1、NHNNONNHNNSONHOOOOONNHNOSNHNNONONNNHNSNHOS13452 NHEt3 ONHNHNH2523NNHNO3452112345NNH34521NO12345NNNH34521N63452 NCH3NH1NNNNNNNNN135121314NN13OHNHN13O2NHNH13ONHN13ONHNH13OOONH2H3C634521NH7634521O7634521S7125NNH3521345467NN1234678867634521NHNN7ONHSA CHCCCHAHHHHAEAEAE+NHOSAEAEAEAEH H+AEHHAEAEAAEHEH HAAA
2、AAAEH H+AEAEAAcONO2AcONO2Ac2O+HNO3+NHAcONO2Ac2O,10oCNHNO2NHNO251%13%+SAcONO2Ac2O-AcOH,0oCSNO2SNO260%10%+OAcONO2 5 30oCONO2AcO碱碱或或ONO2 HOAc OONO2AcOHHBONO2AcOONO2NO2 HOAc+NSO3NSO3+CH2Cl2NH100oCNHSO3HSSH+r.t.SO32Ba2+OH+OSO3H+OSO3HHO3S41%15%90%86%Ba(OH)2NSO3NSO3NSO3r.t.SSSO3HH2SO4r.t.SH2SO4r.t.SSO3H&OO
3、CSSCH3OPhCClOPhCOSnCl2Ac2OBF3NHNHNN PhPhN2 XOBr2/0oC稀溶液OBrSSBrHOAcBr2AGAWAGAWSCH3HNO3/Ac2OSCH3SCH3O2NNO2+70%30%(AcONO2)SNO2HNO3SNO2SNO2O2NO2N+85%15%ONO2HNO3ONO2O2NSHNO3/Ac2OSNO2BrBrSBr2COOHCH3COOHSCOOHBrAG345进入3位进入4位进入5位AGEAGEAGEAGEAGEAGEAGEEEEAW345AWEAWEAWEAWEAWEAWEAWE进入3位E进入4位E进入5位EAG245进入2位进入4位进入
4、5位AGEAGEAGEAGEAGEAGEAGEAGEEEEAW245进入4位进入5位AWEAWEAWEAWEAWEAWEAWEAWE进入2位EEEOSNHH2/PdH2/PdOSNHH2/MoS2SRRRRNiSSCCORORRaney NiRaney NiH2H2CCOROR+NiS+RCRORCRSSSHHSH2Raney NiRCRHHO+CO2CH3CO2CH3OH3CO2CH3CO2CFBrLiOONHHNONHSORCH2CH2RH2O/H+ORCH2CH2RORRCH2OOHORRH+ORRHHORRORROH2OHRROHOHRROHOHRROH+OHRROORROH2O-H-
5、HSAcONO2Ac2O-AcOH,0oCSNO2SNO260%10%+OAcONO2 5 30oCONO2AcO碱 或 ONO2 HOAcOBr2/CH3OHOH3COBrCH3OHOH3COOCH3Br2+2 CH3OHCH3O+Br CH3Br+H2OOBrOBrCH3OOBrH3COOH3COOH3COOCH3OCH3 BrOBr2/CH3OHOH3COBrCH3OHOH3COOCH3H2/PdOH3COOCH3H2OH+OHOHOHBuLior LDAOLiRXOROH3C过过量量OH3CLiOH3CBrHOOHTsOHH3CBrOOOOBuLiBr(CH2)3BrRLiH3CROO
6、OO(1)H(2)OHNHNRRRNH+NHHHNHH+NHHHNHHHNHHHNHnH+NHHHnNHH+NHHHNHNHHHNHHNHHHNHHNHHNHHHHNHHHnNHNRRHROHPhOHNHNK+KH2NNNNNNONKCO2H2OH+NHCOOHCHCl3KOHNHCHOR C ClONCOR150oCNHCORCH3INCH3150oCNHCH3CCCCCNHHHHHNNR3NNKb10-910-410-14HROTs+TsClNROH+NH ClRCH+NC(CO2C2H5)2RCHOCH2(CO2C2H5)2NSO3NSO3+CH2Cl2NSO3NHSO3H(1)(2)H
7、ClNClH+NHSO3H+NN SO3NCH3NCH3II+NCH3300oCHINaOHNCH3NCH3HINCH3NaOH重重排排NCH3INRCClONRCOClROHRCORONClH+NRCOROHNRCOROHRCOORHN+RCORONH+N(CH3)3N(CH3)3NO2发发烟烟 H2SO4发发烟烟 HNO3 /常常温温N发发烟烟 H2SO4发发烟烟 HNO3 /No Reaction发发烟烟 H2SO4发发烟烟 HNO3 /NNO2300oC/24h常常温温NNSO3HNBr浓浓 H2SO4/HgSO4220oC300oCBr2/浮浮石石Friedel-Crafts 反反应
8、应No ReactionNKNO3/浓浓 H2SO4110oCNNO2H3CCH3H3CCH3NNH220oCBr2/HOAcNNH2BrNNNNNN EENENENENEHHH-HNE 位位E 位位NNEHNEHNEHNE-HNGNGNGNG（弱）（强）EEEEEENNHNuNNuNu=NH2,PhNu HN NuNuNuNNH2NHNH2HNH2NNH2+H2NH2NNH+NH3NH2+NNHHNNH2+H2+NHNNNNH2+NaNH2H2NH3 或 PhNMe2NPhLiNPhO2 or PhNO2,(氧氧化化)NPhLiNPhLiHO2 or PhNO2,(氧氧化化芳芳构构化化)NP
