4'-hydroxybifenthrin | 115340-45-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4'-hydroxybifenthrin
• 英文别名: (4'-Hydroxy-2-methyl[biphenyl]-3-yl)methyl (1R,3R)-3-((1Z)-2-chloro-3,3,3-trifluoro-1-propen-1-yl)-2,2-dimethylcyclopropanecarboxylate-rel-；[3-(4-hydroxyphenyl)-2-methylphenyl]methyl (1R,3R)-3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate
• CAS: 115340-45-9
• 化学式: C₂₃H₂₂ClF₃O₃
• 分子量: 438.874
• InChiKey: SCZTZUIYDBOJNV-UZDMBDHZSA-N

反应信息

• 作为产物：
  描述：

  bifenthrin 在 Pb(trifluoroacetate)₄ 、 potassium carbonate 、 三氟乙酸 作用下， 生成 4'-hydroxybifenthrin 、 5-hydroxybifenthrin
  参考文献：
  名称：

  Simple Synthesis of Pyrethroid Metabolites

  摘要：

  The primary metabolism of 3-phenoxybenzyl pyrethroids by microsomal P450 monooxygenases commonly results in hydroxylation at the 2'- or 4'-positions. This paper reports the synthesis of these types of metabolites directly from five pyrethroids: deltamethrin, permethrin, fenvalerate, acrinathrin, and bifenthrin. The reactions were electrophilic substitutions using organometallic reagents. When these pyrethroids were reacted with lead tetrakis(trifluoroacetate) in trifluoroacetic acid followed by hydrolysis in K2CO3, 2'- and 4'-hydroxy derivatives of the 3-phenoxybenzyl group were found as the major products. For bifenthrin, which is a 2-methylbiphenyl-3-yl pyrethroid, 5- and 4'-hydroxy products were formed. This simple synthetic procedure will be valuable for generating authentic standards for pyrethroid metabolism studies.

  DOI：

  10.1021/jf00044a039