[2-Acetyloxy-3-(4-chlorophenoxy)propyl] acetate | 911835-63-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [2-Acetyloxy-3-(4-chlorophenoxy)propyl] acetate
• CAS: 911835-63-7
• 化学式: C₁₃H₁₅ClO₅
• 分子量: 286.712
• InChiKey: HCAAQICZRZSZGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [2-Acetyloxy-3-(4-chlorophenoxy)propyl] acetate 在 ion-exchange resin Wofatit SBW (OH(-)-form) 作用下， 以 甲醇 为溶剂， 生成 1,2-丙二醇,3-(4-氯苯氧基)-,(2R)- 、 (S)-3-(4-chlorophenoxy)propane-1,2-diol
  参考文献：
  名称：

  Kinetic resolution of acyclic 1,2-diols using a sequential lipase-catalyzed transesterification in organic solvents

  摘要：

  A method for the kinetic resolution of 3-(aryloxy)-1,2-propanediols rac-1a-n without additional protection-deprotection steps using a lipase-catalyzed sequential transesterification with lipase amnno PS has been developed. In the first step of this one-pot procedure the racemic 1,2-diols are acylated regioselectively at the primary hydroxy group without enantioselection. The subsequent acylation at the secondary hydroxy group of the formed primary monoacetate is responsible for high enantioselection. The enantioselectivity of this transformation depends significantly on the substitution pattern of the aryl ring and the organic solvent used. 3-(Aryloxy)-1,2-propanediols with substituents in the para-position show a much higher enantioselectivity than the corresponding derivatives with ortho-substituents. Among other substrates, the pharmaceuticals Mephenesin, Guaifenesin, and Chlorphenesin have been resolved. The replacement of the aryloxy by alkyl substituent causes a dramatic decrease of enantioselectivity.

  DOI：

  10.1021/jo00081a018
• 作为产物：
  描述：

  4-氯苯基缩水甘油醚 、 乙酸酐 在 ammonium phosphomolybdate 作用下， 反应 1.0h， 以94%的产率得到[2-Acetyloxy-3-(4-chlorophenoxy)propyl] acetate
  参考文献：
  名称：

  A mild, rapid and highly regioselective ring-opening of epoxides and aziridines with acetic anhydride under solvent-free conditions using ammonium-12-molybdophosphate

  摘要：

  A highly regioselective ring opening of epoxides and aziridines can be carried out efficiently with acetic anhydride to form the acetates of the corresponding 1,2-diols and 2-amino-alcohols, respectively, using ammonium-12-molybdophosphate (AMP) as a heterogeneous catalyst, at room temperature, in the absence of solvent. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.07.055