acetic acid-(16-hydroxy-hexadecyl ester) | 137174-89-1

• 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: acetic acid-(16-hydroxy-hexadecyl ester)
• 英文别名: Essigsaeure-(16-hydroxy-hexadecylester)；16-Hydroxyhexadecyl acetate
• CAS: 137174-89-1
• 化学式: C₁₈H₃₆O₃
• 分子量: 300.482
• InChiKey: RDWAZRGUIVQUKG-UHFFFAOYSA-N

物化性质

• 沸点：
  389.6±15.0 °C(Predicted)
• 密度：
  0.919±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  21
• 可旋转键数：
  17
• 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

• 作为反应物：
  描述：

  acetic acid-(16-hydroxy-hexadecyl ester) 、 氢溴酸 生成 1,16-二溴十六烷 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Chuit; Hausser, Helvetica Chimica Acta, 1929, vol. 12, p. 478

  摘要：

  DOI：
• 作为产物：
  描述：

  1,16-hexadecanediol diacetate 在 HY-Zeolite 作用下， 以 甲醇 为溶剂， 反应 6.5h， 以90%的产率得到acetic acid-(16-hydroxy-hexadecyl ester)
  参考文献：
  名称：

  对称二醇的选择性单乙酰化和对称二乙酸酯的选择性单脱乙酰化使用 HY-沸石作为可重复使用的多相催化剂

  摘要：

  已发现 HY-沸石是一种有效且可重复使用的催化剂，可用于对称二醇的选择性单乙酰化和对称二乙酸酯的选择性单脱乙酰化，以高产率形成产物。

  DOI：

  10.1055/s-2003-42468

文献信息

• Facile and highly selective monoacylation of symmetric diols adsorbed on silica gel with acetyl chloride
  作者：Haruo Ogawa、Misa Amano、Haruo Ogawa、Teiji Chihara

  DOI：10.1039/a707753j

  日期：——

  Monoacetylated alcohols of symmetric 1,n-diols are synthesized quantitatively by refluxing a suspension of the diols adsorbed on silica gel with acetylchloride.

  通过对称1,n-二醇吸附于硅胶上的悬浮液与乙酰氯回流反应，可以定量合成单乙酰化醇。
• Part 148 in the Series “Studies on Novel Synthetic Methodologies:” Selective Acetylation of Alcohols, Phenols and Amines and Selective Deprotection of Aromatic Acetates using Silica-Supported Phosphomolybdic Acid
  作者：Biswanath Das、Ponnaboina Thirupathi、Rathod Aravind Kumar、Keetha Laxminarayana

  DOI：10.1002/adsc.200700292

  日期：2007.12.10

  efficient catalyst for the selective acetylation of alcohols, phenols and amines in the absence of any solvent and also for the chemoselective deprotection of aromatic acetates under very mild conditions. This method has been used for the protection of the hydroxy groups as well as for the deprotection of the acetates of several naturally occurring bioactive phenolic compounds. The catalyst can be easily

  发现环保的二氧化硅负载的磷钼酸是在没有任何溶剂的情况下用于醇，酚和胺的选择性乙酰化以及在非常温和的条件下用于芳族乙酸酯的化学选择性脱保护的高效催化剂。该方法已用于保护羟基以及几种天然存在的生物活性酚类化合物的乙酸酯的脱保护。该催化剂可以容易地回收和再利用。
• 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.