1-benzoyloxy-3-allyloxypropan-2-one | 1375077-59-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-benzoyloxy-3-allyloxypropan-2-one
• 英文别名: (2-Oxo-3-prop-2-enoxypropyl) benzoate；(2-oxo-3-prop-2-enoxypropyl) benzoate
• CAS: 1375077-59-0
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: BUGNUVMXCGXFDN-UHFFFAOYSA-N

物化性质

• 沸点：
  357.4±27.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-benzoyloxy-3-allyloxypropan-2-one 在 辛醇 、 Muchor miehei lipase 作用下， 以 甲基叔丁基醚 、 异丙醚 为溶剂， 反应 24.0h， 生成 1-acetoxy-3-allyloxypropan-2-one
  参考文献：
  名称：

  Enzymatic synthesis of both enantiomeric forms of 3-allyloxy-propane-1,2-diol

  摘要：

  The stereoselective synthesis of (S)- and (R)-3-allyloxy-propane-1,2-diol has been accomplished in four steps from (RS)-3-allyloxy-propane-1,2-diol. Only one intermediate, namely 1-benzoyloxy-3-allyloxy-2-propanone has been prepared by a chemical reaction, that is, pyridinium chlorochromate oxidation of 1-benzoyloxy-3-allyloxypropan-2-ol. All of the remaining reactions (regioselective acylations, asymmetric bioreduction of prochiral ketones, and enzymatic alcoholysis) have been carried out in the presence of biocatalysts. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.03.008
• 作为产物：
  描述：

  3-(allyloxy)-2-hydroxypropyl benzoate 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以64%的产率得到1-benzoyloxy-3-allyloxypropan-2-one
  参考文献：
  名称：

  Enzymatic synthesis of both enantiomeric forms of 3-allyloxy-propane-1,2-diol

  摘要：

  The stereoselective synthesis of (S)- and (R)-3-allyloxy-propane-1,2-diol has been accomplished in four steps from (RS)-3-allyloxy-propane-1,2-diol. Only one intermediate, namely 1-benzoyloxy-3-allyloxy-2-propanone has been prepared by a chemical reaction, that is, pyridinium chlorochromate oxidation of 1-benzoyloxy-3-allyloxypropan-2-ol. All of the remaining reactions (regioselective acylations, asymmetric bioreduction of prochiral ketones, and enzymatic alcoholysis) have been carried out in the presence of biocatalysts. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.03.008

文献信息

• Enzymatic synthesis of both enantiomeric forms of 3-allyloxy-propane-1,2-diol
  作者：Silvana Casati、Enzo Santaniello、Pierangela Ciuffreda

  DOI：10.1016/j.tetasy.2012.03.008

  日期：2012.3

  The stereoselective synthesis of (S)- and (R)-3-allyloxy-propane-1,2-diol has been accomplished in four steps from (RS)-3-allyloxy-propane-1,2-diol. Only one intermediate, namely 1-benzoyloxy-3-allyloxy-2-propanone has been prepared by a chemical reaction, that is, pyridinium chlorochromate oxidation of 1-benzoyloxy-3-allyloxypropan-2-ol. All of the remaining reactions (regioselective acylations, asymmetric bioreduction of prochiral ketones, and enzymatic alcoholysis) have been carried out in the presence of biocatalysts. (C) 2012 Elsevier Ltd. All rights reserved.