有机化学第十六章杂环化合物
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N H
Xiamen University
N CO2Et N
Organic Chemistry
巨杂环
Xiamen University
卟吩环系
N
NH HN N
大环醚
O OO
OO O
N NH H HN
氮穴类化合物
NH H HN N
Organic Chemistry
螺杂环
碳环螺杂环 杂环螺杂环 HN
O
Heterocyclic compounds are common in organic chemistry, and many have XiamenimUnpivoerrtsaitynt biological properties.
Antibiotic: Penicillin
O
Organic Chemistry
C6H5CH2 C NH H
O
H S
N
CH3 CH3
CO2H H
Xiamen University
Penicillin G
Antiulcer agent: Cimetidine
O Organic Chemistry CH3HN C NHCH2CH2 S CH2
N
Cimentidine
Xiamen Unive甲rsi氰ty 咪胍(抗溃疡药)
Natural products: Chlorophyll
Organic Chemistry
CH3
CH2CH3
CH2 CH CH3
N
CH3
N Mg N
N
O
CH3 H
ຫໍສະໝຸດ Baidu
CO2CH3 H HO
O
Xiamen University Chlorophyll a
CH3 H CH3 H
Chlorophyll a
THF cyclic ether)
N Pyridine
(A cyclic amine)
Organic Chemistry
16.1 分类和命名
Classification and Nomenclature
Xiamen University
Organic Chemistry
杂环化合物
Xiamen University
The structure of chlorophyll a was Organic eChsetmabisltirsyhed largely through the work of H.
Fischer(Munich), R. Willstätter(Munich), and J. B. Conant(Harvard). A synthesis of chlorophyll a from simple organic compounds was achieved by R. B. Woodward(Harvard) in 1960. Who won the Nobel Prize in 1965 for his outstanding contributions to synthetic Xiamen Uonrigvearnsiitcy chemistry.
Some heterocycles we’ve encountered
Organic CheOmistry
Epoxide (A cyclic ether)
OO
Lactone (A cyclic ester)
NO H Lactam (A cyclic amide)
O
Xiamen
Universi(tAy
O H
N SO
O
Saccharin
Natural products: Heme
Organic Chemistry
CH3
HO2CCH2CH2
CH3
CH CH2
N N Fe N
N
CH3 CH CH2
HO2CCH2CH2
Xiamen University
CH3
Heme
Organic Chemistry Xiamen University
CH3
N H
Sedative: Phenobarbital
H
Organic Chemistry
ON
N H
O
O CH2CH3
Xiamen University Phenobarbital
Nonnutritive sweetener: Saccharin
Organic Chemistry Xiamen University
编号—— 使杂原子的位号尽可能小 如不 止一个杂原子 则按O S N的顺序编号 对不同程度饱和的杂环化合物 不但要标 明氢化(饱和)的程度 而且要标出氢化的 位置
Xiamen University
O
OrganiFc uChreamnistry 呋喃
N H Pyrrole
吡咯
S
Thiophene 噻吩
NH
O NH
Xiamen University
桥杂环
Organic Chemistry
杂环多面体
Xiamen University
NH OH
H
H
CH3CO2
丁公藤碱
O H
O
OH
O
H
HOCH2
N NH2 N
OH OH H
河豚毒素
单杂环的命名方法
根据每个杂环化合物的英文名称音译 加 Organic “C口hem”字istr旁y 表示环状化合物
单杂环 稠杂环 巨杂环 螺杂环 桥杂环 杂环多面体
Organic Chemistry
单杂环
Xiamen University
三员杂环 O 四员杂环 S
NN S
五员杂环 OO
六员杂环 NN H
七员杂环
N H
苯并杂环
Organic Chemistry
N
碳环并杂环
H
稠杂环
其它碳环并杂环 NN
杂环并杂环 N
N
Pyridine 吡啶
N
N
O
Oxazole Xiamen 噁Un唑iversity
N H Imidazole
咪唑
N
N
S
Thiazole 噻唑
N
Pyrimidine 嘧啶
CH3
N
Organic Chemistry
3-Methylpyridine
第十六章 杂环化合物
Heterocycles
Carbocycles
Cyclic organic compounds
Heterocycles
Organic Chemistry
Carbocyclic rings contain only carbon atoms.
Heterocyclic rings contain one or more different atoms in addition to carbon. N, O, S are the most common heteroatoms.
