几种鳞翅目昆虫性信息素10和11—十二碳烯—1—醇乙酸酯的简便合成

从芥酸出发，经臭氧化还原，乙酰化及四乙酸铅脱羧三步反应合成了茶长卷峨性信息素组分（４），再经ＣｏＣｌ２／Ｐｈ３Ｐ／ＮａＢＨ４体系异构化合成桦广翅小卷峨、豆荚小卷娥等昆虫性信息素组份（５）。     

地老虎性信息素类似物E－7－十五碳烯－1－醇乙酸酯的合成

以紫胶桐酸为原料，经三步反应合成了地老虎性信息素类似物Ｅ－７－十五碳稀－１－醇乙酸酯。关键步骤是１６－羟基－９Ｅ－十六碳烯酸（２）在ＤＢＵ作用下的脱羧反应。     

地老虎性信息素类似物E—7—十五碳烯—1—醇乙酸酯的合成

以紫胶酮酸为原料，经三步反应合成了地老虎性信息素类似物Ｅ－７－十五碳稀－１－醇乙酸酯。关键步骤是１６－羟基－９Ｅ－十六碳烯酸（２）在ＤＢＵ作用下的脱羧反应。     

两种鳞翅目螟蛾科昆虫性信息素组分的合成

以天然产物中含有的大量组分油酸为初始原料合成了2种鳞翅目螟蛾科昆虫性信息素组分顺-9-十八碳烯-1-醇乙酸酯与顺-9-十八碳烯醛,并通过N M R、IR对中间体和目标化合物的结构进行了表征.结果表明,油酸经四氢铝锂还原后,再经乙酸酐酯化得到的顺-9-十八碳烯-1-醇乙酸酯和经氯铬酸吡啶盐(PCC)氧化得到的顺-9-十八...     

鳞翅目斑蛾科昆虫性信息素的合成

鳞翅目斑蛾科昆虫为森林和果树的重要害虫,可利用昆虫性信息素进行斑蛾科害虫的种群预测和直接诱杀.以7-溴庚酸为起始原料,经过二氯亚砜酰氯化、仲丁醇酯化得到7-溴庚酸仲丁醇酯,再与三苯基膦反应得到膦盐,最后与正戊醛进行相转移催化的Wittig反应,合成了鳞翅目斑蛾科昆虫性信息素顺-7-十二碳烯酸仲丁醇酯(Z7-12:COO...     

(Z/E)-8-十二碳烯-1-醇乙酸酯气相色谱分析方法研究

建立了一种用气相色谱测定(Z/E)-8-十二碳烯-1-醇乙酸酯的定量分析方法。采用安捷伦HP-5毛细管柱进行分离,硝基苯作内标物,在柱温100℃保持1 min,速率20℃/min升至250℃,保持5 min的色谱条件下,内标物、Z构型与E构型均可以实现良好分离。该分析方法的线性相关系数为0.999 4,标准偏差为0.002 5,平均回收率为99.39%。     

亚洲玉米螟性信息素的简便合成

以廉价的1,12-十二碳二醇为起始原料,经单边溴代、乙酰化、氧化吡啶氧化和Wittig反应,以36.6%的总收率合成了亚洲玉米螟性信息素(Z/E)-12-十四碳烯醇乙酸酯(Z/E,89/11),接着将顺反异构体混合物在亚硝酸钠和硝酸体系中经构型转化得到顺反比例为17/83的12-十四碳烯醇乙酸酯。产物通过红外光谱、核磁共振光谱数据确证,并采用气相色谱确定了顺反异构体的比例。该方法简单、易操作,而且总产率相对高于文献报道。     

家蝇性信息素Z—9—廿三碳烯的合成进展

综述了家蝇信息素Z—9—廿三碳烯合成方法的最新进展。     

梨小食心虫性信息素的简便合成

[目的]以廉价、易得的原料合成梨小食心虫性信息素(Z/E)-12-十四碳烯醇乙酸酯.[结果]以35.9%的总收率合成了梨小食心虫性信息索(Z/E)-12-十四碳烯醇乙酸酯,GC分析结果表明顺反异构体比例为87/13.将所得的顺反异构体混合物在亚硝酸钠和硝酸体系中经构型转化得到顺反比例为23/77的(Z/E)-12-十四碳烯醇乙酸酯,产物结构经IR、1H NMR等方法确证.[结论]该路线简洁且比大多数文献报道的方法产率略高,值得借鉴.     

