1、CCOCHCORCORORXCCORCOCCORRBrH3CCH3O强强碱碱H3CCH2O低低温温H3CCH2ORH3COC2H5OONaOEtH3COC2H5OOR(1)稀稀OHH3COHOOR(2)H+,H3CCH2ORRBrCO2 H3COC2H5OONaOEt(1)稀 OH(2)H+,H3CORR XH3COC2H5OOR H3CORH3COC2H5OORRRRXNaOEt(1)稀 OH(2)H+,H3COC2H5OONaOEt(1)稀 OH(2)H+,XH3COC2H5OOX(CH2)nX(CH2)nNaOEtH3COC2H5OOH3CO(CH2)n(CH2)nn=2 5(1)稀 O
2、H(2)H+,(CH2)nNaOEtXX(CH2)n 2H3COC2H5OOX(CH2)nH3COC2H5OOH3COC2H5OO(CH2)nH3COH3CONaOEt+H3COC2H5OOH3COC2H5OO 2NaOEt(1)稀 OH(2)H+,H3COH3COH3COH3COCO2EtCO2EtI2H3COC2H5OO H3COEtOONaOEtH3COEtOOIH3COEtOOIIX(CH2)nXn=0X2H3COC2H5OONaOEtRXXX(CH2)nNaOEt(1)稀 OH(2)H+,?H3COC2H5OONaOEtRXNaOEt(1)稀 OH(2)H+,?I2 2 2 2 2
3、NaOEtH3COC2H5OOBrCH2CO2Et(1)稀 OH(2)H+,?H3COC2H5OOROClNaHH3COC2H5OORO(1)稀 OH(2)H+,H3CORONaHRXH3COROR(1)稀 OH(2)H+,H3CCH2ORH3COC2H5OOR(1)浓 OH(2)H+,H3COH2COHOROH+H3COC2H5OOR浓 OHH3COOORO+H3COOOROHH3COOOROHH3COOOOR+水解HH3COC2H5OORO(CH2)nH3COC2H5OOH3COC2H5OOH3COC2H5OORRH3COC2H5OO(CH2)nEtOOEtOONaOEt(1)OH(2)H
4、+,OHORR XEtOOEtOORHOOHOOR-CO2 H+H3COEtOH2COEtOR X(1)(2)OHOR强强碱碱RXNaOEt(2)H+,(1)OHOHOREtOOEtOORRRNaOEt(2)H+,R X EtOOEtOO(1)OHOHOREtOOEtOOREtOOEtOONaOEtXX(CH2)nHOO(CH2)n(1)OH(2)H+,2XX(CH2)nNaOEtEtOOEtOO(1)OH(2)H+,(CH2)nHOOHOO或 I2 HOOHOONaOEtEtOOEtOO(1)OH(2)H+,RNaOEtEtOOEtOORRBrCH2CO2EtXEtOOEtOOROEtONa
5、OEtEtOOEtOORNaOEt 2?XXX(CH2)n或 I2 2C2H5XCC2H5H3C(H2C)3COOEtH3C(H2C)3X+H2CCOOEtCOOEtCOOEtH2CCOOEtCOOEt(CH2)3CH3XNaOEtNaOEtC2H5X(1)OH(2)H+,CHCOOEtCOOEtC2H5CHCOOHH3C(H2C)3C2H5CCOOEtCOOEtH3C(H2C)3C2H5 CHCOOHH3C(H2C)3C2H5CH3OEtO2CI2NaOEtOCH3OCH3EtO2CEtO2C(1)稀OH(2)H+,OCH3OCH3OCH3 OH2 OCH3OCH3OCH3OCH3OCH3E
6、tO2CEtO2CCH3OCO2Et2+I2OCH3OCH3OCH3CH3OEtO2COCH3OCH3EtO2COCH3X+H3CCH2OC2H5OOC2H5OCH2OC2H5OOH3CCH3OC2H5OCH3OOCO2EtRXNaOEtOOCO2EtR(1)稀 NaOH(2)H+,ORRXNaHOR OR1R2OR1R2XX+OR1X(1)LDA/低温(2)OR1(1)LDA/低温(2)R2XOR1R2OR1R2（少少量量）+OR1R2R2X+OR1R2CO2EtOR1CO2Etab+OR1OR1X+bOEtOOEtR1X+OR1CO2EtOCO2Eta重重排排R2XOR1CO2EtOCO2
7、EtR1XOR1R2CO2Et(1)稀 NaOH(2)H+,OR1R2NaOEtOR1CO2EtNaOEtt-BuOK O(1)LDA/低低温温(2)OR1R2XR1XOR1CO2EtOR1R2CO2Et(1)稀 NaOH(2)H+,OR1R2 NaOEtOEtOOEt1.NaH 2.NCO2C2H5OH3CbNCOOC2H5CO2C2H5H3CNH2H3CCH2CCO2C2H5+2HaNH2H3CO+orNH2H3CH3CH3CO+2 HCHO+NOH3CEtOCHOOEtOOOCH3+CH2CHCH2CH2CHCH2XCH3X+CH3aEtOOOOEt+CH3CH2CO2EtEtOCOOC
8、H2CHCH2CO2EtCH3EtOCHOOCO2EtCH3+CH2CHCH2Xb EtOOOOEt+CH3CH2CO2EtNaOEtEtOOOCO2EtCH3NaOEtXEtOOOCH2CHCH2CO2EtCH3(1)稀 OH(2)H+,HOOOCH2CHCH2CH3EtOOOCH2CHCH2CH3酯酯化化CHCOCCOHRX碱碱CRCOCCOHRXCHCOCCOR 碱碱CHCOCCOHRX 2 强强碱碱CCOCCOCHCOCCORH2O/H+RXCH2COH3CCCH3O CHCONaH2CCCH3ONaCH2COCH2CCH3ORNH4ClRCOXNH4ClCH2COCH2CCH3ORCO2 NaNH2H3CCHOO(1)PhCH2Cl(2)H3O+H2CCHOOCH2PhH3CCO2CH3O(1)CH3CH2Br(2)H3O+CH3CH2CH2CO2CH3O2 KNH2H2CCHOKOKNaHH3CCOONaOCH3 BuLiH2CCOLiONaOCH3RO(1)NaH(2)HCO2C2H5ROROCH(1)RX(2)H3O+ROCHOR去-CHORORNaHROCH(1)RX(2)H3O+ROCHORKOHROCHOR2 NaNH2OOROCHORO(1)NaH(2)HCO2C2H5去-CHOKOH
