文章摘要
稳定同位素标记D5-氯氰菊酯的合成
Synthesis of Isotope-labeled D5-Cypermethrin
投稿时间:2019-06-12  修订日期:2019-07-11
DOI:
中文关键词: D5-氯氰菊酯,同位素标记,拟除虫菊酯,合成,表征
英文关键词: D5-cypermethrin  isotope- labeled  pyrethroid  synthesis  characterization
基金项目:食品安全关键技术研发重点专项(2017YFC1601300)
作者单位E-mail
罗勇 上海化工研究院 real-luoyong@hotmail.com 
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中文摘要:
      以丰度98% atom D的D6-苯酚为起始原料,经氘氧化钾在无水甲苯中回流脱水成盐,然后与间溴苯甲醛通过乌尔曼缩合反应得到关键标记中间体D5-间苯氧基苯甲醛,再与氰化钠及DV-菊酰氯通过“相转移催化氰醇一步法”得到稳定同位素标记的D5-氯氰菊酯,以投入的氘代苯酚的物质的量计算产率为20%。目标产物结构经MS、NMR和HPLC等加以表征确认,液相色谱纯度大于98%,液质丰度98% atom D,该标记中间体亦可用于其他同位素标记拟除虫菊酯类化合物的合成。
英文摘要:
      This paper describes an novel synthesis of D5-cypermethrin with D6-phenol (98% atom D) as the labeled precursor. D6-phenol was dehydrated by potassium deuterium oxide in anhydrous toluene, and then reacted with 3-bromobenzaldehyde to obtain the key labeled intermediate D5-3-phenoxy-benzaldehyde through Ullmann Condensation Reaction. Finally, D5-cypermethrin was obtained by “phase transfer catalysis cyanohydrins reaction” with sodium cyanide and 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarbonyl chloride by one-step method. The yield based on the amount of substance of deuterium-substituted phenol was 20%. As-synthesized product was con-firmed by MS, NMR and HPLC to be target compound. Its chemical purity is higher than 98%, and isotopic abundance is higher than 98% (atom D). This method could also be used to synthesize other labeled pyrethroids.
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