[(3R)-4,4-dimethyl-2-oxooxolan-3-yl] (2R)-2-phenylpropanoate | 136011-01-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: [(3R)-4,4-dimethyl-2-oxooxolan-3-yl] (2R)-2-phenylpropanoate
• CAS: 136011-01-3
• 化学式: C₁₅H₁₈O₄
• 分子量: 262.306
• InChiKey: UEOTULQYSUHHHH-PWSUYJOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  苯乙酸甲酯 在 氯化亚砜 、 二甲基十二/十四烷基叔胺 、 sodium hydride 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 6.5h， 生成 [(3R)-4,4-dimethyl-2-oxooxolan-3-yl] (2R)-2-phenylpropanoate
  参考文献：
  名称：

  An Alternative Mechanism for the 1,4-Asymmetric Induction in the Stereoselective Addition of (R)-Pantolactone to 2-Phenylpropylketene

  摘要：

  An alternative mechanism for the 1,4-assymmetric induction in the stereoselective addition of (R)-pantolactone to 2-phenylpropylketene was theoretically investigated. A mechanism involving an intermolecular proton transfer assisted by two amine molecules was proposed, which considered the active participation of the dimethylethylamine and its ion as proton transfer agents. In the first step, a neutral dimethylethylamine interacts with the seven-membered ring of the enol intermediate. A specific acid-base interaction is established between the hydroxyl group of the enol and the nitrogen atom of the dimethylethylamine. The neutral dimethylethylamine is basic enough to remove the proton. Another protonated dimethylethylamine is considered to donate its proton to the C=C double bond to give the desired products. The stereochemical outcome was defined by the way that the neutral and protonated dimethylethylamine approached to the enol. The diastereoisomeric ratio found is in good agreement with experiments [for (S, R) and (R, R) it is 99:1].

  DOI：

  10.1590/s0103-50532011000400020