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Synthesis of chiral calixarenes and application as functional organic catalysts

Synthesis of chiral calixarenes and application as functional organic catalysts
手性杯芳烃的合成及其作为功能有机催化剂的应用
批准号:
17560685
负责人:
GOTO Koichi
金额:
$2.05万
依托单位:
依托单位国家:
日本
项目类别:
Grant-in-Aid for Scientific Research (C)
财政年份:
2005
资助国家:
日本
项目状态:
已结题
起止时间:
2005 至 2006

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中文摘要
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英文摘要
The racemic mixture of chiral calix [4]arenes (5-tert-butyl-11-methyl-17,23-diphenyl-25,26,27,28-tetrahydroxycalix [4]arene) with three different upper rim substituents was synthesized by the fragmentation-condensation of p-substituted phenol dimmers (2-(5-methylsalicyl)-4-tert-butylphenol and 3-(3-hydroxymethyl-5-phenylsalicyl)-5-phenyl-2-hydroxybenzyl alchol) according to K. No and coworkers' multi-step method. On the other hand, amino acid esters (Z-D(L)-Ala-PNP, Z-D(L)-Trp-PNP) were prepared from N-(benzyloxycarbonyl)-D(L)-amino acids by esterification of the COOH group with p-nitrophenol and dicyclohexylcarbodiimide. The calix[4]arenes and amino acid esters were confirmed by elemental analysis, specific rotation, IR and NMR spectroscopic measurements. With respect to the hydrolysis of Z-D(L)-Trp-PNP mediated by the calix[4]arenes in the presence of Z-L-Phe-OH, a little inhibition effect was observed on the basis of the rate constants. Particularly, the hydrolysis of D-substrate tended to be slightly slower than that of L-substrate. Furthermore, the computer modeling (molecular mechanics) studies indicated that the calix[4]arene would adopt a "cone" conformation. These results suggest that the calix[4]arenes could form inclusion complexes with Z-D(L)-Trp-PNP. Probably, the stereochemical arrangements of the chiral calix[4]arenes may induce the enantioselectivity for the hydrolysis of Z-D(L)-Trp-PNP.
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海外基金