(E)-(3-(trifluoromethoxy)prop-1-en-1-yl)benzene | 1241960-07-5

• 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: (E)-(3-(trifluoromethoxy)prop-1-en-1-yl)benzene
• 英文别名: [(E)-3-(trifluoromethoxy)prop-1-enyl]benzene
• CAS: 1241960-07-5
• 化学式: C₁₀H₉F₃O
• 分子量: 202.176
• InChiKey: AKLKYQCXVJZVCM-QPJJXVBHSA-N

物化性质

• 沸点：
  207.4±40.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  三氟甲烷磺酸三氟甲酯 、 Cinnamyl bromide 在 silver fluoride 作用下， 以 乙腈 为溶剂， 反应 26.5h， 以47%的产率得到(E)-(3-(trifluoromethoxy)prop-1-en-1-yl)benzene
  参考文献：
  名称：

  A deeper insight into direct trifluoromethoxylation with trifluoromethyl triflate

  摘要：

  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.

  DOI：

  10.1016/j.jfluchem.2009.11.006

文献信息

• Direct Dehydroxytrifluoromethoxylation of Alcohols
  作者：Xiaohuan Jiang、Zhijie Deng、Pingping Tang

  DOI：10.1002/anie.201711050

  日期：2018.1.2

  developed. This method generated an alkyl fluoroformate in situ from alcohols, followed by nucleophilic trifluoromethoxylation with trifluoromethyl arylsulfonate (TFMS) as the trifluoromethoxylation reagent. The reaction is operationally simple and scalable, and it proceeds under mild reaction conditions to provide access to a wide range of trifluoromethyl ethers from alcohols. In addition, this method

  已经开发出醇直接脱羟基三氟甲氧基化的第一个例子。该方法由醇原位生成氟代甲酸烷基酯，然后用三氟甲基芳基磺酸酯（TFMS）作为三氟甲氧基化试剂进行亲核性三氟甲氧基化。该反应操作简单且可扩展，并且在温和的反应条件下进行以提供从醇类中获得各种三氟甲基醚的途径。此外，该方法适用于复杂小分子的后期三氟甲氧基化。
• Facile Access to AgOCF₃and Its New Applications as a Reservoir for OCF₂for the Direct Synthesis of N−CF₃, Aryl or Alkyl Carbamoyl Fluorides
  作者：Abdurrahman Turksoy、Thomas Scattolin、Samir Bouayad‐Gervais、Franziska Schoenebeck

  DOI：10.1002/chem.202000116

  日期：2020.2.17

  showcase its performance in trifluoromethoxylations or as reservoir for O=CF2. This enabled the direct, practical and safe synthesis of valuable N‐alkyl/aryl and N−CF3 carbamoyl fluorides from secondary amines and isothiocyanides, respectively. Our mechanistic data indicate that AgOCF3 does not liberate O=CF2 until it is activated by a nucleophilic co‐reagent, reinforcing the stability of the salt under

  创新氟化策略的发展在很大程度上还取决于现有氟化试剂的可用性，安全性和实用性。我们在本文中显示了在室温下制备有价值的AgOCF 3的直接和定量策略，并展示了其在三氟甲氧基化中或作为O = CF 2的储库的性能。这样就可以分别从仲胺和异硫氰化物直接，实用和安全地合成有价值的N-烷基/芳基和N-CF 3氨基甲酰氟。我们的机理数据表明，AgOCF 3不会释放O = CF 2 直至其被亲核助剂激活，从而在我们的新制备策略下增强了盐的稳定性。
• Catalytic Oxidative Trifluoromethoxylation of Allylic C−H Bonds Using a Palladium Catalyst
  作者：Xiaoxu Qi、Pinhong Chen、Guosheng Liu

  DOI：10.1002/anie.201703841

  日期：2017.8.1

  A catalytic intermolecular allylic C−H trifluoromethoxylation reaction of alkenes has been developed based on the use of a palladium catalyst, CsOCF3 as the trifluoromethoxide source, and benzoquinone as the oxidant. This reaction provides an efficient route for directly accessing allylic trifluoromethoxy derivatives with excellent regioselectivities from terminal alkenes via an allylic C−H bond activation

  基于钯催化剂，CsOCF 3作为三氟甲醇盐源和苯醌作为氧化剂，已经开发了烯烃的分子间烯丙基CH-H三氟甲氧基化反应。该反应提供了一种有效的途径，可以通过烯丙基CH键活化过程直接从末端烯烃中获得具有极好的区域选择性的烯丙基三氟甲氧基衍生物。
• 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。
• A New and Direct Trifluoromethoxylation of Aliphatic Substrates with 2,4-Dinitro(trifluoromethoxy)benzene
  作者：Olivier Marrec、Thierry Billard、Jean-Pierre Vors、Sergii Pazenok、Bernard R. Langlois

  DOI：10.1002/adsc.201000488

  日期：2010.11.2

  The reaction of tetrabutylammonium triphenyldifluorosilicate with 2,4-dinitro(trifluoromethoxy)benzene, in acetonitrile and under microwave irradiation, generates a trifluoromethoxide anion which is able to substitute activated bromides (benzyl bromide, cinnamyl bromide), as well as, to some extent, alkyl iodides. Aliphatic trifluoromethyl ethers are thus formed. This is the first example of the nucleophilic

  四丁基三苯基二氟硅酸铵与2,4-二硝基（三氟甲氧基）苯在乙腈中并在微波辐射下反应生成三氟甲氧基阴离子，它可以取代活化的溴化物（苄基溴化物，肉桂基溴化物），以及在一定程度上烷基碘。由此形成脂肪族三氟甲基醚。这是三氟甲氧基从活化的芳环亲核取代的第一个例子。