2'-hydroxyfenvalerate | 72120-17-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2'-hydroxyfenvalerate
• 英文别名: Cyano[3-(2-hydroxyphenoxy)phenyl]methyl 2-(4-chlorophenyl)-3-methylbutanoate；[cyano-[3-(2-hydroxyphenoxy)phenyl]methyl] 2-(4-chlorophenyl)-3-methylbutanoate
• CAS: 72120-17-3
• 化学式: C₂₅H₂₂ClNO₄
• 分子量: 435.907
• InChiKey: DGQZGRIBSTXBJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  79.6
• 氢给体数：
  1
• 氢受体数：
  5

ADMET

代谢

2'-羟基-乙螨唑是乙螨唑的一个已知人体代谢物。

2'-hydroxy-esfenvalerate is a known human metabolite of Esfenvalerate.

来源:NORMAN Suspect List Exchange

反应信息

• 作为产物：
  描述：

  氰戊菊酯 在 Pb(trifluoroacetate)₄ 、 potassium carbonate 、 三氟乙酸 作用下， 生成 4'-hydroxyfenvalerate 、 2'-hydroxyfenvalerate
  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