4-(1-Hydroxy-propyl)-furan-3-carboxylic acid methyl ester | 137304-08-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 4-(1-Hydroxy-propyl)-furan-3-carboxylic acid methyl ester
• 英文别名: Methyl 4-(1-hydroxypropyl)furan-3-carboxylate
• CAS: 137304-08-6
• 化学式: C₉H₁₂O₄
• 分子量: 184.192
• InChiKey: ZKTPHDQVCJKRGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(tert-Butyl-dimethyl-silanyl)-furan-3-carboxylic acid 在 四丁基氟化铵 作用下， 反应 12.0h， 生成 4-(1-Hydroxy-propyl)-furan-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Yu, Shuyuan; Keay, Brian A., Journal of the Chemical Society. Perkin transactions I, 1991, # 4, p. 2600 - 2601

  摘要：

  DOI：

文献信息

• Regioselective Preparation of 2,4-, 3,4-, and 2,3,4-Substituted Furan Rings. 2.¹ Regioselective Lithiation of 2-Silylated-3-substituted Furan Rings
  作者：Edward Bures、James A. Nieman、Shuyuan Yu、Patrick G. Spinazzé、Jean-Louis J. Bontront、Ian R. Hunt、Arvi Rauk、Brian A. Keay

  DOI：10.1021/jo971098b

  日期：1997.12.1

  A new method for the preparation of 3,4- and 2,5-disubstituted furan rings is described. A variety of 2-silylated-3-(hydroxymethyl)furans and 2-silylated-3-furoic acids lithiate exclusively at C-4 when treated with 2.2 equivs of BuLi. The resulting dianions were quenched with a variety of electrophiles to provide 2-silylated-3-(hydroxymethyl)-substituted furans and 2-silylated-4-substituted 3-furoic acids in good to excellent yields. Removal of the silyl group (n-Bu4NF) provided a variety of 4-substituted-3-(hydroxymethyl)furans and methyl 4-substituted-3-furoates, respectively. The latter esters were prepared due to difficulties encountered in isolating 4-substituted-3-furoic acids. The site of lithiation was altered by protecting the 3-hydroxyl group with a triethylsilane. Lithiation of 2-silylated-3-(((triethylsilyl)oxy)methyl)furan with 1.2 equivs of BuLi followed by the addition of electrophiles provided 2-silylated-3-(((triethylsilyl)oxy)methyl)-5-substituted furan rings. Subsequent removal of both silyl groups provided 2,4-disubstituted furan rings in moderate to good yields. A rationale is provided to explain why protection of the hydroxyl group at C-3 leads to a change in lithiation from the C-4 to the C-5 position of the furan ring. In addition, an explanation for the observed effect of adding HMPA or LiCl to the solution during the lithiation of 2-(tert-butyldimethylsilyl)-3-(hydroxymethyl)furan is provided.