2-acetoxy-3-phenylpropan-1-ol | 179052-75-6

• 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: 2-acetoxy-3-phenylpropan-1-ol
• 英文别名: (1-Hydroxy-3-phenylpropan-2-yl) acetate；(1-hydroxy-3-phenylpropan-2-yl) acetate
• CAS: 179052-75-6
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: XTVCIQUYTSLWLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-acetoxy-3-phenylpropan-1-ol 生成 (R)-2-acetoxy-3-phenylpropan-1-ol
  参考文献：
  名称：

  Kinetic resolution of 2-acylated-1,2-diols by lipase-catalyzed enantiomer selective acylation

  摘要：

  Enantiomer selectivity of lipase catalyzed acylation of 2-acylated 1,2-diols was studied. First, acylation of 2-acetoxyheptan-1-ol rac-3b with vinyl acetate was investigated by varying the enzyme and the solvent, showing the highest enantiomer selectivity by using lipase from Pseudomonas fluorescens (PfL) in hexane-vinyl acetate (VA). We have found varying or even reversed enantiomer selectivity for different secondary acyl moieties in 2-acyloxyheptan-1-ols rac-3bA-F. Next, all six possible types of enantiomer selective biotransformations (hydrolysis of diacetate and the two kinds of monoacetetes; acylation of diol and the two kinds of monoacetates) were compared on two model diols rac-4b,d. Among the transformations investigated, acetylation of secondary monoacetates rac-3b,d showed the highest enantiomer selectivity. Finally, PfL catalyzed acetylations of several 2-acetylated 1,2-diols rac-3a-g were investigated under our optimum conditions. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00161-9
• 作为产物：
  描述：

  1-(benzyloxy)-3-phenylpropan-2-ol 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 氢气 作用下， 以 正己烷 、 二氯甲烷 、 异丙醇 为溶剂， 生成 2-acetoxy-3-phenylpropan-1-ol
  参考文献：
  名称：

  Kinetic resolution of 2-acylated-1,2-diols by lipase-catalyzed enantiomer selective acylation

  摘要：

  Enantiomer selectivity of lipase catalyzed acylation of 2-acylated 1,2-diols was studied. First, acylation of 2-acetoxyheptan-1-ol rac-3b with vinyl acetate was investigated by varying the enzyme and the solvent, showing the highest enantiomer selectivity by using lipase from Pseudomonas fluorescens (PfL) in hexane-vinyl acetate (VA). We have found varying or even reversed enantiomer selectivity for different secondary acyl moieties in 2-acyloxyheptan-1-ols rac-3bA-F. Next, all six possible types of enantiomer selective biotransformations (hydrolysis of diacetate and the two kinds of monoacetetes; acylation of diol and the two kinds of monoacetates) were compared on two model diols rac-4b,d. Among the transformations investigated, acetylation of secondary monoacetates rac-3b,d showed the highest enantiomer selectivity. Finally, PfL catalyzed acetylations of several 2-acetylated 1,2-diols rac-3a-g were investigated under our optimum conditions. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00161-9

文献信息

• Kinetic resolution of 2-acylated-1,2-diols by lipase-catalyzed enantiomer selective acylation
  作者：Gabriella Egri、Eszter Baitz-Gács、László Poppe

  DOI：10.1016/0957-4166(96)00161-9

  日期：1996.5

  Enantiomer selectivity of lipase catalyzed acylation of 2-acylated 1,2-diols was studied. First, acylation of 2-acetoxyheptan-1-ol rac-3b with vinyl acetate was investigated by varying the enzyme and the solvent, showing the highest enantiomer selectivity by using lipase from Pseudomonas fluorescens (PfL) in hexane-vinyl acetate (VA). We have found varying or even reversed enantiomer selectivity for different secondary acyl moieties in 2-acyloxyheptan-1-ols rac-3bA-F. Next, all six possible types of enantiomer selective biotransformations (hydrolysis of diacetate and the two kinds of monoacetetes; acylation of diol and the two kinds of monoacetates) were compared on two model diols rac-4b,d. Among the transformations investigated, acetylation of secondary monoacetates rac-3b,d showed the highest enantiomer selectivity. Finally, PfL catalyzed acetylations of several 2-acetylated 1,2-diols rac-3a-g were investigated under our optimum conditions. Copyright (C) 1996 Elsevier Science Ltd