双柱[5]芳烃初步合成研究探讨
摘要
杯芳烃是一类由取代苯酚和甲醛缩合而成的大环化合物,它具有独特的空腔结构和丰富的反应点,可制备具有各种官能团、构象确定、π空腔大小可调的衍生物,在分子识别、模拟酶催化、物质的检测和分离等方面都显示出其作为超分子化学中的一类重要的受体化合物的特殊价值,引起了人们的关注,被誉为继冠醚和环糊精之后的第三代超分子主体化合物。
传统杯芳烃中连接苯环亚甲基在同一苯环中互为间位,T. Ogoshi等首次报道用BF3·Et2O催化下1,4-二甲氧基苯和多聚甲醛反应得到环状五聚体,命名为1,4-甲氧基柱[5]芳烃,脱甲基得到柱[5]芳烃。我们课题组用1,4-二烷氧基-2,5-二(烷氧基甲基)苯46在对甲苯磺酸催化下反应,得到1,4-甲氧基柱[5]芳烃43,产率最高可达90%以上。近来对柱[5]芳烃的研究主要集中在分子识别,发光性质,1,4-烷氧基不对称柱[5]芳烃的合成及其构象分析等。
本论文采用我们课题组的合成方法,以对羟基苯甲醚为原料,通过不同基团连接得到二聚体,经历氯甲基化、甲氧基化,得到具有四个甲氧基甲基的化合物,并探讨在对甲苯磺酸催化下一步法合成双柱[5]芳烃的合成,实验未能获得双柱[5]芳烃,而是得到一聚合物。
此外,1,4-烷氧基柱[5]芳烃与NBS反应,经历开环反应,ipso取代反应,得到二-(4-溴-2,5-二烷氧基苯基)甲烷44,其与硝酸反应得到二-(4-硝基-2,5-二甲氧基苯基)甲烷47。该反应方法操作简单,反应条件温和,选择性好,产率中等,为制备二-(4-溴-2,5-二烷氧基苯基)甲烷衍生物提供了一条新途径。
Calixarenes are macrocyclic compounds which are generally formed by condensation of aldehydes and substituted phenols. Because calixarenes have a calix-shape, hydrophobic cavity and several reactable positions, they have attracted considerable attentions. They are broadly used as building blocks to construct well preorganized host molecules which have widely potential applications in the field of molecular recognition, enzyme mimics, etc. Therefore they are considered as the third host molecule after crown ethers and cyclodextrins in supramolecular chemistry.
Tradictional calixarenes were connected by methylene groups in meta position. T. Ogoshi first reported a new calixar[5]arene named 1,4-dimethoxypillar[5]arene, which was synthesized by a Lewis acid-catalyzed reaction using 1,4-dimethoxybenzene and formaldehyde in the presence of BF3·Et2O. The methylene groups were in para position. They also got pillar[5]arenes by demethylation of 1,4-dimethoxypillar[5]arenes. But the yeilds were poor. Our research group found a simple method for the synthesis of pillar[5]arene. 2,5-Bis(ethoxymethyl)-1,4-dialkoxybenzene was treated with catalytic amount of p-toluenesulfonic acid in boiling dichloromethane to give 1,4-dialkoxypillar[5]arenes in high yield. Recent research on pillar[5]arenes included molecular recognition, spectral properties, nonsymmetric pillar[5]arene, conformation analyses.
In this article, we applied our synthetic method to synthesize bispillar[5]arene. 4-Methoxyphenol reacted with dihalo-compounds to form a dimer; then chloromethylation and methoxylation of the dimer gave the intermediate with four methoxymethyl groups. The intermediate was treated with catalytic amount of p-toluenesulfonic acid. However, bispillar[5]arene was not found. We have tried many mehtods, but failed.
