Taylor W G, Schreck C E
J Pharm Sci. 1985 May;74(5):534-9. doi: 10.1002/jps.2600740508.
Fourteen stereoisomeric mixtures of six oxazolidine heterocycles and one amino alcohol were obtained from commercial samples of (+)-, (-), or (+/-)-citronellol and evaluated in a cloth test system as mosquito repellents. A technical sample of 3-acetyl-2-(2',6'-dimethyl-5'-heptenyl)oxazolidine, evaluated initially as a mixture of two pairs of enantiomers, was an effective repellent against two of the three species of mosquitoes. To study repellency-stereochemistry relationships, 1 was isolated as fractions G-1, G-2, I-1, and I-2, corresponding to representative samples of the four possible stereoisomers. The enantiomeric composition of 1, but not of the other derivatives, could be determined by chiral-phase capillary gas chromatography with Chirasil-Val. Two chiral phases showed that experimental samples of 1, and hence the commercial samples of 2, were composed of not more than 90% of one enantiomer. Differences in repellency of isomerically enriched samples were generally small. Fraction G, a mixture of diastereoisomers readily prepared from (+)-2, was considerably more effective than standard insect repellents in bioassays with three mosquito species.
从（+）-、（-）-或（±）-香茅醇的市售样品中获得了六种恶唑烷杂环和一种氨基醇的十四种立体异构体混合物，并在布测试系统中作为驱蚊剂进行了评估。一种最初作为两对对映体混合物评估的3-乙酰基-2-（2'，6'-二甲基-5'-庚烯基）恶唑烷工业样品，对三种蚊子中的两种具有有效的驱避作用。为了研究驱避性与立体化学的关系，将1分离为馏分G-1、G-2、I-1和I-2，分别对应四种可能立体异构体的代表性样品。1的对映体组成，而非其他衍生物的对映体组成，可通过使用Chirasil-Val的手性相毛细管气相色谱法测定。两种手性相表明，1的实验样品以及2的市售样品中，一种对映体的含量不超过90%。异构体富集样品的驱避性差异通常较小。馏分G是一种容易由（+）-2制备的非对映异构体混合物，在对三种蚊子的生物测定中，其效果比标准驱虫剂好得多。
