1,16-hexadecanediol diacetate | 42237-30-9

• 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: 1,16-hexadecanediol diacetate
• 英文别名: n-Hexadecandiyl-diacetat；1,16-diacetoxy-hexadecane；1,16-Diacetoxy-hexadecan；16-acetyloxyhexadecyl acetate
• CAS: 42237-30-9
• 化学式: C₂₀H₃₈O₄
• 分子量: 342.519
• InChiKey: CBUWFIQHLBJQLJ-UHFFFAOYSA-N

物化性质

• 沸点：
  375.2±10.0 °C(Predicted)
• 密度：
  0.936±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  24
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1,16-二甲氧基-十六烷 在 氢溴酸 、 溶剂黄146 作用下， 生成 1,16-hexadecanediol diacetate
  参考文献：
  名称：

  Chuit, Helvetica Chimica Acta, 1926, vol. 9, p. 265

  摘要：

  DOI：

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.
• Chuit; Hausser, Helvetica Chimica Acta, 1929, vol. 12, p. 478
  作者：Chuit、Hausser

  DOI：——

  日期：——
• ——
  作者：Gary N. Ross、Henry M. Fales、Helen A. Lloyd、Tappey Jones、Edward A. Sokoloski、Kimberly Marshall-Batty、Murray S. Blum

  DOI：10.1023/a:1010372114144

  日期：——

  Abdominal defensive glands of both sexes of the Gulf fritillary butterfly, Agraulis vanillae (Linnaeus) (Nymphalidae:Heliconiinae) emit a pronounced odor when disturbed. We have identified 6-methyl-5-hepten-2-one; oleic, palmitic, and stearic esters of the corresponding alcohol 6-methyl-5-hepten-2-ol; hexadecyl acetate; 1,16-hexadecanediol diacetate; and 1,15-hexadecanediol diacetate in the glandular exudate. Since we have determined that free-flying birds or birds in a butterfly conservatory discriminate against A. vanillae as prey, we suggest that the constituents in the glands may play a defensive role against potential avian predators.
• US4233230A
  申请人：——

  公开号：US4233230A

  公开（公告）日：1980-11-11