(E)-2-bromo-6-fluorobenzaldehyde O-methyloxime | 914311-48-1

• 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: (E)-2-bromo-6-fluorobenzaldehyde O-methyloxime
• 英文别名: (E)-1-(2-bromo-6-fluorophenyl)-N-methoxymethanimine
• CAS: 914311-48-1
• 化学式: C₈H₇BrFNO
• 分子量: 232.052
• InChiKey: BRYDQMABMZXAJU-VZUCSPMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-fluorobenzaldehyde O-methyloxime 在 N-溴代丁二酰亚胺(NBS) 、 Ag^(1-)*C₂F₃O₂^(1-) 、 palladium diacetate 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 5.0h， 生成 (E)-2-bromo-6-fluorobenzaldehyde O-methyloxime 、 (Z)-2-bromo-6-fluorobenzaldehyde O-Methyloxime
  参考文献：
  名称：

  Selectiveortho-Bromination of Substituted Benzaldoximes Using Pd-Catalyzed C–H Activation: Application to the Synthesis of Substituted 2-Bromobenzaldehydes

  摘要：

  Substituted 2-bromobenzaldehydes were synthesized from benzaldehydes using a three-step sequence involving a selective palladium-catalyzed ortho-bromination as the key step. O-Methyloxime serves as a directing group in this reaction. A rapid deprotection of substituted 2-bromobenzaldoximes afforded substituted 2-bromobenzaldehydes with good overall yields.

  DOI：

  10.1021/jo200853j

文献信息

• New Practical Synthesis of Indazoles via Condensation of <i>o</i>-Fluorobenzaldehydes and Their <i>O</i>-Methyloximes with Hydrazine
  作者：Kirill Lukin、Margaret C. Hsu、Dilinie Fernando、M. Robert Leanna

  DOI：10.1021/jo0613784

  日期：2006.10.1

  The reaction of o-fluorobenzaldehydes and their O-methyloximes with hydrazine has been developed as a new practical synthesis of indazoles. Utilization of the methyloxime derivatives of benzaldehydes (in the form of the major E-isomers) in this condensation effectively eliminated a competitive Wolf-Kishner reduction to fluorotoluenes, which was observed in the direct preparations of indazoles from aldehydes. Reaction of Z-isomers of methyloximes with hydrazine resulted in the formation of 3-aminoindazoles via a benzonitrile intermediate.
• Selective<i>ortho</i>-Bromination of Substituted Benzaldoximes Using Pd-Catalyzed C–H Activation: Application to the Synthesis of Substituted 2-Bromobenzaldehydes
  作者：Emmanuelle Dubost、Christine Fossey、Thomas Cailly、Sylvain Rault、Frederic Fabis

  DOI：10.1021/jo200853j

  日期：2011.8.5

  Substituted 2-bromobenzaldehydes were synthesized from benzaldehydes using a three-step sequence involving a selective palladium-catalyzed ortho-bromination as the key step. O-Methyloxime serves as a directing group in this reaction. A rapid deprotection of substituted 2-bromobenzaldoximes afforded substituted 2-bromobenzaldehydes with good overall yields.