雜環(huán)化合物2優(yōu)秀課件

Chapter14HeterocyclicCompounds（雜環(huán)化合物）Heterocycle/HeterocyclicCompound構(gòu)成環(huán)系的原子除C外，還有其它雜原子。O,S,N.Hetero-atom(雜原子):HeterocycleSaturatedHeterocycles飽和雜環(huán)化合物AromaticHeterocycles芳香雜環(huán)化合物體現(xiàn)各自功能團的性質(zhì)一.Classification&Nomenclature:按環(huán)的大小Five-memberedringSix-memberedring按雜原子的數(shù)目一個雜原子雜環(huán)兩個雜原子雜環(huán)多個雜原子雜環(huán)按環(huán)的拼合形式單雜環(huán)(homo-heterocycle)稠雜環(huán)(fused-heterocycle)pyrrole吡咯thiophene噻吩furan呋喃Classification&NomenclatureFive-memberedringheterocyclesimidazole咪唑pyrazole吡唑oxazole口惡唑thiazole噻唑Isoxazole異口惡唑

Fused-heterocyclesClassification&Nomenclaturequinoline喹啉iso-quinoline*異喹啉Purine*嘌呤Indole吲哚

蝶啶pteridine口丫啶acridine吩嗪phenazinecarbazole咔唑Phenothiazine吩噻嗪Classification&NomenclatureAttention!“指示氫”or“標(biāo)氫”—最多的非累積雙鍵外的飽和氫沒有達到最多的非累積雙鍵，“外加氫”的標(biāo)注Classification&Nomenclature取代雜環(huán)的命名：編號原則：單雜環(huán)、稠雜環(huán)；最小編號和優(yōu)先順序法則iso-quinoline*異喹啉Purine*嘌呤5-硝基-2-呋喃甲醛4-氨基嘧啶N,N-二乙基-3-吡啶甲酰胺1,3,7-三甲基嘌呤-2,6-二酮3-甲基-5-氯喹啉7-碘-8-羥基喹啉-5-磺酸Classification&Nomenclature拼合雜環(huán)的命名：非特定稠環(huán)基本環(huán)附加環(huán)稠合邊的表示呋喃并[2,3-b]噻吩吡咯并[3,2-b]噻吩Classification&Nomenclature拼合雜環(huán)的命名：整體稠環(huán)編號，取代基位置5-苯基咪唑并[2,1-b]噻唑6H-吡唑并[4,5-d]口惡唑二.Six-memberedHeterocycliccompoundsPyridine吡啶1.Structure:

C5H5N芳香性較強的堿性2.Physicalproperties(1)(偶極矩)Dipolemoment=7.4110-38c.m3.9010-38c.mIC方向一致Six-memberedHeterocycliccompounds(2)Solubility:

吡啶可以與水以任意比例互溶3.Chemicalreactionsa.BasicityofPyridineBasicitySix-memberedHeterocycliccompoundsSix-memberedHeterocycliccompoundsPyr.SO3磺化試劑酰化試劑甲基化試劑Six-memberedHeterocycliccompounds不穩(wěn)定取代2-位取代3-位Six-memberedHeterocycliccompounds-PyridineSix-memberedHeterocycliccompoundsc.NucleophilicSubstitution2,4,6-位的影響—X的取代Six-memberedHeterocycliccompounds-PyridineSix-memberedHeterocycliccompoundsE.Chichibabin

ReactionH-的取代Six-memberedHeterocycliccompounds-PyridineSix-memberedHeterocycliccompounds-Pyridined.ReactionsofsidechainSideChainAcidityof-HSix-memberedHeterocycliccompounds2-位甲基3-位甲基4-位甲基八隅體八隅體Six-memberedHeterocycliccompoundse.Oxidations&Reductions側(cè)鏈的氧化煙堿煙酸煙酰胺N-氧化物Pyridine-N-oxide3-甲基吡啶N-氧化物Six-memberedHeterocycliccompounds-PyridinePyridine-N-oxide:Substitution/PositionSix-memberedHeterocycliccompounds-Pyridine-attack-attack-attackSix-memberedHeterocycliccompounds-PyridinepiperidineReductionSix-memberedHeterocycliccompounds-PyrimidineVitaminB2SulfadiazineSD磺胺嘧啶苯巴比妥PhenobarbitalMoxonidine莫索尼定Six-memberedHeterocycliccompounds-PyrimidineAntimetabolicAgentsFluorouracil5-FUTegafurCytarabine阿糖胞苷司他夫定StavudineZidovudine齊多夫定拉米夫定LamivudineAntiviralAgentsSix-memberedHeterocycliccompounds-QuinolineandIsoquinolineQuinolineandIsoquinolinequinoline喹啉iso-quinoline*異喹啉雜化sp2堿性取代反應(yīng)：E.S.N.S.位置Six-memberedHeterocycliccompounds-QuinolineandIsoquinolineElectrophilicSubstitution異環(huán)取代5-，8-位Six-memberedHeterocycliccompounds-QuinolineandIsoquinolineNucleophilicSubstitution發(fā)生在吡啶環(huán)上，2(1)、4位上Six-memberedHeterocycliccompounds-QuinolineandIsoquinolineTheReactionsofSideChain2(1),4位側(cè)鏈-HSix-memberedHeterocycliccompounds-QuinolineandIsoquinolineOxidation&Reduction氧化苯環(huán)還原吡啶環(huán)Six-member