methyl N-trifluoroacetylisonipecotate

• 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: methyl N-trifluoroacetylisonipecotate
• 英文别名: Methyl 1-(2,2,2-trifluoroacetyl)piperidine-4-carboxylate
• 化学式: C₉H₁₂F₃NO₃
• 分子量: 239.194
• InChiKey: XMQKYZLKJIKXOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl N-trifluoroacetylisonipecotate 在 三氟化硼四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 以71%的产率得到[1-(2,2,2-三氟乙基)哌啶-4-基]甲醇
  参考文献：
  名称：

  Design of fluorinated 5-HT4R antagonists: Influence of the basicity and lipophilicity toward the 5-HT4R binding affinities

  摘要：

  Analogues of potent 5-HT4R antagonists possessing a fluorinated N-alkyl chain have been synthesized in order to investigate the effect of the resulting change in basicity and lipophilicity on the affinity and selectivity profile. We demonstrate that for this series, the affinity is decreased with decreased basicity of the piperidine's nitrogen atom. In contrast, the resulting increase in lipophilicity has minimal impact on binding affinity and selectivity. 3,3,3-Trifluoropropyl and 4,4,4-trifluorobutyl derivatives 6d and 6e have shown to bind to the 5-HT4R while maintaining their pharmacological profile and selectivity toward other 5-HT receptors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.08.061
• 作为产物：
  描述：

  4-哌啶甲酸甲酯 、 三氯三氟乙烷 在 四丁基高氯酸铵 、 cobalt(2+);methyl 3-[(1S,2S,3S,5Z,7S,8S,13S,15Z,17R,18R,19R)-2,7,18-tris(2-methoxy-2-oxoethyl)-3,13,17-tris(3-methoxy-3-oxopropyl)-1,2,5,7,12,12,15,17-octamethyl-8,13,18,19-tetrahydro-3H-corrin-24-id-8-yl]propanoate;perchlorate 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以79%的产率得到methyl N-trifluoroacetylisonipecotate
  参考文献：
  名称：

  Electrochemical approach to trifluoroacetamide synthesis from 1,1,1-trichloro-2,2,2-trifluoroethane (CFC-113a) catalyzed by B₁₂ complex

  摘要：

  以 B[式：见正文]络合物为催化剂，采用电化学方法，在室温露天的温和条件下，开发出了生产三氟乙酰胺的一锅合成法。从 1,1,1-三氯-2,2,2-三氟乙烷（CFC-113a）中合成了 30 例三氟乙酰胺，收率从中等到良好。这种便于使用的方法适用于多种三氟乙酰胺的合成。

  DOI：

  10.1142/s1088424621500292

文献信息

• Design of fluorinated 5-HT4R antagonists: Influence of the basicity and lipophilicity toward the 5-HT4R binding affinities
  作者：Clement Q. Fontenelle、Zhong Wang、Christine Fossey、Thomas Cailly、Bruno Linclau、Frederic Fabis

  DOI：10.1016/j.bmc.2013.08.061

  日期：2013.12

  Analogues of potent 5-HT4R antagonists possessing a fluorinated N-alkyl chain have been synthesized in order to investigate the effect of the resulting change in basicity and lipophilicity on the affinity and selectivity profile. We demonstrate that for this series, the affinity is decreased with decreased basicity of the piperidine's nitrogen atom. In contrast, the resulting increase in lipophilicity has minimal impact on binding affinity and selectivity. 3,3,3-Trifluoropropyl and 4,4,4-trifluorobutyl derivatives 6d and 6e have shown to bind to the 5-HT4R while maintaining their pharmacological profile and selectivity toward other 5-HT receptors. (C) 2013 Elsevier Ltd. All rights reserved.
• Electrochemical approach to trifluoroacetamide synthesis from 1,1,1-trichloro-2,2,2-trifluoroethane (CFC-113a) catalyzed by B₁₂ complex
  作者：Mohammad Moniruzzaman、Yoshio Yano、Toshikazu Ono、Yoshio Hisaeda、Hisashi Shimakoshi

  DOI：10.1142/s1088424621500292

  日期：2022.6

  One-pot synthetic approach to produce trifluoroacetamide has been developed using an electrochemical method with the B[Formula: see text] complex as a catalyst under mild conditions, in open air at room temperature. Thirty examples of trifluoroacetamide were synthesized from 1,1,1-trichloro-2,2,2-trifluoroethane (CFC-113a) in moderate to good yields. This user-friendly strategy is compatible with a broad range of trifluoroacetamide syntheses.

  以 B[式：见正文]络合物为催化剂，采用电化学方法，在室温露天的温和条件下，开发出了生产三氟乙酰胺的一锅合成法。从 1,1,1-三氯-2,2,2-三氟乙烷（CFC-113a）中合成了 30 例三氟乙酰胺，收率从中等到良好。这种便于使用的方法适用于多种三氟乙酰胺的合成。