1-甲氧基-3-[2-(4-硝基苯基)乙烯基]苯 | 14064-58-5

• 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: 1-甲氧基-3-[2-(4-硝基苯基)乙烯基]苯
• 英文名称: (E)-1-methoxy-3-[2-(4-nitrophenyl)ethenyl]benzene
• 英文别名: (E)-1-methoxy-3-(4-nitrostyryl)benzene；(E)-3-Methoxy-4'-nitrostilbene；methyl-(4'-nitro-stilben-3-yl)-ether；Methyl-(4'-nitro-stilben-3-yl)-aether；4'-Nitro-3-methoxy-stilben；trans-4-Nitro-3'-methoxy-stilben；1-methoxy-3-[(E)-2-(4-nitrophenyl)ethenyl]benzene
• CAS: 14064-58-5
• 化学式: C₁₅H₁₃NO₃
• 分子量: 255.273
• InChiKey: ZKWGCQHPGYOCSV-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2909309090

反应信息

• 作为反应物：
  描述：

  1-甲氧基-3-[2-(4-硝基苯基)乙烯基]苯 在 sodium hydride 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 9.5h， 生成 (E)-2-(4-(3-methoxystyryl)phenyl)benzo[d][1,2]selenazol-3(2H)-one
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of benzoselenazole-stilbene hybrids as multi-target-directed anti-cancer agents

  摘要：

  To identify novel multi-target-directed drug candidates for the treatment of cancer, a series of benzoselenazole-stilbene hybrids were synthesised by combining the pharmacophores of resveratrol and ebselen. The biological assay indicated that all of the hybrids exhibited antiproliferative activities against four human cancer cell lines and demonstrated good TrxR inhibitory activities. The mechanism of cell apoptosis was investigated in G2/M cell cycle arrest induced by compound 6e and the apoptosis of the human liver carcinoma Bel-7402 cell line. The significant increase in intracellular ROS confirmed that compound 6e was capable of causing oxidative stress-induced apoptosis in cancer cells. Our results support the potential of compound 6e as a candidate for further studies examining the development of novel drugs for cancer treatment. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.03.030
• 作为产物：
  描述：

  三苯胂 生成 1-甲氧基-3-[2-(4-硝基苯基)乙烯基]苯
  参考文献：
  名称：

  烷基化物的研究：用（对硝基亚苄基）三苯基砷烷进行羰基烯化

  摘要：

  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。

  DOI：

  10.1016/s0022-328x(00)80646-4

文献信息

• Discovery of efficient stimulators for adult hippocampal neurogenesis based on scaffolds in dragon's blood
  作者：Jian-Hua Liang、Liang Yang、Si Wu、Si-Si Liu、Mark Cushman、Jing Tian、Nuo-Min Li、Qing-Hu Yang、He-Ao Zhang、Yun-Jie Qiu、Lin Xiang、Cong-Xuan Ma、Xue-Meng Li、Hong Qing

  DOI：10.1016/j.ejmech.2017.05.025

  日期：2017.8

  discovered to efficiently stimulate adult rats' neurogenesis. In-depth structure-activity relationship studies proved the necessity of a stilbene scaffold that is absent in highly cytotoxic analogs such as chalcones and heteroaryl rings and inactive analogs such as diphenyl acetylene and diphenyl ethane, and validated the importance of an NH in the carboxamide and a methylenedioxy substituent on the

  由衰老和神经系统疾病引起的海马神经发生减少会损害神经回路并导致记忆丧失。一种新的铅化合物（ñ -反式-3'，4'- methylenedioxystilben -4-基乙酰胺27）已发现有效地刺激成年大鼠的神经发生。深入的结构-活性关系研究证明，在高度细胞毒性类似物（如查耳酮和杂芳基环）和无活性类似物（如二苯乙炔和二苯乙烷）中不存在二苯乙烯骨架的必要性，并验证了氨甲酰胺和苯环上的亚甲二氧基取代基。免疫组织化学染色和生化分析表明，与先前报道的神经保护化学物质相比，N-二苯乙烯基羧酰胺具有神经增殖型神经发生的额外能力，从而为提高成年哺乳动物脑的可塑性提供了基础。
• 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
• Scope and limitations of the Heck–Matsuda-coupling of phenol diazonium salts and styrenes: a protecting-group economic synthesis of phenolic stilbenes
  作者：Bernd Schmidt、Nelli Elizarov、René Berger、Frank Hölter

  DOI：10.1039/c3ob40420j

  日期：——

  4-Phenol diazonium salts undergo Pd-catalyzed Heck reactions with various styrenes to 4′-hydroxy stilbenes. In almost all cases higher yields and fewer side products were observed, compared to the analogous 4-methoxy benzene diazonium salts. In contrast, the reaction fails completely with 2- and 3-phenol diazonium salts. For these substitution patterns the methoxy-substituted derivatives are superior

  4-苯酚重氮盐与各种苯乙烯进行Pd催化的Heck反应，生成4'-羟基苯乙烯。与类似的4-甲氧基苯重氮盐相比，几乎在所有情况下均观察到更高的收率和更少的副产物。相反，用2-和3-苯酚重氮盐使反应完全失败。对于这些取代方式，甲氧基取代的衍生物是优越的。
• Mechanically activated synthesis of (E)-stilbene derivatives by high-speed ball milling
  作者：Xingyi Zhu、Jun Liu、Tao Chen、Weike Su

  DOI：10.1002/aoc.2827

  日期：2012.3

  An efficient mechanically activated solvent‐free synthesis of (E)‐stilbene derivatives by high‐speed ball milling is described. This method has notable advantages in terms of good yield, short reaction time and high selectivity. Copyright © 2012 John Wiley & Sons, Ltd.

  描述了通过高速球磨进行的高效机械活化的无溶剂合成（E）-二苯乙烯衍生物。该方法在产率高，反应时间短和选择性高方面具有显着的优点。版权所有©2012 John Wiley＆Sons，Ltd.
• Olefination of<i>N</i>-Sulfinylimines under Mild Conditions
  作者：Shubhendu Dhara、Charles E. Diesendruck

  DOI：10.1002/ejoc.201601577

  日期：2017.2.24

  A very simple and efficient diastereoselective synthesis of 1,2-disubstituted alkenes has been achieved under mild conditions. The sulfoxide stabilised N-sulfinylimine reacted with in situ generated phosphonate carbanion to give 1, 2-disubtituted alkenes in good to excellent yields. Different aryl phosphonate reacted with a range of electronically diverse N-sulfinylimine to afford in almost greater

  1,2-二取代烯烃的非对映选择性合成已在温和条件下实现，非常简单有效。亚砜稳定的 N-亚磺酰亚胺与原位生成的膦酸碳负离子反应，以良好到极好的收率得到 1, 2-二取代的烯烃。不同的芳基膦酸酯与一系列电子不同的 N-亚磺酰亚胺反应，得到几乎大于 99:1 的 E-选择性烯烃。该协议最重要的特点是该反应可以在室温下进行，使用廉价的氢化钠作为最有效的碱来生成反应性膦酸酯碳负离子，产生高达 85% 的分离的 E 选择性烯烃。