trans-4-hydroxymethyl-2-(2-furyl)-1,3-dioxolane | 1258153-55-7

• 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: trans-4-hydroxymethyl-2-(2-furyl)-1,3-dioxolane
• 英文别名: trans-2-(2-Furyl)-4-hydroxymethyl-1,3-dioxolane；[(2R,4R)-2-(furan-2-yl)-1,3-dioxolan-4-yl]methanol
• CAS: 1258153-55-7
• 化学式: C₈H₁₀O₄
• 分子量: 170.165
• InChiKey: BKRXMKVDYAWYHS-HTRCEHHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  糠醛 、 甘油 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 生成 trans-2-(2-furyl)-5-hydroxy-1,3-dioxane 、 cis-2-(2-furyl)-5-hydroxy-1,3-dioxane 、 trans-4-hydroxymethyl-2-(2-furyl)-1,3-dioxolane 、 cis-4-hydroxymethyl-2-(2-furyl)-1,3-dioxolane
  参考文献：
  名称：

  Nucleophilic addition to acetylenes in superbasic catalytic systems: XVII. Vinyl ethers with furyl and cycloacetal fragments: Synthesis and structure

  摘要：

  4-Hydroxymethyl-2-(2-furyl)-1,3-dioxolane and 5-hydroxy-2-(2-furyl)-1,3-dioxane consisting of mixtures of cis- and trans-isomers react with acetylene in the superbasic catalytic system KOHH-DMSO at the atmospheric or higher pressure (80-85A degrees C, 2-3 h) giving the corresponding vinyl ethers in 88-90% yield. The ratio of the structural and configurational isomers in vinyl ethers remains the same as in the initial compounds.

  DOI：

  10.1134/s1070428010090204

文献信息

• Nucleophilic addition to acetylenes in superbasic catalytic systems: XVII. Vinyl ethers with furyl and cycloacetal fragments: Synthesis and structure
  作者：L. A. Oparina、O. V. Vysotskaya、A. V. Stepanov、N. K. Gusarova、K. A. Chernyshev、L. B. Krivdin、B. A. Trofimov

  DOI：10.1134/s1070428010090204

  日期：2010.9

  4-Hydroxymethyl-2-(2-furyl)-1,3-dioxolane and 5-hydroxy-2-(2-furyl)-1,3-dioxane consisting of mixtures of cis- and trans-isomers react with acetylene in the superbasic catalytic system KOHH-DMSO at the atmospheric or higher pressure (80-85A degrees C, 2-3 h) giving the corresponding vinyl ethers in 88-90% yield. The ratio of the structural and configurational isomers in vinyl ethers remains the same as in the initial compounds.