| 芳基乙酮酸薄荷醇酯的合成及不对称Henry反应 |
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| 引用本文： | 向纪明,李宝林.芳基乙酮酸薄荷醇酯的合成及不对称Henry反应[J].高等学校化学学报,2010,31(1):68-73. |
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| 作者姓名： | 向纪明 李宝林 |
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| 作者单位： | 1. 陕西师范大学化学与材料学院, 药用植物资源与天然药物化学教育部重点实验室, 西安 710062;
2. 安康学院化学化工系, 安康 725000 |
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| 基金项目： | 教育部科学技术研究重点项目(批准号:105153)资助 |
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| 摘 要： | 以钛酸四乙酯为催化剂, 芳基乙酮酸乙酯与天然L-薄荷醇进行酯交换, 合成了8个含手性基团的芳基乙酮酸薄荷醇酯; 在手性基团的立体选择性控制下, 芳基乙酮酸薄荷醇酯与硝基甲烷进行不对称Henry反应, 合成了7个(2R)-2-羟基-2-芳基-3-硝基丙酸薄荷醇酯新化合物, 用IR, 1H NMR, 13C NMR, MS和元素分析表征了化合物结构. 用高效液相色谱经手性柱分析了不对称反应效果, 缩合反应的非对映体过量在46.5%～64.2%之间, 表明可以通过立体选择性控制产物构型.
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| 关 键 词： | α-芳基酮酸酯 L-薄荷醇 酯交换 不对称Henry反应 |
| 收稿时间： | 2009-04-07 |
Synthesis and Asymmetric Henry Reaction of Menthyl Arylglyoxylate |
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| XIANG Ji-Ming,LI Bao-Lin.Synthesis and Asymmetric Henry Reaction of Menthyl Arylglyoxylate[J].Chemical Research In Chinese Universities,2010,31(1):68-73. |
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| Authors: | XIANG Ji-Ming LI Bao-Lin |
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| Institution: | 1. School of Chemistry and Materials Science, Key Laboratory of Medicinal Plant Resource & Natural Pharmaceutical Chemistry of Ministry of Education, Shaanxi Normal University, Xi′an 710062, China;
2. Department of Chemistry and Chemical Engineering, Ankang University, Ankang 725000, China |
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| Abstract: | In the presence of titanium(Ⅳ) tetraethoxide, eight chiral menthyl arylglyoxylates were prepared by transesterification of ethyl arylglyoxylates and the natural (1R,2S,5R)-(-)-menthol. Seven new menthyl (2R)-2-hydroxy-2-aryl-3-nitropropionates were synthesized by the Henry reaction of menthyl arlglyoxylates and nitromethane. The structures of the products were characterized by IR, ~1H NMR, ~(13)C NMR spectroscopy, MS and elemental analysis. The diastereoselectivities were analyzed by HPLC with chiral column. The diastereomeric excess(d.e.) of the condensation reactions were between 46.5%-64.2%, achieve diastereoselectivities control to the structure. |
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| Keywords: | L-Menthol Transesterification Asymmetric Henry reaction |
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