[(E)-3,3,3-trifluoro-1-propen-1-yl]-4-benzaldehyde | 1404363-19-4

• 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)-3,3,3-trifluoro-1-propen-1-yl]-4-benzaldehyde
• 英文别名: (E)-4-formylphenethenyltrifluoromethane；(E)-4-(3,3,3-trifluoroprop-1-en-1-yl)benzaldehyde；4-[(E)-3,3,3-trifluoroprop-1-enyl]benzaldehyde
• CAS: 1404363-19-4
• 化学式: C₁₀H₇F₃O
• 分子量: 200.16
• InChiKey: SRLIJPYGTSMAJC-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-碘-3,3,3-三氟丙烷 、 4-碘苯甲醛 在 palladium diacetate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 以73%的产率得到[(E)-3,3,3-trifluoro-1-propen-1-yl]-4-benzaldehyde
  参考文献：
  名称：

  Rapid Syntheses of [¹¹C]Arylvinyltrifluoromethanes through Treatment of (E)-Arylvinyl(phenyl)iodonium Tosylates with [¹¹C]Trifluoromethylcopper(I)

  摘要：

  We report a method for labeling arylvinyltrifluoromethanes with carbon-11 (t(1/2) = 20.4 min) as representatives of a new radiolabeled chemotype that has potential for developing radiotracers for biomedical imaging with positron emission tomography. Treatment of (E)-arylvinyl(phenyl)iodonium tosylates (1a - 1k) with [C-11]CuCF3 gave the corresponding [C-11]arylvinyltrifluoromethanes ([C-11]2a-[C-11]2k) in high radiochemical yields (90-97%) under rapid (2 min) and mild (60 degrees C) conditions.

  DOI：

  10.1021/acs.orglett.0c01705

文献信息

• Electrochemical Decarboxylative Trifluoromethylation of <i>α, β‐</i> Unsaturated Carboxylic Acids with CF ₃ SO ₂ Na
  作者：Fang‐Yuan Li、Dian‐Zhao Lin、Tian‐Jun He、Wei‐Qiang Zhong、Jing‐Mei Huang

  DOI：10.1002/cctc.201900438

  日期：2019.5.7

  A new method for the synthesis of vinyl trifluoromethyl compounds from α, β‐unsaturated carboxylic acids and CF3SO2Na has been developed. This electrochemical decarboxylative trifluoro‐methylation was found to be highly stereoselective and afforded products in good yields with wide substrate scope under metal‐free and external chemical oxidant‐free conditions.

  已开发出一种由α，β-不饱和羧酸和CF 3 SO 2 Na合成乙烯基三氟甲基化合物的新方法。发现这种电化学脱羧三氟甲基化反应具有高度的立体选择性，并且在无金属和无外部化学氧化剂的条件下，可以提供高收率的产品，具有广泛的底物范围。
• 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。
• 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）。
• Rapid Syntheses of [¹¹C]Arylvinyltrifluoromethanes through Treatment of (<i>E</i>)-Arylvinyl(phenyl)iodonium Tosylates with [¹¹C]Trifluoromethylcopper(I)
  作者：Susovan Jana、Sanjay Telu、Bo Yeun Yang、Mohammad B. Haskali、Jimmy E. Jakobsson、Victor W. Pike

  DOI：10.1021/acs.orglett.0c01705

  日期：2020.6.5

  We report a method for labeling arylvinyltrifluoromethanes with carbon-11 (t(1/2) = 20.4 min) as representatives of a new radiolabeled chemotype that has potential for developing radiotracers for biomedical imaging with positron emission tomography. Treatment of (E)-arylvinyl(phenyl)iodonium tosylates (1a - 1k) with [C-11]CuCF3 gave the corresponding [C-11]arylvinyltrifluoromethanes ([C-11]2a-[C-11]2k) in high radiochemical yields (90-97%) under rapid (2 min) and mild (60 degrees C) conditions.