1,1,2,2,3,3,4,4,5,5,6,6-dodecafluoro-1,8-diiodooctane | 6145-01-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机碘化物
• 英文名称: 1,1,2,2,3,3,4,4,5,5,6,6-dodecafluoro-1,8-diiodooctane
• 英文别名: 1,1,2,2,3,3,4,4,5,5,6,6-Dodecafluoro-1,8-diiodo-octane
• CAS: 6145-01-3
• 化学式: C₈H₄F₁₂I₂
• 分子量: 581.91
• InChiKey: HNFRZWUSPAMSKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1,1,2,2,3,3,4,4,5,5,6,6-dodecafluoro-1,8-diiodooctane 、 prop-2-en-1-yl-2,3,6-tri-O-acetyl-4-O-(α-D-2',3',4',6'-tetra-O-acetyl-glucopyranosyl)-β D-glucopyranoside 在 锌 作用下， 以 二氯甲烷 为溶剂， 以66%的产率得到Acetic acid (2R,3R,4S,5R,6R)-4-acetoxy-6-acetoxymethyl-2-(4,4,5,5,6,6,7,7,8,8,9,9-dodecafluoro-2,11-diiodo-undecyloxy)-5-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  麦芽糖衍生的氟化和半氟化表面活性剂：合成及其在水溶液中处理膜蛋白的应用。

  摘要：

  通过自由基反应将碳氟化合物或乙基封端的碳氟化合物链接枝到β-D-烯丙基麦芽糖的双键上，已获得了两种新型的氟化表面活性剂。如此获得的两种化合物在水中形成多分散聚集体。它们可以使膜蛋白保持水溶性，但是蛋白/表面活性剂复合物是多分散的，既不影响蛋白的天然状态也不影响蛋白的稳定性。

  DOI：

  10.1016/j.bmcl.2006.08.070
• 作为产物：
  描述：

  乙烯 、 1,6-二碘代十二氟己烷 在 copper(l) iodide 作用下， 以80%的产率得到1,1,2,2,3,3,4,4,5,5,6,6-dodecafluoro-1,8-diiodooctane
  参考文献：
  名称：

  麦芽糖衍生的氟化和半氟化表面活性剂：合成及其在水溶液中处理膜蛋白的应用。

  摘要：

  通过自由基反应将碳氟化合物或乙基封端的碳氟化合物链接枝到β-D-烯丙基麦芽糖的双键上，已获得了两种新型的氟化表面活性剂。如此获得的两种化合物在水中形成多分散聚集体。它们可以使膜蛋白保持水溶性，但是蛋白/表面活性剂复合物是多分散的，既不影响蛋白的天然状态也不影响蛋白的稳定性。

  DOI：

  10.1016/j.bmcl.2006.08.070

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.