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Chapter 14 Heterocyclic Compounds （杂环化合物）

Chapter 14 Heterocyclic Compounds （杂环化合物）. Hetero-atom ( 杂原子 ):. O, S, N. Heterocycle / Heterocyclic Compound 构成环系的原子 除 C 外，还有其它 杂原子 。. Saturated Heterocycles 饱和杂环化合物. 体现各自功能团的性质. Heterocycle. Aromatic Heterocycles 芳香杂环化合物. 一 .Classification & Nomenclature:. Five-membered ring.

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Chapter 14 Heterocyclic Compounds （杂环化合物）

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  1. Chapter 14 Heterocyclic Compounds（杂环化合物） Hetero-atom (杂原子): O, S, N. Heterocycle / Heterocyclic Compound 构成环系的原子除C外，还有其它杂原子。 Saturated Heterocycles 饱和杂环化合物 体现各自功能团的性质 Heterocycle Aromatic Heterocycles 芳香杂环化合物

  2. 一 .Classification & Nomenclature: Five-membered ring 按环的大小 Six-membered ring 一个杂原子杂环 按杂原子的数目 两个杂原子杂环 多个杂原子杂环 单杂环(homo-heterocycle) 按环的拼合形式 稠杂环(fused-heterocycle)

  3. Classification & Nomenclature Five-membered ring heterocycles furan 呋喃 thiophene 噻吩 pyrrole 吡咯 thiazole 噻唑 imidazole 咪唑 pyrazole 吡唑 oxazole 口恶 唑 Isoxazole 异口恶 唑

  4. Classification & Nomenclature Six-membered ring heterocycles 2H-pyran 2H- 吡喃 pyridine 吡啶 Pyridazine 哒嗪 pyrimidine 嘧啶 Pyrazine 吡嗪

  5. Classification & Nomenclature Fused-heterocycles quinoline 喹啉 iso-quinoline* 异 喹啉 Indole 吲哚 Purine* 嘌呤 蝶啶 pteridine 口丫啶 acridine 吩嗪 phenazine carbazole 咔唑 Phenothiazine 吩噻嗪

  6. Classification & Nomenclature Attention!  “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

  7. 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 4-氨基嘧啶 N,N-二乙基-3-吡啶甲酰胺 5-硝基-2-呋喃甲醛 3-甲基-5-氯喹啉 7-碘-8-羟基喹啉-5-磺酸 1,3,7-三甲基嘌呤-2,6-二酮

  8. Classification & 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-甲基吡唑

  9. Classification & Nomenclature 非特定稠环  拼合杂环的命名： 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

  10. 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

  11. 二. Six-membered Heterocyclic compounds Pyridine 吡啶 C5H5N 1. Structure: 芳香性 较强的碱性

  12. Six-membered Heterocyclic compounds Kekule’s structure Aromaticity ? E.S. 变难 N.S. 变易 电子云的分布 Oxidation 难 Reduction 易 Basicity

  13. Six-membered Heterocyclic compounds 2. Physical properties (1)  (偶极矩) Dipole moment I 方向一致 C  = 7.4110-38 c.m 3.90 10-38 c.m (2) Solubility: 吡啶可以与水以任意比例互溶

  14. Six-membered Heterocyclic compounds 3. Chemical reactions a. Basicity of Pyridine Basicity

  15. Six-membered Heterocyclic compounds Pyr.SO3 磺化试剂 甲基化试剂 酰化试剂

  16. Six-membered Heterocyclic compounds b. Electrophilic Substitution: N的-I 钝化环 反应条件剧烈 取代反应发生在3-位（）

  17. Six-membered Heterocyclic compounds Six-membered Heterocyclic compounds-Pyridine 取代2-位 不稳定 取代3-位

  18. Six-membered Heterocyclic compounds Six-membered Heterocyclic compounds-Pyridine c. Nucleophilic Substitution —X的取代 2, 4, 6-位的影响

  19. Six-membered Heterocyclic compounds Six-membered Heterocyclic compounds-Pyridine • E. Chichibabin • Reaction H-的取代

  20. Six-membered Heterocyclic compounds Six-membered Heterocyclic compounds-Pyridine 2-位 (6-位) 八电子氮负离子 3-位 4-位 八电子氮负离子

  21. Six-membered Heterocyclic compounds-Pyridine d. Reactions of side chain Acidity of -H Side Chain

  22. Six-membered Heterocyclic compounds 2-位甲基 八隅体 3-位甲基 4-位甲基 八隅体

  23. Six-membered Heterocyclic compounds Six-membered Heterocyclic compounds-Pyridine e. Oxidations & Reductions 侧链的氧化 烟碱 烟酸 烟酰胺 N-氧化物 Pyridine-N-oxide 3-甲基吡啶N-氧化物 Pyridine-N-oxide: Substitution / Position

  24. Six-membered Heterocyclic compounds-Pyridine Electrophilic Nucleophilic

  25. Six-membered Heterocyclic compounds-Pyridine -attack -attack -attack

  26. Six-membered Heterocyclic compounds-Pyridine Reduction piperidine

  27. Six-membered Heterocyclic compounds-Pyrimidine sp2 嘧啶Pyrimidine 碱性 水溶性 取代反应

  28. Six-membered Heterocyclic compounds-Pyrimidine 2, 4, 6-positions (Uracil, U)尿嘧啶 胞嘧啶 (Cytosine, C) 胸腺嘧啶(Thymine. T) tautomerism

  29. Six-membered Heterocyclic compounds-Pyrimidine Vitamin B2 Sulfadiazine SD 磺胺嘧啶 苯巴比妥 Phenobarbital Moxonidine 莫索尼定

  30. Six-membered Heterocyclic compounds-Pyrimidine Antimetabolic Agents Fluorouracil 5-FU Tegafur Cytarabine阿糖胞苷 Antiviral Agents 司他夫定 Stavudine Zidovudine 齐多夫定 拉米夫定 Lamivudine

  31. Six-membered Heterocyclic compounds-Quinoline and Isoquinoline Quinoline and Isoquinoline iso-quinoline* 异 喹啉 quinoline 喹啉 杂化 sp2 碱性 位置 E.S. N.S. 取代反应：

  32. Six-membered Heterocyclic compounds-Quinoline and Isoquinoline Electrophilic Substitution 异环取代 5-，8-位

  33. Six-membered Heterocyclic compounds-Quinoline and Isoquinoline Nucleophilic Substitution 发生在吡啶环上，2(1)、4位上

  34. Six-membered Heterocyclic compounds-Quinoline and Isoquinoline The Reactions of Side Chain -H 2(1), 4位侧链

  35. Six-membered Heterocyclic compounds-Quinoline and Isoquinoline Oxidation & Reduction 氧化苯环 还原吡啶环

  36. Six-membered Heterocyclic compounds-Pyran Pyran 吡喃 -吡喃酮 2H-吡喃 (-吡喃) 吡喃盐正离子 口恶英嗡盐离子 4H-吡喃 (-吡喃) -吡喃酮 杂化 不饱和环醚——非芳香性 芳香性 稳定性/高反应活性

  37. Six-membered Heterocyclic compounds-Pyran -吡喃酮

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