tert-butyl 2-[N-(p-methoxyphenyl)imino]-3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-pentadecafluorononanoate

• 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: tert-butyl 2-[N-(p-methoxyphenyl)imino]-3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-pentadecafluorononanoate
• 英文别名: Tert-butyl 3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-pentadecafluoro-2-(4-methoxyphenyl)iminononanoate
• 化学式: C₂₀H₁₆F₁₅NO₃
• 分子量: 603.328
• InChiKey: DKOGGINLHDBIPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为产物：
  描述：

  2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-N-(4-methoxyphenyl)octanimidoyl chloride 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 地昔帕明 、 potassium carbonate 、 sodium iodide 作用下， 以 丙酮 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 96.0h， 生成 tert-butyl 2-[N-(p-methoxyphenyl)imino]-3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-pentadecafluorononanoate
  参考文献：
  名称：

  Palladium-Catalyzed tert-Butoxycarbonylation of Trifluoroacetimidoyl Iodides

  摘要：

  A modification and details of the palladium-catalyzed tert-butoxycarbonylation of 2,2,2-trifluoroacetimidoyl iodides 1, which gave the iminocarboxylates 2, one of the promising precursors to fluorinated ol-amino acids, are described. The Pd-catalyzed carbonylation reaction was remarkably promoted by the use of DMF or DMI as an additive, enough to achieve the selective formation of tert-butyl iminoesters. Nucleophilic alkylation of the imine moiety of 2 and subsequent removal of N- and O-protecting groups gave a variety of 2-substituted 2-amino-3,3,3-trifluoropropanoic acid derivatives 3 in high yields.

  DOI：

  10.1021/jo991917n

文献信息

• Palladium-Catalyzed <i>tert</i>-Butoxycarbonylation of Trifluoroacetimidoyl Iodides
  作者：Hideki Amii、Yosuke Kishikawa、Katsuhiko Kageyama、Kenji Uneyama

  DOI：10.1021/jo991917n

  日期：2000.6.1

  A modification and details of the palladium-catalyzed tert-butoxycarbonylation of 2,2,2-trifluoroacetimidoyl iodides 1, which gave the iminocarboxylates 2, one of the promising precursors to fluorinated ol-amino acids, are described. The Pd-catalyzed carbonylation reaction was remarkably promoted by the use of DMF or DMI as an additive, enough to achieve the selective formation of tert-butyl iminoesters. Nucleophilic alkylation of the imine moiety of 2 and subsequent removal of N- and O-protecting groups gave a variety of 2-substituted 2-amino-3,3,3-trifluoropropanoic acid derivatives 3 in high yields.