톱다리개미허리노린재 페로몬, (E)-2-hexenyl (E)-2-hexenoate과 (E)-2-hexenyl (Z)-3-hexenoate의 합성

Abstract

톱다리개미허리노린재의 페로몬 성분인 (E)-2-hexenyl (E)-2-hexenoate (1) 과 (E)-2-hexenyl (Z)-3-hexenoate (2)의 합성에 있어 Steglich 에스테르화 반응의 최적 조건을 검토하였다. (E)-2-헥센산 또는 (Z)-3-헥센산에 대하여 1-1.5 당량의 디사이클로카보다이이미드 (DCC), 1.5-2.0 당량의 (E)-2-헥센놀과 0.1 당량의 4-디메틸아미노피리딘(DMAP)과 반응하였을 때, 각각 76-78% 와 87-91%의 수율로 1과 2를 얻었다. We investigated optimal condition for synthesis of (E)-2-hexenyl (E)-2-hexenoate (1) and (E)-2-hexenyl (Z)-3-hexenoate (2), the pheromone components of Riptortus pedestris, by Steglich esterification. The reaction with 1.1-1.5 equivalent of dicyclohexylcarbodiimide (DCC), 1.5-2.0 equivalent of (E)-2-hexenol, and 0.1 equivalent 4-dimethylaminopyrinde (DMAP) to (E)-2-hexenoic acid in toluene or (Z)-3-hexenoic acid in dichloromethane led 1 and 2 in 76-78% and 87-91% yield, respectively.