Synthesis of 7,8,9,10,11,12,20,21,22,23,24,25-dodecahydrodibenzo[b,m]-[1,4,12,15]tetraoxacyclodocosin, a crown ether
Synthesis of 7,8,9,10,11,12,20,21,22,23,24,25-dodecahydrodibenzo[b,m]-[1,4,12,15]tetraoxacyclodocosin, a crown ether
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冠醚7,8,9,10,11,12,20,21,22,23,24,25-十二氢二苯并[b,m]-[1,4,12,15]四氧环二十二烷的合成
DOI：
10.1039/p19810000336
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发表时间：
1981
期刊：
影响因子：
--
通讯作者：
G. R. Brown
中科院分区：
文献类型：
--
作者：
J. Tyman;J. Grundy;G. R. Brown
由邻苯二酚合成了一些对称的双酯和一种不对称的双酯。在预期分子内形成偶姻的条件下，由一种对称化合物4-（o-乙氧羰基丙氧基苯氧基）丁酸乙酯得到的产物是环状双-β-酮酯，导致分子间Dieckmann环化的合理产率。水解成9，22二酮，并将其还原成7，8，9，10，11，12，20，21，22，23，24，25-十二氢二苯并[B，m][1，4，12，15]四氧杂环二十二烷“二苯并-22-冠-4”，进行顺利。不对称中间体4-（o-乙氧羰基甲氧丙基苯氧基）丁酸甲酯可用于类似的环化反应，初步实验中似乎得到偶姻和β-酮酯产物。该方法代表了对某些类型的冠醚体系的不同方法。
A number of symmetrical diesters and an unsymmetrical type have been synthesised from pyrocatechol. Under conditions in which intramolecular acyloin formation was anticipated the product from one symmetrical compound, ethyl 4-(o-ethoxycarbonylpropoxyphenoxy) butyrate, was a cyclic bis-β-keto-ester resulting in reasonable yield from intermolecular Dieckmann cyclisation. Hydrolysis to the 9,22 diketone, and its reduction to 7,8,9,10,11,12,20,21,22,23,24,25-dodecahydrodibenzo [b,m][1,4,12,15] tetraoxacyclodocosin ‘dibenzo-22-crown-4,’ proceeded smoothly. An unsymmetrical intermediate, methyl 4-(o-ethoxycarbonylmethoxypropylphenoxy) butyrate, was prepared for similar cyclisation and in preliminary experiments appeared to give acyloin and β-keto-ester products. The method represents a different approach to crown ether systems of certain types.