(E)-2-(4-methylphenyl)-1-cyano-1-nitroethene

• 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: (E)-2-(4-methylphenyl)-1-cyano-1-nitroethene
• 英文别名: (E)-3-(4-methylphenyl)-2-nitroprop-2-enenitrile
• 化学式: C₁₀H₈N₂O₂
• 分子量: 188.186
• InChiKey: NNMNWFIHNFHLIG-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  亚甲基环戊烷 、 (E)-2-(4-methylphenyl)-1-cyano-1-nitroethene 以 氯仿 为溶剂， 生成 8-cyano-9-(4-methylphenyl)-6-oxa-7-aza-spiro-[4.5]dec-7-ene 7-oxide
  参考文献：
  名称：

  氰基官能化共轭硝基烯烃参与的非催化杂狄尔斯-阿尔德反应完全选择性合成螺环-1,2-恶嗪氮氧化物

  摘要：

  根据实验和量子化学数据评估了 E-2-芳基-1-氰基-1-硝基乙烯和亚甲基环戊烷参与的杂狄尔斯-阿尔德 (HDA) 反应。研究发现，与大多数已知的 HDA 反应相反，标题过程是在非催化条件下和完全区域控制下实现的。 DFT 研究毫无疑问地表明了极性但单步反应机制。使用键合演化理论 (BET) 技术进行更深入的探索，可以清晰地了解沿反应坐标的电子密度重组序列。第一个 C4-C5 键是在第 VII 阶段通过合并两个单突触盆地创建的，而第二个 O1-C6 键是在最后阶段通过将 O1 的非键电子密度捐赠给 C6 创建的。根据研究，我们可以得出结论，所分析的反应按照两阶段一步机理进行。

  DOI：

  10.3390/molecules28124586
• 作为产物：
  描述：

  硝基乙腈 、 对甲基苯甲醛 在 ammonium chloride 作用下， 以 水 为溶剂， 反应 0.03h， 以87%的产率得到(E)-2-(4-methylphenyl)-1-cyano-1-nitroethene
  参考文献：
  名称：

  Effect of Microwave Irradiation on Reaction of Arylaldehyde Derivatives with Some Active Methylene Compounds in Aqueous Media

  摘要：

  The effect of microwave irradiation on the condensation reactions of arylaldehydes 1 and active methylene compounds 2 in aqueous media was studied and compared with "classical" conditions. The results show that the condensation was carried out only under microwave irradiation in the presence of ammonium chloride as a catalyst, followed by dehydration, to afford (E)-olefins 3. The protocol was used to synthesize coumarins by a condensation reaction of salicylaldehyde or its derivatives with various derivatives of ethylacetate 5 (e.g., (RCH2CO2Et)-C-3; R-3: CO2Et, CO2Me, COMe, CN) in high yields. These investigations will contribute to the development of environmentally friendly and inexpensive processes in organic synthesis.

  DOI：

  10.1081/scc-200050942

文献信息

• Kinetics of the [4+2] cycloaddition of cyclopentadiene with (E)-2-aryl-1-cyano-1-nitroethenes
  作者：Radomir Jasiński、Magdalena Kwiatkowska、Andrzej Barański

  DOI：10.1007/s00706-012-0735-3

  日期：2012.6

  AbstractThe electrophilicity of (E)-2-aryl-1-cyano-1-nitroethenes is not sufficient to induce a zwitterionic course of their [4+2] cycloaddition to cyclopentadiene. The one-step mechanism of these reactions is indicated by the activation parameters, and the substituent and solvent effects on the reaction. Graphical Abstract

  摘要（E）-2-芳基-1-氰基-1-硝基乙烯的亲电子性不足以诱导其[4 + 2]环加成到环戊二烯上的两性离子过程。这些反应的一步机制由活化参数以及取代基和溶剂对反应的影响指示。 图形概要
• A unique example of noncatalyzed [3+2] cycloaddition involving (2E)-3-aryl-2-nitroprop-2-enenitriles
  作者：Magdalena Żmigrodzka、Ewa Dresler、Zofia Hordyjewicz-Baran、Renata Kulesza、Radomir Jasiński

  DOI：10.1007/s10593-017-2186-6

  日期：2017.10

  N-Methylazomethine ylide reacts in boiling benzene with (2E)-3-aryl-2-nitroprop-2-enenitriles via [3+2] cycloaddition scheme. This is an evidently rare case of [3+2] cycloaddition of this group of conjugated nitroalkenes.

