藥物合成6氧化反應(yīng)課件

1、Chapter 6 Oxidation2、Oxidations of Alkyl-compounds1、The Mechanism of Oxidation3、Oxidations of Alcohol4、Oxidations of C-C double bond5、Oxidation of Amines6、Eliminations of Hydrogen7、Oxidation ReagentsWhat is OxidationInorganic Chemistry: loss of electrons increase in oxidation numberOrganic Chemistry

2、: gain of oxygens loss of hydrogens What is Oxidation Oxidation is the conversion of a functional group in a molecule to a higher categoryThe Mechanism of Oxidation1.Direct electron transfer2.Hydride transfer3.Hydrogen-atom transfer4.Formation of ester intermediates5.Displacement mechanism6.Addition

3、-elimination mechanism1.Direct electron transfer4.Formation of ester intermediates5.Displacement mechanism6.Addition-elimination mechanism1.oxidations of alkyl in benzyl1.oxidations of alkyl in benzyl1.oxidations of alkyl in benzyl1.oxidations of alkyl in benzyl1.oxidations of alkyl in benzyl1.oxida

4、tions of alkyl in benzyl2.oxidations of -alkyl in carbonylcompounds2.oxidations of -alkyl in carbonylcompounds2.oxidations of -alkyl in carbonylcompounds2.oxidations of -alkyl in carbonylcompounds2.oxidations of -alkyl in carbonylcompounds3. Oxidations of Alkyl in allyl3. Oxidations of Alkyl in ally

5、l3. Oxidations of Alkyl in allyl3. Oxidations of Alkyl in allylOxidations of Alcohol1.Formation of carbonyl compounds2.Formation of carbonic acids3.Oxidations of 1,2-diolOxidations of Alcohol1.Formation of carbonyl compounds1.Formation of carbonyl compounds1.Formation of carbonyl compounds1.Formatio

6、n of carbonyl compounds1.Formation of carbonyl compounds1.Formation of carbonyl compounds1.Formation of carbonyl compounds1.Formation of carbonyl compounds1.Formation of carbonyl compounds1.Formation of carbonyl compounds1.Formation of carbonyl compounds1.Formation of carbonyl compounds1.Formation o

7、f carbonyl compounds2.Formation of carbonic acids3.Oxidations of 1,2-diol3.Oxidations of 1,2-diol3.Oxidations of 1,2-diolOxidations of C-C double bond1.Formation of epoxy compound2.formation of 1.2-diol3.Cleavage of C-C double bondOxidations of C-C double bond1.Formation of epoxy compound1.Formation

8、 of epoxy compound1.Formation of epoxy compound1.Formation of epoxy compound1.Formation of epoxy compound1.Formation of epoxy compound1.Formation of epoxy compound1.Formation of epoxy compound1.Formation of epoxy compoundacac: acetylacetonateSharpless Reaction: high selectivity for allyl alcohol to

9、epoxide1.Formation of epoxy compound1.Formation of epoxy compound1.Formation of epoxy compound1.Formation of epoxy compound1.Formation of epoxy compound2.formation of 1.2-diol2.formation of 1.2-diol2.formation of 1.2-diol2.formation of 1.2-diol2.formation of 1.2-diol2.formation of 1.2-diol2.formatio

10、n of 1.2-diol2.formation of 1.2-diol2.formation of 1.2-diol2.formation of 1.2-diol3.Cleavage of C=C3.Cleavage of C=COxidation of Amines1. Oxidation of primary amines2. Oxidation of secondary amines3. Oxidation of tertiary amines4. Oxidation of N-alkyl groups1. Oxidation of primary aminesH2O2RCOOOH2.

11、 Oxidation of secondary aminesH2O2RCOOOH3. Oxidation of tertiary aminesH2O2RCOOOHEliminations of Hydrogen1.Formation of ,-unsaturated carbonyl compounds2.Aromatization1.formation of ,-unsaturated carbonyl compound1.formation of ,-unsaturated carbonyl compound1.formation of ,-unsaturated carbonyl com

12、pound1.formation of ,-unsaturated carbonyl compound1.formation of ,-unsaturated carbonyl compound2.AromatizationPd2.Aromatization2.Aromatization2.AromatizationOxidation ReagentsKMnO4MnO2H2CrO4Pb(OAc)4PeroxideRCOOOHHIO4Containing AgDMSOSeO2KMnO4KMnO4KMnO4KMnO4KMnO4MnO2MnO2H2CrO4 and its derivativesH2CrO4 and its derivativesH2CrO4 and it