有机合成路线设计原理.ppt

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1、2023/2/21,1,Introduction to Organic Synthesis有机合成初步,2023/2/21,2,合成化学家在旧的自然界旁又建起了一个新的自然界R.B.Woodward,E.J.CoreyRetro-synthetic analysis逆合成分析 The Noble Prize in 1990,20世纪,The Logic of Chemical Synthesis,2023/2/21,3,1.Retrosynthetic analysis(逆合成分析),In this procedure the target molecule is transformed pr

2、ogressively into simpler structures by disconnecting selected carbon-carbon bonds.These disconnections rest on transforms,which are the reverse of plausible synthetic constructions.Each simpler structure,so generated,becomes the starting point for further disconnections,leading to a branched set of

3、interrelated intermediates.A retrosynthetic transform is depicted by the=symbol,as shown in next slide.Once a complete analysis has been conducted,the desired synthesis may be carried out by application of the reactions underlying the transforms.,2023/2/21,4,Synthon,Equivalent,Disconnection rest on

4、transforms,2023/2/21,5,2023/2/21,6,Synthon Equivalent,PolarInversion,极性反转,2023/2/21,7,Polar Inversion,2023/2/21,8,Symbol,2023/2/21,9,Functional Group transforms,2023/2/21,10,2023/2/21,11,2.Disconnection on TMs without FG adding FG,TM：targeted molecule 目标分子,2023/2/21,12,2023/2/21,13,2023/2/21,14,3.Di

5、sconnection on TMs with mono FG Application of Malonic ester,2023/2/21,15,2023/2/21,16,2023/2/21,17,80%99%,80%,2023/2/21,18,酮式 烯醇式,Application of Ethyl Acetoacetate,pKa 11,2023/2/21,19,2023/2/21,20,2023/2/21,21,2023/2/21,22,Application of Epoxy（环氧）compounds,2023/2/21,23,2023/2/21,24,2023/2/21,25,Dis

6、connection on Cyclohexene,2023/2/21,26,2023/2/21,27,Birch还原,2023/2/21,28,4.Disconnection on Bifunctional groups（1）,-unsaturated compounds,2023/2/21,29,2023/2/21,30,（2）,-unsaturated carboxylic acid,2023/2/21,31,（3）-Hydroxyester,2023/2/21,32,2023/2/21,33,（4）1,3-bicarbonyl,2023/2/21,34,2023/2/21,35,（5）

7、1,4-bicarbonyl,2023/2/21,36,（6）1,5-bicarbonyl,迈克尔（Michael）加成反应,2023/2/21,37,2023/2/21,38,2023/2/21,39,2023/2/21,40,（7）1,6-bicarbonyl,2023/2/21,41,2023/2/21,42,Birch还原,2023/2/21,43,4.Rearrangment,2023/2/21,44,嚬哪醇重排：,2023/2/21,45,2023/2/21,46,5.Examples,2023/2/21,47,2023/2/21,48,2023/2/21,49,2023/2/21

8、,50,2023/2/21,51,2023/2/21,52,2023/2/21,53,2023/2/21,54,2023/2/21,55,2023/2/21,56,A synthesis of N-ethyl-2-aminomethylspiro3.3heptane from starting compounds having no more than three contiguous carbon atoms is required.,2023/2/21,57,A synthesis of 2-acetyl-2-methylbicyclo2.2.2octane from cyclohexen

9、e and other starting compounds having no more than four contiguous carbon atoms is required.,2023/2/21,58,2023/2/21,59,2023/2/21,60,A synthesis of 2,7-dimethyl-4-octanone from starting compounds having no more than four contiguous carbon atoms is required.,2023/2/21,61,A synthesis of 1,4,6-trimethyl

10、naphthalene from para-xylene and other starting compounds having no more than four contiguous carbon atoms is required.,2023/2/21,62,2023/2/21,63,Biomimetic Synthesis仿生合成21世纪,2023/2/21,64,托品酮（Tropinone）的仿生合成,2023/2/21,65,2023/2/21,66,2023/2/21,67,2023/2/21,68,2023/2/21,69,2023/2/21,70,2023/2/21,71,2023/2/21,72,2023/2/21,73,2023/2/21,74,