1-N-methyl-3-(5'-methyl-2'-nitrophenyl)piperidin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-N-methyl-3-(5'-methyl-2'-nitrophenyl)piperidin-2-one
• 英文别名: 1-Methyl-3-(5-methyl-2-nitrophenyl)piperidin-2-one
• 化学式: C₁₃H₁₆N₂O₃
• 分子量: 248.282
• InChiKey: BEFLEWFEVKETSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-硝基甲苯 、 1-methyl-3-trimethylsilanyl-piperidin-2-one 在 三(二甲氨基)锍二氟三甲基硅酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 15.0h， 以53%的产率得到1-N-methyl-3-(5'-methyl-2'-nitrophenyl)piperidin-2-one
  参考文献：
  名称：

  Application of Vicarious Nucleophilic Substitution to the Total Synthesis of dl-Physostigmine

  摘要：

  A concise, highly efficient formal total synthesis of dl-physostigmine is described, using a relatively simple method that should be adaptable to the synthesis of homologous members of this type of alkaloid. The key step in the synthesis is a new vicarious nucleophilic substitution reaction between p-nitroanisole and a C-silylated derivative of N-methylpyrrolidinone. Subsequent conversion of the initial adduct to the tricyclic framework of physostigmine follows a well-established protocol and provides the key intermediate 8 in high yield. The vicarious nucleophilic substitution reaction has also been extended to six-membered lactams, with encouraging results.

  DOI：

  10.1021/jo026438u

文献信息

• Application of Vicarious Nucleophilic Substitution to the Total Synthesis of <i>dl</i>-Physostigmine
  作者：Pankaj D. Rege、Francis Johnson

  DOI：10.1021/jo026438u

  日期：2003.8.1

  A concise, highly efficient formal total synthesis of dl-physostigmine is described, using a relatively simple method that should be adaptable to the synthesis of homologous members of this type of alkaloid. The key step in the synthesis is a new vicarious nucleophilic substitution reaction between p-nitroanisole and a C-silylated derivative of N-methylpyrrolidinone. Subsequent conversion of the initial adduct to the tricyclic framework of physostigmine follows a well-established protocol and provides the key intermediate 8 in high yield. The vicarious nucleophilic substitution reaction has also been extended to six-membered lactams, with encouraging results.