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使用催化有机铜偶联反应合成桔小实蝇引诱剂。

Synthesis of attractants for oriental fruit flyDacus dorsalis Hendel using a catalytic organocopper coupling reaction.

机构信息

U.S. Department of Agriculture, Agricultural Research Service, Insect Chemical Ecology Laboratory, 20705, Beltsville, Maryland.

出版信息

J Chem Ecol. 1993 Dec;19(12):2935-46. doi: 10.1007/BF00980593.

DOI:10.1007/BF00980593
PMID:24248786
Abstract

A general synthetic approach to various catechol derivatives was developed using a copper-catalyzed cross-coupling reaction of 1,2-dimethoxy-4-brornomethyl, 1-ethoxy-2-methoxy-4-bromomethyl- and 2-ethoxy-1-methoxy-4-bromomethylbenzenes with Grignard reagents. Dilithium tetrachlorocuprate was an acceptable catalyst in the dimethoxy series, whereas copper(I) iodide in THF-HMPA was a superior catalyst in all cases due to decreased side reactions, i.e., reduction and reductive coupling. Methyl-substituted analogs of methyl eugenol, a potent attractant of Oriental fruit fly,Dacus dorsalis Hendel, were synthesized by this method and evaluated for attractancy in field tests.

摘要

开发了一种通用的合成方法，可用于各种儿茶酚衍生物，方法是使用铜催化的 1,2-二甲氧基-4-溴甲基、1-乙氧基-2-甲氧基-4-溴甲基和 2-乙氧基-1-甲氧基-4-溴甲基苯与格氏试剂的交叉偶联反应。二锂四氯铜是二甲氧基系列中可接受的催化剂，而在所有情况下，四氢呋喃-HMPA 中的碘化亚铜都是更好的催化剂，因为减少了副反应，即还原和还原偶联。通过这种方法合成了甲基丁香酚的甲基取代类似物，甲基丁香酚是东方果实蝇（Dacus dorsalis Hendel）的一种有效的引诱剂，并在田间试验中评估了其引诱活性。

相似文献

1
Synthesis of attractants for oriental fruit flyDacus dorsalis Hendel using a catalytic organocopper coupling reaction.使用催化有机铜偶联反应合成桔小实蝇引诱剂。
J Chem Ecol. 1993 Dec;19(12):2935-46. doi: 10.1007/BF00980593.
2
Benzyl acetates as attractants for the male oriental fruit fly, Dacus dorsalis, and the male melon fly, Dacus cucurbitae.苯乙酸酯作为东方果实蝇和瓜实蝇雄虫的引诱剂。
Proc Natl Acad Sci U S A. 1986 Mar;83(6):1549-53. doi: 10.1073/pnas.83.6.1549.
3
Di- and tri-fluorinated analogs of methyl eugenol: attraction to and metabolism in the Oriental fruit fly, Bactrocera dorsalis (Hendel).二氟和三氟甲基丁香酚类似物：对东方果实蝇（Bactrocera dorsalis（Hendel））的吸引力及其代谢。
J Chem Ecol. 2011 Jun;37(6):553-64. doi: 10.1007/s10886-011-9963-y. Epub 2011 May 26.
4
Ring-fluorinated analog of methyl eugenol: attractiveness to and metabolism in the oriental fruit fly, Bactrocera dorsalis (Hendel).甲基丁香酚的环氟化类似物：对桔小实蝇（Bactrocera dorsalis (Hendel)）的吸引力及在其体内的代谢
J Chem Ecol. 2009 Feb;35(2):209-18. doi: 10.1007/s10886-008-9581-5. Epub 2009 Feb 6.
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Consumption and metabolism of 1,2-dimethoxy-4-(3-fluoro-2-propenyl)benzene, a fluorine analog of methyl eugenol, in the oriental fruit fly Bactrocera dorsalis (Hendel).甲基丁香酚的氟类似物1,2 - 二甲氧基 - 4 -（3 - 氟 - 2 - 丙烯基）苯在桔小实蝇（Bactrocera dorsalis (Hendel)）中的消耗与代谢
J Chem Ecol. 2006 Jul;32(7):1513-26. doi: 10.1007/s10886-006-9066-3. Epub 2006 Jun 23.
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Attraction of the oriental fruit fly, Dacus dorsalis, to methyl eugenol and related olfactory stimulants.东方果实蝇（橘小实蝇）对甲基丁香酚及相关嗅觉刺激物的趋性
Proc Natl Acad Sci U S A. 1975 Jul;72(7):2501-5. doi: 10.1073/pnas.72.7.2501.
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Saturated and monofluoro analogs of the oriental fruit fly attractant methyl eugenol show reduced genotoxic activities in yeast.东方果实蝇引诱剂甲基丁香酚的饱和及单氟类似物在酵母中显示出降低的遗传毒性活性。
Mutat Res. 1996 Aug 12;369(3-4):175-81. doi: 10.1016/s0165-1218(96)90024-5.
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Pre-release consumption of methyl eugenol increases the mating competitiveness of sterile males of the oriental fruit fly, Bactrocera dorsalis, in large field enclosures.预释放甲基丁香酚可提高东方果实蝇不育雄虫在大型田间围栏中的交配竞争力。
J Insect Sci. 2010;10:8. doi: 10.1673/031.010.0801.
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Evolution of olfactory receptor in oriental fruit fly Dacus dorsalis.桔小实蝇嗅觉受体的进化
Proc Natl Acad Sci U S A. 1979 Apr;76(4):1561-5. doi: 10.1073/pnas.76.4.1561.
10
Relationship of sexual maturation rate to response of oriental fruit fly strains (Diptera: Tephritidae) to methyl eugenol.性成熟率与东方果实蝇品系（双翅目：实蝇科）对甲基丁香酚反应的关系。
J Chem Ecol. 1989 Apr;15(4):1399-405. doi: 10.1007/BF01014839.

