(E)-1-cyano-2-(furan-2'-yl)-1-nitroethene

• 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)-1-cyano-2-(furan-2'-yl)-1-nitroethene
• 英文别名: (E)-2-furyl-1-nitro-1-cyanoethene；(E)-3-(furan-2-yl)-2-nitroprop-2-enenitrile
• 化学式: C₇H₄N₂O₃
• 分子量: 164.12
• InChiKey: ACWCTOVSWXBVHT-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1-cyano-2-(furan-2'-yl)-1-nitroethene 在 叠氮基三甲基硅烷 、 四丁基氟化铵 作用下， 反应 3.0h， 以75%的产率得到5-呋喃-2-基-3H-[1,2,3]三唑-4-甲腈
  参考文献：
  名称：

  Synthesis of 4-Aryl-1H-1,2,3-triazoles through TBAF-Catalyzed [3 + 2] Cycloaddition of 2-Aryl-1-nitroethenes with TMSN₃ under Solvent-Free Conditions

  摘要：

  TBAF-catalyzed [3 + 2] cycloaddition reactions of 2-aryl-1-cyano- or 2-aryl-1-carbethoxy-1-nitroethenes 1 with TMSN3 under SFC allow the corresponding 4-aryl-5-eyano- or 4-aryl-5-carbethoxy-1H-1,2,3-triazoles 2 to be prepared under mild reaction conditions and with good to excellent yields (70-90%). The proposed protocol does not require dried glassware or inert atmosphere.

  DOI：

  10.1021/jo0507845
• 作为产物：
  描述：

  糠醛 、 硝基乙腈 在 iranian dolomite 作用下， 以 水 为溶剂， 反应 0.5h， 以96%的产率得到(E)-1-cyano-2-(furan-2'-yl)-1-nitroethene
  参考文献：
  名称：

  Dolomite (CaMg(CO3)2) as a recyclable natural catalyst in Henry, Knoevenagel, and Michael reactions

  摘要：

  Iranian dolomite (CaMg(CO3)(2)) which consists of double-layered carbonates with Ca2+ and Mg2+ ions was utilized as a heterogeneous base catalyst in the C-C, C-N, and C-S bond forming reactions via the Henry, Knoevenagel, aza-Michael, and thia-Michael transformations under mild conditions in water. Iranian dolomite has been characterized by X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FT-IR), Brunauer Emmett Teller (BET) and XRF chemical analysis, while its basic strength was evaluated by following the Hammett indicators procedure. This water-insoluble natural catalyst demonstrated high activity and was reusable. (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2012.08.027

文献信息

• Dolomite (CaMg(CO3)2) as a recyclable natural catalyst in Henry, Knoevenagel, and Michael reactions
  作者：Fatemeh Tamaddon、Mohammad Tayefi、Elaheh Hosseini、Elham Zare

  DOI：10.1016/j.molcata.2012.08.027

  日期：2013.1

  Iranian dolomite (CaMg(CO3)(2)) which consists of double-layered carbonates with Ca2+ and Mg2+ ions was utilized as a heterogeneous base catalyst in the C-C, C-N, and C-S bond forming reactions via the Henry, Knoevenagel, aza-Michael, and thia-Michael transformations under mild conditions in water. Iranian dolomite has been characterized by X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FT-IR), Brunauer Emmett Teller (BET) and XRF chemical analysis, while its basic strength was evaluated by following the Hammett indicators procedure. This water-insoluble natural catalyst demonstrated high activity and was reusable. (c) 2012 Elsevier B.V. All rights reserved.
• POLYANSKAYA, A. S.;BODINA, R. I.;SHCHADRIN, V. YU.;ABOSKALOVA, N. I., ZH. ORGAN. XIMII, 1984, 20, N 11, 2481-2482
  作者：POLYANSKAYA, A. S.、BODINA, R. I.、SHCHADRIN, V. YU.、ABOSKALOVA, N. I.

  DOI：——

  日期：——
• METCHKOV, T. D.;DEMIREVA, Z. I., J. CHEM. AND ENG. DATA, 1984, 29, N 4, 483-484
  作者：METCHKOV, T. D.、DEMIREVA, Z. I.

  DOI：——

  日期：——
• SOKOLOVA L. N.; POLYANSKAYA A. S.; ABOSKALOVA N. I.; DEMIREVA Z. I.; ABDU+, V SB. 30 GERTSENOVSK. CHTENIYA, XIMIYA,
  作者：SOKOLOVA L. N.、 POLYANSKAYA A. S.、 ABOSKALOVA N. I.、 DEMIREVA Z. I.、 ABDU+

  DOI：——

  日期：——
• Aryl(hetaryl)-containing gem-cyanonitroethenes: Synthesis, structure, and reactions with 2,3-dimethyl-1,3-butadiene
  作者：R. I. Baichurin、N. I. Aboskalova、E. V. Trukhin、V. M. Berestovitskaya

  DOI：10.1134/s1070363215080101

  日期：2015.8

  Methods of aryl(hetaryl)-substituted gem-cyanonitroethenes preparation are summarized, and the products structure elucidation by means of H-1, C-13 NMR, IR, and UV spectroscopy methods is discussed. E-Configuration of the compounds obtained has been proved. Reaction of the studied gem-cyanonitroethenes with 2,3-dimethyl-1,3-butadiene affords the diene synthesis adducts-6-aryl(hetaryl)-3,4-dimethyl-1-nitro-1-cyano- 3-cyclohexenes.