Xiamen University
N CO2Et N
Organic Chemistry
巨杂环
Xiamen University
卟吩环系
N
NH HN N
大环醚
O OO
OO O
N NH H HN
氮穴类化合物
NH H HN N
Organic Chemistry
螺杂环
碳环螺杂环 杂环螺杂环 HN
O
Heterocyclic compounds are common in organic chemistry, and many have XiamenimUnpivoerrtsaitynt biological properties.
Antibiotic: Penicillin
O
Organic Chemistry
C6H5CH2 C NH H
O
H S
N
CH3 CH3
CO2H H
Xiamen University
Penicillin G
Antiulcer agent: Cimetidine
O Organic Chemistry CH3HN C NHCH2CH2 S CH2
N
Cimentidine
Xiamen Unive甲rsi氰ty 咪胍(抗溃疡药)
Natural products: Chlorophyll
Organic Chemistry
CH3
CH2CH3
CH2 CH CH3
N
CH3
N Mg N
N
O
CH3 H
ຫໍສະໝຸດ Baidu
CO2CH3 H HO
O
Xiamen University Chlorophyll a
CH3 H CH3 H
Chlorophyll a
THF cyclic ether)
N Pyridine
(A cyclic amine)
Organic Chemistry
16.1 分类和命名
Classification and Nomenclature
Xiamen University
Organic Chemistry
杂环化合物
Xiamen University
The structure of chlorophyll a was Organic eChsetmabisltirsyhed largely through the work of H.
Fischer(Munich), R. Willstätter(Munich), and J. B. Conant(Harvard). A synthesis of chlorophyll a from simple organic compounds was achieved by R. B. Woodward(Harvard) in 1960. Who won the Nobel Prize in 1965 for his outstanding contributions to synthetic Xiamen Uonrigvearnsiitcy chemistry.
Some heterocycles we’ve encountered
Organic CheOmistry
Epoxide (A cyclic ether)
OO
Lactone (A cyclic ester)
NO H Lactam (A cyclic amide)
O
Xiamen
Universi(tAy
O H
N SO
O
Saccharin
Natural products: Heme
Organic Chemistry
CH3
HO2CCH2CH2
CH3
CH CH2
N N Fe N
N
CH3 CH CH2
HO2CCH2CH2
Xiamen University
CH3
Heme
Organic Chemistry Xiamen University
CH3
N H
Sedative: Phenobarbital
H
Organic Chemistry
ON
N H
O
O CH2CH3
Xiamen University Phenobarbital
Nonnutritive sweetener: Saccharin
Organic Chemistry Xiamen University
编号—— 使杂原子的位号尽可能小 如不 止一个杂原子 则按O S N的顺序编号 对不同程度饱和的杂环化合物 不但要标 明氢化(饱和)的程度 而且要标出氢化的 位置
Xiamen University
O
OrganiFc uChreamnistry 呋喃
N H Pyrrole
吡咯
S
Thiophene 噻吩
NH
O NH
Xiamen University
桥杂环
Organic Chemistry
杂环多面体
Xiamen University
NH OH
H
H
CH3CO2
丁公藤碱
O H
O
OH
O
H
HOCH2
N NH2 N
OH OH H
河豚毒素
单杂环的命名方法
根据每个杂环化合物的英文名称音译 加 Organic “C口hem”字istr旁y 表示环状化合物
单杂环 稠杂环 巨杂环 螺杂环 桥杂环 杂环多面体
Organic Chemistry
单杂环
Xiamen University
三员杂环 O 四员杂环 S
NN S
五员杂环 OO
六员杂环 NN H
七员杂环
N H
苯并杂环
Organic Chemistry
N
碳环并杂环
H
稠杂环
其它碳环并杂环 NN
杂环并杂环 N
N
Pyridine 吡啶
N
N
O
Oxazole Xiamen 噁Un唑iversity
N H Imidazole
咪唑
N
N
S
Thiazole 噻唑
N
Pyrimidine 嘧啶
CH3
N
Organic Chemistry
3-Methylpyridine
第十六章 杂环化合物
Heterocycles
Carbocycles
Cyclic organic compounds
Heterocycles
Organic Chemistry
Carbocyclic rings contain only carbon atoms.
Heterocyclic rings contain one or more different atoms in addition to carbon. N, O, S are the most common heteroatoms.