2-[1-Methyl-pyrrolidin-(2E)-ylidene]-propionic acid ethyl ester | 90407-55-9

• 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: 2-[1-Methyl-pyrrolidin-(2E)-ylidene]-propionic acid ethyl ester
• 英文别名: Ethyl 2-(1-methylpyrrolidin-2-ylidene)propanoate；ethyl 2-(1-methylpyrrolidin-2-ylidene)propanoate
• CAS: 90407-55-9
• 化学式: C₁₀H₁₇NO₂
• 分子量: 183.25
• InChiKey: CIGWHRWSGPMGCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  O-methyl-N-methylpyrrolidonium methylsulfate 在 sodium methylate 、 锌 作用下， 生成 2-[1-Methyl-pyrrolidin-(2E)-ylidene]-propionic acid ethyl ester
  参考文献：
  名称：

  Lactam acetals : Part XXIV reaction with activated haloalkyl compounds with and without zinc

  摘要：

  Reaction of 2-alkoxyimmonium methosulfates (2), and of lactam acetals (3) derived therefrom, with alpha-haloesters in presence of zinc (Reformatsky condition) yielded N-alkyl-2-(alpha-alkyl-alpha-alkoxy-carbonyl)methylene-1-azacycloalkanes (6), while reaction of 3 with alpha-haloesters without zinc gave 3-alkoxycarbonylmethyl-1-azacycloalkane-2-one (5). Similar reaction of; 2 and 3 with 4-bromomethylquinolin-2-one (4) in presence of zinc gave N-alkyl-2-[4-(2-oxoquinolyl)methylene]-1-azacycloalkanes (7), a key intermediate for the synthesis of antimalarial quinoline-4-methanols.

  DOI：

  10.1016/s0040-4039(00)76669-x

文献信息

• Celerier, Jean-Pierre; Deloisy-Marchalant, Elisabeth; Lhommet, Gerard, Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 1633 - 1635
  作者：Celerier, Jean-Pierre、Deloisy-Marchalant, Elisabeth、Lhommet, Gerard

  DOI：——

  日期：——
• Lactam acetals : Part XXIV reaction with activated haloalkyl compounds with and without zinc
  作者：Sanjay Jain、Rahul Jain、Jujhar Singh、Nitya Anand

  DOI：10.1016/s0040-4039(00)76669-x

  日期：1994.5

  Reaction of 2-alkoxyimmonium methosulfates (2), and of lactam acetals (3) derived therefrom, with alpha-haloesters in presence of zinc (Reformatsky condition) yielded N-alkyl-2-(alpha-alkyl-alpha-alkoxy-carbonyl)methylene-1-azacycloalkanes (6), while reaction of 3 with alpha-haloesters without zinc gave 3-alkoxycarbonylmethyl-1-azacycloalkane-2-one (5). Similar reaction of; 2 and 3 with 4-bromomethylquinolin-2-one (4) in presence of zinc gave N-alkyl-2-[4-(2-oxoquinolyl)methylene]-1-azacycloalkanes (7), a key intermediate for the synthesis of antimalarial quinoline-4-methanols.