6-phenethyl-2H-pyran-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 6-phenethyl-2H-pyran-2-one
• 英文别名: 6-(2-Phenylethyl)pyran-2-one
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: JEPSSVCPJNBMFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  6-氯吡喃-2H-酮 在 Pd-BaSO₄ bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 氢气 、 三乙胺 作用下， 以 甲苯 、 苯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 21.0h， 生成 6-phenethyl-2H-pyran-2-one
  参考文献：
  名称：

  6-Chloro-2(2H)-pyranone: a new 2(2H)-pyranone synthon

  摘要：

  6-Chloro-2(2H)-pyranone, which can be prepared in high yield from commercially available trans -glutaconic acid, undergoes facile Pd/Cu-catalyzed reaction with various 1-alkynes to give rise to the corresponding 6-(1-alkynyl)-2(2H)-pyranones in moderate to good yields. These last hitherto unknown compounds have been used as direct precursors to 6-alkyl- and 6-[(Z)-1-alkenyl]-2(2H)-pyranones. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02600-x

文献信息

• Phosphine-Catalyzed Synthesis of 6-Substituted 2-Pyrones:  Manifestation of <i>E</i>/<i>Z</i>-Isomerism in the Zwitterionic Intermediate
  作者：Xue-Feng Zhu、Arnaud-Pierre Schaffner、Ronald C. Li、Ohyun Kwon

  DOI：10.1021/ol050946j

  日期：2005.7.1

  We report a one-step phosphine-catalyzed annulation between aldehydes and ethyl allenoate to form 6-substituted 2-pyrones. The mechanistic rationale for this reaction requires explicit discussion of the EIZ-isomerism of the zwitterionic intermediate formed by the addition of a phosphine to the allenoate. Sterically demanding trialkylphosphines facilitate the shift of equilibrium toward the E-isomeric zwitterion and lead to the formation of 6-substituted 2-pyrones. Various aromatic as well as aliphatic aldehydes undergo the transformation in moderate to excellent yield.
• 5,6-DIHYDROPYRONE DERIVATIVES AS PROTEASE INHIBITORS AND ANTIVIRAL AGENTS
  申请人：PARKE DAVIS & COMPANY

  公开号：EP0729463A1

  公开（公告）日：1996-09-04
• 6-Chloro-2(2H)-pyranone: a new 2(2H)-pyranone synthon
  作者：Matteo Biagetti、Fabio Bellina、Adriano Carpita、Renzo Rossi

  DOI：10.1016/s0040-4039(02)02600-x

  日期：2003.1

  6-Chloro-2(2H)-pyranone, which can be prepared in high yield from commercially available trans -glutaconic acid, undergoes facile Pd/Cu-catalyzed reaction with various 1-alkynes to give rise to the corresponding 6-(1-alkynyl)-2(2H)-pyranones in moderate to good yields. These last hitherto unknown compounds have been used as direct precursors to 6-alkyl- and 6-[(Z)-1-alkenyl]-2(2H)-pyranones. (C) 2002 Elsevier Science Ltd. All rights reserved.