(3R,4R)-2,5-dioxotetrahydrofuran-3,4-diyl dipalmitate | 1245733-18-9

• 英文名称: (3R,4R)-2,5-dioxotetrahydrofuran-3,4-diyl dipalmitate
• CAS: 1245733-18-9
• 化学式: C₃₆H₆₄O₇
• 分子量: 608.9
• InChiKey: IRJAXOINRPUYQU-KKLWWLSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.86
• 重原子数：
  43.0
• 可旋转键数：
  30.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  95.97
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (3R,4R)-2,5-dioxotetrahydrofuran-3,4-diyl dipalmitate 、 维生素 C 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.5h， 以63%的产率得到(2R,3R)-4-((S)-2-((R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl)-2-hydroxyethoxy)-4-oxo-2,3-bis(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-酒石酸 、 棕榈酰氯 反应 24.0h， 以91%的产率得到(3R,4R)-2,5-dioxotetrahydrofuran-3,4-diyl dipalmitate
  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

• Synthesis and Characterization of Novel Surfactants: Combination Products of Fatty Acids, Hydroxycarboxylic Acids and Alcohols
  作者：Hans‐Josef Altenbach、Rachid Ihizane、Bernd Jakob、Karsten Lange、Manfred Schneider、Zeynep Yilmaz、Sukhendu Nandi

  DOI：10.1007/s11743-010-1185-8

  日期：2010.10

  a near quantitative yield. These molecules are excellent electrophiles which react readily with a variety of nucleophiles including alcohols, diols and polyols. Their reaction with triethylene glycol and triethylene glycol monomethyl ether leads to two series of novel anionic surfactants, which are unsymmetrical gemini surfactants. The determination of their properties (CMC, foaming, HLB) revealed

  羟基羧酸（例如柠檬酸，苹果酸和酒石酸）与过量的脂肪酸氯化物的反应产生相应的O一步法制备酰基化的羟基羧酸酐，收率接近定量。这些分子是优异的亲电子试剂，可与多种亲核试剂（包括醇，二醇和多元醇）轻松反应。它们与三甘醇和三甘醇单甲醚的反应产生了两类新型阴离子表面活性剂，它们是不对称的双子表面活性剂。对它们的性能（CMC，起泡，HLB）的测定表明，这些分子（取决于脂肪酸的链长）是优秀的乳化剂，并且它们还表现出令人感兴趣的抗菌活性。这些新颖的功能性表面活性剂对于食品和个人护理产品中的应用以及药物制剂是令人感兴趣的。
• 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.