(Z)-3,3,3-trifluoro-1-(4-nitrophenyl)prop-1-ene

• 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: (Z)-3,3,3-trifluoro-1-(4-nitrophenyl)prop-1-ene
• 英文别名: (Z)-1-nitro-4-(3,3,3-trifluoroprop-1-S7enyl)benzene；(Z)-1-nitro-4-(3,3,3-trifluoroprop-1-en-1-yl)benzene；(Z)-1-(4-nitrophenyl)-3,3,3-trifluoropropene；(Z)-1-(4-nitrophenyl)-3,3,3-trifluoro-1-propene；1-Nitro-4-[(Z)-3,3,3-trifluoro-1-propenyl]benzene；1-nitro-4-[(Z)-3,3,3-trifluoroprop-1-enyl]benzene
• 化学式: C₉H₆F₃NO₂
• 分子量: 217.147
• InChiKey: WGVJEEXBVPTTFU-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对硝基苯酚 、 (E)-1-氯-3,3,3-三氟丙烯 在 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以66.667%的产率得到
  参考文献：
  名称：

  取代酚和醇与（E）-1-氯-3,3,3-三氟丙烯（HFCO-1233zd）的反应

  摘要：

  介绍了从工业产品HFCO-1233zd（CF 3 CH = CHCl）开始的简单方便的一锅法制备ArOCH = CHCF 3，ROCH = CHCF 3和CF 3 CH = CHOArOCH = CHCF 3的方法。这些合成包括在升高的温度下，在DMF或吡啶溶剂中的氢氧化钾存在下，1233zd与酚和醇的反应。

  DOI：

  10.1016/j.jfluchem.2020.109456

文献信息

• Iron(III) Porphyrin Catalyzed Olefination of Aldehydes with 2,2,2-Trifluorodiazoethane (CF₃ CHN₂ )
  作者：Yang Lu、Chuyu Huang、Chao Liu、Yong Guo、Qing-Yun Chen

  DOI：10.1002/ejoc.201800325

  日期：2018.5.15

  An efficient method for the iron(III) porphyrin catalyzed olefination of various aldehydes with 2,2,2‐trifluorodiazoethane (CF3CHN2) under neutral conditions has been developed. This reaction is an important supplement to the synthetic applications of CF3CHN2.

  开发了一种在中性条件下用铁（III）卟啉催化各种醛与2,2,2-三氟重氮乙烷（CF 3 CHN 2）的有效反应的方法。该反应是CF 3 CHN 2合成应用的重要补充。
• 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)
• A Reverse Wittig Coupling with Trifluoroacetaldehyde: A Convenient One-Step Synthesis of Trifluoromethyl Alkenes
  作者：Shainaz Landge、Dmitry Borkin、Bela Torok

  DOI：10.2174/157017809789124795

  日期：2009.9.1

  A novel, mild synthesis of aryl-3,3,3-trifluoropropenes by Wittig olefination of benzylphosphonium ylides with in-situ generated trifluoroacetaldehyde is described. The in-situ formed trifluoroacetaldehyde efficiently traps the Wittig ylides and yields trifluoromethyl alkenes without the troublesome handling. The scope of the reaction was tested in reaction of trifluoroacetaldehyde with a wide variety of benzylphosphonium ylides. The α-trifluoromethyl alkenes were isolated in good to excellent yields in a convenient one step process.

  描述了一种新颖、温和的芳基 3,3,3-三氟丙烯合成方法，通过苄基鏻叶立德与原位生成的三氟乙醛进行 Wittig 烯化。原位形成的三氟乙醛有效地捕获维蒂希叶立德并产生三氟甲基烯烃，而无需麻烦的处理。在三氟乙醛与多种苄基鏻叶立德的反应中测试了反应范围。通过一种方便的一步法以良好至优异的产率分离出 α-三氟甲基烯烃。
• Julia–Kocienski approach to trifluoromethyl-substituted alkenes
  作者：Deborah O. Ayeni、Samir K. Mandal、Barbara Zajc

  DOI：10.1016/j.tetlet.2013.08.069

  日期：2013.11

  A Julia-Kocienski approach to trifluoromethyl-substituted alkenes was evaluated in the reactions of 1,3-benzothiazol-2-yl, 1-phenyl-1H-tetrazol-5-yl, and 1-tbutyl-1H-tetrazol-5-yl 2,2,2-trifluoroethyl sulfones with aldehydes. Among the various conditions tested, the best yields were obtained with 1-phenyl-1H-tetrazol-5-yl 2,2,2-trifluoroethyl sulfone, in CsF-mediated, room temperature olefinations in DMSO. Aromatic aldehydes gave (trifluoromethyl)vinyl derivatives in 23-86% yields, with generally moderate stereoselectivity. Straightforward synthesis of the Julia-Kocienski reagent, and conversion to trifluoromethyl-substituted alkenes under mild reaction conditions, are the advantages of this approach. (C) 2013 Elsevier Ltd. All rights reserved.
• 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：2024.6.12

  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.