E-3,4,5,3’,4’,5’-六甲氧基二苯乙烯 | 61240-22-0

• 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-3,4,5,3’,4’,5’-六甲氧基二苯乙烯
• 中文别名: (E)-3,4,5,3',4',5'-六甲氧基二苯乙烯；(E)-1,2-双(3,4,5-三甲氧基苯基)乙烯
• 英文名称: dehydrobrittonin A
• 英文别名: 1,2-Bis(3,4,5-trimethoxyphenyl)ethylene；1,2,3-trimethoxy-5-[(E)-2-(3,4,5-trimethoxyphenyl)ethenyl]benzene
• CAS: 61240-22-0
• 化学式: C₂₀H₂₄O₆
• 分子量: 360.407
• InChiKey: DUESHOUIPOUGCU-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  E-3,4,5,3’,4’,5’-六甲氧基二苯乙烯 在 sodium 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以69%的产率得到3,3',5,5'-四甲氧基-联苄基
  参考文献：
  名称：

  Regioselective reductive demethoxylation of 3,4,5-trimethoxystilbenes

  摘要：

  Selective removal of the 4-methoxy group of 3,4,5-trimethoxystilbenes was performed under electron transfer conditions from Na metal in THF. Careful control of reaction conditions and quenching procedure allowed the synthesis of either (E)-3,5-dimethoxystilbenes or 3,5-dimethoxybibenzyls. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.08.009
• 作为产物：
  描述：

  3,4,5-三甲氧基甲苯 在 N-溴代丁二酰亚胺(NBS) 、 三(2-吡啶基甲基)胺 、 铜 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 E-3,4,5,3’,4’,5’-六甲氧基二苯乙烯
  参考文献：
  名称：

  铜/多胺促进的苄基宝石-二溴化物立体选择性还原偶联合成的E-二苯乙烯衍生物

  摘要：

  铜/多胺促进的苄基宝石二溴化物的立体选择性还原偶联反应在温和的条件下以高收率生成了E-二苯乙烯衍生物。它提供了使用便宜的试剂和不含烯基的起始原料并易于加工来合成对称和不对称E-苯乙烯衍生物的捷径。

  DOI：

  10.1016/j.tetlet.2017.05.072

文献信息

• Synthesis of styrene and stilbene derivatives by the palladium-catalysed arylation of ethylene with aroyl chlorides
  作者：Alwyn Spencer

  DOI：10.1016/s0022-328x(00)98836-3

  日期：1983.5

  with aroyl chlorides, catalysed by palladium(II) acetate, leads to styrene and stilbene derivatives. By appropriate choice of reaction conditions, particularly the ethylene pressure, the reaction can be made to produce either styrene or stilbene derivatives selectively. The reaction tolerates those common substituents which do not react with aroyl chlorides. Only trans-stilbene derivatives are formed

  在乙酸钯（II）的催化下，乙烯与芳酰氯发生芳基化反应，生成苯乙烯和二苯乙烯衍生物。通过反应条件，特别是将乙烯压力适当选择，反应可以进行，以选择性地产生任一苯乙烯或茋衍生物。该反应容许不与芳酰氯反应的那些常见的取代基。仅形成反式-二苯乙烯衍生物。
• Process for the preparation of styrene derivatives and/or stilbene
  申请人：Ciba-Geigy Corporation

  公开号：US04533505A1

  公开（公告）日：1985-08-06

  Compounds of the formulae Z--CH.dbd.CH--Z.sub.1 (Ia) or CH.sub.2 .dbd.CH--Z.sub.2 --CH.dbd.CH.sub.2 (Ib), in which Z represents unsubstituted or substituted phenyl or naphthyl, Z.sub.1 represents hydrogen or has the same meaning as Z and Z.sub.2 represents unsubstituted or substituted phenylene, naphthylene or p-biphenylene or an unsubstituted or substituted stilbene radical, can be obtained in a simple and economical manner in accordance with a novel process by reacting ethylene, under a pressure of 0.1 to 20 bar, in the presence of a base and with the addition of specific palladium catalysts, such as palladium acetate, with appropriate acid halides. The compounds of the formulae Ia and Ib are valuable intermediates, in particular for the preparation of fluorescent brighteners or scintillators.

