rac-5-Hydroxy-5,6-dimethyl-2-heptanone | 132561-76-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: rac-5-Hydroxy-5,6-dimethyl-2-heptanone
• 英文别名: 5-Hydroxy-5,6-dimethylheptan-2-one
• CAS: 132561-76-3
• 化学式: C₉H₁₈O₂
• 分子量: 158.241
• InChiKey: YQGSPFCEYYECBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,3-二甲基-1,2-丁二醇 在 吡啶 、 正丁基锂 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 生成 rac-5-Hydroxy-5,6-dimethyl-2-heptanone
  参考文献：
  名称：

  Synthesis of (R)-2,3-dihydro-2,5-dimethyl-2-isopropylfuran

  摘要：

  The synthesis of (R)-2,3-dihydro-2,5-dimethyl-2-isopropylfuran (1), an insect pheromone, via a 1,3-oxathiane is reported. Key steps are the preparation of (S)-2,3-dimethylbutane-1,2-diol (7) from isobutyryloxathiane 5 and reaction of lithiated acetone dimethylhydrazone with tosylated diol 8. NMR spectra of the key tautomeric precursors, 2/2'/3, to 1 have been analyzed in detail, and the enantiomeric excess of these precursors was determined by a chiral shift C-13 NMR experiment.

  DOI：

  10.1021/jo00006a022

文献信息

• Synthesis of (R)-2,3-dihydro-2,5-dimethyl-2-isopropylfuran
  作者：Xu Bai、Ernest L. Eliel

  DOI：10.1021/jo00006a022

  日期：1991.3

  The synthesis of (R)-2,3-dihydro-2,5-dimethyl-2-isopropylfuran (1), an insect pheromone, via a 1,3-oxathiane is reported. Key steps are the preparation of (S)-2,3-dimethylbutane-1,2-diol (7) from isobutyryloxathiane 5 and reaction of lithiated acetone dimethylhydrazone with tosylated diol 8. NMR spectra of the key tautomeric precursors, 2/2'/3, to 1 have been analyzed in detail, and the enantiomeric excess of these precursors was determined by a chiral shift C-13 NMR experiment.