2-[(E)-3-(4-Nitro-phenyl)-allylidene]-malononitrile | 73077-88-0

• 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-[(E)-3-(4-Nitro-phenyl)-allylidene]-malononitrile
• 英文别名: 2-[3-(4-Nitrophenyl)prop-2-enylidene]propanedinitrile
• CAS: 73077-88-0
• 化学式: C₁₂H₇N₃O₂
• 分子量: 225.206
• InChiKey: UKQFDVVUFPXOGV-UHFFFAOYSA-N

物化性质

• 熔点：
  184 °C
• 沸点：
  413.5±40.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  93.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(E)-3-(4-Nitro-phenyl)-allylidene]-malononitrile 在 氢气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、200.0 kPa 条件下， 生成 2-(3-(4-aminophenyl)allylidene)malononitrile
  参考文献：
  名称：

  Core–Shell Palladium Nanoparticle@Metal–Organic Frameworks as Multifunctional Catalysts for Cascade Reactions

  摘要：

  Uniform core-shell Pd@IRMOF-3 nanostructures, where single Pd nanoparticle core is surrounded by amino-functionalized IRMOF-3 shell, are prepared by a facile mixed solvothermal method. When used as multifunctional catalysts, the Pd@IRMOF-3 nanocomposites exhibit high activity, enhanced selectivity, and excellent stability in the cascade reaction. Both experimental evidence and theoretical calculations reveal that the high catalytic performance of Pd@IRMOF-3 nanocomposites originates from their unique core-shell structures.

  DOI：

  10.1021/ja411468e
• 作为产物：
  描述：

  4-硝基肉桂醛 、 丙二腈 在 哌啶 作用下， 生成 2-[(E)-3-(4-Nitro-phenyl)-allylidene]-malononitrile
  参考文献：
  名称：

  四烷氧基乙烯的化学。第七部分 1-氰基丁二烯的热[2 + 2]环加成

  摘要：

  在C-1处具有第二个吸电子取代基的无环1-氰基丁二烯（2）像同等取代的简单烯烃一样对四烷氧基乙烯（1）起作用。正常乘积是[2 + 2]，而不是[4 + 2]环加成产物。这些贫电子的烯烃和丁二烯对亲核四烷氧基乙烯的反应性的对应性进一步通过取代基对环加成的相似作用来例证。给出了可能的解释。

  DOI：

  10.1039/p19760001538

文献信息

• ‘On water’ organocatalyzed enantioselective synthesis of highly functionalized cyclohexanones with an all-carbon quaternary centre from allylidene malononitriles and enones
  作者：Ganga B. Vamisetti、Raghunath Chowdhury、Mukesh Kumar、Sunil K. Ghosh

  DOI：10.1016/j.tetasy.2016.12.012

  日期：2017.2

  An organocatalyzed endo [4+2] cycloaddition between enones as pro-diene and allylidene malononitrile as dienophile leading to cyclohexanones with two 1,3-related stereogenic centres and an all-carbon quaternary centre has been developed. The reactions were performed under 'green reaction' conditions using water as the reaction medium and ambient conditions. When allylidene cyanoacetate was used as the dienophile, cyclohexanones with three contiguous stereogenic centres, one of which is an all-carbon quaternary centre, were formed. The products were obtained in high yield and with acceptable diastereo-and enantioselectivity. (C) 2016 Elsevier Ltd. All rights reserved.