4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl methanesulfonate | 908833-73-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl methanesulfonate
• 英文别名: 3-(perfluorooctyl)propanyl methylsulfonate；methyl 3-(perfluorooctyl)propanylsulfonate；3-(perfluorooctyl)propyl methylsulfonate；3-(Perfluorooctyl)propanyl methyl sulfonate
• CAS: 908833-73-8
• 化学式: C₁₂H₉F₁₇O₃S
• 分子量: 556.241
• InChiKey: LEHGEQAXQIZCHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl methanesulfonate 在 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 32.0h， 生成 1-(((5-((4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl)oxy)-2-nitrobenzyl)oxy)carbonyl)-3-methyl-1H-imidazol-3-ium trifluoromethanesulfonate
  参考文献：
  名称：

  Synthesis of Fluorous Photolabile Aldehyde and Carbamate and Alkyl Carbamate Protecting Groups for Carbohydrate-Associated Amines

  摘要：

  Two new fluorous photolabile-protecting groups (FNBC and FNB) and a new base-labile protecting group (FOC) for the masking of amines are reported. The protecting groups survive a wide range of common reaction conditions used in oligosaccharide synthesis and render the attached molecules amenable to fluorous solid-phase extraction (FSPE). A glycosyl acceptor containing the FNB group is shown to be useful in the synthesis of carbohydrates tagged with free deactivated secondary amines.

  DOI：

  10.1021/ol500023y
• 作为产物：
  描述：

  全氟辛基碘烷 在 偶氮二异丁腈 、 三正丁基氢锡 、 三乙胺 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 34.25h， 生成 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl methanesulfonate
  参考文献：
  名称：

  Self-assembled monolayers on gold generated from terminally perfluorinated alkanethiols bearing propyl vs. ethyl hydrocarbon spacers

  摘要：

  This paper examines the structural and interfacial properties of terminally perfluorinated self-assembled monolayers (FSAMs) on gold generated from the adsorption of a new series of terminally perfluorinated propanethiols F(CF2)(n)CH2)(3)SH, where n = 8, 10, and 12. Analysis of these FSAMs by ellipsometry and X-ray photoelectron spectroscopy (XPS) confirmed the formation of the monolayer films. The contact angles of water and n-hexadecane on these FSAMs indicated a high degree of hydrophobicity and oleophobicity. Polarization modulation infrared reflection-adsorption spectroscopy (PM-IRRAS) analysis of the films revealed that the fluorinated chains are oriented largely perpendicular to the gold surface. In addition, the FSAMs formed from the new adsorbates were compared to known FSAMs derived from F(CF2)(n)(CH2)(2)SH, where n = 8, 10, and 12, to examine the influence of the number of CH2 groups in the short alkyl spacer upon the conformational order and packing structure of the films. Analysis of the XPS spectra for the normalized peak intensity of the F 1s and S 2p binding energies for both types of films suggest a slight increase in packing density for the chains having the propyl vs. the ethyl hydrocarbon spacer. This conclusion is consistent with the observed decrease in the wetting behavior of hexadecane on the FSAMs formed from the new adsorbates. However, the preponderance of the data indicates that these two series of partially fluorinated alkanethiols form films with highly similar structure/packing characteristics with no discernible "odd-even" effect between the two series. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2014.09.003

文献信息

• Synthesis, Characterization, and Applications of Hemifluorinated Dibranched Amphiphiles
  作者：Maria Cristina Parlato、Jun-Pil Jee、Motti Teshite、Sandro Mecozzi

  DOI：10.1021/jo200835y

  日期：2011.8.19

  the synthesis and the physicochemical and preliminary pharmaceutical assessment of a novel class of hemifluorinated dibranched derivatives: M1diHxFy. These compounds have the remarkable ability to completely stop the Ostwald ripening commonly associated with nanoemulsions. The developed synthesis is modular and allows easy incremental structural variations in the fluorophilic (fluorous chains), lipophilic

