1-甲基-2-(三氟甲基)喹啉-4-酮 | 139439-36-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 1-甲基-2-(三氟甲基)喹啉-4-酮
• 英文名称: N-methyl-2-trifluoromethyl-4-quinolone
• 英文别名: 1-methyl-2-(trifluoromethyl)quinolin-4(1H)-one；1-methyl-2-(trifluoromethyl)quinolin-4-one
• CAS: 139439-36-4
• 化学式: C₁₁H₈F₃NO
• 分子量: 227.186
• InChiKey: BTNVTJCFFUGWGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-甲基-2-(三氟甲基)喹啉-4-酮 在 盐酸 、 四甲基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 24.25h， 生成 1-methyl-2,2-bis(trifluoromethyl)-2,3-dihydroquinolin-4(1H)-one
  参考文献：
  名称：

  Regioselective Nucleophilic 1,4-Trifluoromethylation of 2-Polyfluoroalkylchromones with (Trifluoromethyl)trimethylsilane. Synthesis of Fluorinated Analogs of Natural 2,2-Dimethylchroman-4-ones and 2,2-Dimethylchromenes

  摘要：

  Reactions of 2-polyfluoroalkylchromones with (perfluoroalkyl)trimethylsilanes proceed as a 1,4-nucleophilic perfluoroalkylation to give 2,2-bis(polyfluoroalkyl)chroman-4-ones with high regioselectivity and good yields after acid hydrolysis. Oxidation of 6-methyl-2,2-bis(trifluoromethyl)chroman-4-one with a mixture of K2S2O8 and CuSO4 in aqueous acetonitrile leads to fluorinated analogues of natural lactarochromal and the corresponding acid. Reduction of substituted 2,2-bis(trifluoromethyl)chroman-4-one with sodium borohydride in methanol and subsequent dehydration of chromanols in refluxing xylene in the presence of p-toluene sulfonic acid gives 2,2-bis(trifluoromethyl)chromenes, which are fluorinated analogues of natural precocenes.

  DOI：

  10.1021/jo034591y
• 作为产物：
  描述：

  3,3-dihydroxy-1-(2-trifluoroacetamidophenyl)-4,4,4-trifluorobutan-1-one 在 硫酸 、 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 1.25h， 生成 1-甲基-2-(三氟甲基)喹啉-4-酮
  参考文献：
  名称：

  摘要：

  The condensation of 2-aminoacetophenone with (RCO2Et)-C-F (R-F = CF3, CF2H, CF2CF2H) in the presence of LiH in THF or (BuOK)-O-t in (BuOH)-O-t affords either 2-polyfluoroalkyl-4-quinolones or 1-(2-polyfluoroacylaminophenyl)-3-polyfluoroalkylpropane-1,3-diones, depending on the ratio of the initial reactants. The latter are hydrolyzed in an acidic medium to produce 2-polyfluoroalkyl-4-quinolones. N-Methyl-2-trifluoromethyl-4-quinolone was synthesized from 2-aminoacetophenone, CF3CO2Et, and MeI in the presence of (BuOK)-O-t.

  DOI：

  10.1023/a:1021632531255

文献信息

• 一种二氟烷基取代的吡啶酮或吡喃酮的合成方法
  申请人：遵义医学院

  公开号：CN105669546A

  公开（公告）日：2016-06-15

  本发明公开了一种简便条件下一种二氟烷基取代的吡啶酮或吡喃酮的合成方法。具体地说，由简单的吡啶酮、吡喃酮和卤代二氟烷基化合物(氯代，溴代，碘代)出发，在光照条件下，用以铱或钌为核心的配合物充当催化剂，高收率地得到各种二氟烷基取代的吡啶酮或吡喃酮的方法。该方法使用简单易得的吡啶酮和吡喃酮和卤代二氟烷基化合物(氯代，溴代，碘代)为原料，具有催化剂用量少，底物适用范围广，操作简便，反应效率高等优点。所得的结构是目前一些重要的含氟砌块，在生物医药领域具有较大的应用前景。
• 6-Aryl aminomethyl quinoline derivatives and their use as anti-tumour agents
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0318225A2

