2-(Acetylamino)-N-methoxy-4-pentenamide | 138566-08-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(Acetylamino)-N-methoxy-4-pentenamide
• 英文别名: 2-acetamido-N-methoxypent-4-enamide
• CAS: 138566-08-2
• 化学式: C₈H₁₄N₂O₃
• mdl: MFCD24390988
• 分子量: 186.211
• InChiKey: MZXMNMYBAPQULW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙酸酐 、 2-((Allyloxycarbonyl)amino)-N-methoxy-4-pentenamide 在 四(三苯基膦)钯 三正丁基氢锡 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以58%的产率得到2-(Acetylamino)-N-methoxy-4-pentenamide
  参考文献：
  名称：

  Palladium-Catalyzed Transprotection of Allyloxycarbonyl-Protected Amines: Efficient One-Pot Formation of Amides and Dipeptides

  摘要：

  The synthetic utility of the N-(allyloxycarbonyl) (Alloc) substituent in alpha-amino acid derivatives is substantially extended beyond its well-known function as an amine protecting group. When the palladium-catalyzed deprotection is carried out by using tributyltin hydride as nucleophile (the Guibe method) in the presence of an active acylating agent a new acyl group is introduced on nitrogen. Successful acylating agents include carboxylic acid anhydrides, acid chlorides, and activated esters. A useful example of this methodology is the removal of the Alloc group in the presence of tert-butyl dicarbonate, which in essence amounts to a ''transprotection'' to a Boc-protected alpha-amino acid derivative. More importantly, the use of activated N-protected alpha-amino ester derivatives (e.g., pentafluorophenyl esters) leads to dipeptides. This new method for peptide coupling proceeds very fast under mild conditions, in good to excellent yields, and without noticeable racemization.

  DOI：

  10.1021/jo00111a035

文献信息

• Palladium-catalyzed synthesis of amides and peptides
  作者：Eric C. Roos、Pablo Bernabé、Henk Hiemstra、W.Nico Speckamp、Bernard Kaptein、Wilhelmus H.J. Boesten

  DOI：10.1016/0040-4039(91)80241-w

  日期：1991.11

  When the Pd(0)-catalyzed hydrostannolysis of the N-allyloxycarbonyl group is carried out in the presence of an activated carbonyl compound, a coupling product is formed. This new method appears to be applicable to the synthesis of a wide range of amides and peptides.
• Palladium-Catalyzed Transprotection of Allyloxycarbonyl-Protected Amines: Efficient One-Pot Formation of Amides and Dipeptides
  作者：Eric C. Roos、Pablo Bernabe、Henk Hiemstra、W. Nico Speckamp、Bernard Kaptein、Wilhelmus H. J. Boesten

  DOI：10.1021/jo00111a035

  日期：1995.3

  The synthetic utility of the N-(allyloxycarbonyl) (Alloc) substituent in alpha-amino acid derivatives is substantially extended beyond its well-known function as an amine protecting group. When the palladium-catalyzed deprotection is carried out by using tributyltin hydride as nucleophile (the Guibe method) in the presence of an active acylating agent a new acyl group is introduced on nitrogen. Successful acylating agents include carboxylic acid anhydrides, acid chlorides, and activated esters. A useful example of this methodology is the removal of the Alloc group in the presence of tert-butyl dicarbonate, which in essence amounts to a ''transprotection'' to a Boc-protected alpha-amino acid derivative. More importantly, the use of activated N-protected alpha-amino ester derivatives (e.g., pentafluorophenyl esters) leads to dipeptides. This new method for peptide coupling proceeds very fast under mild conditions, in good to excellent yields, and without noticeable racemization.