dimethyl rel-(2R,3R,4S,5S)-2,5-dicyano-1-phthalimidopyrrolidine-3,4-dicarboxylate | 1154559-14-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: dimethyl rel-(2R,3R,4S,5S)-2,5-dicyano-1-phthalimidopyrrolidine-3,4-dicarboxylate
• CAS: 1154559-14-4
• 化学式: C₁₈H₁₄N₄O₆
• 分子量: 382.332
• InChiKey: ZDJUZXDNOFBRSR-KPWCQOOUSA-N

物化性质

• 熔点：
  204 °C
• 沸点：
  629.0±65.0 °C(predicted)
• 密度：
  1.52±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为产物：
  描述：

  trans-1-phthalimidoaziridine-2,3-dicarbonitrile 、 马来酸二甲酯 以 氯苯 为溶剂， 反应 3.0h， 以77%的产率得到dimethyl rel-(2R,3R,4S,5S)-2,5-dicyano-1-phthalimidopyrrolidine-3,4-dicarboxylate
  参考文献：
  名称：

  Thermolysis of 1-phthalimidoaziridine-2-carbonitriles in the presence of dipolarophiles

  摘要：

  Thermolysis of trans-3-phenyl-1-phthalimidoaziridine-2-carbonitrile and trans-1-phthalimidoaziridine-2,3-dicarbonitrile in the presence of several dipolarophiles involves 1,3-dipolar cycloaddition to intermediate azomethine ylides and leads to 1-phthalimidopyrrolidine derivatives with good yields and high stereoselectivity. Thermally induced opening of the three-membered ring in trans-2,3-disubstituted 1-phthalimidoaziridines occurs in conrotatory mode to produce the corresponding cis-azomethine ylides in keeping with the orbital symmetry conservation rules. The relative configuration of substituents in the dipolarophiles is retained, which implies concerted mechanism of the addition.

  DOI：

  10.1134/s1070428008120105