4,4,5,5,6,6,7,7,8,8,8-十一氟辛酸 | 914637-49-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 4,4,5,5,6,6,7,7,8,8,8-十一氟辛酸
• 中文别名: 2H，2H，3H，3H-全氟辛酸
• 英文名称: 2H,2H,3H,3H-perfluorooctanoic acid
• 英文别名: 4,4,5,5,6,6,7,7,8,8,8-undecafluorooctanoic acid
• CAS: 914637-49-3
• 化学式: C₈H₅F₁₁O₂
• 分子量: 342.109
• InChiKey: ABFCFCPCGMHSRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  4,4,5,5,6,6,7,7,8,8,8-十一氟辛酸 在 吡啶 、 氯化亚砜 、 三氟乙酸 作用下， 以 氯仿 、 水 为溶剂， 反应 24.5h， 生成 5-O-<3'-(F-pentyl)propanoyl>xylitol
  参考文献：
  名称：

  Synthesis of perfluoroalkylated xylitol ethers and esters: new surfactants for biomedical uses

  摘要：

  New, well-defined surfactants and cosurfactants were synthesized with the objective of enhancing the stability of fluorocarbon emulsions destined to serve as oxygen carriers for biomedical applications. Monoperfluoroalkylated ethers of xylitol were achieved by addition of perfluoroalkyl iodide on the double bond of a protected xylitol allyl ether in a one-step addition-elimination reaction. Monoesters were obtained specifically on position 5 by treating 1,2:3,4-di-O-isopropylidenexylitol with perfluoroalkylated acid chlorides of various chain lengths in pyridine at room temperature. The products display strong surface activity and produce a remarkable synergistic stabilization of a fluorocarbon/Pluronic F-68 type emulsion. Biocompatibility data are reported, which include in vitro toxicity tests on Namalva cell cultures and hemolysis tests on human blood cells; the latter was found to decrease as the length of the F-alkyl chain increased. IV injection in mice (n = 10) showed that these products were innocuous at 400-1000 mg/kg of body weight. Preliminary exchange-perfusion experiments on rats with an emulsion containing the F-octyl xylitol ether were encouraging.

  DOI：

  10.1021/jm00166a028
• 作为产物：
  描述：

  Ethyl 3-F-pentyl propynoate 在 palladium on activated charcoal 氢气 作用下， 生成 4,4,5,5,6,6,7,7,8,8,8-十一氟辛酸
  参考文献：
  名称：

  Synthesis of perfluoroalkylated xylitol ethers and esters: new surfactants for biomedical uses

  摘要：

  New, well-defined surfactants and cosurfactants were synthesized with the objective of enhancing the stability of fluorocarbon emulsions destined to serve as oxygen carriers for biomedical applications. Monoperfluoroalkylated ethers of xylitol were achieved by addition of perfluoroalkyl iodide on the double bond of a protected xylitol allyl ether in a one-step addition-elimination reaction. Monoesters were obtained specifically on position 5 by treating 1,2:3,4-di-O-isopropylidenexylitol with perfluoroalkylated acid chlorides of various chain lengths in pyridine at room temperature. The products display strong surface activity and produce a remarkable synergistic stabilization of a fluorocarbon/Pluronic F-68 type emulsion. Biocompatibility data are reported, which include in vitro toxicity tests on Namalva cell cultures and hemolysis tests on human blood cells; the latter was found to decrease as the length of the F-alkyl chain increased. IV injection in mice (n = 10) showed that these products were innocuous at 400-1000 mg/kg of body weight. Preliminary exchange-perfusion experiments on rats with an emulsion containing the F-octyl xylitol ether were encouraging.

  DOI：

  10.1021/jm00166a028

文献信息

• Hybrid Fluorocarbon–Hydrocarbon Surfactants: Synthesis and Colloidal Characterization
  作者：Emilie Grousson、Florian Mahler、Sandro Keller、Christiane Contino-Pépin、Grégory Durand

  DOI：10.1021/acs.joc.1c01493

  日期：2021.11.5

  Four double-tailed hybrid fluorocarbon–hydrocarbon (F–H) surfactants with a poly(ethylene glycol) (PEG) polar headgroup were synthesized. The hydrophobic scaffold consists of an amino acid core, onto which were grafted both fluorocarbon and hydrocarbon chains of different lengths. The PEG polar head was connected to the hydrophobic scaffold through a copper(I)-mediated click reaction. The four derivatives

  合成了四种具有聚（乙二醇）（PEG）极性头基的双尾杂化碳氟烃（F-H）表面活性剂。疏水支架由氨基酸核心组成，其上接枝了不同长度的碳氟化合物链和烃链。PEG 极性头通过铜 (I) 介导的点击反应连接到疏水支架。如等温滴定量热法 (ITC)、表面张力 (ST) 测量和稳态荧光所证明的，四种衍生物的水溶性 >100 g/L 并自组装成具有微摩尔临界胶束浓度 (CMC) 值的胶束聚集体光谱学。每增加一对 CH 2，CMC 值就会降低约 6 倍组，而当 PEG 极性头的大小从 2000 减少到 750 g/mol 时，观察到减少了 ~2.5 倍。动态光散射 (DLS) 显示流体动力学直径为 10-15 nm 的单峰胶束群，与从尺寸排阻色谱 (SEC) 获得的结果一致。聚集数随着烃链长度的增加而增加，但随着 PEG 链长度的增加而减少。低 CMC 和高水溶性的一种分子设计的组合使这些新型表面活性剂有希望用于新型药物递送系统。
• POLYCARBONATE-BASE POLYMER, PRODUCTION PROCESS, RESIN COATING FLUID PREPARED THEREFROM, AND ELECTROPHOTOGRAPHIC PHOTORECEPTOR PREPARED THEREFROM
  申请人：IDEMITSU KOSAN COMPANY LIMITED

