1-(4-methylstyryl)-2-nitrobenzene | 131534-72-0

• 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: 1-(4-methylstyryl)-2-nitrobenzene
• 英文别名: 1-[2-(4-Methylphenyl)ethenyl]-2-nitrobenzene；1-[2-(4-methylphenyl)ethenyl]-2-nitrobenzene
• CAS: 131534-72-0
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: BOEQYEBHKXREIP-UHFFFAOYSA-N

物化性质

• 沸点：
  385.5±27.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-methylstyryl)-2-nitrobenzene 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 6.0h， 以95%的产率得到2-nitro 4'-bromomethyl stilbene
  参考文献：
  名称：

  Synthesis and calcium antagonistic activity of diethyl styrylbenzylphosphonates

  摘要：

  Twenty-three new phosphonic ester derivatives of stilbene exhibiting structural analogies with fostedil are described. Examination of calcium antagonism showed that this activity could not be increased by introducing electron-withdrawing, electron-releasing or lipophilic substituents. Only compounds containing fluorine at the 2 or 4 positions exhibited similar activity to the model.

  DOI：

  10.1016/0223-5234(94)90204-6
• 作为产物：
  描述：

  4-甲基苄基膦酸二乙酯 、 邻硝基苯甲醛 在 sodium hydride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 10.0h， 以18%的产率得到1-(4-methylstyryl)-2-nitrobenzene
  参考文献：
  名称：

  Synthesis and calcium antagonistic activity of diethyl styrylbenzylphosphonates

  摘要：

  Twenty-three new phosphonic ester derivatives of stilbene exhibiting structural analogies with fostedil are described. Examination of calcium antagonism showed that this activity could not be increased by introducing electron-withdrawing, electron-releasing or lipophilic substituents. Only compounds containing fluorine at the 2 or 4 positions exhibited similar activity to the model.

  DOI：

  10.1016/0223-5234(94)90204-6

文献信息

• Development of Tetrachlorophthalimides as Liver X Receptor β (LXRβ)-Selective Agonists
  作者：Sayaka Nomura、Kaori Endo-Umeda、Makoto Makishima、Yuichi Hashimoto、Minoru Ishikawa

  DOI：10.1002/cmdc.201600305

  日期：2016.10.19

  lipogenesis in liver, and selective LXRβ activation improves RCT in mice. Therefore, LXRβ‐selective agonists are promising candidates to improve atherosclerosis without increasing plasma or hepatic TG levels. However, the ligand‐binding domains in the two LXR isoforms α/β share high sequence identity, and few LXR ligands show subtype selectivity. In this study we identified a tetrachlorophthalimide analogue

  肝X受体（LXR）激动剂是通过诱导ABCA1（ATP结合盒A1）基因表达来治疗动脉粥样硬化的候选药物，该基因表达有助于逆转胆固醇转运（RCT）并促进肝脏和肠道中胆固醇的排出。但是，LXR激动剂也会诱导参与脂肪形成的基因，例如SREBP-1c（固醇调节结合元件蛋白1c）和FAS（脂肪酸合酶），从而引起血浆和肝甘油三酯（TG）水平的不良增加。最近的研究表明，LXRα有助于肝脏中的脂肪生成，选择性LXRβ活化可改善小鼠的RCT。因此，LXRβ选择性激动剂有望在不增加血浆或肝TG水平的情况下改善动脉粥样硬化。但是，两个LXR同工型α/β中的配体结合结构域具有较高的序列同一性，几乎没有LXR配体显示出亚型选择性。在这项研究中，我们确定了四氯邻苯二甲酰亚胺类似物作为LXRβ选择性激动剂。结构发展导致（E）-4,5,6,7-四氯-2-（2-苯乙烯基苯基）异吲哚啉-1,3-二酮（24 a），这在报告基因测
• Immobilized Pd on (<i>S</i>)-methyl histidinate-modified multi-walled carbon nanotubes: a powerful and recyclable catalyst for Mizoroki-Heck and Suzuki-Miyaura C-C cross-coupling reactions in green solvents and under mild conditions
  作者：Abdol R. Hajipour、Zahra Khorsandi

