Structure, stereochemistry, and thermal isomerization of the male sex pheromone of the longhorn beetle Anaglyptus subfasciatus.

Leal WS; Shi X; Nakamuta K; Ono M; Meinwald J

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Structure, stereochemistry, and thermal isomerization of the male sex pheromone of the longhorn beetle Anaglyptus subfasciatus.

机译：长角甲虫Anaglyptus subfasciatus雄性信息素的结构，立体化学和热异构化。

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摘要

Male-released sex pheromone constituents of the longhorn beetle Anaglyptus subfasciatus (Coleoptera: Cerambycidae) are identified by GC-MS and GC-Fourier transform infrared as a 7:1 molar mixture of 3-hydroxy-2-hexanone and 3-hydroxy-2-octanone. These two compounds undergo thermal isomerization during GC analyses to give the corresponding 2-hydroxy-3-alkanones. Comparison of GC retention times of the natural products with those of synthesized enantiomerically pure compounds revealed that both semiochemicals have (R)-stereochemistry. These absolute configurations were confirmed by comparisons of the (R)-methoxy(trifluoromethyl)phenylacetic acid esters of insect-derived and synthetic samples.

机译：通过GC-MS和GC-傅立叶变换红外光谱法鉴定了长角甲虫Anaglyptus subfasciatus（鞘翅目：Cerambycidae）的男性释放性信息素成分为3-羟基-2-己酮和3-羟基-2的7：1摩尔混合物。 -辛酮。这两种化合物在GC分析过程中进行热异构化反应，得到相应的2-羟基-3-链烷酮。天然产物与合成对映体纯化合物的GC保留时间的比较表明，两种化学信息素均具有（R）-立体化学。通过比较昆虫和合成样品中的（R）-甲氧基（三氟甲基）苯基乙酸酯，可以确认这些绝对构型。

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来源
《Proceedings of the National Academy of Sciences of the United States of America》 |1995年第4期|P.1038-1042|共5页
作者
Leal WS; Shi X; Nakamuta K; Ono M; Meinwald J;
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作者单位

Department of Chemistry, Cornell University, Ithaca, NY 14853.;

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收录信息美国《科学引文索引》(SCI);美国《生物学医学文摘》(MEDLINE);美国《化学文摘》(CA);
原文格式 PDF
正文语种 eng
中图分类自然科学总论;
关键词
Beetles; Hexanones; Ketones; Sex Attractants; 3-hydroxy-2-hexanone; 3-hydroxy-2-octanone; 甲虫; 己酮类; 酮类; 性诱引剂;

机译：Beetles;Hexanones;Ketones;Sex Attractants;3-hydroxy-2-hexanone;3-hydroxy-2-octanone;甲虫;己酮类;酮类;性诱引剂;

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6. Structure stereochemistry and thermal isomerization of the male sex pheromone of the longhorn beetle Anaglyptus subfasciatus. [O] . W S Leal, X Shi, K Nakamuta, 1995

机译：长角甲虫Anaglyptus subfasciatus雄性信息素的结构立体化学和热异构化。
7. Structure, stereochemistry, and thermal isomerization of the male sex pheromone of the longhorn beetle Anaglyptus subfasciatus. [O] . Leal, W S, Shi, X, Nakamuta, K, 1995

机译：长角甲虫Anaglyptus subfasciatus雄性信息素的结构，立体化学和热异构化。

Structure, stereochemistry, and thermal isomerization of the male sex pheromone of the longhorn beetle Anaglyptus subfasciatus.

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