trans-3,3',4,4'-Tetrachlorostilbene | 36888-19-4

• 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: trans-3,3',4,4'-Tetrachlorostilbene
• 英文别名: 1,2-Dichloro-4-((E)-2-(3,4-dichlorophenyl)ethenyl)benzene；1,2-dichloro-4-[(E)-2-(3,4-dichlorophenyl)ethenyl]benzene
• CAS: 36888-19-4
• 化学式: C₁₄H₈Cl₄
• 分子量: 318.03
• InChiKey: SEYMIRJSQDOFDO-OWOJBTEDSA-N

物化性质

• 熔点：
  186-187 °C
• 沸点：
  429.9±45.0 °C(Predicted)
• 密度：
  1.442±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  四氯苯醌 、 trans-3,3',4,4'-Tetrachlorostilbene 以 1,4-二氧六环 为溶剂， 反应 50.0h， 以98%的产率得到5,6,8,9-tetrachloro-2-(3,4-dichlorophenyl)-3-(3,4-dichlorophenyl)-1-oxaspiro<3,5>nona-5,8-dien-7-one
  参考文献：
  名称：

  Oxetanes from [2+2] Cycloaddition of Stilbenes to Quinone via Photoinduced Electron Transfer

  摘要：

  The photochemical coupling of various stilbenes (S) and chloranil (Q) is effected by the specific charge-transfer (CT) activation of the precursor electron donor-acceptor (EDA) complex [S, Q], and the [2+2] cycloaddition is established by X-ray structure elucidation of the crystalline trans-oxetanes formed selectively in high yields. Time-resolved (fs/ps) spectroscopy reveals the (singlet) ion-radical pair (1)[S.+, Q(.-)] to be the primary reaction intermediate and thus unambiguously establishes for the first time the electron-transfer pathway for this typical Paterno-Buchi transformation. The alternative cycloaddition via the specific activation of the carbonyl component (as a commonly applied procedure in Paterno-Buchi couplings) leads to the same oxetane regioisomers in identical molar ratios. As such, we conclude that a common electron-transfer mechanism applies via the quenching of the photoactivated quinone acceptor by the stilbene donor to afford triplet ion-radical pairs (3)[S.+, Q(.-)] which appear on the ns/mu s time scale. The spin multiplicities of the critical ion-pair intermediate [S.+, Q(.-)] in the two photoactivation methodologies determine the time scale of the reaction sequences (which are otherwise the same), and thus the efficiency of the relatively slow ion-pair collapses (k(c) similar or equal to 10(8) s(-1)) to the 1,4-biradical that ultimately leads to the oxetane product.

  DOI：

  10.1021/jo981754n
• 作为产物：
  描述：

  3,4-二氯苯甲醛 在 四氯化硅 、 锌 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以33%的产率得到trans-3,3',4,4'-Tetrachlorostilbene
  参考文献：
  名称：

  SiCl4–Zn induced reductive coupling of carbonyl compounds: novel and efficient routes for one-pot syntheses of 1,2,3-triaryl-2-propen-1-ones and pinacolones at room temperature

  摘要：

  An unprecedented one-pot reductive trimerization of aromatic aldehydes to 1,2,3-triaryl-2-propen-1-ones as well as tandem reductive coupling-rearrangements of aryl ketones to pinacolone analogues was efficiently achieved using tetrachlorosilane-zinc at room temperature. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.04.092

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。
• Synthesis of Styrenes and <i>E‐</i>Stilbenes by Palladium‐Catalyzed Vinylation of Aryl Iodides with 1,2‐Dibromoethane
  作者：Guangfa Shi、Xiaotian Ma、Qiongqiong Zhu、Yanghui Zhang

  DOI：10.1002/adsc.202301146

  日期：2024.3.8

  The Pd-catalyzed vinylation reactions of aryl iodides using 1,2-dibromoethane is developed for the synthesis of styrenes and stilbenes. In these reactions, vinyl bromide is generated from 1,2-dibromoethane and then undergoes reductive cross-coupling with aryl iodides, affording styrene products. Under slightly modified reaction conditions, styrenes can continue reacting with vinyl bromide to form E-stilbenes

  使用 1,2-二溴乙烷的钯催化芳基碘化物乙烯基化反应被开发用于合成苯乙烯和茋。在这些反应中，溴乙烯由 1,2-二溴乙烷产生，然后与芳基碘进行还原交叉偶联，得到苯乙烯产物。在稍加修改的反应条件下，苯乙烯可以继续与溴乙烯反应生成E-二苯乙烯，这提供了二苯乙烯的一锅合成方法。醇，包括异丙醇和甲醇，在这些还原交叉偶联反应中用作还原剂。
• SPENCER, A., J. ORGANOMET. CHEM., 1983, 247, N 1, 117-122
  作者：SPENCER, A.

  DOI：——

  日期：——
• Verfahren zur Herstellung von Styrol- und/oder Stilbenderivaten
  申请人：CIBA-GEIGY AG

  公开号：EP0062005B1

  公开（公告）日：1985-06-26