1、RCOOHRCOXRCOORCOORRCONH2(R)CROCOGR CH3COClPh COClCH3CH2CHCOBrBrCOClCOClOCH2PhCOClCH3COOCCH3OCH3COOCCH2CH3OOOOPhCOOC2H5OH3COCH2COOC2H5COC2H5OCH2COOC2H5COH3C COXRCH2COOCOORCONH2(R)CRORCH2RCH2RCH2RCHCOLHRCOLNuRCONu+Lor HNuHLorRCOLRCOOHH2OH or OHROHRNH2RCOORRCONHRH or OHRCOLNuRCONu+ LRCONuL親親核核加加成成消消除除R

2、COHLHNuRCOHNu+RCOHNuL親親核核加加成成消消除除HRCOHNuLHLH堿性條件堿性條件酸性條件酸性條件COXRCOOCOORCONH2(R)CRORRRRCOOHH2OHX+HOCROHORNH3(R)H2OH or OHH2OH or OHH2OH or OHorRCOORCOClRCOORCOORRCONH2(R)CRORCOL XOORNH2(R)CROH2ORCOHORH2ORCOHORRCOHOH HORRCOOHRCOORHHORCOHORH HHOR烯烯烴烴H2O HRCOHORCOOHRCOORHRR+RCOORCOORRCOORHOROHRCOO+OR OH

3、HROHRCOORRCOCl+Et3N or 吡啶Et3NH ClNHClorHClROHRCOORRCOClEt3N or 吡啶RCOOHSOCl2RCOOHRCOOCROROHRCOOR+C2H5OHSCH2OH(CH3CO)2OCH3COONaSCH2OCCH3OOOOCOOEtCOOH二二酸酸單單酯酯COOEtCOOEt二二酸酸二二酯酯 H2CCHCOOCH3n-BuOHTsOHH2CCHCOOBun+ CH3OHOCOHOCH3NaOCH3CH3OOHCOCH3OCH3COCH3+CHCH2CHCH2OAcOAcnCH3OHOHCHCH2CHCH2OHOHnCCH3OO+CH3COC

4、H3ORCOORRCOORROHHorRO+ROH+RCOORRCONHRROH+RNH2+H or OHNHROR 化化學學計計量量）NaOC2H5CH2CH2CO2C2H5NCH2CH2CO2H2H5H3CHClNCO2C2H5OH3CHClNaOC2H5（ 化化學學計計量量）（ 化化學學計計量量）RCNH2OBr2 / NaOHRNH2+CO2RCNHOHOHRCNHOBrBrRCNOBrHRCNOBrOHR2C缺電子中心缺電子中心RCNOBrRCNO- - BrRCNOR遷遷移移異異氰氰酸酸酯酯消消除除和和重重排排同同時時進進行行RCNOOHRCHNOORHNRH2NOHHCO2+OH

5、OH CO2RCNH2OBr2 / NaOHRNH2*+CNOBrCNOCNOBr CR1R2R3CR1R2R3CR1R2R3 Br庫爾提斯庫爾提斯施密特施密特 N2RH2NRCNONNRCNO+CO2+H2ON2R遷遷移移RCClORNH2+RCNONNRCOHOH2ON2NaN3HN3H2SO4CO2+ CNCNCOOEtCNH2CCHCNRCNRCRHCN 不飽和，可不飽和，可加成和還原加成和還原有弱酸性，可有弱酸性，可與強堿作用與強堿作用RCONH2RCNRXKCNORRHCNHORRCNP2O5+H2ORCNRCNH2, Raney NiRCH2NH21. LiAlH4NH32. H

6、2ORCNRCH2NH2H2RCHNHH2 不飽和，不飽和，可加成可加成NuRCNH2OH2OH+OHRCOOHRCONH2H2OH2OH+OHRCOOH2CCHCNH2OCNCNH2O, H2SO4CONH2CONH290 - 100oCH2CCHCONH2ZnCl2H3CCCH3OHCNH3CCCH3OHCNH2SO4, HOCH3H2CCCH3CNH2SO4, HOCH3H2CCCH3COOCH3H2O RCNH+RCRCNH2ORH2OH+ROHOORRMgXRCNRRCNMgXRCNHRH2OH+RCORH2ORCORRCH2ONRMgXH+R-C-OHOR-C-XOR-C-NH2OR-C-OROR-C-O-C-ROOPX3或SOCl2P2O5/ ROH/H+NH3/H+P2O5RCNH2OH2OH2O/OH-H2O/H+或OH-H2O/H+或OH-RCOONaROHROHROHROHROHNH3NH3NH3NH3R-C-NH2NHRNH2OOOHTsOH1. t-BuOK2. PhCH2BrH2O, H+1. LiAlH4(CH3)2C(OCH3)2(C6H14O3)（三三醇醇）（二二醇醇）2. H2O*AC(C9H18O3)(C16H24O3)DB(C13H20O3)OCROR1