(E)-4-(4-硝基苯乙烯基)苯甲腈 | 74518-94-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: (E)-4-(4-硝基苯乙烯基)苯甲腈
• 英文名称: (E)-4-[2-(4-nitrophenyl)ethenyl]benzonitrile
• 英文别名: (E)-4-(4-nitrostyryl)benzonitrile；(E)-4-Cyano-4'-nitrostilbene；4'-nitro-trans-stilbene-carbonitrile-(4)；4'-Nitro-trans-stilben-carbonitril-(4)；4-(4-Nitro-trans-styryl)-benzonitril；4-[(E)-2-(4-nitrophenyl)ethenyl]benzonitrile
• CAS: 74518-94-8
• 化学式: C₁₅H₁₀N₂O₂
• 分子量: 250.257
• InChiKey: AVUPZCWYUFGWKE-OWOJBTEDSA-N

物化性质

• 熔点：
  255-256 °C
• 沸点：
  418.9±24.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• 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)-4-(4-硝基苯乙烯基)苯甲腈 在 盐酸 、 tin(ll) chloride 作用下， 以 溶剂黄146 为溶剂， 以76%的产率得到4-[2-(4-aminophenyl)ethenyl]benzonitrile
  参考文献：
  名称：

  代谢N-羟基化。利用取代基变化来调节4-乙酰氨基苯乙二酸酯的体外生物活化。

  摘要：

  N-羟基化是致癌性芳基酰胺生物活化中的重要步骤。该实验室以前的报道表明，反式-4-乙酰氨基二苯乙烯（1）的4​​'取代基的变化对其体外微粒体N-羟基化的速率有显着影响。为了进一步研究电负性和脂肪族取代基的作用，合成了1的4'-CN，4'-CH3、4'-C（CH3）3和4'-CF3类似物，并通过仓鼠进行了代谢转化肝微粒体。每种化合物均以放射性标记形式合成，并通过TLC，质谱和液体闪烁计数对代谢物进行鉴定和定量。4'-CN类似物的N-羟基化的Vmax为24％，Km为1的11％。乙醇酰胺是4'-CN的次要代谢物。-CN化合物。4'-CH3化合物的主要代谢产物是4'-CH2OH衍生物，少量生成N-羟基化产物。类似地，代谢4'-C（CH3）3类似物以产生反式-4'-[2-（羟甲基）-2-丙基] -4-乙酰氨基sti（26）以及痕量的异羟肟酸。4'-CF3底物产生少量的N-羟基化物质，作为唯一可检测的

  DOI：

  10.1021/jm00183a014
• 作为产物：
  描述：

  4-氰基苯甲醛 在 碘 、 三苯基膦 作用下， 以 甲醇 、 氯仿 、 甲苯 为溶剂， 生成 (E)-4-(4-硝基苯乙烯基)苯甲腈
  参考文献：
  名称：

  Zn(II)-Induced Ground-State π-Deconjugation and Excited-State Electron Transfer in N,N-Bis(2-pyridyl)amino-Substituted Arenes

  摘要：

  The synthesis and X-ray crystal structures of two N,N-bis(2-pyridyl)amino (dpa)-substituted aromatic systems (Ar-dpa) 1 (Ar = 4,4'-disubstituted trans-stilbene) and 2 (Ar = 1,4-disubstituted benzene) and their ZnCl2 complexes (1/ZnCl2 and 2/ZnCl2) are reported. The fluoroionophoric behavior of 1-2 in response to Zn(II) in acetonitrile also has been investigated. In addition, compound 3DPA has been prepared and served as a pi-deconjugated model for 1DPA. The observed crystal structures for 1/ZnCl2 and 2/ZnCl2 Could be divided into two distinct types, the planar and the twisted forms, depending on the aryl-dpa (C-ph-NC3) dihedral angle. The twisted form is more favorable for these complexes unless the arene has a strong "push-pull" character. Nonetheless, the degree of pi-conjugation between the N-pyridyl and the N-aryl group is reduced in both complex forms when compared with the free ligands. Such a Zn(II)-induced pi-deconjugation not only directly affects the internal charge transfer (ICT) fluorescence of the dpa-substituted stilbenes but also facilitates the occurrence of photoinduced electron transfer (PET) from the stilbene donor to the dpa/Zn(II) acceptor. The PET process is particularly important in accounting for the observed Zn(II)-induced fluorescence quenching for 1DPA as well as 3DPA.

