5-phenyl-2,3-dihydro-furan-3,4-dicarboxylic acid diethyl ester | 1239712-14-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 5-phenyl-2,3-dihydro-furan-3,4-dicarboxylic acid diethyl ester
• 英文别名: Diethyl 5-phenyl-2,3-dihydrofuran-3,4-dicarboxylate；diethyl 5-phenyl-2,3-dihydrofuran-3,4-dicarboxylate
• CAS: 1239712-14-1
• 化学式: C₁₆H₁₈O₅
• 分子量: 290.316
• InChiKey: LRTIUFPJQCLVFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  碘甲醇苯甲酸酯 、 富马酸二乙酯 在 三氟化硼乙醚 、 Dimethylzinc 、 氧气 、 草酸 、 silica gel 作用下， 以 正庚烷 、 二氯甲烷 为溶剂， 反应 28.0h， 以68%的产率得到5-phenyl-2,3-dihydro-furan-3,4-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  A Flexible, Stereoselective Dimethylzinc-Mediated Radical-Anionic Cascade: Dramatic Influence of Additional Lewis Acids

  摘要：

  Dimethylzinc-mediated addition of acyloxymethyl radicals to diethyl fumarate led to the highly stereoselective formation of disubstituted gamma-lactones in mean to good yields; this cascade provides a new example of a one-pot process mediated by dimethylzinc involving a tandem radical-anionic reaction; the chemoselectivity of the reaction was totally modified by additional Lewis acids.

  DOI：

  10.1021/ol101519w

文献信息

• A Flexible, Stereoselective Dimethylzinc-Mediated Radical-Anionic Cascade: Dramatic Influence of Additional Lewis Acids
  作者：Julien Maury、Laurence Feray、Patricia Perfetti、Michèle P. Bertrand

  DOI：10.1021/ol101519w

  日期：2010.8.20

  Dimethylzinc-mediated addition of acyloxymethyl radicals to diethyl fumarate led to the highly stereoselective formation of disubstituted gamma-lactones in mean to good yields; this cascade provides a new example of a one-pot process mediated by dimethylzinc involving a tandem radical-anionic reaction; the chemoselectivity of the reaction was totally modified by additional Lewis acids.