4,4'-diacetylstilbene | 6536-02-3

• 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: 4,4'-diacetylstilbene
• 英文别名: 4,4'-Diacetyl-stilben；1-[4-[2-(4-acetylphenyl)ethenyl]phenyl]ethanone
• CAS: 6536-02-3
• 化学式: C₁₈H₁₆O₂
• 分子量: 264.324
• InChiKey: JOYWKYJBQZBXHD-UHFFFAOYSA-N

物化性质

• 沸点：
  455.0±34.0 °C(Predicted)
• 密度：
  1.121±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,4'-diacetylstilbene 生成 4,4'-Diaethinyl-stilben
  参考文献：
  名称：

  Polyacetylene compounds, derivatives of di-, tri- and tetraphenylethylene

  摘要：

  DOI：

  10.1007/bf00845919
• 作为产物：
  描述：

  对甲基苯乙酮 在 potassium tert-butylate 、 氧气 作用下， 以 二甲基亚砜 、 叔丁醇 为溶剂， 生成 4-乙酰基苯甲酸 、 4,4'-diacetylstilbene
  参考文献：
  名称：

  Autoxidation and Condensation Reactions of Carbanions in Dimethyl Sulfoxide Solution

  摘要：

  DOI：

  10.1021/ja00872a044

文献信息

• Stereoselective Synthesis of (<i>E</i>)- and (<i>Z</i>)-Triethoxy(vinyl-<i>d</i>₂)silanes by Hydrosilylation of Acetylene-<i>d</i>₂
  作者：Álvaro Gordillo、Johan Forigua、Carmen López-Mardomingo、Ernesto de Jesús

  DOI：10.1021/om101127t

  日期：2011.1.24

  acetylene with triethoxysilane can be directed to the synthesis of either cis or trans triethoxy(vinyl-d2)silanes by an appropriate choice of metal catalyst. In addition, we have demonstrated the viability of designing hydrosilylation−arylation sequential processes in which acetylene can be converted into styrenes or stilbenes using the same Pd catalyst for both reactions.

  用三乙氧基硅烷氘化乙炔的氢化硅烷化可涉及任一的合成顺式或反式三乙氧基（乙烯基- d 2通过金属催化剂的一种合适的选择）硅烷。另外，我们证明了设计氢化硅烷化-芳基化顺序过程的可行性，其中乙炔可以在两个反应中使用相同的Pd催化剂转化为苯乙烯或对苯乙烯。
• Palladium-Catalyzed Cross-Coupling Reactions of Potassium Alkenyltrifluoroborates with Organic Halides in Aqueous Media
  作者：Emilio Alacid、Carmen Nájera

  DOI：10.1021/jo802356n

  日期：2009.3.20

  cross-coupled with aryl and heteroaryl bromides using 1 mol % Pd loading of 4-hydroxyacetophenone oxime derived palladacycle or Pd(OAc)2 as precatalysts, K2CO3 as base, and TBAB as additive and water reflux under conventional or microwave heating to afford styrenes, stilbenoids, and alkenylbenzenes. These borates can be cross-coupled diastereoselectively with allyl and benzyl chlorides using KOH as base

  乙烯基和烯基三氟硼酸钾与芳基和杂芳基溴化物进行交叉偶联，使用1摩尔％的4-羟基苯乙酮肟衍生的palladacycle或Pd（OAc）2作为Pd的前催化剂，K 2 CO 3在常规或微波加热下，作为碱和TBAB作为添加剂并进行水回流，得到苯乙烯，二苯乙烯类化合物和烯基苯。这些硼酸盐可以在丙酮水（3：2）中，在50°C和0.1 mol％Pd负载下，使用KOH作为碱，与烯丙基氯和苄基氯进行非对映选择性交联，分别得到相应的1,4-二烯和烯丙基芳烃。这些简单的无膦反应条件允许通过萃取分离包含58-105 ppm Pd的产物，在多达五次运行中从水相中回收钯。
• The effect of vicinyl olefinic halogens on cross-coupling reactions using Pd(0) catalysis
  作者：Michael G. Organ、Haleh Ghasemi、Cory Valente

  DOI：10.1016/j.tet.2004.08.006

  日期：2004.10

  products reliably under all reaction conditions. Compound 5 did not provide cross coupled products under any of the reaction conditions used. The Negishi reaction was the only one that worked for templates 4 and 11. Studies indicate that oxidative addition of the most reactive carbon–halogen bond to Pd(0) is followed by elimination of the second halide, when the second halide is a bromide or an iodide

  （反式）1-氯-2-碘乙烯（3），（反式）1-溴-2-碘乙烯（4），（反式）1,2-二碘乙烯（5）和（顺式和反式）1,2-二溴乙烯（11）在Puz催化下，在Suzuki，Sonogashira和Negishi交叉偶联条件下反应以获得单偶联产物。在所有反应条件下，只有烯烃模板3才能可靠地提供所需的偶联产物。在使用的任何反应条件下，化合物5均不提供交叉偶联产物。Negishi反应是唯一适用于模板的反应4和11。研究表明，当第二个卤化物是溴化物或碘化物时，将最具反应性的碳-卤素键氧化加成到Pd（0）上，然后消除第二个卤化物。当第二个卤素是氯化物时，发生的程度要小得多。
• Supported palladium nanoparticles as heterogeneous ligand-free catalysts for the Hiyama C–C coupling of vinylsilanes and halobenzenes leading to styrenes
  作者：Abdessamad Grirrane、Hermenegildo Garcia、Avelino Corma

  DOI：10.1016/j.jcat.2013.02.019

  日期：2013.6

  The Hiyama C-C coupling reaction of a wide range of aryl iodides and vinylsilanes has been performed using ligand-free solid catalysts based on supported palladium nanoparticles. Among the supports tested (Mg, TiO2, CeO2 and active carbon), the most active catalysts were those in which palladium is supported on MgO and TiO2. Analogous Pt and Au materials were inefficient to promote this reaction. Leaching tests suggest that there is some contribution of dissolved Pd since Pd in solution has been detected and the scavenging test decreases the initial reaction rate. Although the solid Pd catalysts can be reused, it was, however, observed that they undergo a certain deactivation upon use that can be attributed to several factors including the presence of inorganic compounds on the catalyst, Pd leaching or agglomeration of Pd NPs. (c) 2013 Elsevier Inc. All rights reserved.
• New Antiviral Compounds with Considerable Activity in Vivo. IV. Aromatic α-Keto Aldehydes
  作者：G. Cavallini

  DOI：10.1021/jm00333a003

  日期：1964.5