  在这里，我们描述了一类新型半氟化二支化衍生物的合成、物理化学和初步药物评估：M 1 diH x F y. 这些化合物具有完全阻止通常与纳米乳液相关的奥斯特瓦尔德熟化的非凡能力。开发的合成是模块化的，允许在亲氟（氟链）、亲油（烷基间隔头）和亲水（极性头）域中轻松增加结构变化。此外，合成可以很容易地扩大规模，并且可以通过硅胶和氟硅胶柱色谱轻松获得高纯度的化合物，而无需使用 HPLC 或其他耗时的技术。胶束形成、临界聚集浓度 (CAC) 和乳液稳定性研究等表面特性证明了二支化半氟化表面活性剂 M 1 diH x F y的不同行为相对于单链半氟化类似物 M z F y。值得注意的是，新聚合物 M 1 diH 3 F 8在超过 1 年的时间里显着减缓了常用氟化麻醉剂七氟醚纳米乳液的成熟。在此期间，纳米液滴尺寸没有增加到超过 400 nm。这一结果非常有希望通过静脉内输送挥发性麻醉剂来诱导和维持全身麻
• Noncovalent fluorous interactions for the synthesis of carbohydrate microarrays
  作者：Sreeman K. Mamidyala、Kwang-Seuk Ko、Firoz A. Jaipuri、Gisun Park、Nicola L. Pohl

  DOI：10.1016/j.jfluchem.2006.01.001

  日期：2006.5

  A surface patterning method based on noncovalent immobilization of fluorous-tagged sugars on fluorous-derivatized glass slides allows the facile fabrication of carbohydrate microarrays. To expand the scope of these arrays, the first syntheses are reported of arabinose, rhamnose, lactose, maltose, and glucosamine tagged with a single C8F17-tail for ease of purification as well as array formation. Screening

  一种基于氟标签化的糖在氟衍生化的载玻片上的非共价固定化的表面图案化方法，可轻松制造碳水化合物微阵列。为了扩大这些阵列的范围，报道了用单个C 8 F 17尾标记的阿拉伯糖，鼠李糖，乳糖，麦芽糖和葡糖胺的首次合成，以易于纯化和形成阵列。对来自普通小麦（WGA）和花生花生（PNA）的凝集素的这些碳水化合物微阵列的筛选表明，在生物学测定条件下，非共价氟-氟相互作用足以保留单糖和二糖。
• Fluorous-based microarrays
  申请人：Pohl Lucia Nicola

  公开号：US20060199211A1

  公开（公告）日：2006-09-07

  A novel means of arraying fluorous tagged probes is disclosed. The method involves fluorous-tagging probes and attaching the same to a substrate having a fluorous surface. Target molecules are then identified and analyzed following attachment to the microarray.

  披露了一种新型的排列含氟标记探针的方法。该方法涉及将含氟标记探针附着在具有氟表面的基质上。随后，将目标分子附着到微阵列上进行识别和分析。
• Synthesis of Fluorous Tags for Incorporation of Reducing Sugars into a Quantitative Microarray Platform
  作者：Guo-Song Chen、Nicola L. Pohl

  DOI：10.1021/ol702915e

  日期：2008.3.1

  Carbohydrate microarrays can map out key interactions of carbohydrates and proteins in a high-throughput manner, but require the inclusion of a range of sugars for their optimal use. Here we present the synthesis and use of a new hydroxylamine-modified fluorous tag that allows the facile incorporation of reducing sugars into a noncovalent fluorous-based microarray after simple purification by fluorous solid-phase extraction (FSPE). The microarray supports quantitative screening against carbohydrate-binding proteins.
• Fluorous-based carbohydrate Quartz Crystal Microbalance
  作者：Lei Chen、Pengfei Sun、Guosong Chen

  DOI：10.1016/j.carres.2014.07.023

  日期：2015.3

  Fluorous chemistry has brought many applications from catalysis to separation science, from supramolecular materials to analytical chemistry. However, fluorous-based Quartz Crystal Microbalance (QCM) has not been reported so far. In the current paper, fluorous interaction has been firstly utilized in QCM, and carbohydrate-protein interaction and carbohydrate-carbohydrate interaction have been detected afterward. (C) 2014 Elsevier Ltd. All rights reserved.