| 手性杯[4]丝氨酸衍生物的合成及其催化性能 |
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| 引用本文： | 李正义,郑崇谦,陈远,殷乐,王治明,孙小强.手性杯[4]丝氨酸衍生物的合成及其催化性能[J].合成化学,2017,25(3). |
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| 作者姓名： | 李正义 郑崇谦 陈远 殷乐 王治明 孙小强 |
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| 作者单位： | 常州大学 石油化工学院,江苏 常州,213164 |
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| 基金项目： | 国家自然科学基金资助项目，江苏省高校自然科学研究重大项目，常州大学江苏省先进催化与绿色制造协同创新中心资助项目 |
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| 摘 要： | 以对叔丁基苯酚为原料,经环化缩合、脱叔丁基、酚羟基醚化、甲酰化和氧化反应制得5-羧基-25,26,27,28-四正丙基杯4]芳烃(5);5与O-苄基-N-苄氧羰基丝氨酸反应制得5-(O-丝氨酸)-25,26,27,28-四正丙基杯4]甲酸酯(7),其结构经~1H NMR,~(13)C NMR和MS(ESI)表征。研究了溶剂和水的用量对7催化性能的影响。结果表明:水为溶剂,其用量为10 eq.时,收率和非对映选择性分别为95%和3∶97 dr;当水的用量为30 eq.时,收率和非对映选择性分别为93%和98∶2 dr。
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| 关 键 词： | 对叔丁基苯酚 杯[4]丝氨酸 合成 催化 Mannich反应 催化性能 |
Synthesis and Catalytic Properties of Chiral Calix[4]serine Derivative |
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| LI Zheng-yi,ZHENG Chong-qian,CHEN Yuan,YIN Yue,WANG Zhi-ming,SUN Xiao-qiang.Synthesis and Catalytic Properties of Chiral Calix[4]serine Derivative[J].Chinese Journal of Synthetic Chemistry,2017,25(3). |
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| Authors: | LI Zheng-yi ZHENG Chong-qian CHEN Yuan YIN Yue WANG Zhi-ming SUN Xiao-qiang |
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| Abstract: | 5-Carboxyl-25,26,27,28-tetra(1-propyloxy)calix4]arene(5) was synthesized by serial reactions of cyclizative condensation, elimination of tert-butyl, etherification of phenolic hydroxyl, formylation and oxidation reaction from para tert-butyl phenol.5-(O-serine)-25,26,27,28-tetra(1-propyloxy)calix4]arene formate(7) was prepared by reaction of 5 with O-benzyl-N-(benzyloxy)carbonyl]serinate.The structure was characterized by 1H NMR, 13C NMR, and MS(ESI).Catalytic properties of 7 were investigated by screening different solvents and loading of water.The results illustrated that 95% yield and 3 ∶97 dr were observed when the reaction was performed in 10 eq.water while 93% yield and 98 ∶2 dr were obtained by using 30 eq.water. |
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| Keywords: | para tert-butyl phenol calix[4]serine synthesis catalysis Mannich reaction catalytic property |
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