北大有机课件第十四章-杂环化合物

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1、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):Heterocycle杂环SaturatedHeterocycles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

2、单杂环(homo-heterocycle)稠杂环(fused-heterocycle)pyrrole吡咯thiophene噻吩furan呋喃Classification&NomenclatureFive-memberedringheterocyclesimidazole咪唑pyrazole吡唑oxazole口恶唑thiazole噻唑Isoxazole异口恶唑Six-memberedringheterocyclesClassification&Nomenclaturepyridine吡啶pyrimidine嘧啶2H-pyran2H-吡喃Pyridazine哒嗪Pyrazine

3、吡嗪4H-pyran4H-吡喃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”的标注命名顺序:-SO3H>-COOH>-COOR>-CONH2>-CN>-CHO>-C

4、OR>-OH>-NH2>-R>-NO2>-XClassification&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,-二甲基嘌呤-2,6-二酮3-甲基-5-氯喹啉7-碘-8-羟基喹啉-5-磺酸Classification&NomenclatureClassification&Nomenclature互变异构的存在，编号及名称的改变7H-嘌呤9H-嘌呤2,4-二羟基嘧啶嘧啶-2,4-二酮5-甲基吡唑3-甲基吡

5、唑尿嘧啶(U)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6-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Kekule’sstructureAromaticity?电子云的分布E.S.变难N.S.变易Oxidation难

6、Reduction易BasicitySix-memberedHeterocycliccompounds2.Physicalproperties(1)(偶极矩)Dipolemoment=7.4110-38c.m3.9010-38c.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-memberedHeterocyclicco

7、mpoundsPyr.SO3磺化试剂酰化试剂甲基化试剂b.ElectrophilicSubstitution:N的-I钝化环反应条件剧烈取代反应发生在3-位（）Six-memberedHeterocycliccompoundsSix-memberedHeterocycliccompounds不稳定取代2-位取代3-位