9、h NClNOHCl ClNOHOHNClNOHNaOHNHO异异构构化化NHONNH2(1)NaNO2,HCl(2)H2O,NOHNHO异异构构化化NNaNH2NNH2NClNH3,ZnCl2NClPhNH2NNHPhNBrNH3NNH2BrBrNOCH3NClNaOCH3 HOCH3,NNH3NClNH3,ZnCl2ZnCl2ClNNH2ZnClCl-HClNNH2 ZnCl2NH2,Pt0.3 MPNHNNHNHSn/HClor Na/EtOHH2,NiNCH3KMnO4NCOOHNNCH3NCOOHHNO3 R3NH2O2R3NONH2O2HOAcNON发烟 H2SO4发烟 HNO3N
10、NO2300oC/24h NO发烟HNO3发烟H2SO490oCNONO2NNO2POCl3+PCl3NO(1)PhMgX(2)H2ONOHPhHAc2ONPhNPhLiNPhO2 or PhNO2,(氧氧化化)NONONONOONO NONONONONNO NONOHNO2NOHNO2NONO2 H+NONO2PCl3NNO2+OPCl3NO2PCl3NOPhMgXNOMgXPhHH2ONOHPhHAc2ONOAcPhH HOAcNPhNCH2BHNCH2NCH2NH2CHBNCH2NCH2NCH2NH2NCH2HPhCPhOH2ONCH2PhCPhONCH2PhCPhOHNCH3PhC P
11、hONCH2NaNH2PhCPhOHNCH3N RLiCNCNNCH21.2.H2ONCH2CH3CH3NCH2CH3CH2CH3NCH2CH3CH2NaNH2CH3INCH3ZnCl2NCH2ZnClClHNCH2ZnClH CHONCH2ZnClCH2OH2O HClNCH2CH2OHNCH3H CHONCH2CH2OHZnCl2NHOS123456712345671234567AEAEAEorAEAEHAE进进2位位 H+AEAEAEHHAE进进3位位 H+NHNSO3NHSO3HSSCOCH3Ac2O主主要要产产物物+OHNO3HOAcONO2AlCl3NSO3HOHNO2少少量量SC
12、OCH3N12345678N12345678NNNNNNN N12345678ENN+EEN N12345678NHNO3NNO2NNO252%48%Br2AgSO4/H2SO4NBrNBr51%49%H2SO4+NH2SO4,SO390oCNSO3HH2SO4300oCNHO3SNE进进入入5位位NENENENENENENENENENENE进进入入8位位NBr2,CCl4NBr吡吡啶啶NBrBrNBr Br BrNBrBrBrBrNBrBrBrHNBrBrBr HB Br2NBrBN1.NaNH2NNH21.n-BuLi2.H2ONBu-nNPh2.H2ONPhNH2PhNO21.NaNH2
13、2.H2ONNClCH3ONa,CH3OHNOCH3NClClNCHCNClNaCHCNPhPhNKMnO4HOOCHOOCNNNH2 mol H2Pt3 mol H2PtNHHNCH3EtOCCOEtO ONaOEt/HOEtNCH2CCOOEtONNNNNNNNN NuEN浓 HNO3浓 H2SO4NN+NO2NO20oC100oC72%8%65%10%N发烟 H2SO4NSO3H300oCNBr2,75oCNBrAlCl3NBrBr BrBrBr Br2BNBr BrNBrBrBrNBrBrHHHBrNBrBrHNBrNBr2,CCl4NBr吡啶NNNH2H2ONLiBunH2ONBun
14、KNH2NH3PhNO2NClClNCH(CO2Et)2ClNaHCH2(CO2Et)2NCH3PhCHO,ZnCl2100oC,2hNCHCHPhNCH3PhCHO,ZnCl2165oC,7 天CHPhNCHNH2+CH2CH CH2OH OHOHNH2SO4PhNO2CH2CHCH2OHOHOHH2SO4HCCHCH2OHOH H2OHCCH2CH2OHOH2SO4HCCHCH2OHCCHCH2OH H2OHNH2H2CCHOH HNH2OHHNHOHNHOHHNHOHNH氧氧化化芳芳构构化化PhNO2N+NH2NHOH2HOSO3HHHHO3SOCH2CHCH2OHOHOHNH2+NH2
15、SO4OHOHNO2OHNH2+NH2SO456H3AsO4CH2CHCH2OHOHOHNH2+NH2SO4PhNO2HCCHCH2ONH2+N浓浓 HClPhNO22 CH3CHOCH3CHOH3CHNO2NCH3NH3CBrNH2NH2H2N+CH2CHCH2OHOHOH+CH2CHCH2OHOHOH2H2SO4NO2H2SO4NO2O2N人有了知识，就会具备各种分析能力，人有了知识，就会具备各种分析能力，明辨是非的能力。明辨是非的能力。所以我们要勤恳读书，广泛阅读，所以我们要勤恳读书，广泛阅读，古人说古人说“书中自有黄金屋。书中自有黄金屋。”通过阅读科技书籍，我们能丰富知识，通过阅读科技书籍，我们能丰富知识，培养逻辑思维能力；培养逻辑思维能力；通过阅读文学作品，我们能提高文学鉴赏水平，通过阅读文学作品，我们能提高文学鉴赏水平，培养文学情趣；培养文学情趣；通过阅读报刊，我们能增长见识，扩大自己的知识面。通过阅读报刊，我们能增长见识，扩大自己的知识面。有许多书籍还能培养我们的道德情操，有许多书籍还能培养我们的道德情操，给我们巨大的精神力量，给我们巨大的精神力量，鼓舞我们前进鼓舞我们前进。
