Faculty of Advanced Life Science, Frontier Research Center for the Post-Genome Science and Technology, Hokkaido University, Sapporo, Japan.
Chirality. 2009;21 Suppl 1:E110-5. doi: 10.1002/chir.20788.
A mixture of tautomers with unique keto-enol structures, 5-ethyl-4-hydroxy-2-methylfuran-3(2H)-one and 2-ethyl-4-hydroxy-5-methylfuran-3(2H)-one (EHMF, homofuraneol, 1a and 1b), comprises four structural isomers including their enantiomers. The four isomers were successfully separated by chromatographic optical resolution, and their odor evaluation was performed. Determination of the absolute chemistry of 1a and 1b were accomplished for the first time by direct measurement of the VCD spectra of their methyl ether derivatives 4a and 4b compared with the calculated ones as well as chemical relay reaction. The relationship between odor characteristics and stereochemistry was also examined.
一种具有独特酮式-烯醇结构的互变异构体混合物，5-乙基-4-羟基-2-甲基-2H-呋喃-3-酮和 2-乙基-4-羟基-5-甲基-2H-呋喃-3-酮（EHMF，同呋喃酮，1a 和 1b），包括四个立体异构体，包括它们的对映异构体。通过色谱光学拆分成功地分离了这四个异构体，并对它们的气味进行了评估。首次通过直接测量其甲酯衍生物 4a 和 4b 的 VCD 光谱，并与计算光谱以及化学接力反应进行比较，确定了 1a 和 1b 的绝对化学性质。还研究了气味特征与立体化学之间的关系。
