2-羟甲基-3-呋喃羧酸甲酯 | 420115-87-3

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 中文名称: 2-羟甲基-3-呋喃羧酸甲酯
• 中文别名: 2-羟甲基-呋喃-3-甲酸甲酯
• 英文名称: 2-Hydroxymethyl-furan-3-carboxylic acid methyl ester
• 英文别名: Methyl 2-(hydroxymethyl)furan-3-carboxylate
• CAS: 420115-87-3
• 化学式: C₇H₈O₄
• 分子量: 156.138
• InChiKey: VVKYQFMKCWGDEM-UHFFFAOYSA-N

物化性质

• 沸点：
  281.6±30.0 °C(Predicted)
• 密度：
  1.259±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-羟甲基-3-呋喃羧酸甲酯 在 chromium(VI) oxide 作用下， 以 吡啶 、 水 为溶剂， 以46%的产率得到methyl 2-formyl-3-furancarboxylate
  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

文献信息

• ——
  作者：L. M. Pevzner

  DOI：10.1023/a:1013149519992

  日期：——

  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.