(E)-3-(furan-2-yl)-2-nitroacrylaldehyde | 1019636-32-8

• 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)-3-(furan-2-yl)-2-nitroacrylaldehyde
• 英文别名: 3-(furan-2-yl)-2-nitroacrylaldehyde；(E)-3-(furan-2-yl)-2-nitroprop-2-enal
• CAS: 1019636-32-8
• 化学式: C₇H₅NO₄
• 分子量: 167.121
• InChiKey: VALXWELVPDCSSA-GQCTYLIASA-N

物化性质

• 熔点：
  86 °C(Solvent: Diethyl ether)
• 沸点：
  298.9±30.0 °C(Predicted)
• 密度：
  1.357±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 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：
  76
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (E)-3-(furan-2-yl)-2-nitroprop-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)-3-(furan-2-yl)-2-nitroacrylaldehyde 、 (E)-3-(furan-2-yl)-2-nitroacrylaldehyde
  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

文献信息

• Chemoenzymatic Synthesis of Advanced Intermediates for Formal Total Syntheses of Tetrodotoxin
  作者：Daler Baidilov、Lukas Rycek、John F. Trant、Jordan Froese、Brennan Murphy、Tomas Hudlicky

  DOI：10.1002/anie.201804602

  日期：2018.8.20

  Advanced intermediates for the syntheses of tetrodotoxin reported by the groups of Fukuyama, Alonso, and Sato were prepared. Key steps include the toluene dioxygenase mediated dihydroxylation of either iodobenzene or benzyl acetate. The resulting diene diols were transformed into Fukuyama's intermediate in six steps, into Alonso's intermediate in nine steps, and into Sato's intermediate in ten steps

  制备了由福山，阿隆索和佐藤小组报告的河豚毒素合成的高级中间体。关键步骤包括碘代苯或乙酸苄酯的甲苯双加氧酶介导的二羟基化。所得的二烯二醇经六步转化为福山中间体，经九步转化为阿隆索的中间体，并经十步转化为佐藤的中间体。
• A Cascade Annulation Based Convergent Approach to Racemic Tetrodotoxin
  作者：Fernando Cagide-Fagín、Ricardo Alonso

  DOI：10.1002/ejoc.201001159

  日期：2010.12

  synthetic power of the recently developed cascade annulations of β-(hetero)aryl-α-nitro-α,β-enals with the pyrrolidine-derived enamine of 2,2-dimethyl-1,3-dioxan-5-one is demonstrated by the first convergent route to (±)-tetrodotoxin.

  证明了最近开发的 β-（杂）芳基-α-硝基-α,β-烯醛与吡咯烷衍生的 2,2-二甲基-1,3-二恶烷-5-one 烯胺的级联环化的合成能力通过第一个趋同途径（±）-河豚毒素。
• SYNTHESIS OF POLYOXYGENATED NITROGEN SYSTEMS, COMPRISING REACTIONS BETWEEN ENAMINES OF 1,3-DIOXAN-5-ONES AND NITROOLEFINS
  申请人：UNIVERSIDADE DE SANTIAGO DE COMPOSTELA

  公开号：EP1783123B1

  公开（公告）日：2010-03-17
• SITKIN A. I.; KLIMENKO V. I.; FRIDMAN A. L., ZH. ORGAN. XIMII <ZORK-AE>, 1975, 11, HO 11, 2452-2453
  作者：SITKIN A. I.、 KLIMENKO V. I.、 FRIDMAN A. L.

  DOI：——

  日期：——
• Synthesis, Structure, and <i>E</i>−<i>Z</i> Isomerization of β-(Hetero)aryl-α-nitro-α,β-enals
  作者：Patricia Martínez-Bescos、Fernando Cagide-Fagín、Luis F. Roa、Juan Carlos Ortiz-Lara、Krzysztof Kierus、Lidia Ozores-Viturro、Marta Fernández-González、Ricardo Alonso

  DOI：10.1021/jo702731b

  日期：2008.5.1

  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.