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4-氧代-(E)-2-己烯醛及其同系物的简短合成:半翅目的信息素成分和防御性化合物

Short and simple syntheses of 4-oxo-(E)-2-hexenal and homologs: pheromone components and defensive compounds of Hemiptera.

作者信息

Moreira Jardel A, Millar Jocelyn G

机构信息

Department of Entomology, University of California, Riverside, CA 92521, USA.

出版信息

J Chem Ecol. 2005 Apr;31(4):965-8. doi: 10.1007/s10886-004-1978-1.

DOI:10.1007/s10886-004-1978-1
PMID:16124263
Abstract

One-step syntheses of 4-oxo-(E)-2-hexenal and 4-oxo-(E)-2-octenal from commercially available 2-ethyl- and 2-butylfuran are described. A two-step synthesis of the homolog 4-oxo-(E)-2-decenal from furan is also reported. These compounds are common components of true bug defensive secretions, and recently have been identified as pheromone components for several species. The simple syntheses reported here will make these compounds readily available for further research.

摘要

本文描述了由市售的2-乙基呋喃和2-丁基呋喃一步合成4-氧代-(E)-2-己烯醛和4-氧代-(E)-2-辛烯醛的方法。还报道了由呋喃两步合成同系物4-氧代-(E)-2-癸烯醛的方法。这些化合物是蝽类防御分泌物的常见成分,最近已被鉴定为几种物种的信息素成分。本文报道的简单合成方法将使这些化合物易于获得,以便进行进一步研究。

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本文引用的文献

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J Chem Ecol. 2004 Aug;30(8):1509-29. doi: 10.1023/b:joec.0000042065.19044.6d.
2
Chemical and physical signals mediating conspecific and heterospecific aggregation behavior of first instar stink bugs.介导初龄椿象同种和异种聚集行为的化学和物理信号。
J Chem Ecol. 2004 Jun;30(6):1257-69. doi: 10.1023/b:joec.0000030276.32665.cb.
3
Efficient Conditions for Conversion of 2-Substituted Furans into 4-Oxygenated 2-Enoic Acids and Its Application to Synthesis of (+)-Aspicilin, (+)-Patulolide A, and (-)-Pyrenophorin.
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J Pestic Sci. 2019 Feb 20;44(1):15-19. doi: 10.1584/jpestics.D18-053.
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PLoS One. 2018 Jan 17;13(1):e0191223. doi: 10.1371/journal.pone.0191223. eCollection 2018.
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