(1-(trifluoromethoxy)ethyl)benzene | 767607-36-3

• 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: (1-(trifluoromethoxy)ethyl)benzene
• 英文别名: 1-(Trifluoromethoxy)ethylbenzene
• CAS: 767607-36-3
• 化学式: C₉H₉F₃O
• 分子量: 190.165
• InChiKey: CFVATUSHCXMGNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,4-二硝基三氟甲氧基苯 在 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 5.0h， 生成 (1-(trifluoromethoxy)ethyl)benzene
  参考文献：
  名称：

  Isolable Pyridinium Trifluoromethoxide Salt for Nucleophilic Trifluoromethoxylation

  摘要：

  DOI：

  10.1021/acs.orglett.1c01664

文献信息

• Silver-Catalyzed Trifluoromethoxylation of Alkyl Trifluoroborates
  作者：Xiaohuan Jiang、Pingping Tang

  DOI：10.1021/acs.orglett.0c01741

  日期：2020.7.2

  A silver-catalyzed trifluoromethoxylation of alkyl trifluoroborates with trifluoromethyl arylsulfonate as the trifluoromethoxylation reagent has been reported for the first time. This reaction is performed under mild reaction conditions and has wide functional group compatibility. In addition, the mechanism of this site-specific trifluoromethoxylation is proposed as a radical pathway.

  首次报道了用三氟甲基芳基磺酸盐作为三氟甲氧基化试剂的银催化的三氟硼酸烷基酯的三氟甲氧基化。该反应在温和的反应条件下进行，并且具有广泛的官能团相容性。另外，该位点特异性三氟甲氧基化的机制被提议为自由基途径。
• Direct Trifluoromethylation of Alcohols Using a Hypervalent Iodosulfoximine Reagent
  作者：Jorna Kalim、Thibaut Duhail、Ewa Pietrasiak、Elsa Anselmi、Emmanuel Magnier、Antonio Togni

  DOI：10.1002/chem.202005104

  日期：2021.2.5

  direct trifluoromethylation of a variety of aliphatic alcohols using a hypervalent iodosulfoximine reagent afforded the corresponding ethers in moderate to good yields (14–72 %). Primary, secondary, and even tertiary alcohols, including examples derived from natural products, underwent this transformation in the presence of catalytic amounts of zinc bis(triflimide). Typical reaction conditions involved

  使用高价碘亚磺酰亚胺试剂对各种脂肪醇进行直接三氟甲基化，可以以中等至良好的收率（14-72％）提供相应的醚。伯，仲，甚至叔醇，包括衍生自天然产物的实例，在催化量的双（三氟酰亚胺）锌存在下进行了这种转化。典型的反应条件包括6.0当量的醇与1.0当量的试剂的纯净混合物，大多数反应在2小时内用2.5 mol％的路易斯酸催化剂完成。此外，提供了实验证据表明，通过醇与碘原子的配位以及随后的还原消除，可以形成C-O键。
• Comprehensive Study and Development of a Metal‐Free and Mild Nucleophilic Trifluoromethoxylation
  作者：Clémence Bonnefoy、Armen Panossian、Gilles Hanquet、Frédéric R. Leroux、Fabien Toulgoat、Thierry Billard

  DOI：10.1002/chem.202301513

  日期：2023.8.15

  Among the general interest in fluorinated compounds, trifluoromethoxylated molecules play a specific role. However, despite this interest, the development of efficient reagents to perform trifluoromethoxylation reactions remains a challenge. Here, 2,4‐dinitro‐trifluoromethoxybenzene (DNTFB) is used as a trifluoromethoxylating reagent to perform nucleophilic substitution under mild metal‐free conditions with different leaving groups, including direct dehydroxytrifluoromethoxylation. A mechanistic study rationalized the reaction and subsequently proposed only three reaction conditions, depending on the reactivity of the starting substrates.

  摘要 在人们对含氟化合物的普遍兴趣中，三氟甲氧基化分子扮演着特殊的角色。然而，尽管人们对三氟甲氧基化反应很感兴趣，但开发高效的试剂仍是一项挑战。本文以 2,4-二硝基三氟甲氧基苯（DNTFB）为三氟甲氧基化试剂，在温和的无金属条件下与不同的离去基团进行亲核取代反应，包括直接脱羟基三氟甲氧基化反应。一项机理研究对该反应进行了合理化，随后根据起始底物的反应活性提出了三种反应条件。
• Silver(i) Perfluoroalcoholates: Synthesis, Structure, and their Use as Transfer Reagents
  作者：Paul Golz、Kamar Shakeri、Lilian Maas、Marius Balizs、Alberto Pérez-Bitrián、Helen D. Kemmler、Merlin Kleoff、Patrick Voßnacker、Mathias Christmann、Sebastian Hasenstab-Riedel

  DOI：10.1002/chem.202400861

  日期：——

  Therefore, the OCF3 group is emerging as a degradable group for a variety of applications, while higher perfluoroalkoxy groups are still of interest for agrochemicals or pharmaceuticals. The silver(I) perfluoroalcoholates can provide valuable reagents for incorporation into organic molecules.

  可降解的氟化基团是未来的一个机会，因为 ECHA 正在考虑在未来几年对持久性 PFAS 进行监管。因此，OCF 3基团正在作为一种可降解基团出现在各种应用中，而更高的全氟烷氧基基团仍然对农用化学品或药物感兴趣。全氟醇银(I)可以为掺入有机分子提供有价值的试剂。
• A deeper insight into direct trifluoromethoxylation with trifluoromethyl triflate
  作者：Olivier Marrec、Thierry Billard、Jean-Pierre Vors、Sergii Pazenok、Bernard R. Langlois

  DOI：10.1016/j.jfluchem.2009.11.006

  日期：2010.2

  Commercially available fluorides (silver fluoride and n-tetrabutylammonium triphenyldifluorosilicate), combined with TFMT, allow a simple generation, in situ, of silver and n-tetrabutylammonium trifluoromethoxides which were able to react with electrophilic substrates. Silver trifluoromethoxide, which is usually more efficient than n-tetrabutylammonium trifluoromethoxide, converts, under mild conditions, primary aliphatic bromides and iodides, as well as primary and secondary benzylic or allylic bromides to the corresponding trifluoromethoxylated compounds. Several trifluoromethyl ethers, which could be valuable building-blocks, were prepared in such a way. (C) 2009 Elsevier B.V. All rights reserved.