(RS)-ethyl 2-acetyl-2-hydroxy-4-phenylbutanoate | 1338127-62-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: (RS)-ethyl 2-acetyl-2-hydroxy-4-phenylbutanoate
• 英文别名: Ethyl 2-hydroxy-3-oxo-2-(2-phenylethyl)butanoate
• CAS: 1338127-62-0
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: MXYDNUYMBOXVEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-苯基-2-氧代丙酸乙酯 、 2,3-丁二酮 在 3-苄基羟乙基甲基噻唑氯化锂 、 三乙胺 作用下， 以 PEG₄₀₀ 为溶剂， 以58%的产率得到(RS)-ethyl 2-acetyl-2-hydroxy-4-phenylbutanoate
  参考文献：
  名称：

  α-Diketones as acyl anion equivalents: a non-enzymatic thiamine-promoted route to aldehyde–ketone coupling in PEG400 as recyclable medium

  摘要：

  By mimicking the peculiar behavior of thiamine diphosphate-dependent acetylacetoin synthase, it has been demonstrated that thiamine hydrochloride 2a and its simple analogue thiazolium salt 2b are able to activate alpha-diketones as acyl anion equivalents in nucleophilic acylations, such as the homo-coupling of alpha-diketones and the hitherto unreported cross-coupling between a-diketones and alpha-ketoesters. These carboligation reactions were optimized under stoichiometric (2a) and catalytic conditions (2b) by using eco-friendly PEG400 as the reaction medium, thus allowing both solvent and thiazolium salt recycling. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.056