(R)-3-Acetyl-1,3-dimethyl-4-methylene-pyrrolidin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (R)-3-Acetyl-1,3-dimethyl-4-methylene-pyrrolidin-2-one
• 英文别名: (3R)-3-acetyl-1,3-dimethyl-4-methylidenepyrrolidin-2-one
• 化学式: C₉H₁₃NO₂
• 分子量: 167.208
• InChiKey: RDMSDUFKURBWMB-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-methyl-N-propargyl-2-methyl-3-oxobutanamide 在 manganese triacetate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以40%的产率得到(R)-3-Acetyl-1,3-dimethyl-4-methylene-pyrrolidin-2-one
  参考文献：
  名称：

  Metallic Salt Promoted Radical Cyclization of β-Keto Carboxamides and Their Corresponding β-Enamino Carboxamides

  摘要：

  Substituted lactams and spirolactams were obtained by Mn(III)-induced radical cyclization of unsaturated beta -keto carboxamides. Treatment of the corresponding tertiary enamines under similar reaction conditions and in the presence of K2CO3 afforded the same cyclized products but with inversion of diastereoselectivity. The oxidation of optically pure secondary enamines leads to diastereomeric spirolactams in an approximately 3:1 ratio.

  DOI：

  10.1021/jo000084u

文献信息

• Metallic Salt Promoted Radical Cyclization of β-Keto Carboxamides and Their Corresponding β-Enamino Carboxamides
  作者：Janine Cossy、Abderrahim Bouzide、Catherine Leblanc

  DOI：10.1021/jo000084u

  日期：2000.11.1

  Substituted lactams and spirolactams were obtained by Mn(III)-induced radical cyclization of unsaturated beta -keto carboxamides. Treatment of the corresponding tertiary enamines under similar reaction conditions and in the presence of K2CO3 afforded the same cyclized products but with inversion of diastereoselectivity. The oxidation of optically pure secondary enamines leads to diastereomeric spirolactams in an approximately 3:1 ratio.