星天牛聚集信息素合成研究
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摘要
以价廉易得的四氢呋喃和1-庚醇为起始原料,分别经过开环反应、保护反应、取代反应、去保护反应和氧化反应,合成了星天牛聚集信息素4-(正庚氧基)-1-丁醇和4-(正庚氧基)-1-丁醛,二者的总收率分别为47%和41%;产物结构利用核磁共振氢谱进行了表征,产品的纯度利用气相色谱仪进行检测。本工艺原料易得,反应条件温和可控,无安全隐患,易于操作,适合放大生产。
The aggregation pheromone of anoplophora chinensis,4-( n-heptyloxy) butan-1-ol and 4-heptyloxy-butyraldehyde,were syhthesized from tetrahydrofuran and 1-heptanol as the the starting materials by the ring opening reaction,protection reaction,nucleophilic substitution reaction,deprotection reaction and oxidation reaction,the overall yields of the products were 47% and 41%,and the products were charaterized by HNMR and GC. This method offered several advantages such as normal materials,simple experimental and scale-up procedures.
The aggregation pheromone of anoplophora chinensis,4-( n-heptyloxy) butan-1-ol and 4-heptyloxy-butyraldehyde,were syhthesized from tetrahydrofuran and 1-heptanol as the the starting materials by the ring opening reaction,protection reaction,nucleophilic substitution reaction,deprotection reaction and oxidation reaction,the overall yields of the products were 47% and 41%,and the products were charaterized by HNMR and GC. This method offered several advantages such as normal materials,simple experimental and scale-up procedures.
引文
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[4]何学友,黄金水,叶剑雄,等.星天牛行为及控制技术研究II.星天牛控制技术的研究[J].福建林业科技,2003,30(2):1-4.
[5]魏建荣,赵文霞,张永安.星天牛研究进展[J].植物检疫,2011,25(5):81-85.
[6]姚万军,杨忠岐.利用管氏肿腿蜂防治光肩星天牛技术研究[J].环境昆虫学报,2008,30(2):127-134.
[7]朱宁,张冬勇,吴利平,等.聚集信息素和寄主植物挥发物对光肩星天牛和星天牛的引诱作用[J].昆虫学报,2017,60(4):421-430.
[8] Laura Hansen,Tian Xu,Jacob Wickham,et al. Identification of a Male-Produced Pheromone Component of the Citrus Longhorned Beetle,Anoplophora chinensis[J]. Plos one,2015,10(8):e0134358.
[9] Aijun Zhang,James E Olivera,Jeffrey R Aldricha,et al. Stimulatory Beetle Volatiles for the Asian Longhorned Beetle Anoplophora glabripennis(Motschulsky)[J]. Z Naturforsch,2002,57c:553-558.
[10] Donald S,Hixon R M. Tetramethylene chlorohydrin[1-Butanol,4-chloro-][M]. Org. Syn.,1943(2):571.
[11] Nakamura K,Kitayama T,Inoue Y,et al. Asymmetric synthesis of a pheromone for Andrena haemorrhoa F from a chiral nitro alcohol obtained by the yeast reduction of a nitro ketone[J]. Tetrahedron,1990,46(21):7471-7481.
[2]嵇保中,刘曙雯.天牛防治措施与对策分析[J].林业科技开发,2001,15(2):7-9.
[3]嵇保中,魏勇,黄振裕.天牛成虫行为研究的现状与展望[J].南京林业大学学报,2002,26(2):79-83.
[4]何学友,黄金水,叶剑雄,等.星天牛行为及控制技术研究II.星天牛控制技术的研究[J].福建林业科技,2003,30(2):1-4.
[5]魏建荣,赵文霞,张永安.星天牛研究进展[J].植物检疫,2011,25(5):81-85.
[6]姚万军,杨忠岐.利用管氏肿腿蜂防治光肩星天牛技术研究[J].环境昆虫学报,2008,30(2):127-134.
[7]朱宁,张冬勇,吴利平,等.聚集信息素和寄主植物挥发物对光肩星天牛和星天牛的引诱作用[J].昆虫学报,2017,60(4):421-430.
[8] Laura Hansen,Tian Xu,Jacob Wickham,et al. Identification of a Male-Produced Pheromone Component of the Citrus Longhorned Beetle,Anoplophora chinensis[J]. Plos one,2015,10(8):e0134358.
[9] Aijun Zhang,James E Olivera,Jeffrey R Aldricha,et al. Stimulatory Beetle Volatiles for the Asian Longhorned Beetle Anoplophora glabripennis(Motschulsky)[J]. Z Naturforsch,2002,57c:553-558.
[10] Donald S,Hixon R M. Tetramethylene chlorohydrin[1-Butanol,4-chloro-][M]. Org. Syn.,1943(2):571.
[11] Nakamura K,Kitayama T,Inoue Y,et al. Asymmetric synthesis of a pheromone for Andrena haemorrhoa F from a chiral nitro alcohol obtained by the yeast reduction of a nitro ketone[J]. Tetrahedron,1990,46(21):7471-7481.