ethyl (2R,3S)-2-oxo-5-phenyltetrahydrofuran-3-carboxylate

• 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: ethyl (2R,3S)-2-oxo-5-phenyltetrahydrofuran-3-carboxylate
• 英文别名: ethyl (3R,5S)-2-oxo-5-phenyloxolane-3-carboxylate
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: JLMUYIBFRBFHBR-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  苯乙烯 、 溴代丙二酸二乙酯 在 lithium tetrafluoroborate 、 fac-Ir(ppy)₃ 作用下， 以 水 、 乙腈 为溶剂， 反应 24.0h， 生成 ethyl (2R,3S)-2-oxo-5-phenyltetrahydrofuran-3-carboxylate 、 ethyl (2S,3S)-2-oxo-5-phenyltetrahydrofuran-3-carboxylate
  参考文献：
  名称：

  A Novel Intermolecular Synthesis of γ-Lactones via Visible-Light Photoredox Catalysis

  摘要：

  Direct gamma-lactone formation via visible-light photoredox catalysis has been achieved efficiently including hydroxylalkylation of aromatic alkenes and transesterification. The present photocatalytic protocol has good regioselectivity and substrate compatibility, affording a novel way to intermolecular gamma-lactone synthesis by the reaction of styrenes with alpha-bromo esters in the absence of any external oxidants.

  DOI：

  10.1021/ol402954t

文献信息

• A Novel Intermolecular Synthesis of γ-Lactones via Visible-Light Photoredox Catalysis
  作者：Xiao-Jing Wei、Deng-Tao Yang、Lin Wang、Tao Song、Li-Zhu Wu、Qiang Liu

  DOI：10.1021/ol402954t

  日期：2013.12.6

  Direct gamma-lactone formation via visible-light photoredox catalysis has been achieved efficiently including hydroxylalkylation of aromatic alkenes and transesterification. The present photocatalytic protocol has good regioselectivity and substrate compatibility, affording a novel way to intermolecular gamma-lactone synthesis by the reaction of styrenes with alpha-bromo esters in the absence of any external oxidants.