2,6-bis(4-fluorophenyl)-4H-pyran-4-one | 331840-68-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2,6-bis(4-fluorophenyl)-4H-pyran-4-one
• 英文别名: 2,6-Bis(4-fluorophenyl)pyran-4-one
• CAS: 331840-68-7
• 化学式: C₁₇H₁₀F₂O₂
• 分子量: 284.262
• InChiKey: STUFZCLYJBYJQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 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-fluorophenyl)-4H-pyran-4-one 在 potassium carbonate 、 三氯氧磷 作用下， 以 N-甲基吡咯烷酮 、 甲苯 为溶剂， 生成 4-(10H-phenothiazin-10-yl)-2,6-bis(4-(p-tolyloxy)phenyl)pyrylium perchlorate
  参考文献：
  名称：

  Functional Aromatic Polyethers: Polymers with Tunable Chromogenic and Fluorogenic Properties

  摘要：

  This paper describes the preparation and chemical modification of pyranone-based aromatic polyethers to yield polymers that contain pyrylium rings, which permit the design of high performance materials with "a la carte" chromogenic and fluorescence behavior. These materials can be used for innovative applications such as luminescent converter (LUCO) materials for hybrid light-emitting diodes (LEDs) or the preparation of selective chromogenic and fluorogenic sensing materials for the preparation of sensing devices. The fluorescence emission maxima of polyether films ranged from 514 to 561 nm, allowing the future development of LUCO-LED devices. Moreover, the interaction of polyether films with different amines leads to color changes and variations in the intensity and emission maxima of fluorescence, which permits the development of amine sensing materials.

  DOI：

  10.1021/ma101106a
• 作为产物：
  描述：

  1-(4-氟苯基)-1,3-丁二酮 在 sodium hydride 作用下， 以 乙二醇二甲醚 为溶剂， 生成 2,6-bis(4-fluorophenyl)-4H-pyran-4-one
  参考文献：
  名称：

  Functional Aromatic Polyethers: Polymers with Tunable Chromogenic and Fluorogenic Properties

  摘要：

  This paper describes the preparation and chemical modification of pyranone-based aromatic polyethers to yield polymers that contain pyrylium rings, which permit the design of high performance materials with "a la carte" chromogenic and fluorescence behavior. These materials can be used for innovative applications such as luminescent converter (LUCO) materials for hybrid light-emitting diodes (LEDs) or the preparation of selective chromogenic and fluorogenic sensing materials for the preparation of sensing devices. The fluorescence emission maxima of polyether films ranged from 514 to 561 nm, allowing the future development of LUCO-LED devices. Moreover, the interaction of polyether films with different amines leads to color changes and variations in the intensity and emission maxima of fluorescence, which permits the development of amine sensing materials.

  DOI：

  10.1021/ma101106a

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。
• Brønsted Acid Catalyzed and NIS-Promoted Cyclization of Diynones: Selective Synthesis of 4-Pyrone, 4-Pyridone, and 3-Pyrrolone Derivatives
  作者：Yi-Feng Qiu、Fang Yang、Zi-Hang Qiu、Mei-Jin Zhong、Li-Jing Wang、Yu-Ying Ye、Bo Song、Yong-Min Liang

  DOI：10.1021/jo402055a

  日期：2013.12.6

  Brønsted acid catalyzed tandem cyclization was found to be highly effective for the preparation of a series of polysubstituted 4-pyrones from diynones (yield up to 99%). 4-Pyridone and 3-pyrrolone derivatives were also selectively synthesized by employing NIS and/or Brønsted acid. NIS as an electrophilic reagent could promote these reactions efficiently and rapidly under very mild reaction conditions

  发现布朗斯台德酸催化的串联环化对于从二炔酮制备一系列多取代的4-吡喃酮非常有效（收率高达99％）。还通过使用NIS和/或布朗斯台德酸选择性地合成了4-吡啶酮和3-吡咯烷酮衍生物。NIS作为亲电子试剂可以在非常温和的反应条件下有效而迅速地促进这些反应。
• 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。
• Synthesis of γ-Pyrones and <i>N</i>-Methyl-4-pyridones via the Au Nanoparticle-Catalyzed Cyclization of Skipped Diynones in the Presence of Water or Aqueous Methylamine
  作者：Elisavet-Maria Zantioti-Chatzouda、Vasiliki Kotzabasaki、Manolis Stratakis

  DOI：10.1021/acs.joc.2c00627

  日期：2022.7.1

  were not seen. The reaction does not proceed via the initial 1,3-transposition of the skipped diynones to their corresponding conjugated 1,3-diynone isomers. If aqueous methylamine is added, N-methyl-4-pyridones are exclusively formed in 69–79% yields via an analogous hydroamination/Au-catalyzed 6-endo cyclization pathway.

  负载在 TiO 2上的 Au 纳米颗粒通过三键活化催化跳过的二炔酮在含水二恶烷中水合/6-内环化为 γ-吡喃酮。没有看到可以使用均相离子 Au(I) 催化剂通过竞争且通常占主导地位的 5-外环化途径形成的异构 3(2 H )-呋喃酮。该反应不会通过跳过的二炔酮的初始 1,3-转位为其相应的共轭 1,3-二炔酮异构体进行。如果加入甲胺水溶液，则通过类似的加氢胺化/Au 催化的 6-内环化途径仅以 69-79% 的产率形成N-甲基-4-吡啶酮。
• New Strong Base Synthesis of Symmetrical 1,5-Diaryl-1,3,5-pentanetriones from Acetone and Benzoate Esters
  作者：John D. Knight、Clyde R. Metz、Charles F. Beam、William T. Pennington、Donald G. VanDerveer

  DOI：10.1080/00397910802138488

  日期：2008.6.27

  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.