Diethyl α-methyl-N-methyl-2-pyrrolemalonate | 144194-94-5

• 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: Diethyl α-methyl-N-methyl-2-pyrrolemalonate
• 英文别名: Diethyl 2-methyl-2-(1-methylpyrrol-2-yl)propanedioate
• CAS: 144194-94-5
• 化学式: C₁₃H₁₉NO₄
• 分子量: 253.298
• InChiKey: UDCJRZFYTWVHSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  57.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-甲基吡咯 、 diethyl 2-iodo-2-methylmalonate 在 双氧水 、 iron(II) sulfate 、 二甲基亚砜 作用下， 以89%的产率得到Diethyl α-methyl-N-methyl-2-pyrrolemalonate
  参考文献：
  名称：

  Homolytic substitution reactions of electron-rich pentatomic heteroaromatics by electrophilic carbon-centered radicals. Synthesis of .alpha.-heteroarylacetic acids

  摘要：

  Efficient and selective homolytic substitutions (yields between 55 and 90%) of pyrrole, indole, and some pyrrole derivatives have been carried out using ambiphilic and electrophilic carbon centered radicals, generated in DMSO by Fe2+/H2O2 and alpha-cyano-, alpha-carbonyl-, and alpha,alpha'-dicarbonylalkyl iodides. The reaction is highly successful also with pyrroles substituted by electron-withdrawing groups, which has allowed an efficient synthesis of Tolmetin. A few extensions of this reaction to furan and thiophene are described.

  DOI：

  10.1021/jo00051a027

文献信息

• Homolytic substitution reactions of electron-rich pentatomic heteroaromatics by electrophilic carbon-centered radicals. Synthesis of .alpha.-heteroarylacetic acids
  作者：Enrico Baciocchi、Ester Muraglia、Giancarlo Sleiter

  DOI：10.1021/jo00051a027

  日期：1992.12

  Efficient and selective homolytic substitutions (yields between 55 and 90%) of pyrrole, indole, and some pyrrole derivatives have been carried out using ambiphilic and electrophilic carbon centered radicals, generated in DMSO by Fe2+/H2O2 and alpha-cyano-, alpha-carbonyl-, and alpha,alpha'-dicarbonylalkyl iodides. The reaction is highly successful also with pyrroles substituted by electron-withdrawing groups, which has allowed an efficient synthesis of Tolmetin. A few extensions of this reaction to furan and thiophene are described.