2,6-bis(4-methoxyphenyl)-4H-pyran-4-one | 1678-14-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,6-bis(4-methoxyphenyl)-4H-pyran-4-one
• 英文别名: 4H-Pyran-4-one, 2,6-bis(p-methoxyphenyl)-；2,6-bis(4-methoxyphenyl)pyran-4-one
• CAS: 1678-14-4
• 化学式: C₁₉H₁₆O₄
• 分子量: 308.334
• InChiKey: LECSSHUYKZKQDD-UHFFFAOYSA-N

物化性质

• 熔点：
  189-190 °C(Solv: benzene (71-43-2); ligroine (8032-32-4))
• 沸点：
  528.3±50.0 °C(Predicted)
• 密度：
  1.218±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  2,6-bis(4-methoxyphenyl)-4H-pyran-4-one 在 phosphorous (V) sulfide 、 苯 作用下， 生成 2,6-bis-(4-methoxy-phenyl)-pyran-4-thione
  参考文献：
  名称：

  Experiments with 4-Thiopyrones and with 2,2',6,6'-Tetraphenyl-4,4'-dipyrylene. The Piezochromism of Diflavylene

  摘要：

  DOI：

  10.1021/ja01556a037
• 作为产物：
  描述：

  1,5-bis(4-methoxyphenyl)-1,3,5-pentanetrione 在 硫酸 作用下， 以83%的产率得到2,6-bis(4-methoxyphenyl)-4H-pyran-4-one
  参考文献：
  名称：

  New Strong Base Synthesis of Symmetrical 1,5-Diaryl-1,3,5-pentanetriones from Acetone and Benzoate Esters

  摘要：

  Lithium hexamethyldisilazide (LiHMDS) was used to condense substituted benzoate esters with acetone to afford symmetrical 1,5-diaryl-1,3,5-pentanetriones that were isolated, characterized (including a representative X-ray crystallographic analysis), and acid cyclized to the respective 2,6-diaryl-4H-pyran-4-ones.

  DOI：

  10.1080/00397910802138488

文献信息

• Regiodivergent Hydration–Cyclization of Diynones under Gold Catalysis
  作者：Marta Solas、Miguel A. Muñoz、Samuel Suárez-Pantiga、Roberto Sanz

  DOI：10.1021/acs.orglett.0c02892

  日期：2020.10.2

  Skipped diynones, efficiently prepared from biomass-derived ethyl lactate, undergo a tandem hydration–oxacyclization reaction under gold(I) catalysis. Reaction conditions have been developed for a switchable process that allows selective access to 4-pyrones or 3(2H)-furanones from the same starting diynones. Further application of this methodology in the total synthesis of polyporapyranone B was demonstrated

  由生物质衍生的乳酸乙酯有效制备的已跳过的二炔酮，在金（I）催化下经历了串联水合-氧环化反应。已经开发了用于可切换过程的反应条件，该过程允许从相同的起始二炔酮选择性地获得4-吡喃酮或3（2 H）-呋喃酮。证明了该方法在聚吡喃酮B的全合成中的进一步应用。
• Synthesis of γ-pyrones via decarboxylative condensation of β-ketoacids
  作者：Jérémy Merad、Thomas Maier、Catarina A. B. Rodrigues、Nuno Maulide

  DOI：10.1007/s00706-016-1851-2

  日期：2017.1

  AbstractThis manuscript describes the convergent synthesis of aryl- and alkyl-disubstituted γ-pyrones from β-ketoacids. The reaction proceeds in the presence of trifluoromethanesulfonic anhydride via an unprecedented decarboxylative auto-condensation of the starting material. Herein, the scope and limitations of this transformation are reported. Graphical abstract

  摘要该手稿描述了由β-酮酸聚合合成芳基和烷基二取代的γ-吡喃酮。反应在三氟甲磺酸酐的存在下通过原料的空前的脱羧自动缩合而进行。在此，报道了这种转变的范围和局限性。 图形概要
• Thermal Addition Reaction of Aroylketene with 1-Aryl-1-trimethylsilyloxyethylenes: Aromatic Substituent Effects of Aroylketene and Aryltrimethylsilyloxyethylene on Their Reactivity.
  作者：Toshiaki SAITOH、Taichi OYAMA、Kiyomi SAKURAI、Yosihiro NIIMURA、Mitsuru HINATA、Yoshie HORIGUCHI、Jun TODA、Takehiro SANO

  DOI：10.1248/cpb.44.956

  日期：——

  The thermal addition reaction of various aroylketenes (C) generated by the thermolysis of 5-aryldioxofurans (A) to 1-aryl-1-trimethylsilyloxyethylenes gave 1, 5-diarylpentane-1, 3, 5-triones (D) and 2, 6-diaryl-4H-pyran-4-ones (E). The introduction of electron withdrawing substituents in the aroylketene and of electron donating substituents facilitated the addition reaction. The observed substituent effects and the reaction mechanism are interpreted in terms of molecular orbital analyses.

  通过对5-芳基二氧呋喃（A）的热分解生成的多种芳酰基酮（C）与1-芳基-1-三甲基硅氧基乙烯的热加成反应，生成了1, 5-二芳基戊烷-1, 3, 5-三酮（D）和2, 6-二芳基-4H-吡喃-4-酮（E）。在芳酰基酮中引入电子拉电子取代基以及在反应中引入电子给体取代基促进了加成反应。观察到的取代基效应和反应机制通过分子轨道分析进行了解释。
• Compositions And Methods For Visible-Light-Controlled Ruthenium-Catalyzed Olefin Metathesis
  申请人：The Trustees of Columbia University In The City of New York

  公开号：US20200108381A1

  公开（公告）日：2020-04-09

  The present disclosure provides compositions and methods for metathesizing a first alkenyl or alkynyl group with a second alkenyl or alkynyl group, the composition comprising a ruthenium metathesis catalyst and a photoredox catalyst that is activated by visible light.

  本公开提供了一种用于将第一烯基或炔基与第二烯基或炔基进行交换反应的组合物和方法，所述组合物包括一种钌交换催化剂和一种可被可见光激活的光还原催化剂。
• Atom-Economic Synthesis of 4-Pyrones from Diynones and Water
  作者：Yan-Li Xu、Qing-Hu Teng、Wei Tong、Heng-Shan Wang、Ying-Ming Pan、Xian-Li Ma

  DOI：10.3390/molecules22010109

  日期：——

  Transition-metal-free synthesis of 4-pyrones via TfOH-promoted nucleophilic addition/cyclization of diynones and water has been developed. This transformation is simple, atom economical and environmentally benign, providing rapid and efficient access to substituted 4-pyrones.

  已经开发出通过 TfOH 促进二炔酮和水的亲核加成/环化来无过渡金属合成 4-吡喃酮。这种转化简单、原子经济且环境友好，可快速有效地获得取代的 4-吡喃酮。