Chromatographic Optical Resolution by Optically Active Poly(diphenyl-2-pyridylmethyl methacrylate) with a Highly One-Handed Helical Structure
Chromatographic Optical Resolution by Optically Active Poly(diphenyl-2-pyridylmethyl methacrylate) with a Highly One-Handed Helical Structure
复制标题
具有高度单手螺旋结构的光学活性聚（二苯基-2-吡啶基甲基丙烯酸甲酯）的色谱光学拆分
DOI：
10.1295/polymj.21.439
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发表时间：
1989
期刊：
影响因子：
2.8
通讯作者：
K. Hatada
中科院分区：
文献类型：
--
作者：
Y. Okamoto;Haruhiko Mohri;K. Hatada
研究了高单手螺旋度的聚（-）-甲基丙烯酸二苯基-2-吡啶甲酯（PD 2 PyMA）作为高效液相色谱手性固定相的光学拆分能力。用（+）-（2S，3S）-二甲氧基-1，4-双（1-全氢氮杂卓基）丁烷有机锂配合物制备了光学活性聚合物。当使用甲醇作为洗脱剂，PD 2 PyMA解决了许多外消旋化合物完全和一些联萘衍生物更好地解决比在决议由光学活性的聚（甲基丙烯酸三苯基甲酯）（PTrMA）。当使用非极性洗脱剂己烷-2-丙醇混合物时，PD 2 PyMA对几种醇的光学分辨能力比PTrMA高。这归因于PD 2 PyMA的2-吡啶基与非极性洗脱液中外消旋体的羟基之间的强相互作用。为了评价柱在甲醇中的耐久性，测定了单体和手性固定相的溶剂分解速率。这表明PD 2 PyMA在甲醇中的耐久性比PTrMA高。
The ability of optical resolution of (−)-poly(diphenyl-2-pyridylmethyl methacrylate) (PD2PyMA) with highly one-handed helicity was investigated by using it as a chiral stationary phase for high-performance liquid chromatography. The optically active polymer was prepared with an organolithium complex of (+)-(2S,3S)-dimethoxy-1,4-bis(1-perhydroazepinyl)-butane. When methanol was used as an eluent, PD2PyMA resolved many racemic compounds completely and several binaphthyl derivatives were better resolved than in resolution by optically active poly(triphenylmethyl methacrylate) (PTrMA). When a non-polar eluent, hexane-2-propanol mixture was used, PD2PyMA exhibited higher optical resolving power to several alcohols than PTrMA. This was ascribed to the strong interaction between the 2-pyridyl group of the PD2PyMA and the hydroxy group of the racemate in the non-polar eluent. In order to evaluate the durability of the column in methanol, the solvolysis rates of the monomer and chiral stationary phase were measured. This revealed that PD2PyMA has higher durability in methanol than PTrMA.