2-(3-Formyl-4-fluorophenyl)-1,3-dioxolane | 146137-77-1

• 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: 2-(3-Formyl-4-fluorophenyl)-1,3-dioxolane
• 英文别名: 5-(1,3-Dioxolan-2-YL)-2-fluorobenzaldehyde
• CAS: 146137-77-1
• 化学式: C₁₀H₉FO₃
• 分子量: 196.178
• InChiKey: YKDPLUKRMOJQKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3-Formyl-4-fluorophenyl)-1,3-dioxolane 在 盐酸 、 sodium hydroxide 、 盐酸羟胺 、 四丁基溴化铵 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 8.0h， 生成 4-Fluoro-3-[(methoxyimino)methyl]benzaldehyde
  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 三氟甲磺酸三甲基硅酯 、 叔丁基锂 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.17h， 生成 2-(3-Formyl-4-fluorophenyl)-1,3-dioxolane
  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

文献信息

• Fluorine as an ortho-directing group in aromatic metalation: A two step preparation of substituted benzo[b]thiophene-2-carboxylates
  作者：Alexander J. Bridges、Arthur Lee、Emmanuel C. Maduakor、C.Eric Schwartz

  DOI：10.1016/s0040-4039(00)60806-7

  日期：——

  A simple 2-step synthesis of B-ring substituted benzo[b]thiophene-2-carboxylates from aryl fluorides has been developed. The route involves a selective lithiation ortho to fluorine, followed by formylation, and subsequently, displacement of fluorine with thioglycollate and base-induced ring closure in a single operation.

  已经开发了由芳基氟化物简单地两步合成B环取代的苯并[b]噻吩-2-羧酸酯的方法。该路线涉及对氟的邻位选择性锂化，然后进行甲酰化，随后在一次操作中用硫代乙醇酸酯置换氟并进行碱诱导的闭环。