(R)-(+)-5,6-dimethyl-5-hydroxy-2-heptanone | 92735-46-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-(+)-5,6-dimethyl-5-hydroxy-2-heptanone
• 英文别名: (R)-5-Hydroxy-5,6-dimethyl-2-heptanone；(5R)-5-hydroxy-5,6-dimethylheptan-2-one
• CAS: 92735-46-1
• 化学式: C₉H₁₈O₂
• 分子量: 158.241
• InChiKey: YQGSPFCEYYECBL-SECBINFHSA-N

物化性质

• 沸点：
  243.0±23.0 °C(Predicted)
• 密度：
  0.919±0.06 g/cm3(Predicted)

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

• 作为反应物：
  描述：

  (R)-(+)-5,6-dimethyl-5-hydroxy-2-heptanone 生成 (R)-(-)-2,3-dihydro-2-isopropyl-2,5-dimethylfuran
  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
• 作为产物：
  描述：

  (+/-)-2-hydroxy-2,3-dimethylbutanenitrile 在 吡啶 、 盐酸 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 氧气 、 copper(l) chloride 、 palladium dichloride 作用下， 以 四氢呋喃 、 乙醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 243.5h， 生成 (R)-(+)-5,6-dimethyl-5-hydroxy-2-heptanone
  参考文献：
  名称：

  Pheromone synthesis—63 Synthesis of both the enantiomers of 2,3-dihydro-2- isopropyl-2,5-dimethylfuran, a sex specific compound in females of the beetle hylecoetus dermestoidesL

  摘要：

  DOI：

  10.1016/s0040-4020(01)91128-7

文献信息

• BAI, XU;ELIEL, ERNEST L., J. ORG. CHEM., 56,(1991) N, C. 2086-2089
  作者：BAI, XU、ELIEL, ERNEST L.

  DOI：——

  日期：——
• 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.
• Pheromone synthesis—63 Synthesis of both the enantiomers of 2,3-dihydro-2- isopropyl-2,5-dimethylfuran, a sex specific compound in females of the beetle hylecoetus dermestoidesL
  作者：Kenji Mori、Takashi Ebata、Shozo Takechi

  DOI：10.1016/s0040-4020(01)91128-7

  日期：1984.1