2,5-dimethylstilbene | 21162-42-5

• 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: 2,5-dimethylstilbene
• 英文别名: β-(2,5-dimethylphenyl)styrene；2,5-Dimethylstilben；1,4-Dimethyl-2-(2-phenylethenyl)benzene
• CAS: 21162-42-5
• 化学式: C₁₆H₁₆
• 分子量: 208.303
• InChiKey: BICHQQURPIQMIX-UHFFFAOYSA-N

物化性质

• 沸点：
  317.5±27.0 °C(Predicted)
• 密度：
  1.015±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  2,5-dimethylstilbene 在 9-硼双环[3.3.1]壬烷 、 亚硝基叔丁烷 作用下， 以 四氢呋喃 为溶剂， 反应 1.83h， 以73%的产率得到(E)-2,5-dimethyl-1-styrylbenzene
  参考文献：
  名称：

  通过可逆的硼氢化反应对苯乙烯和苯乙烯类化合物进行电子选择性异构化

  摘要：

  E和Z的Stilbenes和Stilbenoids的混合物进行氢硼化后，进行消除反应，得到具有高立体选择性的E异构体。该反应容许具有不同立体电子性质的芳族取代基，发生在一个罐中，并且仅需要可商购的试剂。给出了白藜芦醇（一种生物活性抗氧化剂）的合成中的异构化反应的说明。

  DOI：

  10.1016/j.tetlet.2011.09.046
• 作为产物：
  描述：

  溴苯 、 2,5-二甲基苯乙烯 在 potassium phosphate 、 四丁基溴化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以80%的产率得到2,5-dimethylstilbene
  参考文献：
  名称：

  通过纳米颗粒的钯催化的（杂）芳基氯化物和溴化物配体和铜-自由的Sonogashira和的Heck偶联支撑在原位生成的Al（OH）3 †

  摘要：

  （Het）芳基卤化物（Br和Cl）与各种末端炔烃的无配体和无铜Sonogashira反应以及（Het）芳基卤化物（Br和Cl）与一系列烯烃的Heck偶联，负载的钯纳米粒子在新生成的Al（OH）3上进行了研究。该催化剂可以容易地回收并重复使用6次，而不会显着降低活性和钯的浸出。

  DOI：

  10.1039/c6ra25416k

文献信息

• Synthesis of Highly Substituted Arenes via Cyclohexadiene–Alkene C–H Cross Coupling and Aromatization
  作者：Anup Bhunia、Armido Studer

  DOI：10.1021/acscatal.8b00083

  日期：2018.2.2

  The development of a cross-coupling method for the regioselective β-alkenylation of 2,5-cyclohexadiene carboxylic acid derivatives to form ortho-alkenylarenes through in situ decarboxylation and aromatization is described. The carboxylic acid functionality is used as a traceless directing group for efficient and mild β-alkenylation. The modular sequence comprises a reductive Birch α-alkylation, ionic

  描述了交叉偶联方法的发展，该交叉偶联方法用于2，5-环己二烯羧酸衍生物的区域选择性β-烯基化以通过原位脱羧和芳构化形成邻烯基芳烃。羧酸官能团用作有效且温和的β-烯基化反应的无痕导向基团。模块化序列包括还原桦木α烷基化，离子δ烷基化，接着通过Pd催化的脱羧β烯基化，随后芳构化导致整体三倍本位-对位-邻位容易访问的苯甲酸衍生物的官能化。提出了在温和条件下以中等至极好的收率高效合成各种烷基-烯基芳烃的方法。
• Orthopalladated complexes of phosphorus ylide: Poly( <i>N</i> ‐vinyl‐2‐pyrrolidone)‐stabilized palladium nanoparticles as reusable heterogeneous catalyst for Suzuki and Heck cross‐coupling reactions
  作者：Kazem Karami、Sedigheh Abedanzadeh、Omolbanin Vahidnia、Pablo Herves、Janusz Lipkowski、Krzysztof Lyczko

  DOI：10.1002/aoc.3768

  日期：2017.11

  C‐orthometallated complex [Pdκ2(C,C)‐C6H4PPh2C(H)CO(C6H4‐NO2–4)}(μ‐OAc)]2, which underwent bridge exchange reaction with NaN3, NaCl, KBr and KI, respectively, to afford the binuclear C,C‐orthopalladated complexes [Pdκ2(C,C)‐C6H4PPh2C(H)CO(C6H4‐NO2–4)}(μ‐X)]2 (X = N3 (1), Cl (2), Br (3) and I (4)). The complexes were identified using spectroscopy (infrared and NMR), CHNS technique and single‐crystal X‐ray structure

