N-(2,2-difluoro-1-phenylethylidene)isopropylamine | 914801-74-4

• 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: N-(2,2-difluoro-1-phenylethylidene)isopropylamine
• 英文别名: 2,2-difluoro-1-phenyl-N-propan-2-ylethanimine
• CAS: 914801-74-4
• 化学式: C₁₁H₁₃F₂N
• 分子量: 197.228
• InChiKey: PKTKSBXCXQJLOG-UHFFFAOYSA-N

物化性质

• 沸点：
  210.9±40.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2,2-difluoro-1-phenylethylidene)isopropylamine 、 1-叠氮基-3-碘丙烷 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 15.5h， 生成 N-((1E)-5-azido-2,2-difluoro-1-phenylpentylidene)isopropylamine
  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：

  2,2-二氟苯乙酮 、 异丙胺 在 四氯化钛 作用下， 以 乙醚 为溶剂， 反应 15.0h， 以92%的产率得到N-(2,2-difluoro-1-phenylethylidene)isopropylamine
  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

文献信息

• One-pot synthesis of α,α-difluoroimines from alkynes through tandem catalytic diboration/fluorination/imination reaction
  作者：Jesús Ramírez、Elena Fernández

  DOI：10.1016/j.tetlet.2007.03.155

  日期：2007.5

  Tandem catalytic diboration/fluorination/imination of arylacetylenes leads to the formation of α,α-difluoroimines, where the adjacent CN and C–F2 bonds are formed simultaneously. The convenient one-pot protocol involves a Pt(0)-catalyzed diboration of terminal or internal arylalkynes followed by electrophilic fluorination with Selectfluor in the presence of primary amines and a dehydrating agent. A

  芳基乙炔的串联催化二硼化/氟化/亚胺化导致形成α，α-二氟亚胺，同时形成相邻的CN和CF 2键。方便的一锅操作方案涉及末端或内部芳基炔烃的Pt（0）催化二硼化，然后在伯胺和脱水剂存在下用Selectfluor进行亲电氟化。根据基材的电子特性，提出了三个连续步骤（硼化/氟化/亚胺化）的合理机理。炔烃/催化二硼化/烯基二硼酸酯/ Selectfluor /亲电子氟化/α，α-二氟亚胺。