5,5-difluoro-6-phenyl-2,3,4,5-tetrahydropyridine | 951408-28-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5,5-difluoro-6-phenyl-2,3,4,5-tetrahydropyridine
• 英文别名: 5,5-difluoro-6-phenyl-3,4-dihydro-2H-pyridine
• CAS: 951408-28-9
• 化学式: C₁₁H₁₁F₂N
• 分子量: 195.212
• InChiKey: ZXSCYUULFHOSSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• 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：

  5,5-difluoro-6-phenyl-2,3,4,5-tetrahydropyridine 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以97%的产率得到3,3-difluoro-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
• 作为产物：
  描述：

  4,4-difluoro-5-oxo-5-phenylpentanenitrile 在 raney nickel 作用下， 以 甲醇 为溶剂， 50.0 ℃ 、5.0 MPa 条件下， 生成 5,5-difluoro-6-phenyl-2,3,4,5-tetrahydropyridine
  参考文献：
  名称：

  从易得的原料中制备 3,3-二氟哌啶的新方法和新型磷酸二酯酶抑制剂的合成

  摘要：

  已开发出一种合成 3,3-二氟哌啶的新方法。目标化合物采用稳健的方案和简单的起始材料分三步制备。氟的掺入是通过使用廉价且易于获得的 2-溴-2,2-二氟乙酸乙酯作为结构单元来实现的。使用这种方法，已经制备了一种新的有效的体外磷酸二酯酶 2A (PDE2A) 抑制剂，其中包含功能化的氟化哌啶支架。

  DOI：

  10.1055/s-0036-1588313

文献信息

• METAL COMPLEX, LIGHT-EMITTING DEVICE, AND DISPLAY APPARATUS
  申请人：Hashimoto Masashi

  公开号：US20070228940A1

  公开（公告）日：2007-10-04

  A metal complex is provided which is used for an organic EL device and an organic light-emitting device which outputs light with high luminance and high efficiency. The metal complex has a structure in which a nitrogen atom in a 6- to 8-membered non-aromatic cyclic group is bonded to a metal atom. The organic light-emitting device includes a pair of electrodes which are an anode and a cathode, and an organic compound layer interposed between the electrodes. The organic compound layer contains the metal complex represented by the following structural formula.
• US7964292B2
  申请人：——

  公开号：US7964292B2

  公开（公告）日：2011-06-21
• Novel Approach toward 3,3-Difluoropiperidines from Easily Available Starting Materials and Synthesis of a New Phosphodiesterase Inhibitor
  作者：Mauro Marigo、Jessica Giacoboni、Rasmus Clausen

  DOI：10.1055/s-0036-1588313

  日期：——

  for the synthesis of 3,3-difluoropiperidines has been developed. The target compounds are prepared in three steps using a robust protocol and simple starting materials. The incorporation of the fluorine is achieved by using the cheap and easily available ethyl 2-bromo-2,2-difluoroacetate as building block. Using this methodology, a new potent in vitro phosphodiesterase 2A (PDE2A) inhibitor containing

  已开发出一种合成 3,3-二氟哌啶的新方法。目标化合物采用稳健的方案和简单的起始材料分三步制备。氟的掺入是通过使用廉价且易于获得的 2-溴-2,2-二氟乙酸乙酯作为结构单元来实现的。使用这种方法，已经制备了一种新的有效的体外磷酸二酯酶 2A (PDE2A) 抑制剂，其中包含功能化的氟化哌啶支架。
• 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.