(S)-3-(Pyridin-4-yloxy)-propane-1,2-diol | 143145-80-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-3-(Pyridin-4-yloxy)-propane-1,2-diol
• 英文别名: (2S)-3-pyridin-4-yloxypropane-1,2-diol
• CAS: 143145-80-6
• 化学式: C₈H₁₁NO₃
• 分子量: 169.18
• InChiKey: IKKZUFIWBUAHTM-ZETCQYMHSA-N

物化性质

• 沸点：
  369.0±27.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  62.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-(Pyridin-4-yloxy)-propane-1,2-diol 在 盐酸 作用下， 生成 8
  参考文献：
  名称：

  Acid catalyzed racemization of 1-(heterocyclyloxy)-2,3-propanediols

  摘要：

  A number of enantiomerically pure heterocyclic ketals 5 have been prepared, and their acid-catalyzed hydrolysis to the corresponding diols 6 has been studied. During this reaction a rearrangement may occur to give racemic products, and so the kinetics of the two competing reactions have been studied to establish optimum conditions. The rate of rearrangement is independent of pH below the pK(a) of the heterocycle, whereas the rate of ketal continues to increase as pH is lowered. Brief treatment with strong acid has allowed the formation of very pure diols in high yield.

  DOI：

  10.1021/jo00045a030
• 作为产物：
  描述：

  4-氯吡啶 在 盐酸 、 potassium tert-butylate 作用下， 反应 18.25h， 生成 (S)-3-(Pyridin-4-yloxy)-propane-1,2-diol
  参考文献：
  名称：

  Acid catalyzed racemization of 1-(heterocyclyloxy)-2,3-propanediols

  摘要：

  A number of enantiomerically pure heterocyclic ketals 5 have been prepared, and their acid-catalyzed hydrolysis to the corresponding diols 6 has been studied. During this reaction a rearrangement may occur to give racemic products, and so the kinetics of the two competing reactions have been studied to establish optimum conditions. The rate of rearrangement is independent of pH below the pK(a) of the heterocycle, whereas the rate of ketal continues to increase as pH is lowered. Brief treatment with strong acid has allowed the formation of very pure diols in high yield.

  DOI：

  10.1021/jo00045a030

文献信息

• SUBSTITUTED BRIDGED UREA ANALOGS AS SIRTUIN MODULATORS
  申请人：GlaxoSmithKline Intellectual Property (No. 2) Limited

  公开号：EP3221317B1

  公开（公告）日：2020-07-22
• Acid catalyzed racemization of 1-(heterocyclyloxy)-2,3-propanediols
  作者：Jeffrey J. Barlow、Michael H. Block、Julian A. Hudson、Alison Leach、Jethro L. Longridge、Brian G. Main、Stuart Nicholson

  DOI：10.1021/jo00045a030

  日期：1992.9

  A number of enantiomerically pure heterocyclic ketals 5 have been prepared, and their acid-catalyzed hydrolysis to the corresponding diols 6 has been studied. During this reaction a rearrangement may occur to give racemic products, and so the kinetics of the two competing reactions have been studied to establish optimum conditions. The rate of rearrangement is independent of pH below the pK(a) of the heterocycle, whereas the rate of ketal continues to increase as pH is lowered. Brief treatment with strong acid has allowed the formation of very pure diols in high yield.