6-(4-hydroxybenzyl)-tetrahydropyran-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 6-(4-hydroxybenzyl)-tetrahydropyran-2-one
• 英文别名: 6-[(4-Hydroxyphenyl)methyl]oxan-2-one；6-[(4-hydroxyphenyl)methyl]oxan-2-one
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: FHFZEPKHVUXENK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-己烯酸 、 对氯苯酚 以 水 、 乙腈 为溶剂， 反应 14.0h， 以53%的产率得到6-(4-hydroxybenzyl)-tetrahydropyran-2-one
  参考文献：
  名称：

  Benzyl (Phenyl) γ- and δ-lactones via Photoinduced Tandem Ar−C, C−O Bond Formation

  摘要：

  A convenient metal-free procedure for the preparation of benzyl (phenyl) gamma- and delta-lactones is illustrated. This method is based on the photochemical generation of phenyl cations and their reaction with 3, 4, or 5-alkenoic acids. This leads to a phenyl- or benzyl-substituted lactone by tandem formation of an aryl-C and C-O bond. The intermediacy of a phenonium ion imparts a full regio- and stereoselectivity to the reaction.

  DOI：

  10.1021/ja0627287

文献信息

• Benzyl (Phenyl) γ- and δ-lactones via Photoinduced Tandem Ar−C, C−O Bond Formation
  作者：Stefano Protti、Maurizio Fagnoni、Angelo Albini

  DOI：10.1021/ja0627287

  日期：2006.8.1

  A convenient metal-free procedure for the preparation of benzyl (phenyl) gamma- and delta-lactones is illustrated. This method is based on the photochemical generation of phenyl cations and their reaction with 3, 4, or 5-alkenoic acids. This leads to a phenyl- or benzyl-substituted lactone by tandem formation of an aryl-C and C-O bond. The intermediacy of a phenonium ion imparts a full regio- and stereoselectivity to the reaction.