(4aRS,9bRS)-4a,9b-dihydro-2,6,8,9b-tetramethyl-4H-dibenzofuran-3-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: (4aRS,9bRS)-4a,9b-dihydro-2,6,8,9b-tetramethyl-4H-dibenzofuran-3-one
• 英文别名: cis-2,6,8,9b-tetramethyl-4a,9b-dihydrodibenzo[b,d]furan-3(4H)-one；(4aS,9bS)-2,6,8,9b-tetramethyl-4,4a-dihydrodibenzofuran-3-one
• 化学式: C₁₆H₁₈O₂
• 分子量: 242.318
• InChiKey: XZDYSEGWQBESNQ-HOCLYGCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,4-二甲基苯酚 在 potassium phosphate 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以30%的产率得到(4aRS,9bRS)-4a,9b-dihydro-2,6,8,9b-tetramethyl-4H-dibenzofuran-3-one
  参考文献：
  名称：

  碘代苯促进的氧化酚偶联反应合成Pummerer's酮及其类似物

  摘要：

  已经开发了由碘代苯促进的分子间酚偶联，导致了Pummerer的酮及其类似物。该反应允许以优异的非对映选择性制备具有多种取代模式的衍生自酚和萘酚的产物。Pummerer的酮类化合物是唯一的低分子量产物，与简单的实验条件一起使该反应成为进入该重要分子基序的便捷途径。

  DOI：

  10.1016/j.tetlet.2020.152459

文献信息

• Novel Template-Directed Anodic Phenol-Coupling Reaction
  作者：Itamar M. Malkowsky、Christina E. Rommel、Roland Fröhlich、Ulrich Griesbach、Hermann Pütter、Siegfried R. Waldvogel

  DOI：10.1002/chem.200600375

  日期：2006.9.25

  Substituted phenols were anodically coupled to the corresponding 2,2'-biphenols via tetraphenoxy borate derivatives. This electrochemical method is particularly useful for methyl-substituted substrates, such as 2,4-dimethyl phenol. The selective ortho-coupling reaction can be easily performed on a multikilogram scale.

  通过四苯氧基硼酸酯衍生物将取代的酚与相应的2,2'-双酚进行阳极偶联。该电化学方法对于甲基取代的底物，例如2，4-二甲基苯酚特别有用。选择性邻位偶联反应可以轻松地在几千克规模上进行。
• Facile and Highly Diastereoselective Formation of a Novel Pentacyclic Scaffold by Direct Anodic Oxidation of 2,4-Dimethylphenol
  作者：Itamar M. Malkowsky、Christina E. Rommel、Katrin Wedeking、Roland Fröhlich、Klaus Bergander、Martin Nieger、Claudia Quaiser、Ulrich Griesbach、Hermann Pütter、Siegfried R. Waldvogel

  DOI：10.1002/ejoc.200500517

  日期：2006.1

  Electrochemical oxidation of 2,4-dimethylphenol directly provides pentacyclic systems being generated by an oxidative trimerization. The major pentacyclic scaffold is exclusively formed as a single diastereoisomer and is easily isolated. Three further pentacyclic compounds which occur in minor quantities were also fully characterized including their solid-state structures. (© Wiley-VCH Verlag GmbH

  2,4-二甲基苯酚的电化学氧化直接提供了通过氧化三聚反应生成的五环系统。主要的五环支架完全以单一的非对映异构体形式形成，并且很容易分离。另外三种少量出现的五环化合物也被完全表征，包括它们的固态结构。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Unexpected Highly Chemoselective Anodicortho-Coupling Reaction of2,4-Dimethylphenol on Boron-Doped Diamond Electrodes
  作者：Itamar M. Malkowsky、Ulrich Griesbach、Hermann Pütter、Siegfried R. Waldvogel

  DOI：10.1002/ejoc.200600466

  日期：2006.10

  Anodic conversion of 2,4-dimethylphenol on boron-doped diamond (BDD) electrodes under solvent-free conditions results in an unusual highly selective formation of the desired 2,2′-biphenol, representing the best electrochemical synthesis for this particular compound. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

  在无溶剂条件下，2,4-二甲基苯酚在掺硼金刚石 (BDD) 电极上的阳极转化导致所需的 2,2'-双酚的异常高选择性形成，代表了这种特定化合物的最佳电化学合成。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Synthesis of Pummerer’s ketone and its analogs by iodosobenzene-promoted oxidative phenolic coupling
  作者：Sudeep Sarkar、Manoj K. Ghosh、Marcin Kalek

  DOI：10.1016/j.tetlet.2020.152459

  日期：2020.10

  An intermolecular phenolic coupling promoted by iodosobenzene leading to Pummerer’s ketone and its analogs has been developed. The reaction allows for the preparation of products derived from both phenols and naphthols, bearing various substitution patterns, in excellent diasteroselectivity. The Pummerer’s ketone-type compounds form as sole low molecular weight products, which together with simple

  已经开发了由碘代苯促进的分子间酚偶联，导致了Pummerer的酮及其类似物。该反应允许以优异的非对映选择性制备具有多种取代模式的衍生自酚和萘酚的产物。Pummerer的酮类化合物是唯一的低分子量产物，与简单的实验条件一起使该反应成为进入该重要分子基序的便捷途径。