1,4-Alkoxylpillar[5]arenes reacted with NBS to give bis(4-bromo-2,5-dialkoxyphenyl)methane, undergoing ring opening reaction, ipso substituted reaction. Nitration of 1,4-methylpillar[5]arenes with nitric acid gave bis(4-nitro-2,5-dimethoxyphenyl)methane. This synthetic method for preparation of such a compound has some advantages, such as mild reaction conditions, simple operation, high selectivity and good yield.
传统杯芳烃中连接苯环亚甲基在同一苯环中互为间位,T. Ogoshi等首次报道用BF3·Et2O催化下1,4-二甲氧基苯和多聚甲醛反应得到环状五聚体,命名为1,4-甲氧基柱[5]芳烃,脱甲基得到柱[5]芳烃。我们课题组用1,4-二烷氧基-2,5-二(烷氧基甲基)苯46在对甲苯磺酸催化下反应,得到1,4-甲氧基柱[5]芳烃43,产率最高可达90%以上。近来对柱[5]芳烃的研究主要集中在分子识别,发光性质,1,4-烷氧基不对称柱[5]芳烃的合成及其构象分析等。
本论文采用我们课题组的合成方法,以对羟基苯甲醚为原料,通过不同基团连接得到二聚体,经历氯甲基化、甲氧基化,得到具有四个甲氧基甲基的化合物,并探讨在对甲苯磺酸催化下一步法合成双柱[5]芳烃的合成,实验未能获得双柱[5]芳烃,而是得到一聚合物。
此外,1,4-烷氧基柱[5]芳烃与NBS反应,经历开环反应,ipso取代反应,得到二-(4-溴-2,5-二烷氧基苯基)甲烷44,其与硝酸反应得到二-(4-硝基-2,5-二甲氧基苯基)甲烷47。该反应方法操作简单,反应条件温和,选择性好,产率中等,为制备二-(4-溴-2,5-二烷氧基苯基)甲烷衍生物提供了一条新途径。
Calixarenes are macrocyclic compounds which are generally formed by condensation of aldehydes and substituted phenols. Because calixarenes have a calix-shape, hydrophobic cavity and several reactable positions, they have attracted considerable attentions. They are broadly used as building blocks to construct well preorganized host molecules which have widely potential applications in the field of molecular recognition, enzyme mimics, etc. Therefore they are considered as the third host molecule after crown ethers and cyclodextrins in supramolecular chemistry.
Tradictional calixarenes were connected by methylene groups in meta position. T. Ogoshi first reported a new calixar[5]arene named 1,4-dimethoxypillar[5]arene, which was synthesized by a Lewis acid-catalyzed reaction using 1,4-dimethoxybenzene and formaldehyde in the presence of BF3·Et2O. The methylene groups were in para position. They also got pillar[5]arenes by demethylation of 1,4-dimethoxypillar[5]arenes. But the yeilds were poor. Our research group found a simple method for the synthesis of pillar[5]arene. 2,5-Bis(ethoxymethyl)-1,4-dialkoxybenzene was treated with catalytic amount of p-toluenesulfonic acid in boiling dichloromethane to give 1,4-dialkoxypillar[5]arenes in high yield. Recent research on pillar[5]arenes included molecular recognition, spectral properties, nonsymmetric pillar[5]arene, conformation analyses.
In this article, we applied our synthetic method to synthesize bispillar[5]arene. 4-Methoxyphenol reacted with dihalo-compounds to form a dimer; then chloromethylation and methoxylation of the dimer gave the intermediate with four methoxymethyl groups. The intermediate was treated with catalytic amount of p-toluenesulfonic acid. However, bispillar[5]arene was not found. We have tried many mehtods, but failed.
1,4-Alkoxylpillar[5]arenes reacted with NBS to give bis(4-bromo-2,5-dialkoxyphenyl)methane, undergoing ring opening reaction, ipso substituted reaction. Nitration of 1,4-methylpillar[5]arenes with nitric acid gave bis(4-nitro-2,5-dimethoxyphenyl)methane. This synthetic method for preparation of such a compound has some advantages, such as mild reaction conditions, simple operation, high selectivity and good yield.
引文
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