機能性ホスト化合物の分子設計と有機化学への応用 : (第1報)機能性カリックスレゾルシン[4]アレーン誘導体の合成とその機能化
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Since the concept of "Host-Guest Chemisty" was established, the syntheses and application of artificially designed host compounds have been extensively developed. Many cyclic compounds, such as crown ethers and calixarenes have been reported to be superior artificial host molecules, because the cyclic structure has advantages for host molecules. In this report, various C-substituted calixresorcin [4] arenes are synthesized through acid-catalyzed reactions of resorcinol and aldehydes to elucidate their properties. Aliphatic and aromatic aldehydes can be used successfully under controlled reaction conditions, such as temperature and time. Calixresorcin [4] arenes have 2 stereoisomes, all-cis and cis-trans isomes. The pure all-cis isomer, thermodynamic controlled isomer, can be easily obtained. But the isolation of pure cis-trans isomer, kinetic controlled isomer, was very difficult. Only cyclic tetramers of calixresorcinarenes have been reported. In order to obtain calixresorcin[n]arenes (n is not 4), lanthanide triflates were used as Lewis acid catalyts. Some template effects can be expected by coordination of substrates (aldehydes and resorcinol) to lanthanides metal ions. The catalytic activity of the lanthanide triflates was significantly high. They gave kinetic controlled cis-trans isomer to a considerable extent, but no calixresorcin[n]arenes except for tetramer could not be detected. Thus, no template effect has been observed. Acetyl, methyl and benzyl groups have been introduced on hydoroxy group of calixresorcin [4] arenes.
- 久留米工業大学の論文
- 2000-12-20
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関連論文
- 機能性ホスト化合物の分子設計と有機化学への応用 : (第2報)機能性カリックスレゾルシン[4]アレーン誘導体の分子認識能と包接挙動について
- 機能性ホスト化合物の分子設計と有機化学への応用 : (第1報)機能性カリックスレゾルシン[4]アレーン誘導体の合成とその機能化