12-Hydroxydodecyl 2-methylpropanoate | 137174-92-6

• 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: 12-Hydroxydodecyl 2-methylpropanoate
• CAS: 137174-92-6
• 化学式: C₁₆H₃₂O₃
• 分子量: 272.428
• InChiKey: NXLCEKUKGYKOGC-UHFFFAOYSA-N

物化性质

• 沸点：
  355.0±15.0 °C(Predicted)
• 密度：
  0.926±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  19
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  异丁酸甲酯 、 1,12-十二烷二醇 在 sodium hydrogen sulfate 、 silica gel 作用下， 以 正辛烷 为溶剂， 反应 4.5h， 以9%的产率得到12-(2-methylpropanoyloxy)dodecyl 2-methylpropanoate
  参考文献：
  名称：

  Highly selective monoacylation of symmetric diols catalyzed by metal sulfates supported on silica gel

  摘要：

  Several 1,n-diols, ranging from 1,2-ethanediol to 1,16-hexadecanediol, were monoacylated with high selectivity by reaction with esters in the presence of metal sulfates or hydrogen sulfates, like Ce(SO4)2 and NaHSO4, supported on silica gel. Symmetrical secondary diols were also selectively monoformylated, by reaction with ethyl formate. This method of selective esterification is simple and practical. The yield of monoester depends upon both the composition and the volume of the solvent (an ester/alkane mixture). Unsupported NaHSO4 also catalyzed monoacylation, but the selectivity was less than in monoacylations catalyzed by the supported reagent. The selectivity can be explained by the following reasons: (1) monoacylated products are formed selectively because the diol, but not the monoester, is preferentially adsorbed on the surface of the catalysts, where esterification then occurs, and (2) thin diol layers are formed on the surface of the catalysts due to limited solubility of the diols in the solvent.

  DOI：

  10.1021/jo00027a054