2-[(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)sulfanyl]ethanol | 36097-00-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-[(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)sulfanyl]ethanol
• 英文别名: 2-(1H,1H,2H,2H-tridecafluoro-octylsulfanyl)-ethanol；2-(Perfluorhexyl)ethyl-2'-hydroxyethylsulfid；C6F13CH2CH2Sch2CH2OH；2-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctylsulfanyl)ethanol
• CAS: 36097-00-4
• 化学式: C₁₀H₉F₁₃OS
• 分子量: 424.226
• InChiKey: IYBHIXBUMCGHIM-UHFFFAOYSA-N

物化性质

• 沸点：
  80-83 °C(Press: 1.20 Torr)
• 密度：
  1.535±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  2-[(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)sulfanyl]ethanol 在 sodium periodate 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 11.0h， 生成 2-[(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)sulfinyl]ethyl methacrylate
  参考文献：
  名称：

  New perfluoroalkylated amphiphilic methacrylates bearing sulfinyl group as monomers for biomedical applications: water content and oxygen permeability of their copolymers with DEGMA

  摘要：

  Perfluoroalkylated methacrylates 7a-c bearing sulfinyl group within a straight-chain ester group, i.e. CH2=C(CH3)CO2CH2CH2S(O)CH2CH2CF2(CF2CF2)(n)CF3 (n = 1-3) were prepared by two alternative synthetic sequences from 2-[(polyfluoroalkyl)sulfanyl]ethanols HOCH2CH2SCH2CH2CF2(CF2CF2)(n)CF3 (n = 1-3) in overall yields of 88-91%. Copolymers of 7a-c with diethylene glycol methacrylate (DEGMA) prepared in bulk under radical conditions display high transparency, increased water content and good oxygen permeability properties, which are advantageous for their application in ophthalmology and as prosthetic materials. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.06.003
• 作为产物：
  描述：

  3,3,4,4,5,5,6,6,7,7,8,8,8-十三氟-1-辛硫醇 、 2-氯乙醇 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以85%的产率得到2-[(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)sulfanyl]ethanol
  参考文献：
  名称：

  张力合成非烷基F-烷基单分散体

  摘要：

  单分散氟化非离子表面活性剂的合成通常是困难的，漫长的和昂贵的。我们发现了一种新的合成策略，该策略很容易从市售产品中得到应用，这使我们能够以高收率获得均一系列的纯净和单分散双序列非离子全氟烷基表面活性剂。

  DOI：

  10.1016/s0022-1139(00)81027-1

文献信息

• Synthèse de nouveaux silanes F-alkyles dérivés de tensioactifs non-ioniques F-alkyles
  作者：J. Bommelaer、F. Szönyi、A. Cambon

  DOI：10.1016/s0022-1139(00)81255-5

  日期：1991.11

  Additivity of the properties due to the SiOSiO bonding and to the perfluorinated chain is observed in the field of the fluorinated silicones. In this work we report the synthesis of new silanes derived from a series of non-ionic F-alkylated monodisperse surfactants allowing modulation of their degree of crosslinking and their HLB (hydrophilic lipophilic balance).

  在氟化硅氧烷领域中观察到由于SiOSiO键和全氟化链引起的性质的可加性。在这项工作中，我们报告了由一系列非离子型F烷基化单分散表面活性剂衍生的新硅烷的合成，这些表面活性剂可调节其交联度和HLB（亲水亲脂平衡）。
• Perfluoroalkyl alkylene vinyl sulfoxides and sulfones
  申请人：Ciba-Geigy Corporation

  公开号：US04517384A1

  公开（公告）日：1985-05-14

  Perfluoroalkyl alkylene vinyl sulfoxides and sulfones of the formula ##STR1## wherein R.sub.f is perfluoroalkyl of 3 to 18 carbon atoms, R.sub.1 is hydrogen or lower alkyl, m is 1 to 3 and n is 1 or 2, intermediates thereof, methods for their preparation, and the uses of such compounds to render cellulosic, and natural and synthetic polyamide, materials hydrophobic and oleophobic are described.

  本发明涉及一种化合物，其为公式##STR1##中的全氟烷基烷基乙烯基亚砜和亚磺酰化合物，其中R.sub.f是3到18个碳原子的全氟烷基，R.sub.1是氢或低碳基，m为1到3，n为1或2，以及其中间体，制备它们的方法以及使用这些化合物使纤维素和天然和合成聚酰胺材料疏水和疏油的方法。
• New polyfluorothiopropanoyloxy derivatives of 5β-cholan-24-oic acid designed as drug absorption modifiers
  作者：Lech Mrózek、Lenka Coufalová、Lucie Rárová、Lukáš Plaček、Radka Opatřilová、Jiří Dohnal、Katarína Kráľová、Oldřich Paleta、Vladimír Král、Pavel Drašar、Josef Jampílek

  DOI：10.1016/j.steroids.2013.05.012

  日期：2013.9

  A series of final six propanoyloxy derivatives of 5 beta-cholan-24-oic acid (tridecafluoroctylsulfanyl- and tridecafluoroctylsulfinylethoxycarbonylpropanoyloxy derivatives) as potential drug absorption promoters (skin penetration enhancers, intestinal absorption promoters) was generated by multistep synthesis. Structure confirmation of all generated compounds was accomplished by H-1 NMR, C-13 NMR, IR and MS spectroscopy methods. All the prepared compounds were analyzed using RP-TLC, and their lipophilicity (R-M) was determined. The hydrophobicity (log P), solubility (log S), polar surface area (PSA) and molar volume (MV) of the studied compounds were also calculated. All the target compounds were tested for their in vitro transdermal penetration effect and as potential intestinal absorption enhancers. The cytotoxicity of all the evaluated compounds was evaluated against normal human skin fibroblast cells. Their anti-proliferative activity was also assessed against human cancer cell lines: T-lymphoblastic leukaemia cell line and breast adenocarcinoma cell line. One compound showed high selective cytotoxicity against human skin fibroblast cells and another compound possessed high cytotoxicity against breast adenocarcinoma cell line and skin fibroblast cells. Only one compound expressed anti-proliferative effect on leukaemia and breast adenocarcinoma cells without affecting the growth of normal cells, which should be promising in potential development of new drugs. Most of the target compounds showed minimal anti-proliferative activity (IC50 > 37 mu M), indicating they would have moderate cytotoxicity when administered as chemical absorption modifiers. The relationships between the lipophilicity/polarity and the chemical structure of the studied compounds as well as the relationships between their chemical structure and penetration enhancement effect are discussed in this article. (C) 2013 Elsevier Inc. All rights reserved.
• Nucleophilic displacements on .beta.-(perfluoroalkyl)ethyl iodides. Synthesis of acrylates containing heteroatoms
  作者：Christian S. Rondestvedt、Gordon L. Thayer

  DOI：10.1021/jo00436a005

  日期：1977.8
• SZONYI, F.;CAMBON, A., J. FLUOR. CHEM., 36,(1987) N 2, 195-209
  作者：SZONYI, F.、CAMBON, A.

  DOI：——

  日期：——