16-Hydroxyhexadecyl propanoate | 137174-88-0

• 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: 16-Hydroxyhexadecyl propanoate
• CAS: 137174-88-0
• 化学式: C₁₉H₃₈O₃
• 分子量: 314.509
• InChiKey: CRVNBWMRSQVFLS-UHFFFAOYSA-N

物化性质

• 沸点：
  404.1±18.0 °C(Predicted)
• 密度：
  0.916±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  22
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 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：

  1,16-十六烷二醇 、 丙酸乙酯 在 Dowex 50W 作用下， 以 正辛烷 为溶剂， 反应 3.67h， 以72%的产率得到16-Hydroxyhexadecyl propanoate
  参考文献：
  名称：

  Convenient Selective Monoacylation of 1,n-Diols Catalyzed by Ion-Exchange Resins

  摘要：

  Several 1,n-diols, ranging from 1,2-ethanediol to 1,16-hexadecanediol, were selectively monoacylated by transesterification in ester/octane solvent mixtures catalyzed by strongly acidic ion-exchange resins. This method of selective esterification is quite simple and practical. The selectivity for monoester formation and initial rates of monoester formation depended on the ester/octane ratio of the solvents. The reasons for the selectivity are as follows: (1) The sulfonic acid-type ion-exchange resins usually contain 50-80% water, and a strongly acidic aqueous layer is formed on the surface of the resins. (2) A partition equilibrium between the aqueous layer and the aprotic ester/octane layer is setup, and diols have higher partition coefficients than the product monoesters. (3) Acylation of the alcohols occurs in the aqueous layer and/or at the interface between the aqueous and the nonaqueous liquid layer. (4) The formed monoesters move away from the aqueous layer into the aprotic layer.

  DOI：

  10.1021/jo00084a043

文献信息

• Highly selective monoacylation of symmetric diols catalyzed by metal sulfates supported on silica gel
  作者：Takeshi Nishiguchi、Katsumi Kawamine、Tomoko Ohtsuka

  DOI：10.1021/jo00027a054

  日期：1992.1

  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.