  DOI：

  10.1021/jo049902z

文献信息

• Substituent effects on the genotoxicity of 4-nitrostilbene derivatives
  作者：B.H. Hooberman、M.D. Brezzell、S.K. Das、Z. You、J.E. Sinsheimer

  DOI：10.1016/0165-1218(94)90024-8

  日期：1994.11

  4-Nitrostilbene and twelve of its derivatives (eleven E-stilbenes and two Z-stilbenes) were examined for possible quantitative structure-activity relationships of their in vitro and in vivo genotoxicity. Relative mutagenicity was studied with and without S9 activation in Salmonella strains TA98 and TA100, as well as in the nitroreductase deficient strains TA98/NR and TA100/NR. Chromosomal aberrations

  检查了4-硝基二苯乙烯及其十二种衍生物（十一种E-苯乙烯和两个Z-苯乙烯）在体外和体内遗传毒性方面可能的定量构效关系。在沙门氏菌菌株TA98和TA100以及硝基还原酶缺陷型菌株TA98 / NR和TA100 / NR中，研究了有和没有S9活化的相对诱变性。观察到腹膜内施用亚硝基苯甲酸酯后，小鼠骨髓细胞中的染色体畸变是体内遗传毒性的指标。除TA100中的4-氨基-4'-亚硝基二苯乙烯外，所有化合物均在没有S9活化的情况下在TA98和TA100中具有活性。NR菌株中的致突变活性大大降低或消除，这与细菌还原酶对化合物的代谢活化相一致。S9的存在降低了大多数亚硝基苯的活性，推测是由于酶促解毒作用。研究了取代基的哈米特值，分配系数和前沿轨道能量（ELUMO和EHOMO）与11种E-芪的致突变性的关系。可以在没有S9激活的TA​​98中的致突变性与Hammet值之间建立相关性。相同的诱变性也可能与EL
• Reactions at high pressure, part 18; volumes of activation and of reaction for the wittig reaction
  作者：Neil S. Isaacs、Obeid Hassan Abed

  DOI：10.1016/s0040-4039(00)84159-3

  日期：1986.1

  between 1 and 1000 bar of reactions between triphenyl-p-nitrobenzylidenephosphorane, and a series of substituted benzaldehydes .Values of ΔV≠ lie in the range −20 to −30 cm3mol−1 and are somewhat solvent-dependent. The corresponding volume of reaction is less negative. These measurements are in agreement with the accepted reaction mechanism and suggest that the scope of the reaction may be extended by the

  活化的卷已经从速率测量1和三苯基-对- nitrobenzylidenephosphorane之间的反应的1000巴，以及一系列ΔV的取代的苯甲醛的.Values之间获得≠范围谎言-20℃至-30厘米3摩尔-1，并且有点溶剂依赖。相应的反应体积较小。这些测量结果与公认的反应机理相一致，表明通过使用高压可以扩大反应范围。
• Reductive coupling of two aldehydes to unsymmetrical <i>E</i>-alkenes <i>via</i> phosphaalkene and phosphinate intermediates
  作者：Juri Mai、Anna I. Arkhypchuk、Arvind Kumar Gupta、Sascha Ott

  DOI：10.1039/c8cc04218g

  日期：——

  directly accessible from an electron-rich and an electron-deficient benzaldehyde in a novel reductive aldehyde cross-coupling reaction. The one-pot procedure is enabled by the oxidation of a transient phosphinite to the corresponding phosphinate which exhibits sufficient reactivity towards deactivated aldehydes.

