3-acetoxy-2-hydroxypropyl benzoate | 1086444-61-2

• 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: 3-acetoxy-2-hydroxypropyl benzoate
• CAS: 1086444-61-2
• 化学式: C₁₂H₁₄O₅
• 分子量: 238.24
• InChiKey: CRJATYHDCRQCKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.77
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  3-acetoxy-2-oxopropyl benzoate 在 dimethyl sulfide borane 、 sodium sulfate 作用下， 以 癸烷 、 二甲基亚砜 为溶剂， 以212 mg的产率得到3-acetoxy-2-hydroxypropyl benzoate
  参考文献：
  名称：

  I₂-Catalyzed Regioselective Oxo- and Hydroxy-acyloxylation of Alkenes and Enol Ethers: A Facile Access to α-Acyloxyketones, Esters, and Diol Derivatives

  摘要：

  I-2-catalyzed oxo-acyloxylation of alkenes and enol ethers with carboxylic acids providing for the high yield synthesis of a-acyloxyketones and esters is described. This unprecedented regioselective oxidative process employs TBHP and Et3N in stoichiometric amounts under metal-free conditions in DMSO as solvent. Additionally, I-2-catalysis allows the direct hydroxy-acyloxylation of alkenes with the sequential addition of BH3 center dot SMe2 leading to monoprotected diol derivatives in excellent yields.

  DOI：

  10.1021/ol5027393

文献信息

• Studies on DMDO-mediated benzylidene acetal oxidation
  作者：David K. Mycock、Alexandra E. Sherlock、Paul A. Glossop、Christopher J. Hayes

  DOI：10.1016/j.tetlet.2008.08.062

  日期：2008.11

  We have shown that dimethyldioxirane (DMDO) can be used to effect an oxidative partial deprotection of benzylidene acetals derived from both 1,2- and 1,3-diols to afford hydroxy benzoate products. A wide range of functional groups are tolerated, and good to excellent yields are usually observed. The reactions are easy to perform and produce little waste other than acetone. (C) 2008 Elsevier Ltd. All rights reserved.
• I₂-Catalyzed Regioselective Oxo- and Hydroxy-acyloxylation of Alkenes and Enol Ethers: A Facile Access to α-Acyloxyketones, Esters, and Diol Derivatives
  作者：Rambabu N. Reddi、Pragati K. Prasad、Arumugam Sudalai

  DOI：10.1021/ol5027393

  日期：2014.11.7

  I-2-catalyzed oxo-acyloxylation of alkenes and enol ethers with carboxylic acids providing for the high yield synthesis of a-acyloxyketones and esters is described. This unprecedented regioselective oxidative process employs TBHP and Et3N in stoichiometric amounts under metal-free conditions in DMSO as solvent. Additionally, I-2-catalysis allows the direct hydroxy-acyloxylation of alkenes with the sequential addition of BH3 center dot SMe2 leading to monoprotected diol derivatives in excellent yields.