3-acetoxy-2-oxopropyl benzoate | 256462-82-5

• 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-oxopropyl benzoate
• 英文别名: (3-Acetyloxy-2-oxopropyl) benzoate；(3-acetyloxy-2-oxopropyl) benzoate
• CAS: 256462-82-5
• 化学式: C₁₂H₁₂O₅
• 分子量: 236.224
• InChiKey: FPSPPPWQZOIRBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-acetoxy-2-oxopropyl benzoate 在 4-二甲氨基吡啶 、 baker's yeast 、 葡萄糖 、 三乙胺 作用下， 以 phosphate buffer 、 乙醇 、 二甲基亚砜 、 乙酸乙酯 为溶剂， 反应 4.5h， 生成 1-benzyloxy-2,3-diacetoxypropane
  参考文献：
  名称：

  Baker's yeast mediated reduction of dihydroxyacetone derivatives

  摘要：

  Several monoprotected dihydroxyacetone derivatives 4a-d and their acetates 5a-d were prepared and subjected to biotransformation with baker's yeast. The simple chemical modification of the substrates (i.e. transforming the relatively small hydrophilic hydroxymethyl group into a larger hydrophobic acetoxymethyl moiety) inverted the sense of enantiotope selectivity of these reductions yielding optically active diols 6a-d, or their enantiomeric acetates (7a-d) and diols (ent-6a-d), respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00415-2
• 作为产物：
  描述：

  苯甲酸酐 在 水 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 50.0 ℃ 、101.33 kPa 条件下， 反应 10.25h， 生成 3-acetoxy-2-oxopropyl benzoate
  参考文献：
  名称：

  邻羰基辅助的丙炔基羧酸盐的氧乙酰氧基化在无金属条件下保持手性

  摘要：

  提出了保留手性的伯，仲和叔炔丙基羧酸的无金属氧乙酰氧基化方法。该反应通过烷基炔酮中间体上相邻羰基的分子内亲核攻击而进行。该方法是一般的，具有广泛的底物范围，并且适用于包括从天然产物获得的那些炔丙基羧酸酯。通过同位素标记（使用H 2 O 18和D 2 O）洞察机械途径，并确认了对照实验。

  DOI：

  10.1002/adsc.201900314

文献信息

• 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.
• Neighboring Carbonyl Group Assisted Oxyacetoxylation of Propargylic Carboxylates with Retention of Chirality under Metal Free Condition
  作者：Tapas R. Pradhan、Debendra K. Mohapatra

  DOI：10.1002/adsc.201900314

  日期：2019.8.5

  reaction proceeds through the intramolecular nucleophilic attack of the neighboring carbonyl group on an alkynyliodonium intermediate. The process is general with broad substrate scope and is amenable for application to a variety of propargyl carboxylates including those obtained from natural products. Insight into the mechanistic pathway by isotopic labelling (using H2O18 and D2O) and controlled experiments

  提出了保留手性的伯，仲和叔炔丙基羧酸的无金属氧乙酰氧基化方法。该反应通过烷基炔酮中间体上相邻羰基的分子内亲核攻击而进行。该方法是一般的，具有广泛的底物范围，并且适用于包括从天然产物获得的那些炔丙基羧酸酯。通过同位素标记（使用H 2 O 18和D 2 O）洞察机械途径，并确认了对照实验。
• Baker's yeast mediated reduction of dihydroxyacetone derivatives
  作者：József Bálint、Gabriella Egri、Attila Kolbert、Csilla Dianóczky、Elemér Fogassy、Lajos Novák、László Poppe

  DOI：10.1016/s0957-4166(99)00415-2

  日期：1999.10

  Several monoprotected dihydroxyacetone derivatives 4a-d and their acetates 5a-d were prepared and subjected to biotransformation with baker's yeast. The simple chemical modification of the substrates (i.e. transforming the relatively small hydrophilic hydroxymethyl group into a larger hydrophobic acetoxymethyl moiety) inverted the sense of enantiotope selectivity of these reductions yielding optically active diols 6a-d, or their enantiomeric acetates (7a-d) and diols (ent-6a-d), respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.