  通过[3 + 2]环加成方案，N-甲基偶氮甲亚胺叶立德在沸腾的苯中与（2 E）-3-芳基-2-硝基丙-2-烯腈反应。这是这组共轭硝基烯烃的[3 + 2]环加成反应的罕见情况。
• Effect of Microwave Irradiation on Reaction of Arylaldehyde Derivatives with Some Active Methylene Compounds in Aqueous Media
  作者：Hassan Valizadeh、Manouchehr Mamaghani、Abed Badrian

  DOI：10.1081/scc-200050942

  日期：2005.3

  The effect of microwave irradiation on the condensation reactions of arylaldehydes 1 and active methylene compounds 2 in aqueous media was studied and compared with "classical" conditions. The results show that the condensation was carried out only under microwave irradiation in the presence of ammonium chloride as a catalyst, followed by dehydration, to afford (E)-olefins 3. The protocol was used to synthesize coumarins by a condensation reaction of salicylaldehyde or its derivatives with various derivatives of ethylacetate 5 (e.g., (RCH2CO2Et)-C-3; R-3: CO2Et, CO2Me, COMe, CN) in high yields. These investigations will contribute to the development of environmentally friendly and inexpensive processes in organic synthesis.
• Novel synthesis scheme and <i>in vitro</i> antimicrobial evaluation of a panel of (E)-2-aryl-1-cyano-1-nitroethenes
  作者：Anna Boguszewska-Czubara、Agnieszka Lapczuk-Krygier、Konrad Rykala、Anna Biernasiuk、Artur Wnorowski、Lukasz Popiolek、Agata Maziarka、Anna Hordyjewska、Radomir Jasiński

  DOI：10.3109/14756366.2015.1070264

  日期：2016.11.1

  Drug resistance has become a major concern in the field of infection management, therefore searching for new antibacterial agents is getting more challenging. Our study presents an optimized and eco-friendly synthesis scheme for a panel of nitroalkenes bearing various functional groups in the aromatic moiety and bromine or cyano substituents in 1 position of nitrovinyl moiety. The presence of nitrolefine group outside the ring minimalizes genotoxic properties while conjugation of aryl group with nitrovinyl moiety increases stability of the compounds. Then our research focused on evaluation of biological properties of such obtained (E)-2-aryl-1-cyano-1-nitroethenes. As they exhibit strong bacteriostatic and bactericidal activities against reference bacteria and yeast species with no detectable cytotoxicity towards cultured human HepG2 and HaCaT cells, they could be promising candidates for the replacement of traditional nitrofurane-containing antibacterial drugs. Nevertheless, validation of the obtained data in an in vivo model and additional safety studies on mutagenicity are still required.
• Fully Selective Synthesis of Spirocyclic-1,2-oxazine N-Oxides via Non-Catalysed Hetero Diels-Alder Reactions with the Participation of Cyanofunctionalysed Conjugated Nitroalkenes
  作者：Przemysław Woliński、Agnieszka Kącka-Zych、Aneta Wróblewska、Ewelina Wielgus、Rafał Dolot、Radomir Jasiński

  DOI：10.3390/molecules28124586

  日期：——

  Hetero Diels-Alder (HDA) reactions with the participation of E-2-aryl-1-cyano-1-nitroethenes and methylenecyclopentane were evaluated on the basis of experimental as well as quantumchemical data. It was found that contrary to most known HDA reactions, title processes are realised under non-catalytic conditions and with full regiocontrol. The DFT study shows, without any doubt, the polar but single-step

  根据实验和量子化学数据评估了 E-2-芳基-1-氰基-1-硝基乙烯和亚甲基环戊烷参与的杂狄尔斯-阿尔德 (HDA) 反应。研究发现，与大多数已知的 HDA 反应相反，标题过程是在非催化条件下和完全区域控制下实现的。 DFT 研究毫无疑问地表明了极性但单步反应机制。使用键合演化理论 (BET) 技术进行更深入的探索，可以清晰地了解沿反应坐标的电子密度重组序列。第一个 C4-C5 键是在第 VII 阶段通过合并两个单突触盆地创建的，而第二个 O1-C6 键是在最后阶段通过将 O1 的非键电子密度捐赠给 C6 创建的。根据研究，我们可以得出结论，所分析的反应按照两阶段一步机理进行。