2,6-二(4-氯苯基)吡喃-4-酮 | 1469-91-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 2,6-二(4-氯苯基)吡喃-4-酮
• 中文别名: 2,6-二(4-氯苯基)-4H-吡喃-4-酮
• 英文名称: 2,6-bis(4-chlorophenyl)-4H-pyran-4-one
• 英文别名: 2,6-di-(4-chlorophenyl)-4H-pyran-4-one；2,6-bis-(4-chloro-phenyl)-pyran-4-one；2,6-Bis-<4-chlor-phenyl>-4-pyron；2,6-bis(4-chlorophenyl)pyran-4-one
• CAS: 1469-91-6
• 化学式: C₁₇H₁₀Cl₂O₂
• 分子量: 317.171
• InChiKey: UHCSAGVHHGRIOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 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：
  2

反应信息

• 作为产物：
  描述：

  ((1-(4-chlorophenyl)vinyl)oxy)trimethylsilane 以 乙醚 、 甲苯 为溶剂， 反应 6.0h， 生成 2,6-二(4-氯苯基)吡喃-4-酮
  参考文献：
  名称：

  Thermal Addition Reaction of Aroylketene with 1-Aryl-1-trimethylsilyloxyethylenes: Aromatic Substituent Effects of Aroylketene and Aryltrimethylsilyloxyethylene on Their Reactivity.

  摘要：

  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。

  DOI：

  10.1248/cpb.44.956

文献信息

• 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。
• 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.
• 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。