(S)-2,5-dioxotetrahydrofuran-3-yl palmitate | 1280222-65-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2,5-dioxotetrahydrofuran-3-yl palmitate
• 英文别名: [(3S)-2,5-dioxooxolan-3-yl] hexadecanoate
• CAS: 1280222-65-2
• 化学式: C₂₀H₃₄O₅
• 分子量: 354.487
• InChiKey: KGRNJZIBNBIHNY-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  25
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2,5-dioxotetrahydrofuran-3-yl palmitate 、 维生素 C 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 以84%的产率得到(S)-4-((S)-2-((R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl)-2-hydroxyethoxy)-4-oxo-3-(palmitoyloxy)butanoic acid
  参考文献：
  名称：

  A Novel Class of Organo- (Hydro-) Gelators Based on Ascorbic Acid

  摘要：

  A library of novel, lipid-modified derivatives of ascorbic acid was shown to exhibit highly attractive properties as surfactants, emulsifiers, oil soluble antioxidants, and highly effective gelators in organic solvents and especially water. In these systems, intermolecular hydrogen bonding and van der Weals forces act synergistically to induce gelation as confirmed by spectroscopic studies. The morphology of the formed gel has been characterized by scanning electron microscopy.

  DOI：

  10.1021/ol2003622
• 作为产物：
  描述：

  L-苹果酸 、 棕榈酰氯 反应 4.0h， 以92%的产率得到(S)-2,5-dioxotetrahydrofuran-3-yl palmitate
  参考文献：
  名称：

  A Novel Class of Organo- (Hydro-) Gelators Based on Ascorbic Acid

  摘要：

  A library of novel, lipid-modified derivatives of ascorbic acid was shown to exhibit highly attractive properties as surfactants, emulsifiers, oil soluble antioxidants, and highly effective gelators in organic solvents and especially water. In these systems, intermolecular hydrogen bonding and van der Weals forces act synergistically to induce gelation as confirmed by spectroscopic studies. The morphology of the formed gel has been characterized by scanning electron microscopy.

  DOI：

  10.1021/ol2003622

文献信息

• Amphiphiles Based on <scp>d</scp>-Glucose: Efficient Low Molecular Weight Gelators
  作者：Sukhendu Nandi、Hans-Josef Altenbach、Bernd Jakob、Karsten Lange、Rachid Ihizane、Manfred P. Schneider、Ümit Gün、Andre Mayer

  DOI：10.1021/ol300555a

  日期：2012.8.3

  A series of novel amphiphiles were synthesized based entirely on renewable resources. Besides their efficacy as supramolecular gelators in a wide variety of organic solvents and also water, their surface properties as surfactants and emulsifiers have been determined. A methodical study revealed that the length of the hydrocarbon chains has a dramatic and decisive influence on the thermal stabilities of the obtained hydrogels.