(E)-1-phenoxy-4-(3,3,3-trifluoroprop-1-en-1-yl)benzene | 1404363-17-2

• 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)-1-phenoxy-4-(3,3,3-trifluoroprop-1-en-1-yl)benzene
• 英文别名: 1-phenoxy-4-(3,3,3-trifluoroprop-1-en-1-yl)benzene；1-phenoxy-4-[(E)-3,3,3-trifluoroprop-1-enyl]benzene
• CAS: 1404363-17-2
• 化学式: C₁₅H₁₁F₃O
• 分子量: 264.247
• InChiKey: SHRFVQAOQRUGHR-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1-phenoxy-4-(3,3,3-trifluoroprop-1-en-1-yl)benzene 在 palladium on activated charcoal 、 氢气 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、506.66 kPa 条件下， 以99 %的产率得到1-苯氧基-4-(3,3,3-三氟丙基)苯
  参考文献：
  名称：

  Hydroxylamine‐Mediated C(sp2)−H Trifluoromethylation of Terminal Alkenes

  摘要：

  Introduction of the trifluoromethyl (CF3) group into organic compounds has garnered substantial interest because of its significant role in pharmaceuticals and agrochemicals. Here, we report a hydroxylamine‐mediated radical process for C(sp2)−H trifluoromethylation of terminal alkenes. The reaction shows good reactivity, impressive E/Z selectivity (up to > 20:1), and broad functional group compatibility. Expansion of this approach to perfluoroalkylation and late‐stage trifluoromethylation of bioactive molecules demonstrates its promising application potential. Mechanistic studies suggest that the reaction follows a radical addition and subsequent elimination pathway.

  DOI：

  10.1002/chem.202400995
• 作为产物：
  描述：

  (E)-diphenyl-b-(trifluoromethyl)vinylsulfonium triflate 、 4-苯氧基苯基硼酸 在 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 1,4-二氧六环 为溶剂， 反应 19.0h， 以85%的产率得到(E)-1-phenoxy-4-(3,3,3-trifluoroprop-1-en-1-yl)benzene
  参考文献：
  名称：

  在 (E)-(β-三氟甲基) 乙烯基二苯基锍盐的 Pd 催化偶联中，乙烯基 CS 键相对于芳基 CS 键的高度选择性活化：三氟甲基化烯烃和二烯的制备

  摘要：

  我们描述了 (E)-(β-三氟甲基) 乙烯基二苯基锍盐与芳基硼酸的 Suzuki 偶联反应。高效和选择性的反应为合成三氟甲基化烯烃和二烯烃提供了一种有用且温和的方法。随后的 DFT 研究表明，乙烯基 CS 键的氧化加成过渡态比芳基 CS 键更有利（11.7 kcal?mol1）。

  DOI：

  10.1002/ejoc.201200758

文献信息

• Palladium Catalyzed Vinyltrifluoromethylation of Aryl Halides through Decarboxylative Cross-Coupling with 2-(Trifluoromethyl)acrylic Acid
  作者：Subban Kathiravan、Ian A. Nicholls

  DOI：10.1021/acs.orglett.5b00551

  日期：2015.4.17

  An efficient Pd-catalyzed stereoselective vinyltrifluoromethylation of aryl halides, through decarboxylative cross-coupling with 2-(trifluoromethyl)acrylic acid is described. The ready availability of the starting materials, the high level of functional group tolerance, and excellent E/Z selectivity make this protocol a safe and operationally convenient strategy for efficient synthesis of vinyltrifluoromethyl

  描述了通过与2-（三氟甲基）丙烯酸的脱羧交叉偶联的有效的Pd催化的芳基卤化物的立体选择性乙烯基三氟甲基化。起始材料的随时可用，高水平的官能团耐受性和出色的E / Z选择性使该方案成为有效合成乙烯基三氟甲基衍生物的安全且操作便捷的策略。
• Metal‐Free Visible‐Light‐Mediated Hydrotrifluoromethylation of Unactivated Alkenes and Alkynes in Continuous Flow
  作者：Anne‐Laure Barthelemy、Guillaume Dagousset、Emmanuel Magnier

  DOI：10.1002/ejoc.201901252

  日期：2020.3.15

  photoredox-catalyzed hydrotrifluoromethylation of unsaturated systems under continuous flow. This metal-free method is easily broadened to other perfluoroalkyl groups (RF = CF3, CFCl2, CF2Br, C4F9) thanks to the use of sulfilimino iminiums as sources of ·RF radicals. The mild reaction conditions are compatible with unactivated alkenes bearing a wide range of functionalities, as well as with alkynes for the

  我们在此报告了一种在连续流动下的不饱和系统的新型光氧化还原催化氢三氟甲基化。由于使用硫亚胺鎓作为·RF 自由基的来源，这种无金属方法很容易扩展到其他全氟烷基（RF = CF3、CFCl2、CF2Br、C4F9）。温和的反应条件与具有广泛功能的未活化烯烃相容，并首次与炔烃相容。
• Highly Selective Activation of Vinyl C-S Bonds Over Aryl C-S Bonds in the Pd-Catalyzed Coupling of (E)-(β-Trifluoromethyl)vinyldiphenylsulfonium Salts: Preparation of Trifluoromethylated Alkenes and Dienes
  作者：Hao Lin、Xicheng Dong、Yuxue Li、Qilong Shen、Long Lu

  DOI：10.1002/ejoc.201200758

  日期：2012.9

  We describe the Suzuki coupling reaction of (E)-(beta-trifluoromethyl)vinyldiphenylsulfonium salts with arylboronic acid. The highly efficient and selective reaction provides a useful and mild method for the synthesis of trifluoromethylated alkenes and dienes. Subsequent DFT studies showed that the oxidative addition transition state of the vinyl CS bond is much more favorable (11.7 kcal?mol1) than

  我们描述了 (E)-(β-三氟甲基) 乙烯基二苯基锍盐与芳基硼酸的 Suzuki 偶联反应。高效和选择性的反应为合成三氟甲基化烯烃和二烯烃提供了一种有用且温和的方法。随后的 DFT 研究表明，乙烯基 CS 键的氧化加成过渡态比芳基 CS 键更有利（11.7 kcal?mol1）。
• Hydroxylamine‐Mediated C(sp2)−H Trifluoromethylation of Terminal Alkenes
  作者：Xiao Zhao、Bing Zhong、Likun Dong、Yu-Shan Zhang、Hai-Tian Luo、Jin-Dong Yang、Jin-Pei Cheng

  DOI：10.1002/chem.202400995

  日期：——

  Introduction of the trifluoromethyl (CF3) group into organic compounds has garnered substantial interest because of its significant role in pharmaceuticals and agrochemicals. Here, we report a hydroxylamine‐mediated radical process for C(sp2)−H trifluoromethylation of terminal alkenes. The reaction shows good reactivity, impressive E/Z selectivity (up to > 20:1), and broad functional group compatibility. Expansion of this approach to perfluoroalkylation and late‐stage trifluoromethylation of bioactive molecules demonstrates its promising application potential. Mechanistic studies suggest that the reaction follows a radical addition and subsequent elimination pathway.