  DOI：10.1002/aoc.3425

  日期：2016.5

  thermogravimetric and elemental analyses. This new air‐ and moisture‐stable phosphine‐free palladium catalyst was found to be highly active and reusable in Mizoroki–Heck and Suzuki–Miyaura cross‐coupling reactions in poly(ethylene glycol) and aqueous ethanol as green solvents using an extremely small amount of palladium under mild conditions. Copyright © 2016 John Wiley & Sons, Ltd.

  使用固定在多壁碳纳米管表面的（S）-组氨酸甲酯上的固定钯合成了稳定，功能强大的多相钯催化剂。通过傅里叶变换红外光谱和X射线光电子能谱，透射电子显微镜，X射线粉末衍射和电感耦合等离子体，热重分析和元素分析对催化剂进行了表征。发现这种新型的对空气和湿气稳定的无膦钯催化剂具有很高的活性，并且可以在极少量的聚乙二醇和乙醇水溶液作为绿色溶剂的Mizoroki–Heck和Suzuki–Miyaura交叉偶联反应中重用。在温和条件下的钯。版权所有©2016 John Wiley＆Sons，Ltd.
• Iron-Catalyzed Reductive Cyclization of <i>o</i>-Nitrostyrenes Using Phenylsilane as the Terminal Reductant
  作者：Michael Shevlin、Xinyu Guan、Tom G. Driver

  DOI：10.1021/acscatal.7b01915

  日期：2017.8.4

  catalyze the reductive cyclization of ortho-nitrostyrenes into indoles via nitrosoarene reactive intermediates. This method requires only 1 mol % of Fe(OAc)2 and 1 mol % of 4,7-(MeO)2phen and uses phenylsilane as a convenient terminal reductant. The scope and limitations of the method were illustrated with 21 examples, and an investigation into the kinetics of the reaction revealed first-order behavior

  使用微型高通量实验，发现了一种有效的，地球上富集的菲咯啉铁配合物，可通过亚硝基芳烃反应性中间体催化邻硝基苯乙烯转化为吲哚的还原环化反应。该方法仅需要1mol％的Fe（OAc）2和1mol％的4，7-（MeO）2 phen，并使用苯基硅烷作为方便的末端还原剂。该方法的范围和局限性用21个实例进行了说明，对反应动力学的研究揭示了催化剂和硅烷的一级行为以及相对于硝基苯乙烯的零级行为。
• Pschorr, Chemische Berichte, 1906, vol. 39, p. 3115
  作者：Pschorr

  DOI：——

  日期：——
• Styrylphenylphthalimides as Novel Transrepression-Selective Liver X Receptor (LXR) Modulators
  作者：Sayaka Nomura、Kaori Endo-Umeda、Atsushi Aoyama、Makoto Makishima、Yuichi Hashimoto、Minoru Ishikawa

  DOI：10.1021/acsmedchemlett.5b00170

  日期：2015.8.13

  Anti-inflammatory effects of liver X receptor (LXR) ligands are thought to be largely due to LXR-mediated transrepression, whereas side effects are caused by activation of LXR-responsive gene expression (transactivation). Therefore, selective LXR modulators that preferentially exhibit transrepression activity should exhibit anti-inflammatory properties with fewer side effects. Here, we synthesized a series of styrylphenylphthalirnide analogues and evaluated their structure activity relationships focusing on LXRs-transactivating-agonistic/antagonistic activities and transrepressional activity. Among the compounds examined, 171 showed potent LXR-transrepressional activity with high selectivity over transactivating activity and did not show characteristic side effects of LXR-transactivating agonists in cells. This representative compound, 171, was confirmed to have LXR-dependent transrepressional activity and to bind directly to LXR beta. Compound 171 should be useful not only as a chemical tool for studying the biological functions of LXRs transrepression but also as a candidate for a safer agent to treat inflammatory diseases.