2-(4-Nitro-phenyl)-cyclopent-4-en-1,3-dion | 1140-89-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-Nitro-phenyl)-cyclopent-4-en-1,3-dion
• CAS: 1140-89-2
• 化学式: C₁₁H₇NO₄
• 分子量: 217.181
• InChiKey: DGNXHDKTJHGUFD-UHFFFAOYSA-N

物化性质

• 沸点：
  427.0±45.0 °C(predicted)
• 密度：
  1.437±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  2-(4-Nitro-phenyl)-cyclopent-4-en-1,3-dion 、 (1Z)-1-[(2,6-dichlorophenyl)methylidene]-5,5-dimethyl-3-oxopyrazolidin-1-ium-2-ide 反应 40.0h， 以33%的产率得到rac-(3aR,9S,9aS)-9-(2,6-dichlorophenyl)-7,7-dimethyl-2-(4-nitrophenyl)tetrahydro-5H-pyrazolo-[1,2-a]pyrrolo[3,4-c]pyrazole-1,3,5(2H,3aH)-trione
  参考文献：
  名称：

  Steric hindrances to the cycloaddition of (Z)-1-arylmethylidene-5,5-dimethyl-3-oxopyrazolidin-1-ium-2-ides to N-arylmaleimides

  摘要：

  Sterically hindered cycloaddition of (Z)-1-arylmethylidene-5,5-dimethyl-3-oxopyrazolidin-1-ium-2-ides to 4-mono- and 2,6-disubstituted N-arylmaleimides requires prolonged heating (40-60 h) at similar to 150-155A degrees C and yields mixtures of diastereoisomeric cycloadducts. The observed diastereoselectivity is determined by both electronic and steric interactions, depending on the nature and position of substituents in the azomethine imine and maleimide. The reactions of (Z)-1-(2,6-dichlorobenzylidene)-5,5-dimethyl-3-oxopyrazolidin-1-ium-2-ide with 4-substituted N-arylmaleimides give mainly the corresponding cis adducts as a result of preferential exo attack by the dipolarophile, whereas trans adducts predominate in the cycloaddition of (Z)-1-(4-X-benzylidene)-5,5-dimethyl-3-oxopyrazolidin-1-ium-2-ide and (Z)-1-(2,6-dichlorobenzylidene)-5,5-dimethyl-3-oxopyrazolidin- 1-ium-2-ide to 2,6-disubstituted N-arylmaleimides.

  DOI：

  10.1134/s1070428015070143