正十二碳硫醇的合成

正十二碳硫醇主要用于丁苯橡胶、ABS树脂和丁腈橡胶的制备,对其聚合相对分子量进行调节。简单介绍了正十二碳硫醇的性质、用途及合成方法,以文献为基础,总结了以正十二醇、1-十二烯、1-卤代十二烷等为原料,分别与硫脲、硫化氢等含硫化合物反应合成正十二碳硫醇的方法,并对合成路线进行分析、比较,指出正十二醇为原料的合成路线中硫化氢催化取代法是一个较好的方法。对国内正十二碳硫醇合成研究提出了建议。     

亚洲玉米螟性信息素的合成新方法

以10-羟基癸酸为起始原料,经过四氢铝锂还原、单边溴代、邻苯二甲酸二环乙酯（DHP）保护、格氏试剂偶联、脱DHP及乙酰化、臭氧化反应和Wittig反应,以17.9%的总收率合成了亚洲玉米螟性信息素（Z/E）-12-十四碳烯醇乙酸酯（1,2）和正十四碳醇乙酸酯（3）。与文献报道的方法相比,此方法更经济。     

Sex pheromone ofAdoxophyes orana: Additional components and variability in ratio of (Z)-9- and (Z)-11-tetradecenyl acetate

Twelve products related to the sex pheromone main components (Z)-9- and (Z)-11-tetradecenyl acetate (Z9–14Ac andZ11–14Ac, respectively), were identified in female pheromone gland extracts of the laboratory-reared summerfruit tortrix moth,Adoxophyes orana F.v R. These are the geometric isomers and the alcohols of the main components, (Z)-9-dodecenyl acetate, (Z)-11-hexadecenyl acetate, and saturated acetates of 12–22 carbons. The ratio ofZ9–14Ac toZ11–14Ac in individuals varied from 3.51 to 111 with an average of 6.2; their total added up to 462 ng/female with an average of 182 ng for 2- to 7-day-old individuals. No qualitative or quantitative differences were observed between laboratory and field insects.Z9–14Ac,Z11–14Ac and the corresponding alcohols were also found in female effluvia. Addition of either of the two alcohols to a blend of the two acetates augmented trap catch in the field. The same was true for (Z)-9,(E)-12-tetradecadienyl acetate which was not detected in gland extracts.     

Sex pheromone components of the variegated leafroller moth,Platynota flavedana

Female tip extracts of the variegated leafroller moth,Platynota flavedana (Clemens), were analyzed and found to contain a mixture of (E)-11-tetradecen-1-ol and (Z)-11-tetradecen-1-ol (91), as well as a mixture of (E)-11-tetradecenyl acetate and (Z)-11-tetradecenyl acetate (2-31). Small amounts of tetradecen-1-ol and tetradecyl acetate probably are also present. In the field, a mixture of the two alcohols (8416,EZ ratio) attracted significantly more male moths of this species than any other mixture tested. The data indicate that the acetates are probably not used as pheromone components.Lepidoptera:Tortricidae:Tortricinae.This research was supported in part by the Rockefeller Foundation and by NSF Grant No. GB-38020.     

Some solid-phase syntheses of the sex attractant of the spruce budworm—trans-11-tetradecenal

The sex attractant of the spruce budworm,Choristoneura fumiferana,trans-11-tetradecenal (I), was synthesized on solid phases by three different routes from inexpensive 1,10-decanediol. The preparation of thetrans-alkene I directly on the polymer support was not completely stereoselective.The Use of Polymer Supports in Organic Synthesis, XIII.     

(Z)-9-tetradecen-1-ol acetate

(Z)-9-Tetradecen-1-ol acetate [(Z)-9-TDA], identified originally as the sex pheromone of the fall armyworm,Spodoptera frugiperda (J.E. Smith), acted as a secondary sex pheromone when it was tested in sticky traps in field tests. Low-level synergism was obtained when 2 and 10% quantities of (Z)-9-TDA were added to 100 g of (Z)-9-dodecen-1-ol acetate, which is now considered the primary sex pheromone.Lepidoptera: Noctuidae.In cooperation with the University of Georgia College of Agriculture Experiment Stations, Coastal Plain Station, Tifton, Georgia 31794.Mention of a proprietary product does not constitute endorsement by the USDA.     

