(E)-N-benzyl-4-oxopent-2-enamide | 169170-51-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-N-benzyl-4-oxopent-2-enamide
• 英文别名: (2E)-4-Oxo-N-(phenylmethyl)-2-pentenamide
• CAS: 169170-51-8
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: GSCRWULYWINNGH-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-N-benzyl-4-oxopent-2-enamide 以 甲醇 为溶剂， 以100%的产率得到1-benzyl-5-hydroxy-5-methyl-1H-pyrrol-2(5H)-one
  参考文献：
  名称：

  Preparation of N-alkyl pyrrolidinones via photocyclization of γ-keto-α,β-unsaturated amides

  摘要：

  Photolysis of gamma-keto-alpha,beta-unsaturated amides provides N-alkyl pyrrolidinones in high yield (77-100%). The procedure is applicable to a variety of amides derived from the corresponding gamma-keto acid.

  DOI：

  10.1016/0040-4039(95)00779-c
• 作为产物：
  描述：

  (E)-4-氧代-2-烯酸 、 苄胺 在 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 为溶剂， 以27%的产率得到(E)-N-benzyl-4-oxopent-2-enamide
  参考文献：
  名称：

  Highly Selective Rhodium-Catalyzed Conjugate Addition Reactions of 4-Oxobutenamides

  摘要：

  [GRAPHICS]A variety of 4-oxobutenamides 1 were subjected to rhodium-catalyzed conjugate addition with arylboronic acids providing high regio- and enantioselectivity (97:3 to > 99:1, > 96% ee) and moderate to excellent yields (54-99%). The key to high selectivity is the use of sterically demanding P-chiral diphosphines, such as Tangphos or Duanphos. The product oxobutanamides 2 may be converted to alternate targets by selective derivatization of either the amide or ketone functional group. A stereochemical model predicting the absolute sense of induction was developed based on single-crystal X-ray structures of product and precatalyst.

  DOI：

  10.1021/jo701682c