(E)-ethyl 3-(2,5-dimethoxyphenyl)acrylate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-ethyl 3-(2,5-dimethoxyphenyl)acrylate
• 英文别名: ethyl (E)-3-(2,5-dimethoxyphenyl)acrylate；ethyl (E)-3-(2,5-dimethoxyphenyl)prop-2-enoate
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: XIEVTAMMUAMFIQ-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 3-(2,5-dimethoxyphenyl)acrylate 在 palladium on activated charcoal 氢气 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， -70.0~20.0 ℃ 、101.33 kPa 条件下， 反应 14.75h， 生成 ethyl 2-(2,5-dimethoxybenzyl)pent-4-enoate
  参考文献：
  名称：

  Efficient Approach to 4‐Benzyl‐5,5‐dimethyldihydrofuranones: Total Synthesis of (±_bold;)‐Solafuranone

  摘要：

  DOI：

  10.1080/00397910601163919
• 作为产物：
  描述：

  2,5-二甲氧基苯甲醛 在 acid 作用下， 生成 (E)-ethyl 3-(2,5-dimethoxyphenyl)acrylate
  参考文献：
  名称：

  Solid State Behaviour of Vinyl Quinones

  摘要：

  2,5-Bisvinyl-1,4-benzoquinones 1 and 2-vinyl-1,4-benzoquinones 2 substituted with aryl or ester end groups have been synthesized. The 2,5-bisstyryl-1,4-benzoquinones 1 (R=phenyl, p-tolyl, o-tolyl) crystallize with a 7 Angstrom-stacking axis. But only for the o-tolyl derivative the contacts between the vinyl groups are close enough to allow a four-center type photopolymerization. The ester derivative 1 (R=COOEt) has a layer structure and can be photooligomerized in the crystal. The generated cyclobutane subgroups have twofold symmetry. The vinylquinones 2 (R=aryl) may be dimerized photochemically in the crystal at the vinyl groups to centrosymmetric cyclobutanes. Crystals with 4 Angstrom stacking axis are also photoreactive.

  DOI：

  10.1080/10587259608039394

文献信息

• Nucleophilic Amination of Methoxy Arenes Promoted by a Sodium Hydride/Iodide Composite
  作者：Atsushi Kaga、Hirohito Hayashi、Hiroyuki Hakamata、Miku Oi、Masanobu Uchiyama、Ryo Takita、Shunsuke Chiba

  DOI：10.1002/anie.201705916

  日期：2017.9.18

  Come full circle: A method for the nucleophilic amination of methoxy arenes was established by using sodium hydride (NaH) in the presence of lithium iodide (LiI). This method offers an efficient route to benzannulated nitrogen heterocycles. Mechanistic studies showed that the reaction proceeds through an unusual concerted nucleophilic aromatic substitution.

  围成一圈：在碘化锂（LiI）存在下，使用氢化钠（NaH）建立了甲氧基芳烃的亲核胺化方法。该方法提供了一条有效的途径来制得二环氮杂环。机理研究表明，该反应通过异常的协同的亲核芳族取代进行。
• A Microwave-Accelerated Esterification of?,?-Unsaturated Acids with Alkyl or Aryl Carbonochloridate and Triethylamine in Acetonitrile as a Novel Esterifying Reagent Mixture
  作者：Vinod Pathania、Anuj Sharma、Arun?K. Sinha

  DOI：10.1002/hlca.200590058

  日期：2005.4

  An efficient synthesis of α,β-unsaturated esters by treatment of the corresponding acids with alkyl or aryl carbonochloridate, triethylamine, and acetonitrile was accomplished for the first time under microwave irradiation for 10 min. The esters 1b–24b were isolated in 71–97% yield.

  通过用烷基或芳基碳氯化物，三乙胺和乙腈处理相应的酸，在微波辐射下第一次完成10分钟，可以有效合成α，β-不饱和酯。分离出酯1b - 24b的产率为71-97％。
• Synthesis, structure and catalytic activity of a gold(<scp>i</scp>) complex containing 1,2-bis(diphenylphosphino)benzene monoxide
  作者：Christine Hahn、Leticia Cruz、Amanda Villalobos、Liliana Garza、Samuel Adeosun

  DOI：10.1039/c4dt02116a

  日期：——

  The gold(I) complex [Au(dppbO)Cl] was synthesized by reaction of Na[AuCl4]·2H2O with 1,2-bis(diphenylphosphino)benzene (dppb) in the presence of water. This is a new method for the synthesis of a bisphosphine monoxide gold(I) complex. The new gold(I) complex was characterized by NMR spectroscopy and X-ray crystal structure analysis. In the solid state structure a relatively short contact between the

  金（I）配合物[Au（dppbO）Cl]是在水存在下，通过Na [AuCl 4 ]·2H 2 O与1,2-双（二苯基膦基）苯（dppb）的反应合成的。这是合成双膦一氧化金（I）配合物的新方法。通过NMR光谱和X射线晶体结构分析表征了新的金（I）配合物。在固态结构中，观察到氧化膦基团的氧原子与金中心之间的相对短的接触。测试了[Au（dppbO）Cl]的催化活性，用于三种不同的分子间炔烃加氢官能化反应。四氟硼酸银用作卤化物提取的助催化剂。而一氧化二膦金（I）配合物显示出对各种炔烃的水合和苯基乙炔的氢化胺化的中等活性，对丙炔酸乙酯的氢芳基化观察到了高活性。富电子芳烃可快速添加至C-C三键，但选择性相对较低。
• Synthesis of Bidentate Nitrogen Ligands by Rh-Catalyzed C–H Annulation and Their Application to Pd-Catalyzed Aerobic C–H Alkenylation
  作者：Hyun Tae Kim、Eunsu Kang、Minkyu Kim、Jung Min Joo

  DOI：10.1021/acs.orglett.1c01040

  日期：2021.5.7

  A new class of bidentate ligands was prepared by a modular approach involving Rh-catalyzed C–H annulation reactions. The resulting conformationally constrained ligands enabled the Pd-catalyzed C–H alkenylation at electron-rich and sterically less hindered positions of electron-rich arenes while promoting the facile oxidation of Pd(0) intermediates by oxygen. This newly introduced ligand class is complementary

  通过涉及Rh催化的C–H环化反应的模块化方法，制备了一类新的双齿配体。最终形成的构象受约束的配体使Pd催化的C-H链烯基在富电子和富电子芳烃的位置上受阻较小，同时促进了Pd（0）中间体容易被氧氧化。这种新引入的配体类别与为Pd催化的氧化反应开发的配体互补，并可能在过渡金属催化的反应中找到广泛的应用。
• S,O‐Ligand‐Promoted Pd‐Catalyzed C−H Olefination of Anisole Derivatives
  作者：Verena Sukowski、Wen‐Liang Jia、Rianne Diest、Manuela Borselen、M. Ángeles Fernández‐Ibáñez

  DOI：10.1002/ejoc.202100737

  日期：2021.8.6

  The C−H olefination of substituted anisole derivatives as limiting reagents has been realized by a Pd/S, O-ligand catalyst providing the olefinated products in good yields and site selectivities. The reaction proceeds under mild conditions with a broad range of substituted aryl ethers bearing both electron-donating and electron-withdrawing substituents.

  作为限制试剂的取代苯甲醚衍生物的 CH 烯化已通过 Pd/S、O-配体催化剂实现，以良好的产率和位点选择性提供烯化产物。该反应在温和条件下进行，具有广泛的取代芳基醚，带有给电子和吸电子取代基。