(E)-2-nitro-3-(thiophen-2-yl)acrylaldehyde | 1019636-34-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (E)-2-nitro-3-(thiophen-2-yl)acrylaldehyde
• 英文别名: (E)-2-nitro-3-thiophen-2-ylprop-2-enal
• CAS: 1019636-34-0
• 化学式: C₇H₅NO₃S
• 分子量: 183.188
• InChiKey: KNFXRBPEOPSGGY-GQCTYLIASA-N

反应信息

• 作为产物：
  描述：

  (E)-2-nitro-3-(thiophen-2-yl)prop-2-en-1-ol 在 2-碘酰基苯甲酸 作用下， 以 乙酸乙酯 为溶剂， 生成 (Z)-2-nitro-3-(thiophen-2-yl)acrylaldehyde 、 (E)-2-nitro-3-(thiophen-2-yl)acrylaldehyde
  参考文献：
  名称：

  Synthesis, Structure, and E−Z Isomerization of β-(Hetero)aryl-α-nitro-α,β-enals

  摘要：

  The first general methodology for the gram-scale preparation of previously overlooked beta-(hetero)aryl-alpha-nitro-alpha,beta-enals (3) is reported. Condensation of (hetero) aromatic aldehydes with 2-nitroethanol gave the E-isomers of uncommon beta-(hetero)aryl-alpha-hydroxymethyl-alpha,beta-unsatured-nitroalkenes (2), as determined by NOE and X-ray studies. alpha-Nitro-alpha,beta-enals 3 were subsequently obtained by hypervalent iodine oxidation of 2 as E-Z-mixtures in solid form. They showed varied stability and solvent-dependent thermal-promoted and photopromoted E-Z interconversion. Starting with furfural, experimental conditions were developed to prepare the corresponding nitroenal 3a enriched in either the E or the Z isomer: E-3a/Z-3a approximate to 90/10 and 20/80, respectively. In contrast with other structurally related compounds, nitroenals 3 have their (hetero)aryl-vinyl unit and their formyl and nitro groups all in a planar arrangement, both in solid form and in solution; accordingly, they are colored compounds with predicted high dipole moments. As deduced from solution-NMR and X-ray data, the C=C and the C=O double bonds in 3 are exclusively s-cis-oriented; this disposition corresponds in fact to the DFT-computed most stable conformer.

  DOI：

  10.1021/jo702731b