(+/-)-4-Benzyloxy-5-methyl-2,5-dihydrofuran-2-one | 69556-76-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (+/-)-4-Benzyloxy-5-methyl-2,5-dihydrofuran-2-one
• 英文别名: (RS)-4-benzyloxy-5-methyl-5H-furan-2-one；4-benzyloxy-5-methyl-5H-furan-2-one；4-Benzyloxy-5-methylfuran-2(5H)-on；2-methyl-3-phenylmethoxy-2H-furan-5-one
• CAS: 69556-76-9
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: JCSBFABPKABOBN-UHFFFAOYSA-N

物化性质

• 熔点：
  72 °C(Solv: isopropyl ether (108-20-3))
• 沸点：
  408.8±45.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乳酸苄酯 、 (三苯基膦烯)乙烯酮 以 甲苯 为溶剂， 反应 12.0h， 以92%的产率得到(+/-)-4-Benzyloxy-5-methyl-2,5-dihydrofuran-2-one
  参考文献：
  名称：

  Domino syntheses of five-, six- and seven-membered O-, N- and S-heterocycles from α-, β- and γ-substituted carboxylic esters

  摘要：

  By a one-pot procedure, tetronic acids, tetronates, coumarins, benzoxepinones and their N- and S-analogues are readily accessible from keteneylidene(triphenyl)phosphorane 2 and carboxylic esters bearing OH, NHR or SH groups in an alpha-, beta- or gamma-position by an addition/Wittig olefination/(Claisen rearrangement) sequence. This cascade can be controlled by temperature variation. Extension of this procedure by a further addition step yielding annulated bisheterocycles such as the furoquinolone 28 is possible in some cases.

  DOI：

  10.1039/p19960002799

文献信息

• Gelin, Suzanne; Pollet, Patrick, Synthetic Communications, 1980, vol. 10, # 11, p. 805 - 812
  作者：Gelin, Suzanne、Pollet, Patrick

  DOI：——

  日期：——
• Paintner, Franz F.; Allmendinger, Lars; Bauschke, Gerd, Synlett, 2003, # 1, p. 83 - 86
  作者：Paintner, Franz F.、Allmendinger, Lars、Bauschke, Gerd

  DOI：——

  日期：——
• Domino syntheses of five-, six- and seven-membered O-, N- and S-heterocycles from α-, β- and γ-substituted carboxylic esters
  作者：J. Löffler、R. Schobert

  DOI：10.1039/p19960002799

  日期：——

  By a one-pot procedure, tetronic acids, tetronates, coumarins, benzoxepinones and their N- and S-analogues are readily accessible from keteneylidene(triphenyl)phosphorane 2 and carboxylic esters bearing OH, NHR or SH groups in an alpha-, beta- or gamma-position by an addition/Wittig olefination/(Claisen rearrangement) sequence. This cascade can be controlled by temperature variation. Extension of this procedure by a further addition step yielding annulated bisheterocycles such as the furoquinolone 28 is possible in some cases.