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A facile synthesis of (E)-2-hexenyl (E)-2-hexenoate and (E)-2-hexenyl (Z)-3-hexenoate, pheromone components of Riptortus pedestris

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

  • Kim, Junheon (Division of Applied Life Science (BK21), Gyeongsang National University) ;
  • Park, Chung Gyoo (Institute of Agriculture and Life Sciences, Gyeongsang National University)
  • 김준헌 (경상대학교 응용생명과학부(BK21)) ;
  • 박정규 (경상대학교 농업생명과학연구원)
  • Received : 2012.11.09
  • Accepted : 2013.04.05
  • Published : 2013.08.30

Abstract

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.

Acknowledgement

Supported by : Rural Development Administration

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Cited by

  1. Thunberg (Hemiptera: Coreidae) vol.47, pp.2, 2017, https://doi.org/10.1111/1748-5967.12204
  2. (Hymenoptera: Encyrtidae) pp.09312048, 2017, https://doi.org/10.1111/jen.12468