报道了一种间接缩合法高产率简便合成新型四桥联双杯[4]管道和1,2-3,4-双桥联杯[4]芳烃. 杯[4]二酰肼衍生物2与丁二酸酐发生开环反应, 以95%的产率得到杯[4]羧酸衍生物4. 化合物4在DCC/DMAP/CH2Cl2体系中发生分子间自缩合反应, 以90%产率得到新型四桥联双杯[4]管道6. 改用高度稀释的条件则以26%的产率得到新型1,2-3,4-双桥联杯[4]芳烃5. 新化合物的结构与构象经元素分析、红外、质谱、核磁共振谱等表征证实.
This paper described the indirect and convenient syntheses of novel tetra-bridged calix[4]tube and 1,2-3,4-bis-bridged calix[4]arene in high yields. By the ring-opening reaction of calix[4]-bis-hydrazide derivative 2 with succinic anhydride, calix[4]arene carboxyl derivative 4 was obtained in 95% yield. Under the DCC/DMAP/CH2Cl2 system, novel tetra-bridged calix[4]tube 6 was prepared by the intermolecular self-condensation of compound 4 in 90% yield. Under the same system in high diluted condition, novel 1,2-3,4-bis-bridged calix[4]arene 5 was synthesized in 26% yield as by-product. The structures and conformations of new compounds were characterized by elemental analyses, IR, ESI-MS, 1H NMR, etc.
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(杨发福, 郑林禄, 季衍卿, 郭红玉, 林建荣, 有机化学, 2006, 26, 268.)