  公式为 Z--CH.dbd.CH--Z.sub.1（Ia）或CH.sub.2.dbd.CH--Z.sub.2--CH.dbd.CH.sub.2（Ib）的化合物，其中 Z 代表未取代或取代的苯基或萘基，Z.sub.1 代表氢或与 Z 具有相同的含义，Z.sub.2 代表未取代或取代的苯基、萘基或 p-联苯基或未取代或取代的蒽基，可以通过一种新颖的方法简单经济地获得，该方法是在存在碱和特定钯催化剂（如乙酸钯）的情况下，通过在 0.1 到 20 巴的压力下，以乙烯为原料，并加入适当的酸卤化物进行反应。公式 Ia 和 Ib 的化合物是有价值的中间体，特别适用于制备荧光增白剂或闪烁体。
• Catalytic Wittig Reactions of Semi- and Nonstabilized Ylides Enabled by Ylide Tuning
  作者：Emma E. Coyle、Bryan J. Doonan、Andrew J. Holohan、Killian A. Walsh、Florie Lavigne、Elizabeth H. Krenske、Christopher J. O'Brien

  DOI：10.1002/anie.201406103

  日期：2014.11.17

  The first examples of catalytic Wittig reactions with semistabilized and nonstabilized ylides are reported. These reactions were enabled by utilization of a masked base, sodium tert‐butyl carbonate, and/or ylide tuning. The acidity of the ylide‐forming proton was tuned by varying the electron density at the phosphorus center in the precatalyst, thus facilitating the use of relatively mild bases. Steric

  报道了具有半稳定和不稳定的叶立德的催化Wittig反应的第一个实例。这些反应可以通过使用掩蔽的碱，碳酸叔丁酯钠和/或内酯调节来实现。可以通过改变预催化剂中磷中心的电子密度来调节形成内酯的质子的酸度，从而有利于使用相对温和的碱。对前催化剂结构的立体修饰导致E 选择性显着提高，达到> 95：5（E / Z）。
• Ruthenium nanoparticle-intercalated montmorillonite clay for solvent-free alkene hydrogenation reaction
  作者：Praveenkumar Upadhyay、Vivek Srivastava

  DOI：10.1039/c4ra12324g

  日期：——

  Well-characterized, ruthenium nanoparticle-intercalated montmorillonite clay was used as a catalyst in solvent-free alkene hydrogenation reactions and the corresponding products were obtained in good yields. The catalytic activity of ruthenium nanoparticle-intercalated montmorillonite clay was successfully tested with 16 different functionalized and non-functionalized alkenes. Apart from alkene reduction

  表征良好的钌纳米颗粒插层蒙脱土用作无溶剂烯烃加氢反应的催化剂，并以良好的收率获得了相应的产物。用16种不同的官能化和非官能化烯烃成功地测试了钌纳米粒子插层蒙脱土的催化活性。除烯烃还原外，还在Wittig型反应中测试了钌纳米粒子插层的蒙脱土粘土以获得脱氢布雷顿通素A的作用，脱氢溴通心粉素A是合成布雷顿酮A的重要中间体。发现钌纳米粒子插层的蒙脱石粘土对合成氢溴酸蒙脱石具有活性。脱氢布雷顿酮A和布雷顿通酯A。催化剂循环使用9次的能力以及较低的催化剂负载量，
• Stilbene derivatives and their use in medicaments
  申请人：Szekeres Thomas

  公开号：US20070191627A1

  公开（公告）日：2007-08-16

  The invention relates to stilbene derivatives of general formula (I), in which at least four of the substituents R 1 to R 6 do not represent hydrogen. The substituents are effective radical captors, anti-tumour active ingredients and selective cyclooxygenase-2 inhibitors.

  该发明涉及一般式(I)的stilbene衍生物，其中至少有四个取代基R1至R6不代表氢。这些取代基是有效的自由基捕获剂、抗肿瘤活性成分和选择性环氧合酶-2抑制剂。