3,3,3-trifluoro-1-(2-methoxyphenyl)propan-1-one | 130654-91-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3,3-trifluoro-1-(2-methoxyphenyl)propan-1-one
• 英文别名: 3,3,3-Trifluoro-1-(2-methoxyphenyl)-1-propanone
• CAS: 130654-91-0
• 化学式: C₁₀H₉F₃O₂
• 分子量: 218.175
• InChiKey: JBCXLODHZJAKDB-UHFFFAOYSA-N

物化性质

• 沸点：
  233.1±40.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-氯-2-碘苯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 氯[2-(二叔丁基磷)二苯基]金 、 四甲基乙二胺 、 四丁基氟化铵 、 水 、 silver trifluoromethanesulfonate 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 64.5h， 生成 3,3,3-trifluoro-1-(2-methoxyphenyl)propan-1-one
  参考文献：
  名称：

  Regioselective Gold-Catalyzed Hydration of CF₃- and SF₅-alkynes

  摘要：

  The regioselective gold-catalyzed hydration of CF3- and SF5-alkynes is described. The corresponding trifluoromethylated and pentasulfanylated ketones are obtained in up to 91% yield as single regioisomers showcasing the use of CF3 and SF5 as highly efficient directing groups in this reaction. Notably, this transformation represents the first use of CF3- and SF5-alkynes in gold catalysis.

  DOI：

  10.1021/acs.orglett.9b01379

文献信息

• Copper-mediated trifluoromethylation of propiolic acids: facile synthesis of α-trifluoromethyl ketones
  作者：Zhengbiao He、Rui Zhang、Mingyou Hu、Lingchun Li、Chuanfa Ni、Jinbo Hu

  DOI：10.1039/c3sc51613j

  日期：——

  Copper-mediated decarboxylative trifluoromethylation provides a new protocol for the efficient preparation of α-trifluoromethyl ketones from propiolic acids. It was found that water is involved as a reactant in the reaction, which is significantly different from the previously reported decarboxylative fluoroalkylation reactions.

  铜介导的脱羧三氟甲基化反应提供了一种新方法，可高效制备来自丙炔酸的α-三氟甲基酮。研究发现，水作为反应物参与其中，这与先前报道的脱羧氟代烷基化反应有显著差异。
• Photoredox-catalysed redox-neutral trifluoromethylation of vinyl azides for the synthesis of α-trifluoromethylated ketones
  作者：Hai-Tao Qin、Shu-Wei Wu、Jia-Li Liu、Feng Liu

  DOI：10.1039/c6cc10035j

  日期：——

  A redox-neutral, mild, and simple protocol is developed for the synthesis of [small alpha]-trifluoromethylated ketones from vinyl azides under transition-metal-free conditions. In the presence of organic photoredox catalyst N-methyl-9-mesityl acridinium and...

  开发了一种氧化还原中性，温和且简单的方案，用于在无过渡金属的条件下从乙烯基叠氮化物合成[小α]-三氟甲基化的酮。在有机光氧化还原催化剂的存在下，N-甲基-9-间苯二甲啶cri和...
• Trifluoromethylation of α-Haloketones
  作者：Petr Novák、Anton Lishchynskyi、Vladimir V. Grushin

  DOI：10.1021/ja307783w

  日期：2012.10.3

  The C-X bond (X = Br, Cl) of α-haloketones is smoothly trifluoromethylated with the fluoroform-derived CuCF(3) reagent recently developed in our laboratories. This is the first nucleophilic α-trifluoromethylation reaction of carbonyl compounds and a rare example of CF(3)-C(sp(3)) coupling. The transformation employs only low-cost chemicals and cleanly occurs in up to 99% yield at room temperature,

  α-卤代酮的 CX 键 (X = Br, Cl) 被我们实验室最近开发的氟仿衍生的 CuCF(3) 试剂顺利地三氟甲基化。这是羰基化合物的第一个亲核 α-三氟甲基化反应，也是 CF(3)-C(sp(3)) 偶联的罕见例子。该转化仅使用低成本化学品，并且在室温下以高达 99% 的收率干净地发生，从而为获得有价值的 2,2,2-三氟乙基酮提供了前所未有的轻松入口。
• Fenton reagent-catalyzed trifluoromethylation of enamines of 3-oxocarboxylates with CF3I
  作者：Yuhki Ohtsuka、Daisuke Uraguchi、Kyoko Yamamoto、Kenji Tokuhisa、Tetsu Yamakawa

  DOI：10.1016/j.jfluchem.2015.10.013

  日期：2016.1

  The trifluoromethylation of enamines of ethyl 3-oxocarboxylates catalyzed by Fenton reagent with CF3I was investigated. Trifluoromethylation followed by acid hydrolysis provided 3-oxo-2-(trifluoromethyl)carboxylates in 64–94% yields, which were greater than those obtained by the trifluoromethylation of 3-oxocarboxylates as reported previously. Enamines trifluoromethylated at the 2-position were isolated

  研究了Fenton试剂与CF 3 I催化3-氧代羧酸乙酯的烯胺的三氟甲基化。三氟甲基化再进行酸水解后，可得到64-94％的3-氧代-2-（三氟甲基）羧酸酯，这比先前报道的3-氧代羧酸酯的三氟甲基化所得到的产率更高。分离2-位三氟甲基化的烯胺作为中间体。所获得的3-氧代-2-（三氟甲基）羧酸酯的水解和连续脱羧在酸性条件下以令人满意的产率提供了（2,2,2-三氟乙基）酮。
• Preparation of 1-Aryl- or 1-Alkenyl-2-(perfluoroalkyl)acetylenes
  作者：Norihiko Yoneda、Shigeru Matsuoka、Norio Miyaura、Tsuyoshi Fukuhara、Akira Suzuki

  DOI：10.1246/bcsj.63.2124

  日期：1990.7

  1-Aryl- or 1-alkenyl-2-(perfluoroalkyl)acetylenes were produced in high yields by the coupling reaction of aryl or alkenyl iodides with (perfluoroalkynyl)zinc compounds prepared from the corresponding (perfluoroalkyl)acetylenes in the presence of Pd catalyst.

  1-芳基-或1-烯基-2-(全氟烷基)乙炔通过芳基或烯基碘化物与(全氟炔基)锌化合物在Pd催化剂存在下由相应的(全氟烷基)乙炔制备的偶联反应以高产率制备。