3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-十七氟癸烷磺酰氯 | 27619-90-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 磺酰卤
• 中文名称: 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-十七氟癸烷磺酰氯
• 英文名称: 1H,1H,2H,2H-perfluorodecylsulfonyl chloride
• 英文别名: 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecane-1-sulfonyl chloride；3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorooctanesulfonyl chloride；3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecanesulfonyl chloride；1-Decanesulfonyl chloride, 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-
• CAS: 27619-90-5
• 化学式: C₁₀H₄ClF₁₇O₂S
• 分子量: 546.632
• InChiKey: BXLIWKCKMHDVHE-UHFFFAOYSA-N

物化性质

• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  31
• 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：
  42.5
• 氢给体数：
  0
• 氢受体数：
  19

安全信息

• 海关编码：
  2904909090

反应信息

• 作为反应物：
  描述：

  3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-十七氟癸烷磺酰氯 在 氨 作用下， 以 乙酸乙酯 为溶剂， 反应 0.75h， 以91%的产率得到3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-n-decanesulfonamide
  参考文献：
  名称：

  Synthesis and investigation of inhibition effect of fluorinated sulfonamide derivatives on carbonic anhydrase

  摘要：

  Series of perfluoroalkanesulfonamides 1, sodium salt of perfluoroalkanesulfonamides 2 and poly-fluoroalkanesulfonamides 3 derivatives were synthesized and characterized by H-1 NMR, C-13 NMR, F-19 NMR, IR and HRMS. Inhibition effects of these compounds on bovine carbonic anhydrase (bCA) and human carbonic anhydrase isoenzyme II (hCA) have been investigated. Comparing IC50 values of the synthesized molecules 1, 2 and 3, it has been found that compound 2b is a more potent inhibitor than acetazolamide on hCA. Moreover 2b does not present cellular toxicity on sheep red globules. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.11.052
• 作为产物：
  描述：

  3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl thiocyanate 在 水 、 溶剂黄146 、 磺酰氯 作用下， 反应 1.0h， 生成 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-十七氟癸烷磺酰氯
  参考文献：
  名称：

  烷烃和多氟烷磺酰氯的新合成

  摘要：

  本研究描述了一种通过硫氰酸烷基酯 (1) 与磺酰氯在乙酸和水的混合物中反应合成烷烃磺酰氯 (2) 的新方法。以良好的收率获得链烷磺酰氯。© 2009 Wiley Periodicals, Inc. 杂原子化学 20:355–361, 2009; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20559

  DOI：

  10.1002/hc.20559

文献信息

• Fluorous Synthesis of¹⁸F Radiotracers with the [¹⁸F]Fluoride Ion: Nucleophilic Fluorination as the Detagging Process
  作者：Romain Bejot、Thomas Fowler、Laurence Carroll、Sophie Boldon、Jane E. Moore、Jérôme Declerck、Véronique Gouverneur

  DOI：10.1002/anie.200803897

  日期：2009.1.5

  Tag team: The fluoro‐detagging of fluorous sulfonates by the [18F]fluoride ion was found to be an advantageous strategy for the preparation of various 18F‐labeled prosthetic groups and known radiotracers (see picture). Fluorous solid phase extraction (FSPE) was used to separate the excess fluorous precursor from the labeled material, which suggests that traditional purification protocols such as distillation

  标签小组：发现[ 18 F]氟离子对氟代磺酸盐进行氟脱标记是制备各种18 F标记的修复基团和已知放射性示踪剂的有利策略（参见图片）。荧光固相萃取（FSPE）用于从标记的材料中分离出过量的氟前体，这表明可以避免传统的纯化方案，例如蒸馏或繁琐的分离。
• Use of perfluoro groups in nucleophilic¹⁸F-fluorination
  作者：Elisabeth Blom、Farhad Karimi、Bengt LÃ¥ngström

