N-[1,1-di[(O-β-D-glucopyranosyl)oxymethyl]-2-hydroxyethyl]-5,5,6,6,7,7,8,8,9,9,10,10-dodecafluorododecanamide | 1268600-91-4

• 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: N-[1,1-di[(O-β-D-glucopyranosyl)oxymethyl]-2-hydroxyethyl]-5,5,6,6,7,7,8,8,9,9,10,10-dodecafluorododecanamide
• 英文别名: N-1,1-di[(O-β-D-glucopyranosyl)oxymethyl]hydroxyethyl-5,5,6,6,7,7,8,8,9,9,10,10-dodecafluorododecanamide；5,5,6,6,7,7,8,8,9,9,10,10-dodecafluoro-N-[1-hydroxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]propan-2-yl]dodecanamide
• CAS: 1268600-91-4
• 化学式: C₂₈H₄₁F₁₂NO₁₄
• 分子量: 843.613
• InChiKey: USBXEGBKRJFOOY-PEQRZCQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  55
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  248
• 氢给体数：
  10
• 氢受体数：
  26

反应信息

• 作为产物：
  描述：

  N-(1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl)but-3-enamide 在 吡啶 、 甲醇 、 calcium sulfate 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium methylate 、 mercury(II) cyanide 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 100.5h， 生成 N-[1,1-di[(O-β-D-glucopyranosyl)oxymethyl]-2-hydroxyethyl]-5,5,6,6,7,7,8,8,9,9,10,10-dodecafluorododecanamide
  参考文献：
  名称：

  Propyl-Ended Hemifluorinated Surfactants: Synthesis and Self-Assembling Properties

  摘要：

  The advantages of using hemifluorinated surfactants as an efficient alternative to detergents for manipulating membrane proteins in aqueous solution have been demonstrated in recent reports. However, the large-scale synthesis of these surfactants is still considered as a major matter and has limited their use for biochemical purposes. We report herein the synthesis of a novel series of perfluorohexane-based surfactants endowed with a short propyl hydrocarbon tip and whose polar head size is modulated by the presence of two or three glucose moieties. The synthetic route is based on the radical addition of two alkenes onto the 1,6-diiodoperfluorohexane using AIBN as a radical initiator, affording the surfactants in satisfactory overall yields. The self-assembling properties of these hemifluorinated surfactants were studied by surface tension measurements, dynamic light scattering, as well as their behavior upon reversed-phase chromatography and were compared with those of their perfluorinated analogues. Our findings strongly suggest the predominant influence of the propyl tip on both adsorption and micellization phenomena as well as on the hydrophobic character of the surfactants, whereas as previously observed, the shorter ethyl tip does not greatly affect these properties when compared to the perfluorinated analogues. Moreover, all the surfactants reported here self-assemble into small and monodisperse aggregates, a feature of crucial importance for biochemistry applications.

  DOI：

  10.1021/jo102245c

文献信息

• Propyl-Ended Hemifluorinated Surfactants: Synthesis and Self-Assembling Properties
  作者：Maher Abla、Grégory Durand、Bernard Pucci

  DOI：10.1021/jo102245c

  日期：2011.4.1

  The advantages of using hemifluorinated surfactants as an efficient alternative to detergents for manipulating membrane proteins in aqueous solution have been demonstrated in recent reports. However, the large-scale synthesis of these surfactants is still considered as a major matter and has limited their use for biochemical purposes. We report herein the synthesis of a novel series of perfluorohexane-based surfactants endowed with a short propyl hydrocarbon tip and whose polar head size is modulated by the presence of two or three glucose moieties. The synthetic route is based on the radical addition of two alkenes onto the 1,6-diiodoperfluorohexane using AIBN as a radical initiator, affording the surfactants in satisfactory overall yields. The self-assembling properties of these hemifluorinated surfactants were studied by surface tension measurements, dynamic light scattering, as well as their behavior upon reversed-phase chromatography and were compared with those of their perfluorinated analogues. Our findings strongly suggest the predominant influence of the propyl tip on both adsorption and micellization phenomena as well as on the hydrophobic character of the surfactants, whereas as previously observed, the shorter ethyl tip does not greatly affect these properties when compared to the perfluorinated analogues. Moreover, all the surfactants reported here self-assemble into small and monodisperse aggregates, a feature of crucial importance for biochemistry applications.