3-[cyano-(2,4-dichlorophenylazo)-methylene]hexahydropyrrolizine-1,2-dicarboxylic acid dimethyl ester | 1189588-26-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: 3-[cyano-(2,4-dichlorophenylazo)-methylene]hexahydropyrrolizine-1,2-dicarboxylic acid dimethyl ester
• CAS: 1189588-26-8
• 化学式: C₁₉H₁₈Cl₂N₄O₄
• 分子量: 437.282
• InChiKey: OWKOTGYVXFFORK-UHFFFAOYSA-N

反应信息

• 作为产物：
  描述：

  、 马来酸二甲酯 以 苯 为溶剂， 以35%的产率得到3-[cyano-(2,4-dichlorophenylazo)-methylene]hexahydropyrrolizine-1,2-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  3-Alkylsulfanyl-2-arylazo-3-(pyrrolidin-1-yl)-acrylonitriles as masked 1,3-dipoles

  摘要：

  Reaction of 3-alkylsulfanyl-2-arylazo-3-(pyrrolidin-1-yl)acrylonitriles with maleimides, dimethyl maleate and dimethylacetylene dicarboxylate were carried out to give octahydro-pyrrolo[3,4-alpha]pyrrolizin-4-ylidenes, hexahydro-pyrrolizines and 6,7-dihydro-5H-pyrrolizines. The formation of the synthesized compounds is explained by a 1,3-dipolar cycloaddition of an in situ generated azomethine ylide. The mechanisms of the formation of these active intermediates were discussed with the aid of density functional theory methods with the B3LYP functional 6-31G(+) calculations using the STAN method and chemical experiments. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.114