厦门大学化学化工学院：《有机化学》课程教学资源（授课教案）第十六章 杂环化合物 Heterocycles

第十六章杂环化合 Fe 人 Heteredvdle

第十六章 杂环化合物 Heterocycles

Carbocycles 3. Cyclic organic compounds Heterocycles Carbocyclic rings contain only carbon atoms a Heterocyclic rings contain one or more different atoms in addition to carbon no, s are the most common heteroatoms g heterocyclic compounds are common in organic chemistry and many have d important biological properties

Organic Chemistry Organic Chemistry Xiamen Xiamen University University C ycl i c o r g anic compo unds Ca r b o c y c l e s Heterocycles „ 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. „ Heterocyclic compounds are common in organic chemistry, and many have important biological properties

Antibiotic penicillin O C6H3 CH2-C NH H CH H CH Y CO2H Penicillin g

Organic Chemistry Organic Chemistry Xiamen Xiamen University University Antibiotic: Antibiotic: Penicillin Penicillin S N O H H CO 2 H NH H CH 3 CH 3 C 6 H 5CH2 C O P e n i c illin G

Antiulcer agent: Cimetidine O CH3HN-C-NHCH2 CH2-S-CH2 CH Cimetidine H 甲氰咪胍(抗溃疡药)

Organic Chemistry Organic Chemistry Xiamen Xiamen University University Antiulcer agent: Antiulcer agent: Cimetidine Cimetidine N N CH 3 H C NHC H2CH2 S CH2 O CH 3HN Ci m ent i d i n e 甲氰 咪 胍 (抗溃疡药 )

Sedative: phenobarbital H ON、∠O CH2CH3 H Phenobarbital

Organic Chemistry Organic Chemistry Xiamen Xiamen University University Sedative: Sedative: Phenobarbital Phenobarbital N N CH2CH 3 O O O H H Ph e n o bar b ital

I Nonnutritive sweetener: Saccharin N S Saccharin

Organic Chemistry Organic Chemistry Xiamen Xiamen University University Nonnutritive sweetener: Nonnutritive sweetener: Saccharin Saccharin S N H O O O Sa c cha r i n

Natural products: Heme CH3 CH=CH2 CH CH3 N—Fe—N HOCCHoCH CH-CH HO2 CH2 CH3 Heme

Organic Chemistry Organic Chemistry Xiamen Xiamen University University Natural products: Natural products: Heme N N N N CH 3 CH CH 3 CH CH 3 CH 3 HO 2CCH2CH 2 HO2CCH2CH2 CH 2 CH2 Fe He m e

①D ⑨D

Organic Chemistry Organic Chemistry Xiamen Xiamen University University

3 Natural products: Chlorophyll CH L CH2CH3 CH2-CH CH g CH a COCH 3 CH ①D H CH2h Ch, h Chlorophyll a ⑨D

Organic Chemistry Organic Chemistry Xiamen Xiamen University University Natural products: Natural products: Chlorophyll Chlorophyll N N N N CH 3 CH 2CH 3 CH 3 CH CH 3 H Mg CH 2 CH 3 H O O CH 3 H CH 3 H O CO 2CH 3 H C hloro p h yll a

Chlorophyll a g. The structure of chlorophyll a was established largely through the work of H E Fischer(Munich ),R. Willstatter( 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 organic chemistry

Organic Chemistry Organic Chemistry Xiamen Xiamen University University Chlorophyll a Chlorophyll a „ The structure of chlorophyll a was established largely through the work of H. Fischer(Munich), R. Willst ätter(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 organic chemistry