(E)-3,4'-Dinitrostilbene | 51042-51-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-3,4'-Dinitrostilbene
• 英文别名: 1-nitro-3-[(E)-2-(4-nitrophenyl)ethenyl]benzene
• CAS: 51042-51-4
• 化学式: C₁₄H₁₀N₂O₄
• 分子量: 270.244
• InChiKey: WMOGPQFWQAXCTI-SNAWJCMRSA-N

物化性质

• 熔点：
  224-226 °C
• 沸点：
  413.7±24.0 °C(Predicted)
• 密度：
  1.376±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 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：
  91.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3,4'-Dinitrostilbene 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 以98%的产率得到3-<2-(4-aminophenyl)ethyl>benzenamine
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of resveratrol analogues as aromatase and quinone reductase 2 inhibitors for chemoprevention of cancer

  摘要：

  A series of new resveratrol analogues were designed and synthesized and their inhibitory activities against aromatase were evaluated. The crystal structure of human aromatase (PDB 3eqm) was used to rationalize the mechanism of action of the aromatase inhibitor 32 (IC50 0.59 mu M) through docking, molecular mechanics energy minimization, and computer graphics molecular modeling, and the information was utilized to design several very potent inhibitors, including compounds 82 (IC50 70 nM) and 84 (IC50 36 nM). The aromatase inhibitory activities of these compounds are much more potent than that for the lead compound resveratrol, which has an IC50 of 80 mu M. In addition to aromatase inhibitory activity, compounds 32 and 44 also displayed potent QR2 inhibitory activity (IC50 1.7 mu M and 0.27 mu M, respectively) and the high-resolution X-ray structures of QR2 in complex with these two compounds provide insight into their mechanism of QR2 inhibition. The aromatase and quinone reductase inhibitors resulting from these studies have potential value in the treatment and prevention of cancer. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.042
• 作为产物：
  描述：

  3-硝基溴苄 生成 (E)-3,4'-Dinitrostilbene
  参考文献：
  名称：

  Studies on ylides formation and reactions of ortho- and meta-Nitrobenzylidenetriphenylarsenanes

  摘要：

  DOI：

  10.1016/s0022-328x(00)80697-x

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
• Studies on ylides: Carbonyl olefination with (p-nitro benzylidene)triphenylarsenane
  作者：P.S. Kendurkar、R.S. Tewari

  DOI：10.1016/s0022-328x(00)80646-4

  日期：1973.11

  (p-Nitrobenzylidene)triphenylarsenane, a semistabilized arsonium ylide has been prepared and reacted with carbonyl compounds to yield olefins as opposed to epoxidation products. Treatment of the ylide with a ranged acyl halides gave new disubstituted arsonium ylides. IR and NMR spectral data for the resulting products are reported.

  已经制备了（对硝基亚苄基）三苯基ar烷，一种半稳定的鎓内鎓盐，并与羰基化合物反应生成与环氧化产物相反的烯烃。用一定范围的酰基卤处理该叶立德，得到新的二取代的亚砷基叶立德。报告了所得产物的IR和NMR光谱数据。
• Direct C≡C Triple Bond Formation from the C=C Double Bond and Direct Hydroxylation into the<i>o</i>-Position of a Nitro Group on the Benzene Nucleus with Potassium<i>t</i>-Butoxide in<i>N</i>,<i>N</i>-Dimethylformamide in the Air
  作者：Shuzo Akiyama、Kunihiko Tajima、Shin’ichi Nakatsuji、Kenichiro Nakashima、Kazuko Abiru、Miwa Watanabe

  DOI：10.1246/bcsj.68.2043

  日期：1995.7

  4-diethylamino-4′ -nitrostilbene was measured to identify an anion radical species expected for explanation of the mechanism of the dehydrogenation reaction. Further, cyclic voltammetric measurements of a series of stilbenes and diphenylacetylenes were carried out in connection with the above mechanism. In many cases, interestingly, the use of a large excess of t-BuOK brought about succeeding hydroxylation

  在空气中的 N,N-二甲基甲酰胺中用叔丁醇钾 (t-BuOK) 处理从 C=C 双键直接形成 C≡C 炔键的新方法和简便方法已在 9,10-双(4-取代苯乙烯基)蒽系列、4-取代4'-硝基二苯乙烯系列和1-(对硝基苯基)-4-(对-取代苯基)-1,3-丁二烯系列；已经审查了其范围和局限性。测量针对 4-二乙氨基-4'-硝基二苯乙烯的反应的 ESR 光谱，以确定预期用于解释脱氢反应机理的阴离子自由基种类。此外，结合上述机理进行了一系列二苯乙烯和二苯乙炔的循环伏安测量。在许多情况下，有趣的是，使用大量过量的 t-BuOK 导致后续羟基化到苯核上硝基的邻位。简单的羟基化可用于合成取代的 5-（芳基乙炔基）-2-硝基苯酚，...
• Importance of Direct Metal−π Coupling in Electronic Transport Through Conjugated Single-Molecule Junctions
  作者：Jeffrey S. Meisner、Seokhoon Ahn、Sriharsha V. Aradhya、Markrete Krikorian、Radha Parameswaran、Michael Steigerwald、Latha Venkataraman、Colin Nuckolls

  DOI：10.1021/ja308626m

  日期：2012.12.19

  We study the effects of molecular structure on the electronic transport and mechanical stability of single-molecule junctions formed with Au point contacts. Two types of linear conjugated molecular wires are compared: those functionalized with methylsulfide or amine aurophilic groups at (1) both or (2) only one of its phenyl termini. Using scanning tunneling and atomic force microscope break-junction

  我们研究了分子结构对由 Au 点接触形成的单分子结的电子传输和机械稳定性的影响。比较了两种类型的线性共轭分子线：那些在 (1) 两个或 (2) 只有一个苯基末端用甲基硫化物或胺亲金基团官能化的。使用扫描隧道和原子力显微镜断裂连接技术，研究了单和双功能化分子线的电导及其对连接伸长和断裂力的依赖性。当分子桥通过一端的 S-Au 供体-受体键和另一端相对较弱的 Au-π 相互作用耦合时，可以观察到通过单功能化导线的电荷传输。对于单功能化分子线，可以通过在元位置安装第二个亲金基团来机械稳定连接，然而，这本身不会有助于新的传导途径。这些结果揭示了通过金属-π 相互作用产生的电子耦合与共轭体系上化学取代引入的量子力学效应之间的重要相互作用。这项研究提供了一种通过分子线确定性地调整电气和机械性能的策略。
• Ashley et al., Journal of the Chemical Society, 1942, p. 103,107
  作者：Ashley et al.

  DOI：——

  日期：——