOOR1d isRCOOH+R1O HRCONHR1d isRCOOH+R1N H2ArCOORd

3、isA rH+R C O C lRCH2COR1d isR B r+R1C O C H2C O O E T2 1,2-FGCH3OHCOOHa.CH3OHCOOHFGICH3OHCOOHCH3OHCNOCH3+HCN+CH3OCl2)CH3CH3COOHNH2a.CH3CH3COOHNH2FGICH3CH3CNNH2CH3CH3CHO+NH3+HCNOCH3CH3OHOHTMOCHO+CH3CH3CH3OHOdisCH3CH3CH3OHOFGICHCH2CH3CH3OH+CHCHCH3CH3OdisCHCHCHCNaNaNH2CH3COCH3CHCH2CH3CH3OHH2OCH3CH3CH3O

4、HOOCHOOH-TMS.3 1,3-FGCH3CH3CHOOHa.CH3CH3CHOOHCH3CH3CHOOHCH3CHO+CH3CHOs.CH3CHO2OH-TM2)OCOOC2H5COOEtOOC2H5OO HCOOHO HFG ITMS.O HH N O3OO HCOOHC2H5O HH2SO4COOEtOOC2H5TM(one-flask m ethod)OHC6H5COOHTMO+H5C6COOHReform atsky m ethods.H5C6COOHBr2+PH5C6COOHBrEtOHH2SO4H5C6BrCOOEt1)Zn/ether2)OOHC6H5COOEtNaOHH

5、3O+TM4 1,4-FGCH3CH3OOTMFGACH3CH3OOCOOEtCH3OEtOO+CH3BrOCH3OEtOOEtONaCH3BrOCH3CH3OOCOOEt1)KOH2)H3O+/TMs,CH3OOOFGICH3OEtOOOHCH3OEtOO+OTMCH3OEtOO1)EtONa2)OTMOdis1,3OC H3Odis1,4O+CH3OBrONHN1)B rC H2C O C H32)H3O+OCH3OO H_TMS.TM5 1,5-FGOCH3CH3O1,3OOEtCH3OCH3CH3CH3CH3CH3O+CH3OEtOs.CH3CH3OCH3CH3CH3O1)EtO Na

6、2)COOEtCOOEtCH3CH3OOEtOOC1)KO H/H2O2)H3O+TMTMOC6H5OCH3C6H5OOC H2+CH3C6H5OF G ACH3C6H5OEtOOCF G IONC H3C H3O+C H2O+NHC H3C H3CH3OEtOO+H5C6CH2BrT MOCH2OCH2O+NHCH3CH3CH3OEtOOTM+1）EtONa2)C6H5-CH2-BrCH3OC6H5COOEtOH-OC6H5COOEt1)KOH/H2O2)H3O+/s.+dis 1,3OCOOEtC6H5H5C6dis1,3CH3OCOOEtC6H5C6H5Odis1,5CH3C6H5OCH

7、3COOEtOH5C6OCH3+H5C6OCH3dis1,3CH3OOEtCH3OOEtTMs.CH3OCOOEtC6H5C6H5OCH3C6H5OCH3COOEtOH5C6OCH3CH3OOEt21)NaOC2H52)H3O+C6H5CHOOH-NaOEtOH-TMRobinson ReactionCH3CH3OHOHFGICH3CH3OOdis 1,5CH3CH3COOEtCOOEtCH3Odis 1,3CH3CH3CH3O+COOEtCOOEtCH3CH3CH3Odis 1,3CH3CH3O+CH3CH3OTMS.CH3CH3O2OH-CH3CH3CH3OCH2(C00Et)2NaOEt

8、CH3CH3COOEtOO1)OH-2)H3O+CH3CH3OONaBH4TMH5C6OO HOF G IC6H5F G IC6H5O HO+C6H5M g B rs.O1)M g,E t2OB r2)C6H5O HH3P O4C6H51)K M n O4/H3O+T M6 1,6-FGOHCH3OCOOHCOOHOFGICOOHCOOHCH2CH2+COOHCOOHCOOHCOOHOOOd is 1,3-OEtOOCF G IOCNF G IOOTsF G IOOHF G IOCOOEtF G AOCOOEtCOOEtd is 1,5O+COOEtCOOEtCOOEtCOOEt1)NaOEt2)OOCOOEtCOOEt1)OH-2)H3O+OCOOH1)EtOH,H+2)HOCH2CH2OH,HCl(g)OOCOOEt1)LiAlH42)TsCl,N(C2H5)2OOOTsNaCNOOCNH3O+EtOHOOCOOEt1)NaOEt2)H3O+TMS.