药物合成反应习题.pdf

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1、药物合成反应习题第一章卤化反应1.写出下列反应的主要产物（（（或试剂（或试剂）））①CH3OC6H4HBr2CCloCHH42-5②BrBrOOOOOH3CCH3CCl4ref5hH3CCH3③NBS/DMSO/H2OCH3H3CCCCH2NBS/DMSOHCH3④C8H17I2/CF3COOAg⑤OSiMe3MeNBSTHF0oC⑥(C6H5)3P/I2C6H6refHOH⑦AgFICH2COOMe1⑧OAcOBrBrBrBrEt2O/HClO⑨COCH3Br2/NaOHHClH2O/diox,10°CH3COCOC⑩HBHHCCH3CCH32I2NaOCH3,CH

2、3OH2．．．写出下列反应的可能产物①CH3HBr,100°CH3CCCH2OHCH3②HCOOCH3NBS/(C6H5CO)2O2H3CCH3CCl4ref③OH2Br2KClO3H2OH3CCCCH2CH340-50°C光照④H3CC2H5Cl2,CH3COOHHH23.写出下列反应的主要试剂及条件①C(CH2OH)4C(CH2Br)4②HOOC(CH2)4COOHClCO(CH2)4COCl③PhCH2COCH3PhCHCH2OCH3Cl④OOCOOHI第二章烃化反应1.完成下列反应①COOCH3OHCHI3NaOHOH②OHOHMe2SO4K2CO3COCH3

3、③HCH3OHH2SO4H3CCCH2OCH3OHCH3ONa3④HN(CH2)5Me2SO4C85-95°CO⑤ClNO2PhNH295°CNO2⑥CHCHSOClCH2(COOC2H5)23642HOC2H5ONaC2H5OHH⑦C2H5ONaBr(CH2)5Br+CH2(COOC2H5)2C2H5OH⑧NH2CH2OH加热Raney-Ni⑨OH3CLDA/CH3OCH2CH2OCH3-40~0°C酮过量2.完成下列反应过程①OCC2H5ONaClCH2COOC2H5NCH(COOC2H5)2150-160°CCC2H5OHOHCl.H2OPyCH3COOH4②H

4、COOH2/Raney-Ni+CH3NH2③O(C2H5O)2PHH2CCCH2Br/50%NaOHHClC6H5CH2NH2HCCl4(n-C4H9)4HSO4④NH2OCH3CH3C2H5MgBrH2CCCH2ClC6H6refOrefOrefC(CH3)3第三章酰化反应1.完成下列反应①AlCl3+CH3COClH3COOCH3OCH3②HNHCOCHCl2/CHN66CCCH2OH+CH3(CH2)16COClO2NOHH③H2NSNNClCH2CONHCCOOHNDCC+NOCH3NCH2SNTHFSOCH3COOH5④CH3(CH2)5COClAlCl3C

5、lCH2CH2Cl0°CCH3⑤OCH3OCH3H3COH3COCHOH3COH3COH3COH3CO⑥CH3POCl3+C6H5NCHO90-95°C⑦OOH2140°CCH3CCCOC2H5+HO4~5hr2.完成下列合成路线①OHOC2H5DMFPOCl3COClH2NSCH3NCH3OC2H5OCOONa②以苯和丁二酸酐为起始原料合成四氢萘6第四章缩合反应1.改错（（（只能改动一处（只能改动一处）））①CHOPh3P+-CHCH3+HHCH3②OC3H7CH3CH2CH2CCH3+CH3COOC2H5CCHCOOC2H5H3C③HCHOZn+C6H6CCHCO

6、OC2H5+ClCH2COOC2H5(C2H5)2O2.完成下列反应式①ONO2-OH/H2OCH3+CHO②OH3CHCCHCH3O③OCa(OH)2+CH2O(过量)H2O④7C6H5CHOCOOHCCHC2H5⑤+ClCH2COOCH3H2OHO-CH3ONaOH⑥OH+C6H5CH2CNC6H5CCOC2H5CN⑦CH2CH2CHOONaNH2CH3(C6H5)3PCCCH2H2HC6H6Br⑧CH3CO2CH3ZnCH3CO2HO+++BrCH2CO2CH3C6H6(C2H5)2O,ref.H2OH3CO3.完成下列合成过程①从甲苯COOC2H5CC2H5C

7、OOC2H5②CHH3H2CCCHOCH3CH3CH384.填写下列各部分产物(1)_HCHO/OHHCNa-甲基丙醛AC5H10O2BC6H12O4+H3O+-H2OH3OCC6H10O3DEC9H17NO5+PhCH2OH(2)COCHCH33(C2H5)2NCH2CH2COCH3OACH3ONaCH3OHC6H6HO+KOH3BCH3OH/H2O,ref.(3)OHCZn/BrCH2COOEtNa/EtOH+H3ODHBrSOCl2KCNAlCl3COOH(4)MeHCOOH,HClCH2(COOH)2MeNCO2EtorDMF/POClPip