1-[(E)-2-(4-methylphenyl)ethenyl]-3,5-dimethoxybenzene | 880354-46-1

• 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: 1-[(E)-2-(4-methylphenyl)ethenyl]-3,5-dimethoxybenzene
• 英文别名: (E)-1-(4'-methylphenyl)-2-(3,5-dimethoxyphenyl)ethene；(E)-1,3-dimethoxy-5-(4-methylstyryl)benzene；trans-3,5-dimethoxy-4'-methyl-stilbene；1,3-dimethoxy-5-[(E)-2-(4-methylphenyl)ethenyl]benzene
• CAS: 880354-46-1
• 化学式: C₁₇H₁₈O₂
• 分子量: 254.329
• InChiKey: XMWGAFZFKOMEKV-CMDGGOBGSA-N

物化性质

• 沸点：
  392.4±11.0 °C(Predicted)
• 密度：
  1.073±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[(E)-2-(4-methylphenyl)ethenyl]-3,5-dimethoxybenzene 生成 2,4-dimethoxy-6-methylphenantrene
  参考文献：
  名称：

  The anisotropic effect of 4-substituents on the1H NMR chemical shift of H-5 in phenanthrenes

  摘要：

  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.

  DOI：

  10.1002/mrc.1270160311
• 作为产物：
  描述：

  Alpha-甲基苯乙烯 、 3,5-二甲氧基苯硼酸 在 双(乙腈)氯化钯(II) 、 氧气 、 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以68%的产率得到1-[(E)-2-(4-methylphenyl)ethenyl]-3,5-dimethoxybenzene
  参考文献：
  名称：

  方便快捷地获得白藜芦醇衍生物及其辐射防护活性

  摘要：

  基于芳基硼酸与苯乙烯的钯催化氧化Heck反应，然后以中等至良好的产率脱甲基，可以轻松快速地获得白藜芦醇衍生物。易于合成一系列具有各种官能团的白藜芦醇衍生物。还已经使用大鼠胸腺细胞评估了合成化合物的放射防护活性。结果表明，一些白藜芦醇衍生物有效地保护了胸腺细胞免受辐射诱导的细胞凋亡。

  DOI：

  10.1016/j.bmcl.2016.07.018

文献信息

• Photoinitiated carbonyl-metathesis: deoxygenative reductive olefination of aromatic aldehydes <i>via</i> photoredox catalysis
  作者：Shun Wang、Nanjundappa Lokesh、Johnny Hioe、Ruth M. Gschwind、Burkhard König

  DOI：10.1039/c9sc00711c

  日期：——

  carbonyl groups in a single reaction are less explored. Here, we report a photoredox-catalysis that uses B2pin2 as terminal reductant and oxygen trap allowing for deoxygenative olefination of aromatic aldehydes under mild conditions. This strategy provides access to a diverse range of symmetrical and unsymmetrical alkenes with moderate to high yield (up to 83%) and functional-group tolerance. To follow

  羰基-羰基烯化反应，即 McMurry 反应，代表了构建烯烃的有力策略。然而，在单个反应中直接偶联两个羰基的催化变体的探索较少。在这里，我们报告了一种使用 B 2 pin 2的光氧化还原催化作为末端还原剂和氧阱，允许在温和条件下对芳族醛进行脱氧烯化。该策略提供了获得各种对称和不对称烯烃的途径，具有中等至高产率（高达 83%）和官能团耐受性。为了遵循反应途径，进行了一系列实验，包括自由基抑制、氘标记、荧光猝灭和循环伏安法。此外，结合 NMR 研究和 DFT 计算来检测和分析三种活性中间体：环状三元阴离子物质、α-氧硼基碳负离子和 1,1-苄基二硼酸酯。基于这些结果，我们提出了一种 C C 键生成机制，涉及顺序自由基硼化、“bora-Brook”重排、B 2pin 2介导的脱氧和硼-维蒂希过程。
• Stereospecific Iron-Catalyzed Carbon (sp²)–Carbon (sp²) Cross-Coupling of Aryllithium with Vinyl Halides
  作者：Peng Chen、Zhi-Yong Wang、Xiao-Shui Peng、Henry N.C. Wong

