5,5-dimethyl-4-hydroxymethyl-2-oxo-2,5-dihydrofuran-3-carboxylic acid | 898922-42-4

• 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: 5,5-dimethyl-4-hydroxymethyl-2-oxo-2,5-dihydrofuran-3-carboxylic acid
• 英文别名: 4-(Hydroxymethyl)-5,5-dimethyl-2-oxo-2,5-dihydrofuran-3-carboxylic acid；4-(hydroxymethyl)-5,5-dimethyl-2-oxofuran-3-carboxylic acid
• CAS: 898922-42-4
• 化学式: C₈H₁₀O₅
• 分子量: 186.164
• InChiKey: LAKHCBMFXFCQAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,5-dimethyl-4-hydroxymethyl-2-oxo-2,5-dihydrofuran-3-carboxylic acid 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以69%的产率得到4,4-dimethyl-2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylic acid
  参考文献：
  名称：

  稠合环丙烷环的双环γ-内酯的合成及一些转化

  摘要：

  Reductive cyclization of 4-hydroxymethyl-5,5-dimethyl(or pentamethylene)-2,5-dihydrofuran-2-ones by the action of sodium tetrahydridoborate gave bicyclic compounds in which the lactone ring is fused to a cyclopropane ring. Hydrolysis of the products with aqueous sodium hydroxide resulted in the formation of the corresponding disodium cyclopropane-1,1-dicarboxylates, which reacted with alkyl halides to produce the diesters. Acid hydrolysis of the fused systems was accompanied by opening of the cyclopropane ring with formation of 4-chloromethyl-5,5-dimethyl-2-oxotetrahydrofuran-3-carboxylic acid.

  DOI：

  10.1134/s1070428008120129