引用本文的文献

1
Di- and tri-fluorinated analogs of methyl eugenol: attraction to and metabolism in the Oriental fruit fly, Bactrocera dorsalis (Hendel).二氟和三氟甲基丁香酚类似物：对东方果实蝇（Bactrocera dorsalis（Hendel））的吸引力及其代谢。
J Chem Ecol. 2011 Jun;37(6):553-64. doi: 10.1007/s10886-011-9963-y. Epub 2011 May 26.
2
Ring-fluorinated analog of methyl eugenol: attractiveness to and metabolism in the oriental fruit fly, Bactrocera dorsalis (Hendel).甲基丁香酚的环氟化类似物：对桔小实蝇（Bactrocera dorsalis (Hendel)）的吸引力及在其体内的代谢
J Chem Ecol. 2009 Feb;35(2):209-18. doi: 10.1007/s10886-008-9581-5. Epub 2009 Feb 6.
3

本文引用的文献

1
Alkyl substitution in terminal chain of (Z)-5-decenyl acetate, a pheromone component of turnip moth,Agrotis segetum. Synthesis, single-sensillum recordings, and structure-activity relationships.(Z)-5-癸烯基乙酸酯末端链的烷基取代，黑光灯诱小菜蛾性信息素成分。合成、单感器记录和构效关系。
J Chem Ecol. 1991 Jan;17(1):103-22. doi: 10.1007/BF00994425.
2
Introduction of methyl groups to acetate substituted chain of (Z)-5-decenyl acetate, a pheromone component of turnip moth,agrotis segetum: synthesis, single-sensillum recordings, and structure-activity relationships.向（Z）-5-癸烯基乙酸酯中引入甲基，（Z）-5-癸烯基乙酸酯是萝卜蛾 Agrotis segetum 的一种信息素成分：合成、单感器记录和结构-活性关系。
J Chem Ecol. 1992 Apr;18(4):637-57. doi: 10.1007/BF00987825.
3
Consumption and metabolism of 1,2-dimethoxy-4-(3-fluoro-2-propenyl)benzene, a fluorine analog of methyl eugenol, in the oriental fruit fly Bactrocera dorsalis (Hendel).
甲基丁香酚的氟类似物1,2 - 二甲氧基 - 4 -（3 - 氟 - 2 - 丙烯基）苯在桔小实蝇（Bactrocera dorsalis (Hendel)）中的消耗与代谢
J Chem Ecol. 2006 Jul;32(7):1513-26. doi: 10.1007/s10886-006-9066-3. Epub 2006 Jun 23.
Olfactory receptors in the melon fly Dacus cucurbitae and the oriental fruit fly Dacus dorsalis.瓜实蝇和桔小实蝇的嗅觉受体。
Proc Natl Acad Sci U S A. 1983 Jun;80(11):3143-7. doi: 10.1073/pnas.80.11.3143.
4
Molecular parameters and olfaction in the oriental fruit fly Dacus dorsalis.东方果实蝇 Dacus dorsalis 的分子参数与嗅觉。
Proc Natl Acad Sci U S A. 1981 Jul;78(7):4007-10. doi: 10.1073/pnas.78.7.4007.
5
Structure-activity studies of the carcinogenicities in the mouse and rat of some naturally occurring and synthetic alkenylbenzene derivatives related to safrole and estragole.一些与黄樟素和草蒿脑相关的天然存在及合成的烯基苯衍生物在小鼠和大鼠体内致癌性的构效关系研究。
Cancer Res. 1983 Mar;43(3):1124-34.
6
Genotoxicity of safrole-related chemicals in microbial test systems.黄樟素相关化学品在微生物测试系统中的遗传毒性。
Mutat Res. 1982 Apr;101(2):127-40. doi: 10.1016/0165-1218(82)90003-9.
7
The metabolism of the naturally occurring hepatocarcinogen safrole to 1'-hydroxysafrole and the electrophilic reactivity of 1'-acetoxysafrole.天然存在的肝癌致癌物黄樟素代谢生成1'-羟基黄樟素以及1'-乙酰氧基黄樟素的亲电反应活性。
Cancer Res. 1973 Mar;33(3):575-89.
8
Safrole, eugenol and methyleugenol induce intrachromosomal recombination in yeast.黄樟素、丁香酚和甲基丁香酚可诱导酵母发生染色体内重组。
Mutat Res. 1989 Dec;224(4):427-36. doi: 10.1016/0165-1218(89)90067-0.
9
Hepatotoxicity of eugenol and related compounds in mice depleted of glutathione: structural requirements for toxic potency.谷胱甘肽缺乏小鼠中丁香酚及相关化合物的肝毒性：毒性效力的结构要求
Res Commun Chem Pathol Pharmacol. 1991 Jul;73(1):87-95.
10
Attraction of the oriental fruit fly, Dacus dorsalis, to methyl eugenol and related olfactory stimulants.东方果实蝇（橘小实蝇）对甲基丁香酚及相关嗅觉刺激物的趋性
Proc Natl Acad Sci U S A. 1975 Jul;72(7):2501-5. doi: 10.1073/pnas.72.7.2501.