  DOI：10.1021/acs.orglett.1c01318

  日期：2021.6.4

  We present herein an efficient synthetic protocol involving iron-catalyzed cross-coupling of organolithium compounds with vinyl halides as key coupling partners. More than 30 examples were obtained with moderate to good yields and high stereoselectivities. The practicality of this method is evidenced by a gram-scale synthesis. In addition, a preliminary mechanistic investigation was also performed

  我们在此提出了一种有效的合成方案，涉及有机锂化合物与乙烯基卤化物作为关键偶联伙伴的铁催化交叉偶联。获得了 30 多个具有中等至良好产率和高立体选择性的实例。克级合成证明了该方法的实用性。此外，还进行了初步的机械调查。
• A Simple Access to Biologically Important<i>trans</i>-Stilbenes via Ru-Catalyzed Cross Metathesis
  作者：Hans-Günther Schmalz、Janna Velder、Stefanie Ritter、Johann Lex

  DOI：10.1055/s-2005-918506

  日期：——

  The cross metathesis of methoxy- or acetoxy-substituted styrenes using the Grubbs II catalyst affords unsymmetrical (mixed) E-stilbenes with astonishingly high selectivity (up to 79% yield). This approach offers a short and flexible synthesis of variously substituted stilbenes, which are derivatives or precursors of biologically important compounds such as resveratrol, piceatannol, and pinostilbene

  使用 Grubbs II 催化剂对甲氧基或乙酰氧基取代的苯乙烯进行交叉复分解，得到了具有惊人高选择性（高达 79% 产率）的不对称（混合）E-二苯乙烯。这种方法提供了各种取代的二苯乙烯的短而灵活的合成，它们是生物重要化合物如白藜芦醇、白杉醇和松芪的衍生物或前体。
• An efficient palladium-catalyzed Negishi cross-coupling reaction with arylvinyl iodides: facile regioselective synthesis of E-stilbenes and their analogues
  作者：M. Shahjahan Kabir、Aaron Monte、James M. Cook

  DOI：10.1016/j.tetlet.2007.08.047

  日期：2007.10

  A general synthetic route for the Pd-catalyzed cross-coupling of an arylzinc reagent with arylvinyl iodides (Negishi cross-coupling) has been developed. The system permits efficient and selective preparation of E-stilbenes and their analogues. It also functions effectively at low levels of catalyst loading without the need for an additional ligand and tolerates a wide range of functional groups including

  已经开发出一种通常的合成路线，用于钯催化的芳基锌试剂与芳基乙烯基碘的交叉偶联（Negishi交叉偶联）。该系统允许有效地和选择性地制备E-芪及其类似物。它在催化剂用量低的情况下也能有效发挥功能，而无需其他配体，并能耐受包括杂芳族底物在内的各种官能团。进行了各种参数的系统研究，并将其与催化剂-底物活性相关联。
• COMPOSITION CONTAINING RESVERATROL AND/OR DERIVATIVES THEREOF AND PLANT OIL, PROCESS FOR PRODUCING SAID COMPOSITION, NUTRACEUTICAL AND/OR PHARMACEUTICAL PRODUCT, AND METHOD FOR ENHANCING THE POTENTIAL OF RESVERATROL
  申请人：Souto Andre Arigony

  公开号：US20130040920A1

  公开（公告）日：2013-02-14

  The present invention is a method for obtaining a formulation of resveratrol and rice bran oil. The resulting product in the form of an oil or solid proves to increase the therapeutic potential of resveratrol by the synergistic action of the components of the rice oil. The product obtained through the method of the invention is an active principle which, when incorporated in nutraceutical and/or pharmaceutical compositions, provides antioxidant, anti-inflammatory, antiviral, cardioprotective, neuroprotective and/or cancer chemoprotective action, besides protecting against infections and ischemia, reducing obesity, and preventing illnesses of old age.