1-cyclopentyl-3-hydroxypropan-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-cyclopentyl-3-hydroxypropan-1-one
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: PXKUNQYEMIPADR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  1-环己烯基乙酸 在 lithium aluminium tetrahydride 、 thallium(III) nitrate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.25h， 生成 1-cyclopentyl-3-hydroxypropan-1-one
  参考文献：
  名称：

  Thallium Trinitrate Mediated Oxidation of 3-Alkenols:  Ring Contraction vs Cyclization

  摘要：

  The reaction of a series of six-membered ring 3-alkenols with thallium trinitrate (TTN) in three different experimental conditions was studied. Either cyclization products or ring contraction products were obtained, depending on the structure of the substrate as well as the nature of the solvent. The reaction of a seven-membered ring 3-alkenol with TTN led to the ring contraction product exclusively.

  DOI：

  10.1021/jo011178m

文献信息

• Reaction of 3-Alkenols with Thallium Trinitrate: An Unexpected and Useful Ring Contraction
  作者：Helena M. C. Ferraz、Andréa P. Santos、Luiz F. Silva、Tiago de O. Vieira

  DOI：10.1080/00397910008087377

  日期：2000.2

  The first thallium trinitrate (TTN) mediated ring contraction of cyclic homoallylic alcohols, using a 1:1 mixture of AcOH and H2O as solvent, is described. The reaction or two of these alcohols with excess of TTN in pentane gave alpha-spirocyclopentyl-gamma-butirolactones in reasonable yields.
• Thallium Trinitrate Mediated Oxidation of 3-Alkenols:  Ring Contraction vs Cyclization
  作者：Helena M. C. Ferraz、Luiz S. Longo、Julio Zukerman-Schpector

  DOI：10.1021/jo011178m

  日期：2002.5.1

  The reaction of a series of six-membered ring 3-alkenols with thallium trinitrate (TTN) in three different experimental conditions was studied. Either cyclization products or ring contraction products were obtained, depending on the structure of the substrate as well as the nature of the solvent. The reaction of a seven-membered ring 3-alkenol with TTN led to the ring contraction product exclusively.