  DOI：10.1002/jlcr.1695

  日期：——

  Substrates with leaving groups that contained perfluoro moieties were investigated in labelling chemistry in order to exploit their properties to improve reactivity and purification. [18F](Fluoromethyl)benzene was used as the model target compound. Precursors containing perfluoroalkyl and perfluoroaryl sulfonate moieties were subjected to nucleophilic 18F-fluorination, and the impact of perfluoro groups on the substitution reaction and product purification was investigated. [18F]Fluoride interacted with perfluoroalkyl chains, precluding nucleophilic substitution. When perfluoroaryl groups were used, the substitution proceeded, and the separation of product was explored. The radiolabelled product was obtained in 32% analytical yield and the radiochemical purity was increased to approximately 77% using fluorous solid phase extraction purification. Copyright © 2009 John Wiley & Sons, Ltd.

  含有全氟基团的离去基底在标记化学中进行了研究，以利用其特性提高反应性和纯化。以[18F](氟甲基)苯作为模型目标化合物。含有全氟烷基和全氟芳基磺酸基团的前体经过亲核性18F-氟化，研究了全氟基团对取代反应和产物纯化的影响。[18F]氟化物与全氟烷基链发生相互作用，妨碍了亲核取代反应。当使用全氟芳基基团时，取代反应得以进行，并探讨了产物的分离。最终获得了32%的分析产率，并通过氟固相萃取纯化将放射化学纯度提高至约77%。版权所有 © 2009 John Wiley & Sons, Ltd.
• Synthesis and Evaluation of Fluorous-Tagged and Polystyrene-Supported Precursors for Fluoro-benziodoxole
  作者：John F. Valliant、Graham K. Murphy、Léanne Racicot

  DOI：10.1055/a-2085-3284

  日期：2023.9

  exchange with fluorous- or polystyrene-based sulfonyloxy-benziodoxole precursors. Key to this strategy was the facile O-sulfonylation of a common hydroxy-benziodoxole precursor with sulfonyl chlorides, which enabled the easy synthesis and evaluation of previously unknown fluorous- or polystyrene-based fluoride exchange precursors. Fluorination of a fluorous-tagged iodane led to fluoro-benziodoxole in

  Fluoro-benziodoxole 是一种氟化高价碘 (HVI) 试剂，通过与基于氟或聚苯乙烯的磺酰氧基-benziodoxole 前体进行氟化物交换制备。该策略的关键是用磺酰氯对常见的羟基苯并氧唑前体进行简单的 O-磺酰化，这使得以前未知的氟或聚苯乙烯基氟化物交换前体的合成和评估变得容易。用 TBAF 氟标记的碘烷氟化在 10 分钟内以 67% 的产率生成氟代苯并双酚，而聚苯乙烯支撑的碘烷上的氟化物交换在与 TBAF 反应 10 分钟后以 82 ± 5% 的产率生成氟代苯并双酚.
• [EN] PREPARATION OF FLUORINE-LABELLED COMPOUNDS<br/>[FR] PRÉPARATION DE COMPOSÉS MARQUÉS PAR DU FLUOR
  申请人：ISIS INNOVATION

  公开号：WO2010007363A3

  公开（公告）日：2010-07-01
• Synthesis and investigation of inhibition effect of fluorinated sulfonamide derivatives on carbonic anhydrase
  作者：Zohra Benfodda、Franck Guillen、Bernard Romestand、Abdelkader Dahmani、Hubert Blancou

  DOI：10.1016/j.ejmech.2009.11.052

  日期：2010.3

  Series of perfluoroalkanesulfonamides 1, sodium salt of perfluoroalkanesulfonamides 2 and poly-fluoroalkanesulfonamides 3 derivatives were synthesized and characterized by H-1 NMR, C-13 NMR, F-19 NMR, IR and HRMS. Inhibition effects of these compounds on bovine carbonic anhydrase (bCA) and human carbonic anhydrase isoenzyme II (hCA) have been investigated. Comparing IC50 values of the synthesized molecules 1, 2 and 3, it has been found that compound 2b is a more potent inhibitor than acetazolamide on hCA. Moreover 2b does not present cellular toxicity on sheep red globules. (C) 2009 Elsevier Masson SAS. All rights reserved.