  磷叶立德[PH 3 PCHC（O）C 6 H ^ 4 -NO 2 -4]用Pd（OAC）反应2，得到C，C-orthometallated络合物[钯κ 2（C，C）-C 6 ħ 4 PPh 2 C（H）CO（C 6 H 4 -NO 2 -4）}（μ-OAc）] 2，它们分别与NaN 3，NaCl，KBr和KI进行桥交换反应，得到双核C ，C-orthopalladated配合物[钯κ 2（C，C）-C 6 H ^ 4 PPH 2 C（H）CO（C 6 H ^ 4‐NO 2 –4）}（μ‐X）] 2（X = N 3（1），Cl（2），Br（3）和I（4））。使用光谱学（红外和NMR），CHNS技术和单晶X射线结构分析鉴定复合物。此后，使用碘桥联的原钯配合物4与聚N的回流反应可轻松制备尺寸分布窄的钯纳米颗粒。-乙烯基-2-吡咯烷酮）（PVP）作为保护基。PVP稳定化的钯纳米粒子使用多种技术
• The anisotropic effect of 4-substituents on the1H NMR chemical shift of H-5 in phenanthrenes
  作者：R. M. Letcher

  DOI：10.1002/mrc.1270160311

  日期：1981.7

  AbstractChloro‐, methoxy‐ and methyl‐substituents in the 4‐position of phenanthrenes exert a profound and diagnostic influence on the 1H chemicalshift of H‐5, and from 13C measurements it is considered to be dueto an anisotropic effect.
• Pd-TPPTS catalyzed Mizoroki–Heck coupling in halogen-free ionic liquids [Rmim][p-CH3C6H4SO3]
  作者：Juan Wei、Hai-Yan Fu、Rui-Xiang Li、Hua Chen、Xian-Jun Li

  DOI：10.1016/j.catcom.2011.01.008

  日期：2011.3

  A highly efficient system composed of Pd-TPPTS [TPPTS: trisodium salt of tri(m-sulphonylphenyl)phosphine] and halogen-free ionic liquid ([Rmim][p-CH3C6H4SO3), R = methyl, ethyl, n-butyl, n-hexyl, n-octyl, n-dodecyl) has been established for Heck coupling of aryl halides with styrene. Most of the investigated substrates could give the complete conversions (> 95%) with the catalyst of 1 mol% at 110 degrees C. The resulting products can be easily separated from the ionic liquids by simple liquid-liquid extraction, and the catalyst immobilized by ionic liquids can be consecutively run five times without significant loss in catalytic activity. (c) 2011 Elsevier B.V. All rights reserved.
• Sulphated mesoporous La2O3–ZrO2 composite oxide as an efficient and reusable solid acid catalyst for alkenylation of aromatics with phenylacetylene
  作者：Zhongkui Zhao、Jinfeng Ran

  DOI：10.1016/j.apcata.2015.01.023

  日期：2015.8

  Sulphated mesoporous La2O3-ZrO2 composite oxides (SO42-/meso-La2O3-ZrO2) were firstly prepared by a surfactant-assisted co-precipitation/hydrothermal crystallization with subsequent impregnation method (SACPHC-IM). The prepared SO42-/meso-La2O3-ZrO2 catalyst was employed as solid acid to catalyze direct alkenylation of p-xylene with phenylacetylene for clean production of alpha-arylstyrene. Various characterization techniques such as Ny adsorption-desorption, X-ray diffraction (XRD), FT-IR, NH3 temperature-programmed desorption (NH3-TPD), and pyridine-IR were employed to reveal the relationship between catalyst nature and catalytic performance. The as-prepared SO42-/meso-La2O3-ZrO2 catalyst shows much superior catalytic activity and similar selectivity to SO42-/meso-ZrO2, ascribed to increasing acid properties, enlarging specific surface area and increasing pore volume, reducing average crystalline size resulting from the promoting effect of adding La into ZrO2 matrix. Furthermore, the SO42-/meso-La2O3-ZrO2 catalysts were optimized by varying the atomic ratio of La/(La + Zr) from 0.05 to 0.2. The SO42-/meso-La2O3-ZrO2 catalyst with the 0.1 of optimum L(La + Zr) atomic ratio exhibited excellent catalytic performance, ascribed to the increase in amount acid sites and pore size. The results for stability test demonstrated that close to 100% of maximum conversion can be achieved, and more than 80% of conversion can be maintained with the time on stream up to 780 min. Through simple calcination treatment, the spent catalyst can be almost complete recovered. The developed SO42-/meso-La2O3-ZrO2 catalyst could be a potential candidate for a-arylstyrene production via acid catalyzed direct alkenylation of aromatics with phenylacetylene. (C) 2015 Elsevier B.V. All rights reserved.