5-chloro-2,2-difluoro-1-(3,5-dimethoxyphenyl)pentanone | 1039364-66-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-chloro-2,2-difluoro-1-(3,5-dimethoxyphenyl)pentanone
• CAS: 1039364-66-3
• 化学式: C₁₃H₁₅ClF₂O₃
• 分子量: 292.71
• InChiKey: PYJIFXYZVCRXKI-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  5-chloro-2,2-difluoro-1-(3,5-dimethoxyphenyl)pentanone 、 苄胺 在 四氯化钛 作用下， 以 乙醚 为溶剂， 反应 15.0h， 以74%的产率得到N-((1E)-5-chloro-2,2-difluoro-1-(3,5-dimethoxyphenyl)pentylidene)benzylamine
  参考文献：
  名称：

  New Entries toward 3,3-Difluoropiperidines

  摘要：

  Difluoropiperidines attract considerable interest from organic and medicinal chemists, but their synthesis is often problematic. This paper describes a new synthetic pathway toward valuable 3,3-difluoropiperidines starting from suitable 6-chloro-alpha,alpha-difluoroimines. The latter imines can be synthesized via electrophilic fluorination of the corresponding delta-chloroimines using NFSI (N-fluorodibenzenesulfonimide) in acetonitrile. After hydride reduction of the imino bond and subsequent intramolecular substitution of the chloride atom, new 3,3-difluoropiperidines were obtained in good yields. In addition, this methodology was applied to establish the first synthesis of N-protected 3,3-difluoropipecolic acid, a new fluorinated amino acid.

  DOI：

  10.1021/jo800768q
• 作为产物：
  描述：

  N-(5-chloro-1-(3,5-dimethoxyphenyl)pentylidene)isopropylamine 在 4 A molecular sieve 、 potassium carbonate 、 N-氟代双苯磺酰胺 、 盐酸 作用下， 以 乙腈 、 二氯甲烷 为溶剂， 反应 22.0h， 以47%的产率得到5-chloro-2,2-difluoro-1-(3,5-dimethoxyphenyl)pentanone
  参考文献：
  名称：

  New Entries toward 3,3-Difluoropiperidines

  摘要：

  Difluoropiperidines attract considerable interest from organic and medicinal chemists, but their synthesis is often problematic. This paper describes a new synthetic pathway toward valuable 3,3-difluoropiperidines starting from suitable 6-chloro-alpha,alpha-difluoroimines. The latter imines can be synthesized via electrophilic fluorination of the corresponding delta-chloroimines using NFSI (N-fluorodibenzenesulfonimide) in acetonitrile. After hydride reduction of the imino bond and subsequent intramolecular substitution of the chloride atom, new 3,3-difluoropiperidines were obtained in good yields. In addition, this methodology was applied to establish the first synthesis of N-protected 3,3-difluoropipecolic acid, a new fluorinated amino acid.

  DOI：

  10.1021/jo800768q