药物合成期末复习试题及答案

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1、1.写出下列重排反应的机理:ch3ch3IICH3—CCCHgIIOHOHH+ch3ch3IC—C—CH3IIICH3OPPT2-6(曾四下P116)(1)RRIcIRIcIOHOHC—C—RIIOHOH2©H2O+RRIc-IOHRI■c-(2)R—C—C—R©kOH—C—CH++RCII0C—R2.双分子亲核収代反应和单分子取代反应的反应机理。（汽叫上P238）PPT2-3、51）双分子亲核取代反应机理R1R0+R*—私5--►RO…A--XHH*ROCH2Rf+1）单分子亲核取代反应机理+X0RX+R

2、.OH©R-O-R.3.完成以下合成鲨肝醇的各步反应ch2ohch2ohCHOHch2ohMe2CO/HCICH-0.Cl6h2o〉S:iR-O-R1+HC18H37OTs，KOH/To么>110r,3hCH2OC18H37

3、COOEt)2C7H16CH(COOH)2►-c7h15ch2coohA4.写出下列Beckmann重排的反应机理：PPT5-15(曾四下120)ROHH+9C=N►R-C-NHR，ROHH+C=NR,ZH2O2-H2ORC=N©=NR、-H+C=Nh2o@r*RC=NHO’R*OR-C-NHR'5.PPT1-237.PPT1-21CH32molBr，/hv125C?2hCH，Br(48%*53%)ch3CH：Br稀氢的卤代不常见。PhC三CHNaOH/Br2/H2Or.t”60hPhC=CBr(73%*8

4、3%)8.PPT1-319.PPT1-31SO2C12/CC14r.t.^h1)Br2/NaOHH2O<10C,lh(CH3)3CCOCH3[(CH3)3CCOCBr3】►(CH3)3CCO2H+HCBn2)H7A(71%*74%)COBr11.PPT2-46(61%)2(CH3)2CHCHO-^Si-OHCH3(ch3)2ch-6h-6-choin3(85%)16.PPT4-46•CN(100%)Etz：H2CH2CNKOHZMeOH,CN+CH2=CHCN90-95°EtzH%。=。+(C6H5)3P

5、=C；R4R2+(CgH5)3P=O19.PPT1-44CH，OHSOCKPv扇1〜4h(75%)(TCH.C1CH0Me2SO4/NaOH22.PPT2-28MexNH3+C二On-Pr(90%)RaneyNiMe€HNHn-Pr23.PPT2-31RNH2AlS02CI•RNHSC^ArRX/Na0H!RR*Ns(^ArRr，NhNaOH24.PPT2-50BrCH2CH2CH2CI/NaOEtCH2(COOEt)2*-EtOH(55%)OEtOEt25.PPT4-2500HCHO/HCI►HOAc/H

6、3PO480°,(77%)CHoCOOH26.PPT1-56RCO2Ag+X2RX+AgXI+CO2斗(X=Br,I)27.齊叫下121Br2/OH-oIIrcnh228.PPT5-30CF3CO3H»CH2CI2,25°C29.PPT5-48OCH2CH=CH22(xrc"•Allylphenol(13%)Allylphenylether30.PPT6-1731.Br2/H20•—C—C—+Xj+H2OX2=CI2,Br26Hh^33.PPTI-8Br2/LiBr%BrPhC=CCH3=►C=CPhHOA

7、C/25Cch3BrCH3(98%)BrBr(2%)34.PPT4-11CHO+CH3COCH3=cZH(60—66%)xcoch335.试以丙二酸二乙酯为原料，合成：(注意引入烃基的先后顺序)PPT2-51Me2CHCH2CH2、zCOOEt/◦、EtCOOEtMe2CHCH2CH2Br/NaOEtMe2CHCH2CH2zCOOEtCH2(COOEt)2►}C、EtOH,75-58°,6h(88%)HCOOEtEtBr/NaOEt/EtOHMe2CHCH2CH2zCOOEt35°,10h;65-70°,1

8、hEtzCOOEtPhCH-CH2-C-OEtCH(COOEt)2H=CHCOOH35.写出下列重排反应的机理:0IICH2(COOEt)2+PhCH2=CH-C-OEt36.以下列反应为例，写出Perkin反应的反应机理。1)AcOK,150*+(CH3CO)2OHO2)H3O38./°^人vCH2OHCsH^NHCrOsCI►?NaOAc/CH2CI239.C6H5COOOC(CH3)3/CuBr+BrCH