(E)-1-cyano-2-(4'-chlorophenyl)-1-nitroethene | 98207-42-2

• 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)-1-cyano-2-(4'-chlorophenyl)-1-nitroethene
• 英文别名: (E)-2-(4-chlorophenyl)-1-nitro-1-cyanoethene；4-chloro-α-nitro-cis-cinnamonitrile；4-Chlor-α-nitro-cis-cinnamonitril；E-4-Chlor-α-nitrocinnamonitril；(E)-3-(4-chlorophenyl)-2-nitroprop-2-enenitrile
• CAS: 98207-42-2；37630-65-2
• 化学式: C₉H₅ClN₂O₂
• 分子量: 208.604
• InChiKey: CATPLYDHBHXHSE-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  (E)-1-cyano-2-(4'-chlorophenyl)-1-nitroethene 在 叠氮基三甲基硅烷 、 四丁基氟化铵 作用下， 反应 0.15h， 以90%的产率得到5-(4-chlorophenyl)-2H-1,2,3-triazole-4-carbonitrile
  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：

  硝基乙腈 、 4-氯苯甲醛 在 氯化(1-丁基-3-甲基咪唑) 作用下， 反应 0.08h， 以96%的产率得到(E)-1-cyano-2-(4'-chlorophenyl)-1-nitroethene
  参考文献：
  名称：

  Novel synthesis scheme and in vitro antimicrobial evaluation of a panel of (E)-2-aryl-1-cyano-1-nitroethenes

  摘要：

  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.

  DOI：

  10.3109/14756366.2015.1070264

文献信息

• Conjugated nitroalkenes in cycloaddition reactions. Part 2. Diels–Alder reactions of E-2-aryl-1-cyano-1-nitroethenes with cyclopentadiene
  作者：Radomir Jasiński、Michał Rzyman、Andrzej Barański

  DOI：10.1135/cccc2009562

  日期：——

  The reaction between E-2-aryl-1-cyano-1-nitroethenes 1a–1e and cyclopentadiene (2) occurs according to the carbodiene [4+2]cycloaddition scheme and leads to the corresponding 6-endo-aryl-5-endo-cyano-5-exo-nitronorbornenes 3a–3e and 6-exo-aryl-5-exo-cyano-5-endo-nitronorbornenes 4a–4e as the only reaction products. The attempts to detect the products of heterodiene [4+2]cycloaddition in the reaction environment were not successful.

  E-2-芳基-1-氰基-1-硝基乙烯1a–1e和环戊二烯(2)之间的反应遵循碳二烯[4+2]环加成机制，生成相应的6-内取代芳基-5-内取代氰基-5-外取代硝基-壬二烯3a–3e和6-外取代芳基-5-外取代氰基-5-内取代硝基-壬二烯4a–4e作为唯一的反应产物。在反应环境中检测到异二烯[4+2]环加成的产物尝试失败。
• 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
• Unexpected course of reaction between (E)-2-aryl-1-cyano-1-nitroethenes and diazafluorene: why is there no 1,3-dipolar cycloaddition?
  作者：Radomir Jasiński、Karolina Kula、Agnieszka Kącka、Barbara Mirosław

  DOI：10.1007/s00706-016-1893-5

  日期：2017.5

  AbstractReactions between (E)-2-aryl-1-cyano-1-nitroethenes and diazafluorene lead to acyclic 2,3-diazabuta-1,3-diene derivatives, instead of the expected pyrazoline systems. DFT calculations suggest that this is a consequence of formation of zwitterionic structure in the first stage of the reaction. It must be noted that this is a specific property of the (E)-2-aryl-1-cyano-1-nitroethenes group, in

   抽象的 ( E )-2-芳基-1-氰基-1-硝基乙烯和二氮杂芴之间的反应产生无环2,3-二氮杂丁-1,3-二烯衍生物，而不是预期的吡唑啉体系。 DFT 计算表明这是反应第一阶段形成两性离子结构的结果。必须指出的是，与大多数其他共轭硝基烯烃相比，这是 ( E )-2-芳基-1-氰基-1-硝基乙烯基团的特定性质。  图形概要
• 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。
• 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.