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日本松干蚧性信息素(2E,4E)-(6R,10R)-4,6,10,12-四甲基-2,4-十三碳二烯-7-酮的酶促合成

Enzymatic synthesis of (2E,4E)-(6R,10R)-4,6,10,12-tetramethyl-2,4-tridecadien-7-one, the sex pheromone of Matsucoccus matsumurae Japanese pine bast scale.

作者信息

Lin G Q, Xu W C

机构信息

Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, People's Republic of China.

出版信息

Bioorg Med Chem. 1996 Mar;4(3):375-80. doi: 10.1016/0968-0896(96)00014-4.

DOI:10.1016/0968-0896(96)00014-4
PMID:8733615
Abstract

The sex pheromone of Matsucoccus matsumurae Japanese pine bast scale (2E,4E)-(6R,10R)-4,6,10,12-tetramethyl-2,4-tridecadien-7-one (1) was synthesized with stereocontrol from (2R,4S)-5-acetoxy-2,4-dimethyl-pentanol (3), which in turn was prepared by lipase-catalyzed transesterification of meso-2,4-dimethyl-1,5-propanediol (2).

摘要

日本松干蚧(Matsucoccus matsumurae)的性信息素(2E,4E)-(6R,10R)-4,6,10,12-四甲基-2,4-十三碳二烯-7-酮(1)是由(2R,4S)-5-乙酰氧基-2,4-二甲基戊醇(3)经立体控制合成的,而(2R,4S)-5-乙酰氧基-2,4-二甲基戊醇(3)又是通过脂肪酶催化内消旋-2,4-二甲基-1,5-丙二醇(2)的酯交换反应制备的。

相似文献

1
Enzymatic synthesis of (2E,4E)-(6R,10R)-4,6,10,12-tetramethyl-2,4-tridecadien-7-one, the sex pheromone of Matsucoccus matsumurae Japanese pine bast scale.日本松干蚧性信息素(2E,4E)-(6R,10R)-4,6,10,12-四甲基-2,4-十三碳二烯-7-酮的酶促合成
Bioorg Med Chem. 1996 Mar;4(3):375-80. doi: 10.1016/0968-0896(96)00014-4.
2
Antennal response and field attraction of the predator Elatophilus hebraicus (Hemiptera: Anthocoridae) to sex pheromones and analogues of three Matsucoccus spp. (Homoptera: Matsucoccidae).捕食性昆虫希伯来埃拉特蝽(半翅目:花蝽科)对三种松干蚧(同翅目:珠蚧科)性信息素及其类似物的触角反应和田间吸引力
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Pheromonal and kairomonal activities can be separated: synthesis and bioactivity studies of pine bast scale sex pheromones and their analogues.信息素和利它素活性可以分离:松干蚧性信息素及其类似物的合成与生物活性研究。
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Pheromone syntheses: a tropical approach. Enantioselective synthesis of the (2R,6S,10S) and (2S,6S,10S) isomers of methyl 2,6,10-trimethyldodecanoate.
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引用本文的文献

1
Determination of the Absolute Configuration of the Male-Produced Sex Pheromone of the Stink Bug Pellaea stictica, (2R,4R,8R)-2,4,8,13-Tetramethyltetradecan-1-ol by Stereoselective Synthesis Coupled with Enantiomeric Resolution.通过立体选择性合成与对映体拆分相结合,测定臭虫 Pellaea stictica 雄虫性信息素的绝对构型,(2R,4R,8R)-2,4,8,13-四甲基十四烷-1-醇。
J Chem Ecol. 2022 Jun;48(5-6):502-517. doi: 10.1007/s10886-022-01371-5. Epub 2022 Jul 16.
2
Synthesis and structure-activity relationship of diene modified analogs of Matsucoccus sex pheromones.松干蚧性信息素二烯修饰类似物的合成及其构效关系
Naturwissenschaften. 2003 Jul;90(7):313-7. doi: 10.1007/s00114-003-0429-0. Epub 2003 May 24.