5-(p-tolyl)-2,3-dihydrothieno[3,4-b][1,4]dioxine | 925674-57-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(p-tolyl)-2,3-dihydrothieno[3,4-b][1,4]dioxine
• 英文别名: Thieno[3,4-b]-1,4-dioxin,2,3-dihydro-5-(4-methylphenyl)-；5-(4-methylphenyl)-2,3-dihydrothieno[3,4-b][1,4]dioxine
• CAS: 925674-57-3
• 化学式: C₁₃H₁₂O₂S
• 分子量: 232.303
• InChiKey: OGGMIKKHDAKHBZ-UHFFFAOYSA-N

物化性质

• 沸点：
  362.5±41.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(p-tolyl)-2,3-dihydrothieno[3,4-b][1,4]dioxine 在 potassium tert-butylate 、 三氯氧磷 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 34.0h， 生成 2-((2,3-dihydro-5-p-tolylthieno[3,4-b][1,4]dioxin-7-yl)methylene)malononitrile
  参考文献：
  名称：

  Pd-mediated C–H arylation of EDOT and synthesis of push–pull systems incorporating EDOT

  摘要：

  The direct C-H arylation of 3,4-ethylenedioxythiophene (EDOT) is described under Heck-type experimental conditions. This methodology has been used to synthesize a series of push-pull systems containing EDOT units. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.07.037
• 作为产物：
  描述：

  4-碘甲苯 、 3,4-乙烯二氧噻吩 在 四(三苯基膦)钯 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以45%的产率得到5-(p-tolyl)-2,3-dihydrothieno[3,4-b][1,4]dioxine
  参考文献：
  名称：

  Pd-mediated C–H arylation of EDOT and synthesis of push–pull systems incorporating EDOT

  摘要：

  The direct C-H arylation of 3,4-ethylenedioxythiophene (EDOT) is described under Heck-type experimental conditions. This methodology has been used to synthesize a series of push-pull systems containing EDOT units. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.07.037

文献信息

• Direct C–H Arylation of Thiophenes at Low Catalyst Loading of a Phosphine-Free Bis(alkoxo)palladium Complex
  作者：Yabo Li、Jingran Wang、Mengmeng Huang、Zhiwei Wang、Yusheng Wu、Yangjie Wu

  DOI：10.1021/jo402745b

  日期：2014.4.4

  An efficient phosphine-free direct C–H arylation of thiophenes at the α-position has been developed at low catalyst loading of bis(alkoxo)palladium complex (Cat.I, 0.1–0.2 mol %). The developed synthetic method can be applied to the synthesis of α-aryl/heteroaryl thiophenes from aryl or heteroaryl bromides in good to excellent yields and is compatible with the substrates bearing electron-donating or

  在双（烷氧基）钯配合物（Cat.I，0.1-0.2 mol％）的低催化剂负载下，已开发出一种有效的无磷的噻吩在α位上无膦直接CH芳基化的化合物。所开发的合成方法可用于从芳基或杂芳基溴化物以良好至优异的产率合成α-芳基/杂芳基噻吩，并且与带有给电子或吸电子基团的底物相容。噻吩2位和5位的反应性是相同的，并且在最佳条件下不依赖于空间位阻。该条件还可以以高转化率应用于其他杂环部分，例如苯并噻吩，苯并呋喃和吡咯。
• An Efficient C−Si/C−H Cross‐Coupling Reaction Enabled by a Radical Pathway
  作者：Chunchun Mi、Bei‐Bei Zhang、Guanghao Zhang、Aidong Peng、Zhi‐Xiang Wang、Qinqin Shi、Hui Huang

  DOI：10.1002/chem.202303857

  日期：2024.3.25

  The aryl radical from sulfonium salts have been generated through copper-metal-catalyzed processes, which enable the successful biaryl transformation through the addition to the aryl(trialkyl)silanes for the first time. Given the fast development in the copper catalysis, this method is expected to present new opportunities for exploring aryl(trialkyl)silanes in biaryl synthesis.

  锍盐中的芳基自由基是通过铜金属催化过程产生的，首次通过添加到芳基（三烷基）硅烷中成功实现了联芳基转化。鉴于铜催化的快速发展，该方法有望为探索联芳基合成中的芳基（三烷基）硅烷提供新的机会。
• Synthesis of mono- and bis-arylated 3,4-(ethylenedioxythiophenes) via direct palladium catalyzed arylation reactions
  作者：Arasambattu K. Mohanakrishnan、P. Amaladass、J. Arul Clement

  DOI：10.1016/j.tetlet.2006.11.138

  日期：2007.1

  The synthesis of arylated/heteroarylated 3,4-ethylenedioxythiophene derivatives is reported using a straightforward palladium mediated Heck coupling of 3,4-ethylenedioxythiophene with various aryl/heteroaryl halides. (c) 2006 Elsevier Ltd. All rights reserved.
• Pd-mediated C–H arylation of EDOT and synthesis of push–pull systems incorporating EDOT
  作者：P. Amaladass、J. Arul Clement、Arasambattu K. Mohanakrishnan

  DOI：10.1016/j.tet.2007.07.037

  日期：2007.10

  The direct C-H arylation of 3,4-ethylenedioxythiophene (EDOT) is described under Heck-type experimental conditions. This methodology has been used to synthesize a series of push-pull systems containing EDOT units. (C) 2007 Elsevier Ltd. All rights reserved.