d,l-2,5-dioxohexane-3,4-dicarboxylic acid dimethyl ester | 74536-45-1

• 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: d,l-2,5-dioxohexane-3,4-dicarboxylic acid dimethyl ester
• 英文别名: dimethyl (2R,3R)-2,3-diacetylbutanedioate
• CAS: 74536-45-1；139136-52-0；139136-53-1
• 化学式: C₁₀H₁₄O₆
• 分子量: 230.218
• InChiKey: MFUZXFWVYOMQBM-YUMQZZPRSA-N

物化性质

• 熔点：
  138-140 °C
• 沸点：
  120-135 °C(Press: 1 Torr)
• 密度：
  1.177±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  乙酰乙酸甲酯 在 sodium iodide 作用下， 以 丙酮 为溶剂， 以16%的产率得到d,l-2,5-dioxohexane-3,4-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Electrochemical oxidative dimerization of acetoacetic and benzoylacetic esters in the presence of metal halides

  摘要：

  Acetoacetic and benzoylacetic esters dimerize on electrolysis in the presence of metal halide mediators to form 2,5-dioxohexane-3,4-dicarboxylic and 1,4-dioxo-1,4-diphenylbutane-2,3-dicarboxylic esters in yields up to 90%. Primarily the meso-form of the dimer is produced (up to 90%) under optimal conditions (NaI, -20-degrees-C) in acetone and acetonitrile. Diastereomers of the dimer are produced in comparable amounts in methanol and ethanol.

  DOI：

  10.1007/bf00961039

文献信息

• Electrochemical oxidative dimerization of acetoacetic and benzoylacetic esters in the presence of metal halides
  作者：M. N. �linson、T. L. Lizunova、G. I. Nikishin

  DOI：10.1007/bf00961039

  日期：1991.11

  Acetoacetic and benzoylacetic esters dimerize on electrolysis in the presence of metal halide mediators to form 2,5-dioxohexane-3,4-dicarboxylic and 1,4-dioxo-1,4-diphenylbutane-2,3-dicarboxylic esters in yields up to 90%. Primarily the meso-form of the dimer is produced (up to 90%) under optimal conditions (NaI, -20-degrees-C) in acetone and acetonitrile. Diastereomers of the dimer are produced in comparable amounts in methanol and ethanol.