杂环化合物2优秀课件

Chapter14HeterocyclicCompounds（杂环化合物）Heterocycle/HeterocyclicCompound构成环系的原子除C外，还有其它杂原子。O,S,N.Hetero-atom(杂原子):HeterocycleSaturatedHeterocycles饱和杂环化合物AromaticHeterocycles芳香杂环化合物体现各自功能团的性质一.Classification&Nomenclature:按环的大小Five-memberedringSix-memberedring按杂原子的数目一个杂原子杂环两个杂原子杂环多个杂原子杂环按环的拼合形式单杂环(homo-heterocycle)稠杂环(fused-heterocycle)pyrrole吡咯thiophene噻吩furan呋喃Classification&NomenclatureFive-memberedringheterocyclesimidazole咪唑pyrazole吡唑oxazole口恶唑thiazole噻唑Isoxazole异口恶唑

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

蝶啶pteridine口丫啶acridine吩嗪phenazinecarbazole咔唑Phenothiazine吩噻嗪Classification&NomenclatureAttention!“指示氢”or“标氢”—最多的非累积双键外的饱和氢没有达到最多的非累积双键，“外加氢”的标注Classification&Nomenclature取代杂环的命名：编号原则：单杂环、稠杂环；最小编号和优先顺序法则iso-quinoline*异喹啉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-羟基喹啉-5-磺酸Classification&Nomenclature拼合杂环的命名：非特定稠环基本环附加环稠合边的表示呋喃并[2,3-b]噻吩吡咯并[3,2-b]噻吩Classification&Nomenclature拼合杂环的命名：整体稠环编号，取代基位置5-苯基咪唑并[2,1-b]噻唑6H-吡唑并[4,5-d]口恶唑二.Six-memberedHeterocycliccompoundsPyridine吡啶1.Structure:

C5H5N芳香性较强的碱性2.Physicalproperties(1)(偶极矩)Dipolemoment=7.4110-38c.m3.9010-38c.mIC方向一致Six-memberedHeterocycliccompounds(2)Solubility:

吡啶可以与水以任意比例互溶3.Chemicalreactionsa.BasicityofPyridineBasicitySix-memberedHeterocycliccompoundsSix-memberedHeterocycliccompoundsPyr.SO3磺化试剂酰化试剂甲基化试剂Six-memberedHeterocycliccompounds不稳定取代2-位取代3-位Six-memberedHeterocycliccompounds-PyridineSix-memberedHeterocycliccompoundsc.NucleophilicSubstitution2,4,6-位的影响—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-位甲基八隅体八隅体Six-memberedHeterocycliccompoundse.Oxidations&Reductions侧链的氧化烟碱烟酸烟酰胺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齐多夫定拉米夫定LamivudineAntiviralAgentsSix-memberedHeterocycliccompounds-QuinolineandIsoquinolineQuinolineandIsoquinolinequinoline喹啉iso-quinoline*异喹啉杂化sp2碱性取代反应：E.S.N.S.位置Six-memberedHeterocycliccompounds-QuinolineandIsoquinolineElectrophilicSubstitution异环取代5-，8-位Six-memberedHeterocycliccompounds-QuinolineandIsoquinolineNucleophilicSubstitution发生在吡啶环上，2(1)、4位上Six-memberedHeterocycliccompounds-QuinolineandIsoquinolineTheReactionsofSideChain2(1),4位侧链-HSix-memberedHeterocycliccompounds-QuinolineandIsoquinolineOxidation&Reduction氧化苯环还原吡啶环Six-member