(nonafluorobutyl)benzene | 2398-75-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (nonafluorobutyl)benzene
• 英文别名: nonafluorobutylbenzene；(perfluorobutyl)benzene；Ph-C4F9；C4F9Ph；perfluorobutyl benzene；Perfluorbutyl-benzol；Benzene, (nonafluorobutyl)-；1,1,2,2,3,3,4,4,4-nonafluorobutylbenzene
• CAS: 2398-75-6
• 化学式: C₁₀H₅F₉
• 分子量: 296.135
• InChiKey: PACASBRIKDMTSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  9

安全信息

• 海关编码：
  2903999090

反应信息

• 作为反应物：
  描述：

  (nonafluorobutyl)benzene 在 硫酸 、 硝酸 作用下， 生成 1-nitro-3-(perfluorobutyl)benzene
  参考文献：
  名称：

  The Electronic Properties of Fluoroalkyl Groups. Fluorine p-π Interaction¹

  摘要：

  DOI：

  10.1021/ja01089a020
• 作为产物：
  描述：

  (七氟丁偶基)苯酮 在 sulfur tetrafluoride 作用下， 生成 (nonafluorobutyl)benzene
  参考文献：
  名称：

  The Electronic Properties of Fluoroalkyl Groups. Fluorine p-π Interaction¹

  摘要：

  DOI：

  10.1021/ja01089a020

文献信息

• A general and practical Ni-catalyzed C–H perfluoroalkylation of (hetero)arenes
  作者：Shaoke Zhang、Nicolas Rotta-Loria、Florian Weniger、Jabor Rabeah、Helfried Neumann、Christoph Taeschler、Matthias Beller

  DOI：10.1039/c9cc01971e

  日期：——

  (hetero)arenes using the air- and moisture-stable complex (dppf)Ni(o-tol)Cl was developed (23 examples). The novel procedure allows for the synthesis of various fluorinated products and tolerates sensitive functional groups including aldehydes, free amino groups and several heterocycles.

  开发了使用空气和水分稳定的复合物（dppf）Ni（邻甲苯基）Cl直接对（杂）芳烃进行全氟烷基化的方法（23个例子）。该新颖方法允许合成各种氟化产物并耐受敏感的官能团，包括醛，游离氨基和几个杂环。
• Heterogeneous Platinum-Catalyzed CH Perfluoroalkylation of Arenes and Heteroarenes
  作者：Lin He、Kishore Natte、Jabor Rabeah、Christoph Taeschler、Helfried Neumann、Angelika Brückner、Matthias Beller

  DOI：10.1002/anie.201411066

  日期：2015.3.27

  compounds are gaining increasing interest for life science applications. The replacement of hydrogen in arenes or heteroarenes by a perfluoroalkyl group has a profound influence on the physical and biological properties of such building blocks. Here, an operationally simple protocol for the direct CH perfluoroalkylation of (hetero)arenes with RfI or RfBr has been developed, using a robust supported platinum

  氟化有机化合物在生命科学应用中越来越受到关注。芳烃或杂芳烃中的氢被全氟烷基取代对这种结构单元的物理和生物学特性产生深远的影响。在此，使用R f I或R f对（杂）芳烃进行直接CH全氟烷基化的操作简单协议使用坚固的负载型铂催化剂已开发出Br。起始原料的可用性，优异的底物耐受性和催化剂的可重复使用性使该方法对合成各种全氟烷基取代的芳族化合物具有吸引力。初步的机理研究表明，自由基的形成对反应系统至关重要。
• 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.
• Copper-Catalyzed Oxidative Perfluoroalkylation of Aryl Boronic Acids Using Perfluoroalkylzinc Reagents
  作者：Xifei Bao、Lihua Liu、Junlan Li、Shilu Fan

  DOI：10.1021/acs.joc.7b02557

  日期：2018.1.5

  An efficient and synthetically convenient method for copper-catalyzed cross-coupling of aryl boronic acids with perfluoroalkyl zinc reagents has been described. The reaction proceeds under mild reaction conditions with a high efficiency and broad substrate scope and provides a general access to perfluoroalkylated arenes, which are of interest in life and materials science.

  已经描述了用于铜催化的芳基硼酸与全氟烷基锌试剂的交叉偶联的有效且合成方便的方法。该反应在温和的反应条件下进行，具有较高的效率和广泛的底物范围，并提供了进入全氟烷基化芳烃的一般途径，这是生命科学和材料科学中关注的问题。
• Fluorous-tagged indolylboron for the diversity-oriented synthesis of biologically-attractive bisindole derivatives
  作者：Takahiro Kasahara、Yoshinori Kondo

  DOI：10.1039/b516487g

  日期：——

  The diversity-oriented synthesis of bisindole derivatives to construct concise libraries using consecutive cross-coupling reactions and prepare new sulfonamide type fluorous protecting groups is presented.

  本文介绍了以多样性为导向的双吲哚衍生物合成方法，利用连续的交叉偶联反应构建简洁的化合物库，并制备新的磺酰胺型氟保护基团。