4-[(Z)-2-(4-硝基苯基)乙烯基]苯甲腈 | 159394-73-7

• 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: 4-[(Z)-2-(4-硝基苯基)乙烯基]苯甲腈
• 英文名称: (Z)-4-Cyano-4'-nitrostilbene
• 英文别名: 4-[(Z)-2-(4-nitrophenyl)ethenyl]benzonitrile
• CAS: 159394-73-7
• 化学式: C₁₅H₁₀N₂O₂
• 分子量: 250.257
• InChiKey: AVUPZCWYUFGWKE-UPHRSURJSA-N

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：

  4-[(Z)-2-(4-硝基苯基)乙烯基]苯甲腈 在 碘 、 tin(ll) chloride 作用下， 以 甲醇 、 乙醇 、 氯仿 为溶剂， 反应 18.0h， 生成 4-[2-(4-aminophenyl)ethenyl]benzonitrile
  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
• 作为产物：
  描述：

  4-硝基苄基三苯基溴蓊盐 、 4-氰基苯甲醛 以35%的产率得到4-[(Z)-2-(4-硝基苯基)乙烯基]苯甲腈
  参考文献：
  名称：

  取代基对4-硝基二苯乙烯衍生物的遗传毒性的影响。

  摘要：

  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

  DOI：

  10.1016/0165-1218(94)90024-8

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
• Zn(II)-Induced Ground-State π-Deconjugation and Excited-State Electron Transfer in <i>N,N</i>-Bis(2-pyridyl)amino-Substituted Arenes
  作者：Jye-Shane Yang、Yan-Duo Lin、Yu-Hsi Lin、Fen-Ling Liao

  DOI：10.1021/jo049902z

  日期：2004.5.1

  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.