5-(dioxolan-2-yl)-3-(hydroxymethyl)-2-methylfuran | 420115-94-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: 5-(dioxolan-2-yl)-3-(hydroxymethyl)-2-methylfuran
• 英文别名: 5-(Dioxolan-2-yl)-3-(hydroxymethyl)-2-methyl-furan；[5-(1,3-dioxolan-2-yl)-2-methylfuran-3-yl]methanol
• CAS: 420115-94-2
• 化学式: C₉H₁₂O₄
• 分子量: 184.192
• InChiKey: NPKHMYUZVUQGRO-UHFFFAOYSA-N

物化性质

• 沸点：
  207.1±30.0 °C(Predicted)
• 密度：
  1.245±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(dioxolan-2-yl)-3-(hydroxymethyl)-2-methylfuran 在 吡啶 、 氯化亚砜 、 sodium 作用下， 以 乙醚 、 苯 为溶剂， 反应 12.0h， 生成 3-(diethoxyphosphorylmethyl)-5-(dioxolan-2-yl)-2-methylfuran
  参考文献：
  名称：

  摘要：

  Reaction of formylfurancarboxylates with excess ethylene glycol in the presence of p-toluenesulfonic acid gives rise to (1,3-dioxolan-2-yl)furancarboxylates. Reduction of these products with lithium aluminum hydride proceeds with preservation of the dioxolane ring. Except for 5-(1,3-dioxolan-2-y1)(hydroxymethyl)-2-methyl-3-furan, the obtained alcohols are unstable. Chlorides derived from them decompose under conditions of the Michaelis-Becker reaction, and no phosphorylation products are formed. By contrast, the above-mentioned stable alcohol by treatment with thionyl chloride in the presence of pyridine is converted to a fairly stable chloromethylfuran. The latter compound reacts with sodium diethyl phosphite in benzene to form the corresponding phosphonate that exists as a 1 :4 mixture of two spectroscopically discernible conformers.

  DOI：

  10.1023/a:1013149519992
• 作为产物：
  描述：

  5-羟基甲基-2-甲基呋喃-3-羧酸甲酯 在 chromium(VI) oxide 、 lithium aluminium tetrahydride 、 对甲苯磺酸 、 原甲酸三乙酯 作用下， 以 吡啶 、 乙醚 、 氯仿 、 水 为溶剂， 反应 10.0h， 生成 5-(dioxolan-2-yl)-3-(hydroxymethyl)-2-methylfuran
  参考文献：
  名称：

  摘要：

  Reaction of formylfurancarboxylates with excess ethylene glycol in the presence of p-toluenesulfonic acid gives rise to (1,3-dioxolan-2-yl)furancarboxylates. Reduction of these products with lithium aluminum hydride proceeds with preservation of the dioxolane ring. Except for 5-(1,3-dioxolan-2-y1)(hydroxymethyl)-2-methyl-3-furan, the obtained alcohols are unstable. Chlorides derived from them decompose under conditions of the Michaelis-Becker reaction, and no phosphorylation products are formed. By contrast, the above-mentioned stable alcohol by treatment with thionyl chloride in the presence of pyridine is converted to a fairly stable chloromethylfuran. The latter compound reacts with sodium diethyl phosphite in benzene to form the corresponding phosphonate that exists as a 1 :4 mixture of two spectroscopically discernible conformers.

  DOI：

  10.1023/a:1013149519992