CAJ | 학술논문

以单(6-O-p-甲苯磺酰基)-β-环糊精为反应原料，通过亲核取代合成了3个带苯环的β-环糊精衍生物CD-1～CD-3，收率为9.93%～17.51%，衍生物的结构通过1H NMR和ESI-MS进行了表征确认。将合成的β-环糊精衍生物与Na2MoO4·2H2O络合后应用于催化H2O2氧化苯甲硫醚。结果表明，反应介质的pH值对该反应体系的收率有一定影响。通过1H ROESY NMR发现，CD-1～CD-3的分子内自包结是影响Na2MoO4·2H2O催化氧化苯甲硫醚不对称反应产物ee%值的主要原因。通过量子化学计算对自包结状态进行了证实。
이단(6-O-p-갑분광선기)-β-배호정위반응원료，통과친핵취대합성료3개대분배적β-배호정연생물CD-1～CD-3，수솔위9.93%～17.51%，연생물적결구통과1H NMR화ESI-MS진행료표정학인。장합성적β-배호정연생물여Na2MoO4·2H2O락합후응용우최화H2O2양화분갑류미。결과표명，반응개질적pH치대해반응체계적수솔유일정영향。통과1H ROESY NMR발현，CD-1～CD-3적분자내자포결시영향Na2MoO4·2H2O최화양화분갑류미불대칭반응산물ee%치적주요원인。통과양자화학계산대자포결상태진행료증실。
Three β-cyclodextrin derivatives CD-1 to CD-3 were synthesized via nucleophilic substitution of mono (6-O-toluenesulfonyl)-β-cyclodextrin in the yield of 9.93% to 17.51%. All theβ-cyclodextrin derivatives were characterized by 1H NMR and ESI-MS. Theβ-cyclodextrin derivatives CD-1~CD-3 coordinated with Na2MoO4·2H2O,and the product was used for catalytic oxidation of thioanisole by H2O2. The yield of the reaction was influenced by reaction medium and pH of the reaction system. Asymmetric oxidation of thioanisole by Na2MoO4·2H2O was induced byβ-cyclodextrin derivatives. 1H ROESY NMR characterization showed that intramolecular self-inclusion of CD-1~CD-3 was the main factor limiting the ee%values of the product. The result was verified by quantum chemistry calculation.