5-undecyl-3-(2-hydroxyhexadecyl)[1,2,4]oxadiazole | 1313432-95-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-undecyl-3-(2-hydroxyhexadecyl)[1,2,4]oxadiazole
• 英文别名: 1-(5-Undecyl-1,2,4-oxadiazol-3-yl)hexadecan-1-ol；1-(5-undecyl-1,2,4-oxadiazol-3-yl)hexadecan-1-ol
• CAS: 1313432-95-9
• 化学式: C₂₉H₅₆N₂O₂
• 分子量: 464.776
• InChiKey: PQXTYLRSXKFGAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.6
• 重原子数：
  33
• 可旋转键数：
  25
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (Z)-N-dodecanoyl-2-hydroxy-hexadecylamidoxime 在 吡啶 、 对甲苯磺酰氯 作用下， 反应 7.0h， 以91%的产率得到5-undecyl-3-(2-hydroxyhexadecyl)[1,2,4]oxadiazole
  参考文献：
  名称：

  Synthesis of novel ceramide-like penetration enhancers

  摘要：

  Ceramide-like penetration enhancers have been synthesized by isosteric replacements of the 1-hydroxymethyl and amide moieties of natural ceramides. Metabolically more stable oxime and five-membered heterocyclic (1,2,4-oxadiazole, 1,2,4-triazole, tetrazole) analogues are more polar and possess H-bond acceptor properties, which make them potentially useful in optimizing key intermolecular features in interactions between the modified ceramide structures and the lipid layers of stratum corneum. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.02.024