  公开（公告）日：1989-05-31

  The invention relates to a quinoline of the formula:- wherein each of R¹ and R², which may be the same or different, is hydrogen, halogeno, hydroxy, cyano, carbamoyl, nitro or amino, alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or alkanoylamino each of up to 4 carbon atoms, or substituted alkyl or alkoxy each of up to 3 carbon atoms, provided that both R¹ and R² are not hydrogen; the quinoline ring may bear further substituents; R³ is hydrogen or alkyl of up to 4 carbon atoms; R⁴ is hydrogen, alkyl, alkenyl or alkynyl each of up to 4 carbon atoms or substituted alkyl of up to 3 carbon atoms; Ar is phenylene, naphthylene or heterocyclene which is unsubstituted or which bears one or more substituents; R⁵ is such that R⁵-NH₂ is an amino acid; or a pharmaceutically-acceptable salt or ester thereof. The compounds possess anti-tumour activity.

  本发明涉及一种式如下的喹啉 其中R¹和R²可以相同或不同，各自为氢、卤素、羟基、氰基、氨基甲酰基、硝基或氨基、烷基、烷氧基、烷硫基、烷基氨基、二烷基氨基或烷酰氨基，各自最多为4个碳原子，或取代的烷基或烷氧基，各自最多为3个碳原子，条件是R¹和R²都不是氢； 喹啉环可带有其他取代基； R³ 是氢或最多 4 个碳原子的烷基； R⁴ 是氢、各含最多 4 个碳原子的烷基、烯基或炔基或含最多 3 个碳原子的取代烷基； Ar 是未取代的苯基、萘基或杂环基，或带有一个或多个取代基； R⁵ 是 R⁵-NH₂ 是氨基酸； 或其药学上可接受的盐或酯。 这些化合物具有抗肿瘤活性。
• N-Alkylated 2-Trifluoromethyl-4-quinolones by Addition of Base and an Alkylating Agent to 2-Trifluoroacetylaminoacetophenones
  作者：Donald W. Combs、Marianne S. Reed、Dieter H. Klaubert

  DOI：10.1080/00397919208021309

  日期：1992.1

  2-Trifluoroacetylaminoacetophenones 1 are cyclized to N-alkyl-2-trifluoromethyl-4-quinolones 2 in one pot with concomitant N-alkylation in 40 to 74% yield using potassium hydroxide in acetone containing an alkylating agent.
• Nucleophilic trifluoromethylation of RF-containing 4-quinolones, 8-aza- and 1-thiochromones with (trifluoromethyl)trimethylsilane
  作者：Vyacheslav Ya. Sosnovskikh、Boris I. Usachev、Dmitri V. Sevenard、Gerd-Volker Röschenthaler

  DOI：10.1016/j.jfluchem.2005.03.001

  日期：2005.5

  Reactions of N-substituted 2-polyfluoroalkyl-4-quinolones and 8-aza-5,7-dimethyl-2-polyfluoroalkylchromones with (trifluoromethyl)-trimethylsilane proceed mainly as a 1,4-nucleophilic trifluoromethylation to give N-substituted 2,2-bis(polyfluoroalkyl)-2,3-dihydroquinolin-4(1H)-ones and 5,7-dimethyl-2,2-bis(polyfluoroalkyl)-2,3-dihydro-4H-pyrano[2,3-b]pyridin-4-ones after acid hydrolysis. Similar reaction with 2-trifluoromethyl-4H-thiochromen-4-one proceeds as a 1,2-addition to give 2,4-bis(trifluoromethyl)-4H-thiochromen-4-yl trimethylsilyl ether. (c) 2005 Elsevier B.V. All rights reserved.