  具有推挽式电子学的对苯二甲酸酯可通过新型的还原性醛交叉偶联反应从富电子和缺电子的苯甲醛中直接获得。一锅法是通过将瞬态次膦酸酯氧化成相应的次膦酸酯而实现的，该次膦酸酯对失活的醛具有足够的反应性。
• Metabolic N-hydroxylation. Use of substituent variation to modulate the in vitro bioactivation of 4-acetamidostilbenes
  作者：Patrick E. Hanna、Richard E. Gammans、Russell D. Sehon、Man-Kil Lee

  DOI：10.1021/jm00183a014

  日期：1980.9

  radiolabeled form, and the metabolites were identified and quantified by TLC, mass spectrometry, and liquid scintillation counting. The Vmax for N-hydroxylation of the 4'-CN analogue was 24% and the Km was 11% of that of 1. The glycolamide was a minor metabolite of the 4'-CN compound. The principal metabolite of the 4'-CH3 compound was the 4'-CH2OH derivative, the N-hydroxylated product being formed in small

  N-羟基化是致癌性芳基酰胺生物活化中的重要步骤。该实验室以前的报道表明，反式-4-乙酰氨基二苯乙烯（1）的4​​'取代基的变化对其体外微粒体N-羟基化的速率有显着影响。为了进一步研究电负性和脂肪族取代基的作用，合成了1的4'-CN，4'-CH3、4'-C（CH3）3和4'-CF3类似物，并通过仓鼠进行了代谢转化肝微粒体。每种化合物均以放射性标记形式合成，并通过TLC，质谱和液体闪烁计数对代谢物进行鉴定和定量。4'-CN类似物的N-羟基化的Vmax为24％，Km为1的11％。乙醇酰胺是4'-CN的次要代谢物。-CN化合物。4'-CH3化合物的主要代谢产物是4'-CH2OH衍生物，少量生成N-羟基化产物。类似地，代谢4'-C（CH3）3类似物以产生反式-4'-[2-（羟甲基）-2-丙基] -4-乙酰氨基sti（26）以及痕量的异羟肟酸。4'-CF3底物产生少量的N-羟基化物质，作为唯一可检测的
• Synthesis, Characterisation and Molecular Hyperpolarisabilities of Pseudo‐Octahedral Hydrido(nitrile)iron( <scp>II</scp> ) Complexes for Nonlinear Optics: X‐ray Structure of [Fe(H)(dppe) ₂ (4‐NCC ₆ H ₄ NO ₂ )][PF ₆ ]·CH ₂ Cl ₂
  作者：Maria Paula Robalo、António P. S. Teixeira、Maria Helena Garcia、M. Fátima Minas da Piedade、M. Teresa Duarte、Alberto Romão Dias、Jochen Campo、Wim Wenseleers、Etienne Goovaerts

  DOI：10.1002/ejic.200501050

  日期：2006.6

  2-bis(diphenylphosphanyl)ethane; R = acceptor-substituted conjugated ligand] have been synthesised by chloride abstraction from the starting compound trans-[FeHCl(dppe)2] and fully characterised. First hyperpolarisabilities (β) have been determined by hyper-Rayleigh scattering (HRS) at the fundamental wavelength of 1072 nm and the high near-resonant values obtained (up to 1130 × 10 – 30 esu) are interpreted in

  一系列具有通式 [Fe(H)(dppe)2(4NCR)][PF6] [dppe = 1,2-双（二苯基膦基）乙烷的离子假八面体反式氢化（腈）铁（II）配合物; R = 受体取代的共轭配体] 已通过从起始化合物 trans-[FeHCl(dppe)2] 中提取氯化物合成并充分表征。第一超极化率 (β) 已通过 1072 nm 基本波长的超瑞利散射 (HRS) 确定，并且获得的高近共振值（高达 1130 × 10 – 30 esu）被解释为两级模型 (TLM) 并与 IR 和 NMR 光谱数据相关。波长相关的 HRS 已在