3,3-difluoro-4,4-dihydroxy-1-trifluoroacetylpiperidine | 1206540-62-6

• 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-4,4-dihydroxy-1-trifluoroacetylpiperidine
• 英文别名: 1-(3,3-difluoro-4,4-dihydroxypiperidin-1-yl)-2,2,2-trifluoroethanone
• CAS: 1206540-62-6
• 化学式: C₇H₈F₅NO₃
• 分子量: 249.137
• InChiKey: DXQBGULQEWGIAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,3-difluoro-4,4-dihydroxy-1-trifluoroacetylpiperidine 在 palladium 10% on activated carbon 、 三乙胺 、 sodium iodide 作用下， 以 甲醇 、 甲苯 为溶剂， 120.0 ℃ 、480.01 kPa 条件下， 反应 134.0h， 生成 3,3-difluoro-1-[3-(4-fluorophenoxy)propyl]piperidin-4-amine
  参考文献：
  名称：

  5-HT2B RECEPTOR ANTAGONISTS

  摘要：

  本发明涉及一种新型氟代哌啶衍生物，其具有对5-HT2B受体的拮抗活性，包括这些化合物的制药组合物以及它们作为药物的用途。

  公开号：

  US20130172386A1
• 作为产物：
  描述：

  1-(3,3-difluoro-4-hydroxypiperidin-1-yl)-2,2,2-trifluoroethanone 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以56%的产率得到3,3-difluoro-4,4-dihydroxy-1-trifluoroacetylpiperidine
  参考文献：
  名称：

  Synthesis of 4-Substituted 3,3-Difluoropiperidines

  摘要：

  Synthetic strategies toward 4-substituted 3,3-difluoropiperidines were evaluated. 4-Alkoxymethyl- and 4-aryloxymethyl-3,3-difluoropiperidines were synthesized via 1,4-addition of ethyl bromodifluoroacetate to 3-substituted acrylonitriles in the presence of copper powder, followed by borane reduction of the cyano substituent, lactamization, and reduction of the lactam. This method was applied to establish the synthesis of N-protected 3,3-difluoroisonipecotic acid, a fluorinated gamma-amino, acid. 4-Benzyloxy-3,3-difluoropiperidine was prepared using an analogous methodology and was converted to N-protected 3,3-difluoro-4,4-dihydroxypiperidine, a compound with high potential as a building block in medicinal chemistry.

  DOI：

  10.1021/jo902164z

文献信息

• [EN] 5-HT2B RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DE RÉCEPTEUR DE 5-HT2B
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2012028614A1

  公开（公告）日：2012-03-08

  The present invention relates to novel fluorinated piperidine derivatives having antagonistic activity at the 5-HT2B receptor, pharmaceutical compositions comprising these compounds and their use as a medicine in the treatment or prevention of pulmonary arterial hypertension, pulmonary fibrosis or irritable bowel syndrome.

  本发明涉及新型氟代哌啶衍生物，具有5-HT2B受体拮抗活性，包括这些化合物的制药组合物，以及它们作为药物治疗或预防肺动脉高压、肺纤维化或肠易激综合征的用途。
• 5-HT2B receptor antagonists
  申请人：Janssen Pharmaceutica, NV

  公开号：US08703958B2

  公开（公告）日：2014-04-22

  The present invention relates to novel fluorinated piperidine derivatives having antagonistic activity at the 5-HT2B receptor, pharmaceutical compositions comprising these compounds and their use as a medicine.

  本发明涉及一种新颖的氟代哌啶衍生物，具有5-HT2B受体拮抗活性，其制剂包括这些化合物，并将其用作药物。
• US8703958B2
  申请人：——

  公开号：US8703958B2

  公开（公告）日：2014-04-22
• US9139523B2
  申请人：——

  公开号：US9139523B2

  公开（公告）日：2015-09-22
• Synthesis of 4-Substituted 3,3-Difluoropiperidines
  作者：Riccardo Surmont、Guido Verniest、Jan Willem Thuring、Gregor Macdonald、Frederik Deroose、Norbert De Kimpe

  DOI：10.1021/jo902164z

  日期：2010.2.5

  Synthetic strategies toward 4-substituted 3,3-difluoropiperidines were evaluated. 4-Alkoxymethyl- and 4-aryloxymethyl-3,3-difluoropiperidines were synthesized via 1,4-addition of ethyl bromodifluoroacetate to 3-substituted acrylonitriles in the presence of copper powder, followed by borane reduction of the cyano substituent, lactamization, and reduction of the lactam. This method was applied to establish the synthesis of N-protected 3,3-difluoroisonipecotic acid, a fluorinated gamma-amino, acid. 4-Benzyloxy-3,3-difluoropiperidine was prepared using an analogous methodology and was converted to N-protected 3,3-difluoro-4,4-dihydroxypiperidine, a compound with high potential as a building block in medicinal chemistry.