benzyl (trifluoromethoxy)acetate | 1241960-09-7

• 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: benzyl (trifluoromethoxy)acetate
• 英文别名: benzyl 2-(trifluoromethoxy)acetate
• CAS: 1241960-09-7
• 化学式: C₁₀H₉F₃O₃
• 分子量: 234.175
• InChiKey: SEEFOJKNKRVTTC-UHFFFAOYSA-N

物化性质

• 沸点：
  243.2±35.0 °C(Predicted)
• 密度：
  1.290±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-溴乙酸苄酯 在 silver fluoride 、 sodium iodide 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 18.0h， 生成 benzyl (trifluoromethoxy)acetate
  参考文献：
  名称：

  通过原位产生氟光气进行无 OCF3 载体的直接三氟甲氧基化

  摘要：

  开发了一种高效、原子经济的三氟甲氧基化方法，无需三氟甲氧基化试剂。该方法依赖于原位产生氟光气并将其转化为 OCF 3阴离子以实现对一系列烷基碘的亲核取代。

  DOI：

  10.1002/ejoc.202100429

文献信息

• 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。
• 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.