furan-3-carboxylic acid (1RS,2RS,3SR)-1-(furan-3-yl)-3-hydroxy-2-methylpentyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: furan-3-carboxylic acid (1RS,2RS,3SR)-1-(furan-3-yl)-3-hydroxy-2-methylpentyl ester
• 英文别名: [(1R,2R,3S)-1-(furan-3-yl)-3-hydroxy-2-methylpentyl] furan-3-carboxylate
• 化学式: C₁₅H₁₈O₅
• 分子量: 278.305
• InChiKey: VMKCIJJGLJINKN-DDTOSNHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-糠醛 、 3-戊酮 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以68%的产率得到furan-3-carboxylic acid (1RS,2RS,3SR)-1-(furan-3-yl)-3-hydroxy-2-methylpentyl ester
  参考文献：
  名称：

  Evans−Tishchenko Coupling of Heteroaryl Aldehydes

  摘要：

  The low-temperature Evans-Tishchenko coupling of a range of functionalized heteroaryl aldehydes with beta-hydroxy ketones in the presence of a Sm(III) catalyst has been achieved with high yields (90-99%) and good to excellent diastereoselectivity (90:10 -> 95:5 dr). However, at room temperature a retro-aldol aldol-Tishchenko reaction was found to compete with the desired Evans-Tishchenko reaction. Identification of these byproducts has allowed the corresponding aldol-Tishchenko reaction to be optimized for several heteroaryl aldehydes.

  DOI：

  10.1021/jo1015689

文献信息

• Evans−Tishchenko Coupling of Heteroaryl Aldehydes
  作者：Philip D. Dorgan、Jamie Durrani、Manuel J. Cases-Thomas、Alison N. Hulme

  DOI：10.1021/jo1015689

  日期：2010.11.5

  The low-temperature Evans-Tishchenko coupling of a range of functionalized heteroaryl aldehydes with beta-hydroxy ketones in the presence of a Sm(III) catalyst has been achieved with high yields (90-99%) and good to excellent diastereoselectivity (90:10 -> 95:5 dr). However, at room temperature a retro-aldol aldol-Tishchenko reaction was found to compete with the desired Evans-Tishchenko reaction. Identification of these byproducts has allowed the corresponding aldol-Tishchenko reaction to be optimized for several heteroaryl aldehydes.