α-Cyano-4-fluoro-3-[(methoxyimino)methyl]benzyl alcohol | 166408-36-2

• 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: α-Cyano-4-fluoro-3-[(methoxyimino)methyl]benzyl alcohol
• CAS: 166408-36-2
• 化学式: C₁₀H₉FN₂O₂
• 分子量: 208.192
• InChiKey: AXXGFNGQEXHVES-AWNIVKPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.36
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  65.61
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R-顺式)-3-(2,2-二溴乙烯基)-2,2-二甲基环丙烷甲酸 、 α-Cyano-4-fluoro-3-[(methoxyimino)methyl]benzyl alcohol 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以70%的产率得到α-Cyano-4-fluoro-3-[(methoxyimono)methyl]benzyl (1R)-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate
  参考文献：
  名称：

  The pyrethrins and related compounds. Part XXXVIII-optimisation of insecticidal activity in 3-[(alkoxyimino)methyl]-4-fluorobenzyl esters

  摘要：

  AbstractOptimisation of activity in 3‐[(alkoxyimino)methylbenzyl] esters has been investigated by introducing an α‐cyano group and a fluorine atom in position 4 of the benzylic moiety in conjunction with varying the length and nature of the side chain. Of the five side‐chain variations investigated, the 3‐methoxyiminomethyl was more effective than others. Introduction of fluorine in position 4 of the benzylic moiety generally increased activity, particularly against mustard beetles, as in previous instances. Surprisingly, the effect on insecticidal activity of introducing an α‐CN group ranged from positive to negative depending upon the nature of the alkoxyimino substituent, an effect not observed previously. The most effective esters were derived from α‐cyano‐4‐fluoro‐3‐[(methoxyimino)methyl]benzyl alcohol, which was synthesised from 2‐{4‐fluoro‐3‐[(hydroxyimino)methyl]phenyl}‐1,3‐dioxolane.

  DOI：

  10.1002/ps.2780440309
• 作为产物：
  描述：

  3-溴-4-氟苯甲醛 在 盐酸 、 sodium hydroxide 、 三氟甲磺酸三甲基硅酯 、 盐酸羟胺 、 四丁基溴化铵 、 叔丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 9.17h， 生成 α-Cyano-4-fluoro-3-[(methoxyimino)methyl]benzyl alcohol
  参考文献：
  名称：

  The pyrethrins and related compounds. Part XXXVIII-optimisation of insecticidal activity in 3-[(alkoxyimino)methyl]-4-fluorobenzyl esters

  摘要：

  AbstractOptimisation of activity in 3‐[(alkoxyimino)methylbenzyl] esters has been investigated by introducing an α‐cyano group and a fluorine atom in position 4 of the benzylic moiety in conjunction with varying the length and nature of the side chain. Of the five side‐chain variations investigated, the 3‐methoxyiminomethyl was more effective than others. Introduction of fluorine in position 4 of the benzylic moiety generally increased activity, particularly against mustard beetles, as in previous instances. Surprisingly, the effect on insecticidal activity of introducing an α‐CN group ranged from positive to negative depending upon the nature of the alkoxyimino substituent, an effect not observed previously. The most effective esters were derived from α‐cyano‐4‐fluoro‐3‐[(methoxyimino)methyl]benzyl alcohol, which was synthesised from 2‐{4‐fluoro‐3‐[(hydroxyimino)methyl]phenyl}‐1,3‐dioxolane.

  DOI：

  10.1002/ps.2780440309