6-(3-acetoxypropyl)hexano-6-lactone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 6-(3-acetoxypropyl)hexano-6-lactone
• 英文别名: 3-(7-Oxooxepan-2-yl)propyl acetate
• 化学式: C₁₁H₁₈O₄
• 分子量: 214.262
• InChiKey: PAAWJTSNYKAVJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,4,5,6,7,8-hexahydro-2H-chromene 在 甲酸 、 硫酸 、 双氧水 作用下， 反应 1.33h， 生成 6-(3-acetoxypropyl)hexano-6-lactone
  参考文献：
  名称：

  摘要：

  A new method for the synthesis of n-(3-acyloxypropyl)-substituted six- to thirteen-membered alkan-n-olides was developed. The method is based on the H2SO4-catalyzed reactions of oxabicycloalkenes, obtained from 2-(3-acetoxypropyl)cycloalkanes, with H2O2 and formic or acetic acid. The method includes the subsequent transformations of oxabicycloalkenes; into bicyclic hydroperoxides, peroxy ethers, and, at the final stage, into target lactones formed in 56-71% yields. These transformations are carried as a one-pot reaction.

  DOI：

  10.1023/a:1021336031371

文献信息

• ——
  作者：Yu. N. Ogibin、A. V. Kutkin、A. O. Terent"ev、G. I. Nikishin

  DOI：10.1023/a:1021336031371

  日期：——

  A new method for the synthesis of n-(3-acyloxypropyl)-substituted six- to thirteen-membered alkan-n-olides was developed. The method is based on the H2SO4-catalyzed reactions of oxabicycloalkenes, obtained from 2-(3-acetoxypropyl)cycloalkanes, with H2O2 and formic or acetic acid. The method includes the subsequent transformations of oxabicycloalkenes; into bicyclic hydroperoxides, peroxy ethers, and, at the final stage, into target lactones formed in 56-71% yields. These transformations are carried as a one-pot reaction.