ethyl 2-oxo-6-phenyl-2H-pyran-5-carboxylate | 1476744-04-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: ethyl 2-oxo-6-phenyl-2H-pyran-5-carboxylate
• 英文别名: Ethyl 6-oxo-2-phenylpyran-3-carboxylate；ethyl 6-oxo-2-phenylpyran-3-carboxylate
• CAS: 1476744-04-3
• 化学式: C₁₄H₁₂O₄
• 分子量: 244.247
• InChiKey: KOSHTJCCOPXXID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  丙烯酸 、 苯丙炔酸乙酯 在 氧气 、 palladium diacetate 、 三乙胺 、 copper(ll) bromide 作用下， 以 乙酸酐 、 溶剂黄146 为溶剂， 反应 12.0h， 以78%的产率得到ethyl 2-oxo-6-phenyl-2H-pyran-5-carboxylate
  参考文献：
  名称：

  Palladium-Catalyzed Oxidative Annulation of Acrylic Acid and Amide with Alkynes: A Practical Route to Synthesize α-Pyrones and Pyridones

  摘要：

  A range of internal alkynes smoothly underwent palladium-catalyzed oxidative annulations with acrylic acid and amide to afford alpha-pyrones and pyridones in good to excellent yields with high regioselectivity. The usage of O-2 (1 atm) as a stoichiometric oxidant with H2O as the only byproduct under mild conditions makes this process more attractive and practical.

  DOI：

  10.1021/ol500611d

文献信息

• Ruthenium-Catalyzed Dimerization of Propiolates: A Simple Route to α-Pyrones
  作者：Rajendran Manikandan、Masilamani Jeganmohan

  DOI：10.1021/ol4035929

  日期：2014.2.7

  A ruthenium-catalyzed regioselective intermolecular multistep homo- and heterodimerization of substituted propiolates providing α-pyrone-5-carboxylates and α-pyrone-6-carboxylates is described. The synthetic utilities of α-pyrone derivatives are shown. The proposed mechanism is strongly supported by experimental evidence.

  描述了钌催化的区域选择性分子间多步均聚和异二聚化，提供了α-吡喃酮5-羧酸盐和α-吡喃酮-6-羧酸盐。显示了α-吡喃酮衍生物的合成效用。所提出的机制得到实验证据的有力支持。
• Construction of Functionalized 2<i>H</i>-Pyran-2-ones via N-Heterocyclic Carbene-Catalyzed [3 + 3] Annulation of Alkynyl Esters with Enolizable Ketones
  作者：Zheng Liang、Jibin Li、Lei Wang、Zexuan Wei、Jiahui Huang、Xinrui Wang、Ding Du

  DOI：10.1021/acs.joc.2c02392

  日期：2023.2.3

  A new synthesis of functionalized 2H-pyran-2-ones has been developed through N-heterocyclic carbene-catalyzed formal [3 + 3] annulation of alkynyl esters with enolizable ketones. The key to the success of this protocol relies on the use of an NHC instead of a tertiary amine as the catalyst. This protocol also features a broad substrate scope and mild metal-free conditions, offering simple and rapid

  通过 N-杂环卡宾催化的炔基酯与可烯醇化酮的正式 [3 + 3] 环化，开发了功能化 2 H -pyran-2-ones的新合成方法。该协议成功的关键在于使用 NHC 而不是叔胺作为催化剂。该协议还具有广泛的底物范围和温和的无金属条件，以高度区域选择性的方式提供对目标分子的简单快速访问。
• Rhodium-Catalyzed Decarboxylative and Dehydrogenative Coupling of Maleic Acids with Alkynes and Alkenes
  作者：Masaki Itoh、Masaki Shimizu、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/jo401992d

  日期：2013.11.15

  The dehydrogenative coupling of maleic acids with alkynes proceeds smoothly accompanied by decarboxylation under rhodium catalysis to produce variously substituted a-pyrone derivatives. The catalyst system is also applicable to the coupling with 1,3-diynes and alkenes.
• Palladium-Catalyzed Oxidative Annulation of Acrylic Acid and Amide with Alkynes: A Practical Route to Synthesize α-Pyrones and Pyridones
  作者：Yue Yu、Liangbin Huang、Wanqing Wu、Huanfeng Jiang

  DOI：10.1021/ol500611d

  日期：2014.4.18

  A range of internal alkynes smoothly underwent palladium-catalyzed oxidative annulations with acrylic acid and amide to afford alpha-pyrones and pyridones in good to excellent yields with high regioselectivity. The usage of O-2 (1 atm) as a stoichiometric oxidant with H2O as the only byproduct under mild conditions makes this process more attractive and practical.