3,3-difluoro-1-isopropyl-2-phenylpiperidine | 1039364-53-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3,3-difluoro-1-isopropyl-2-phenylpiperidine
• 英文别名: 3,3-Difluoro-2-phenyl-1-propan-2-ylpiperidine
• CAS: 1039364-53-8
• 化学式: C₁₄H₁₉F₂N
• 分子量: 239.308
• InChiKey: QTRCOQDHJAYSNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-((1E)-5-chloro-2,2-difluoro-1-phenylpentylidene)isopropylamine 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以70%的产率得到3,3-difluoro-1-isopropyl-2-phenylpiperidine
  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

• 10.1016/j.chempr.2024.07.034
  作者：Ma, Xingxing、Zhong, Zihao、Song, Qiuling

  DOI：10.1016/j.chempr.2024.07.034

  日期：——

  deuterated) SCF3-containing alkenes can be assembled in good yields via this strategy. This protocol features tunable synthesis, high stereoselectivity and efficiency, applicability to late-stage modifications of bioactive molecules, and modular introduction of fluorine atoms/fluorinated groups. Additionally, these transformations can perfectly suppress the Zweifel pathway and keep the fluorine atoms/fluorinated

  将氟原子或含氟部分引入有机分子中会极大地影响其性质，从而提高它们作为药物或有机材料结构单元的适用性。在此，我们报道了有趣的氟化亲电拦截实现了各种含氟化合物的合成，其中涉及炔基四配位硼的 1,2-迁移对烯基硼物种的氧化或原脱硼化。显然，α，α-二氟酮在 30 分钟内很容易获得，这可能提供 [18F]α，α-二氟酮的替代方法。同时，通过这种策略，多功能的单氟烯烃、α-SCF3 酮和（高度氘化的）含 SCF3 的烯烃可以以良好的产率组装。该方案具有可调合成、高立体选择性和效率、适用于生物活性分子的后期修饰以及氟原子/氟化基团的模块化引入。此外，这些转化可以完美地抑制 Zweifel 通路并保持氟原子/氟化基团完整而不被消除，并且二氟哌啶支架也可以通过该方案有效地锻造。
• New Entries toward 3,3-Difluoropiperidines
  作者：Guido Verniest、Riccardo Surmont、Eva Van Hende、Arvid Deweweire、Frederik Deroose、Jan Willem Thuring、Norbert De Kimpe

  DOI：10.1021/jo800768q

  日期：2008.7.1

  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.