(E)-2-(3,3,3-trifluoroprop-1-en-1-yl)pyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (E)-2-(3,3,3-trifluoroprop-1-en-1-yl)pyridine
• 英文别名: 2-(3,3,3-Trifluoroprop-1-en-1-yl)pyridine；2-[(E)-3,3,3-trifluoroprop-1-enyl]pyridine
• 化学式: C₈H₆F₃N
• 分子量: 173.138
• InChiKey: OMIMHKSHDOGJTL-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-碘吡啶 、 1-碘-3,3,3-三氟丙烷 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74%的产率得到(E)-2-(3,3,3-trifluoroprop-1-en-1-yl)pyridine
  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。
• Decarboxylative and Denitrative Trifluoromethylation for the Synthesis of C_vinylCF₃Compounds with Togni (II) Reagent
  作者：Jing-jing Ma、Wen-bin Yi、Guo-ping Lu、Chun Cai

  DOI：10.1002/adsc.201500631

  日期：2015.11.16

  A highly efficient dimethylformamide (DMF)-promoted decarboxylative trifluoromethylation of α,β-unsaturated carboxylic acids with Togni (II) reagent under metal-free conditions has been developed. The reactions showed good yields, high stereoselectivities and excellent functional group tolerance. Mechanistic studies confirmed that free-radical processes were involved in this system since the CF3 radical

  在无金属条件下，用Togni（II）试剂开发了高效的二甲基甲酰胺（DMF）促进的α，β-不饱和羧酸的脱羧三氟甲基化反应。反应显示出良好的产率，高的立体选择性和优异的官能团耐受性。机理研究证实，该自由基系统参与了该系统，因为CF 3自由基已被清除剂清楚地捕获。该方法已扩展到在铁（III）催化剂存在下β-硝基苯乙烯的反硝化三氟甲基化反应。
• Room temperature decarboxylative trifluoromethylation of α,β-unsaturated carboxylic acids by photoredox catalysis
  作者：Pan Xu、Ablimit Abdukader、Kaidong Hu、Yixiang Cheng、Chengjian Zhu

  DOI：10.1039/c3cc48598f

  日期：——

  A visible-light-induced decarboxylative trifluoromethylation of alpha,beta-unsaturated carboxylic acids, which uses the Togni reagent as the CF3 source is disclosed. The corresponding trifluoromethylated alkenes were obtained in moderate to high yields with excellent functional group tolerance at ambient temperature. Preliminary mechanistic analyses suggest a radical-type mechanism.

  公开了使用Togni试剂作为CF 3源的可见光诱导的α，β-不饱和羧酸的脱羧三氟甲基化。以中等至高产率获得了相应的三氟甲基化烯烃，其在环境温度下具有优异的官能团耐受性。初步的机械分析表明是一种激进型机制。
• Controlled Trifluoromethylation Reactions of Alkynes through Visible-Light Photoredox Catalysis
  作者：Naeem Iqbal、Jaehun Jung、Sehyun Park、Eun Jin Cho

  DOI：10.1002/anie.201308735

  日期：2014.1.7

  The control of a reaction that can form multiple products is a highly attractive and challenging concept in synthetic chemistry. A set of valuable CF3‐containing molecules, namely trifluoromethylated alkenyl iodides, alkenes, and alkynes, were selectively generated from alkynes and CF3I by environmentally benign and efficient visible‐light photoredox catalysis. Subtle differences in the combination

  在合成化学中，控制可形成多种产物的反应是一个极具吸引力和挑战性的概念。通过对环境无害且有效的可见光光氧化还原催化作用，从炔烃和CF 3 I选择性地生成了一组有价值的含CF 3分子，即三氟甲基化的烯基碘，烯烃和炔烃。催化剂，碱和溶剂的组合之间存在细微差异，因此可以控制炔烃与CF 3 I之间反应的反应性和选择性。
• Synthesis and Reactions of (2,2,2-Trifluoroethyl)triphenylphosphonium Trifluoromethanesulfonate
  作者：Takeshi Hanamoto、Noriko Morita、Keiko Shindo

  DOI：10.1002/ejoc.200300395

  日期：2003.11

  hydroxide gave (2,2-dimethoxyvinyl)triphenylphosphonium triflate (6a) in high yield instead of the corresponding (2,2,2-trifluoroethyl)diphenylphosphane oxide. Furthermore, reactions between 1 and secondary amines exclusively gave the novel (Z)-(2-amino-2-fluorovinyl)triphenylphosphonium triflates (10) in high yields. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  (2,2,2-三氟乙基)三苯基鏻三氟甲磺酸盐 (triflate) (1) 很容易从三苯基膦和 2,2,2-三氟乙基三氟甲磺酸酯以高产率合成。1 与带有吸电子基团的芳香醛在 DMF 中以 CsF 作为碱的 Wittig 烯化反应顺利进行，以良好的收率产生相应的 3,3,3-三氟亚丙基化合物。另一方面，在含有氢氧化钠的甲醇中水解 1 以高产率得到（2,2-二甲氧基乙烯基）三苯基鏻三氟甲磺酸盐（6a），而不是相应的（2,2,2-三氟乙基）二苯基氧化膦。此外，1 和仲胺之间的反应仅以高产率得到新型 (Z)-(2-氨基-2-氟乙烯基)三苯基鏻三氟甲磺酸盐 (10)。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)