methyl 3-(2,2-dimethyl-5-oxotetrahydrofuran-3-yl)propanoate | 99182-04-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 3-(2,2-dimethyl-5-oxotetrahydrofuran-3-yl)propanoate
• 英文别名: Methyl 3-(2,2-dimethyl-5-oxooxolan-3-yl)propanoate；methyl 3-(2,2-dimethyl-5-oxooxolan-3-yl)propanoate
• CAS: 99182-04-4
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: XEJOYWPDWOTPGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  4-(1'-hydroxy-1'-methylethyl)-5-isopropyloxytetrahydrofuran-2-one 在 硫酸 、 palladium on activated charcoal 、 氢气 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 生成 methyl 3-(2,2-dimethyl-5-oxotetrahydrofuran-3-yl)propanoate
  参考文献：
  名称：

  Synthesis and phytotoxicity of 4,5 functionalized tetrahydrofuran-2-ones

  摘要：

  In this work we report a versatile synthesis of fourteen gamma-lactones all structurally related, nine of which are novel compounds, accomplished from the readily available furfural. The phytotoxic activity of the synthesized compounds was evaluated in vitro by the influence on the growth of wheat coleoptiles. The percentages of inhibition were mostly small and not statistically different from control after the third dilution (100 mu mol L-1). In general, alpha,beta-unsaturated lactones presented better activities than the saturated ones. The most active compounds presented 51, 68 and 76% of inhibition in 1000 mu mol L-1. The results indicate that regardless of saturation, the presence of the gamma-lactone moiety is important for the bioactivity, but their presence has no implications with potency.

  DOI：

  10.1590/s0103-50532012001200016