多氟烷基取代和葡萄糖基取代
1018有机化学
、,01.28.2008
分析仪测定.
化合物2和3按照文献【10】方法合成;溴代.2,3,4,6一四.D.乙酰基.a—D.吡喃葡萄糖按照文献[11】方法合成;C6F13C2n4I,C8F17C2I-14I从acros公司购买;无水D.葡萄糖从国药集团购买,三乙胺、DMF按标准方法精制后使用,其他试剂均为市售分析纯.1.2化合物4的合成
将芳香醛(4.0mm01)溶于8mL冰醋酸中,加入化合物3(4.0mm01),磁力搅拌回流30min,冷却,即析出大量固体,抽滤,用少量无水乙醇洗涤,烘干,即得纯品
4a~4i.
4a:白色固体,产率82%,m.P.180~182℃;1H
NMR(CDCls,400MHz)J:7.47~7.52(m,5H,C6H5),7.52~7.57(m,1H,C6H5),7.88~7.90(m,2H,C6H5),7.95~7.97(In,2H,C6H5),10.07(s,1H,CH=N),11.21(s,1H,NH);IR(KBr)v:3028,1603,1543,1502,1363,
1277cm~.Anal.calcdforC15H12N4S:C64.26,H4.31,N19.98;foundC64.23,H4.38,N19.92.
4b:黄色固体,产率78%,m.P.218~220℃;1H
NMR(CDCl3,400MHz)6:7.46~7.54(m,5H,c6I-15),7.82(d,J=7.6Hz,2H,C6H4),7.92(d,J=7.2Hz,2H,C6H4),10.16(s,1H,CH=N),10.94(s,1H,NH);IR(KBr)
v:3030,1599,1539,1500,1356,1281cm~.Anal.calcd
forC15HllClN4S:C57.23,H3.52,N
17.80;foundC
57.15,H3.58,N17.83.
4c:黄色固体,产率80%,m.P.171~173℃;1H
NMR(CDCl3,400MHz)J:3.95(s,3H,OCH3),7.03(d,
J=8.0Hz,1H,C6H5),7.20(dd,-,=1.6,8.4Hz,1H,C6H3),
7.45(d,J=7.2Hz,2H,C6H3),7.50(d,.,=1.6Hz,2H,C6H5),7.88~7.90(m,2H,C6H5),9.70(s,1H,CH=N),11.17(s,1H,NH);IR(KBr)v:3070,1593,1514,1383,
1292cm~.Anal.calcdforC16H14N402S:C58.88,H4.32,N17.17;foundC58.94,H4.28,N17.15.
4d:白色固体,产率84%,m.P.227~229℃;1H
NMR(DMSO一,/6,400MHz)6:6.94(d,J=8.8Hz,2H,C6I-h),7.52~7.54(m,3H,C6H5),7.75(d,J=9.2Hz,2H,C6H4),7.86~7.89(m,2H,C6H5),9.37(s,1H,CH=N),10.42(s,1H,OH),14.16(s,1H,NH);IR(Kar)1,:3030,
1606,1568,1512。1356.1284cm~.Anal.calcd
for
C15H12N40S:C60.79,H4.08,N18.91;foundC60.85,H4.02.N18.87.
4e:白色固体,产率91%,r11.P.225~227℃;1H
NMR(DMSO—d6,400MHz,)J:6.94(t,J=7.6Hz,IH,C6H5),7.00(d,J=8.4Hz,1H,C6H5),7.44(t,J=8.4Hz,lH,C6H4),7.5l~7.54(m,3H,C6H4),7.82~7.88(m,3H,
C6H5),9.93(s,1H,CH=N),10.48(s,1H,OH),14.09(s,1H,NH);IR(KBr)1,:3032,1622,1599,1500,1360,1267