  公开号：EP0837085A1

  公开（公告）日：1998-04-22

  A polymer comprising mainly repeating units (1) and/or repeating units (2), containing optionally terminal groups (3) and/or repeating units (4), and having a reduced viscosity [ηsp/c] of 0.2 to 10.0 dl/g as measured in a 0.5 g/dl solution thereof in methylene chloride at 20°C; a resin coating fluid containing the polymer, a charge-transfer substance and a solvent; and an electrophotographic photoreceptor containing the polymer as a binder resin in a photosensitive layer, wherein Rf1 represents a group that is composed of at least carbon atoms and fluorine atoms and bonded directly to the two oxygen atoms of the carbonate linkage in the general formula (1) without any intervening arylene group; and Rf2 represents a group that is composed of at least carbon atoms and fluorine atoms and bonded directly to one of the oxygen atoms of the carbonate linkage in the general formula (3) without any intervening arylene group.

  一种主要由重复单元（1）和/或重复单元（2）组成的聚合物，含有任选的末端基团（3）和/或重复单元（4），在 0.其中 Rf1 代表至少由碳原子和氟原子组成并直接与通式（1）中碳酸酯连接的两个氧原子键合的基团，而没有任何芳基介入；Rf2 代表一个至少由碳原子和氟原子组成的基团，直接与通式（3）中碳酸酯链节的一个氧原子键合，中间不含任何芳烯基。
• METHOD FOR FORMING MULTILAYER RESIST
  申请人：DAIKIN INDUSTRIES, LTD.

  公开号：EP1686425A1

  公开（公告）日：2006-08-02

  There is formed a laminated resist which exhibits sufficient reflection reducing effect in a photolithography process using light of vacuum ultraviolet region and also has sufficient developing characteristics in a developing process. The method of forming the laminated photoresist comprises (I) a step for forming the photoresist layer (L1) on a substrate and (II) a step for forming the antireflection layer (L2) on the photoresist layer (L1) by applying the coating composition containing the fluorine-containing polymer (A) having hydrophilic group Y. The fluorine-containing polymer (A) contains a structural unit derived from a fluorine-containing ethylenic monomer having hydrophilic group Y and is characterized in that (i) the hydrophilic group Y contains an acidic OH group having a pKa value of not more than 11, (ii) a fluorine content is not less than 50 % by mass, and (iii) the number of moles of the hydrophilic group Y in 100 g of the fluorine-containing polymer (A) is not less than 0.14.

  形成了一种层状光刻胶，它在使用真空紫外区光的光刻工艺中显示出足够的减反射效果，并且在显影工艺中具有足够的显影特性。形成层状光刻胶的方法包括：(I) 在基底上形成光刻胶层 (L1) 的步骤；(II) 在光刻胶层 (L1) 上形成抗反射层 (L2) 的步骤，该步骤通过涂敷含有亲水基团 Y 的含氟聚合物 (A) 的涂层组合物来实现。含氟聚合物(A)含有由具有亲水基团 Y 的含氟乙烯单体衍生的结构单元，其特征在于：(i) 亲水基团 Y 含有 pKa 值不大于 11 的酸性 OH 基团；(ii) 氟含量不小于 50%（按质量计）；(iii) 100 克含氟聚合物(A)中亲水基团 Y 的摩尔数不小于 0.14。
• Low-Temperature Mineralization of Fluorotelomers with Diverse Polar Head Groups
  作者：Richard J. Monsky、Yuli Li、K. N. Houk、William R. Dichtel

  DOI：10.1021/jacs.4c03117

  日期：2024.6.26

  groups–carboxylic acids, sulfonic acids, alcohols, and phosphonic acids, which are the most common polar head groups used in commercial and industrial applications. The degradation intermediates and byproducts were characterized using 1H, 13C, and 19F NMR spectroscopy. Density functional theory computations at the M06-2X/6-311 + G(2d,p)-SMD-(DMSO) level were consistent with the observed intermediates and guided

  全氟烷基物质和多氟烷基物质 (PFAS) 是持久性环境污染物，会对健康产生有害影响。目前采用的 PFAS 销毁方法是能源密集型的，并且经常产生短链且顽固的部分氟化副产物。我们报告了五种含氟调聚物化合物在 DMSO:H 2 O (8:1 v/v) 混合物中使用 NaOH 和温和温度 (120 °C) 进行碱介导降解的矿化。研究的含氟调聚物具有不同的极性头基——羧酸、磺酸、醇和膦酸，它们是商业和工业应用中最常见的极性头基。使用 1H、13C 和 19F NMR 光谱对降解中间体和副产物进行了表征。 M06-2 X /6-311 + G(2d,p)-SMD-(DMSO) 水平的密度泛函理论计算与观察到的中间体一致，并指导了整体机制假设。每种含氟调聚物的降解通过类似的过程发生，其中非氟化碳和第一氟化碳从剩余的全氟烷基片段中裂解，该片段通过先前确定的途径降解。这些发现为 PFAS 降解过程提供了重要
• Perfluoroalkylated monoesters of 1,4-D-sorbitan, isosorbide and isomannide: new surfactants for biomedical applications
  作者：Leila Zarif、Jacques Greiner、Jean G. Riess

  DOI：10.1016/s0022-1139(00)84372-9

  日期：1989.7