Sex pheromone components of the fruit-tree leaf roller,Archips argyrospilus (Walker) (Lepidoptera: Tortricidae), in British Columbia

In field experiments in the Okanagan Valley, British Columbia, the pheromone blend of (11Z)-tetradecen-1-ol acetate (Z11-14:OAc), (11E)-tetradecen-1-ol acetate (E 11-14:OAc), (9Z)-tetradecen-1-ol acetate (Z9-14:OAc) and dodecan-1-ol acetate (12: OAc) at a 1006421 ratio (western FTLR blend) attracted significantly more male fruit-tree leaf roller (FTLR),Archips argyrospilus (Walker), than did the previously reported four-component blend and modifications thereof. Addition of (11Z)-tetradecen-1-ol (Z11-14:OH) to the western FTLR blend in a ratio of 4% relative toZ11-14: OAc further significantly enhanced attraction. Compounds were identified and their ratio determined by coupled gas chromatographic-electroantennographic (GC-EAD) and coupled GC-mass spectrometric analyses of female FTLR pheromone gland extracts and by retention index calculations of candidate pheromone components. Determination and use of geographically specific pheromonal blends may be required for optimal, semiochemical-based biorational control of FTLR and other lepidopteran orchard pests.     

Sex pheromone of hickory shuckwormCydia caryana Development of an effective field Lure

Extracts of the sex pheromone glands of femaleCydia caryana were evaluated by electroantennography and gas chromatography-mass spectrometry. These studies suggested the following compounds were potential sex pheromone components: (Z)-8- and/or (E)-9-dodecenyl acetate (50 pg/female), dodecyl acetate (40 pg/female), and (E, E)-8,10-dodecadienyl acetate (25 pg/female). In field tests only the diene produced trap catch, and when the other components were added to the diene, trap catch was not increased. When the diene was formulated in red natural rubber septa, only transient and low catches were obtained, but when gray halobutyl isoprene elastomeric septa were used, high and consistent catches were obtained for eight weeks. Catches depended on the ratio of (E, E)-8,10 to (E, Z)-8,10 isomers. High catches were obtained for anEE toEZ ratio of 100 0.6, and insignificant catches were obtained when the ratio was 100 3. Equivalent catches were obtained for dosages of 50, 100, and 200 g/septum.     

2-甲基-3-(2-呋喃基)-2-丙烯-1-醇的合成研究

本文报道了利用交叉Cannizzaro反应,合成2-甲基-3-(2-呋喃基)-2-丙烯-1-醇的一种新方法。该合成法,步骤简单;原料易得,价廉;在最佳反应条件下,产率可达58．1％。较已有文献报道的产率44％有较大幅度的提高。     

Female Sex Pheromone of Brinjal Fruit and Shoot Borer, Leucinodes orbonalis Blend Optimization

The brinjal fruit and shoot borer, Leucinodes orbonalis is the major pest of eggplant in South Asia. Analysis of female pheromone gland extracts prepared from insects of Indian and Taiwanese origin confirmed (E)-11-hexadecenyl acetate (E11-16:Ac) as the major pheromone component with 0.8 to 2.8% of the related (E)-11-hexadecen-1-ol (E11-16:OH), as previously reported from Sri Lanka. The average quantity of E11-16:Ac extracted per female was estimated to be 33 ng, with a range of 18.9 to 46.4 ng when collected 2 to 3 hr into the scotophase. In field trials conducted in India, blends containing between 1 and 10% E11-16:OH caught more male L. orbonalis than E11-16:Ac alone. At the 1000 g dose, on white rubber septa, addition of 1% E11-16:OH to E11-16:Ac was found to be more attractive to male L. orbonalis than either 0.1 or 10% E11-16:OH. Trap catch was found to be positively correlated with pheromone release rate, with the highest dose tested, 3000 g, on white rubber septa catching more male moths than lower doses. Field and wind tunnel release rate studies confirmed that E11-16:OH released from white rubber septa and polyethylene vials at approximately twice the rate of E11-16:Ac and that the release rate of both compounds was doubled in polyethylene vials compared to white rubber septa. This difference in release rate was reflected in field trials conducted in Bangladesh where polyethylene vial dispensers caught more male moths than either black or white rubber septa, each loaded with the same 100 : 1 blend of E11-16:Ac and E11-16:OH in a 3000 g loading.     

10-(异丙基-2-醇)-9,10-二氢-9-氧杂-10-膦杂菲-10-氧化物的合成

以9,10-二氢-9-氧杂-10-膦杂菲-10-氧化物(DOPO)和丙酮为原料,合成10-(异丙基-2-醇)-9,10-二氢-9-氧杂-10-膦杂菲-10-氧化物。考察了原料摩尔比、反应温度和反应时间对产物收率的影响。结果表明,较优工艺条件为:n(丙酮)∶n(DOPO)=12∶1,反应温度为50℃,反应时间为30 min时,DOPO的转化率为99%,目标产物收率为90%。