5,7-dimethyl-2-trifluoromethyl-4H-pyrano[2,3-b]pyridin-4-one | 540743-12-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃吡啶类
• 英文名称: 5,7-dimethyl-2-trifluoromethyl-4H-pyrano[2,3-b]pyridin-4-one
• 英文别名: 5,7-dimethyl-2-trifluoromethyl-8-azachroman-4-one；5,7-dimethyl-2-trifluoromethyl-8-azachromone；8-aza-5,7-dimethyl-2-trifluoromethylchromone；5,7-Dimethyl-2-(trifluoromethyl)pyrano[2,3-b]pyridin-4-one
• CAS: 540743-12-2
• 化学式: C₁₁H₈F₃NO₂
• mdl: MFCD05042244
• 分子量: 243.185
• InChiKey: KDJHPFVIODTZQU-UHFFFAOYSA-N

物化性质

• 熔点：
  123-124 °C
• 沸点：
  283.7±40.0 °C(Predicted)
• 密度：
  1.398±0.06 g/cm3(Predicted)
• 溶解度：
  17.3 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,7-dimethyl-2-trifluoromethyl-4H-pyrano[2,3-b]pyridin-4-one 在 硫化氢 、 三乙胺 作用下， 以 异丙醇 为溶剂， 反应 2.0h， 以61%的产率得到3-{2-[4-(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-ylcarbonyl)-3,5-bis(trifluoromethyl)-1,2-dithiolan-3-yl]acetyl}-4,6-
  参考文献：
  名称：

  Unexpected dimerization of 5,7-dimethyl-2-trifluoromethyl-8-azachromone induced by hydrogen sulfide

  摘要：

  根据反应条件，5,7-二甲基-2-三氟甲基-8-氮杂色原酮与硫化氢反应生成具有S-S键的环状和线状二聚体。反应产物的区域和立体化学结构通过1H和13C NMR光谱测定。

  DOI：

  10.1007/s11172-010-0360-4
• 作为产物：
  描述：

  3-乙酰基-4,6-二甲基-2(1H)-吡啶酮 在 硫酸 、 lithium hydride 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 5,7-dimethyl-2-trifluoromethyl-4H-pyrano[2,3-b]pyridin-4-one
  参考文献：
  名称：

  The first synthesis of 8-aza-2-polyfluoroalkylchromones

  摘要：

  The condensation of 3-acetyl-4,6-dimethyl-2-pyridone with RFCO2Et in the presence of LiH in dioxane affords corresponding R-F-containing beta-diketones, whose dehydration under the action of conc. H2SO4 gives 8-aza-5,7-dimethyl-2-polyfluoroalkylchromones. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(02)00280-4

文献信息

• A Simple One-Pot Synthesis of 2,6-Disubstituted 4-(Polyfluoroalkyl)pyridines and -pyrimidines by Reaction of 2-Polyfluoroalkylchromones with Aromatic Methyl Ketimines and Amidines
  作者：Vyacheslav Ya. Sosnovskikh、Boris I. Usachev、Aleksei Yu. Sizov、Mikhail A. Barabanov

  DOI：10.1055/s-2004-822321

  日期：——

  The reaction of 2-polyfluoroalkylchromones with ketimines, derived from aromatic methyl ketones and isopropyl­amine, gives 2,6-diaryl-4-polyfluoroalkylpyridines in moderate to low yields. Benzamidine and guanidine also react with 2-polyfluoroalkylchromones to afford the corresponding 2,6-disubstituted 4-polyfluoroalkylpyrimidines.

  2-聚氟烷基铬酮与源自芳香性甲基酮和异丙胺的酮亚胺反应，得到2,6-二芳基-4-聚氟烷基吡啶，产率为中等到偏低。苄氨基和鸟氨酸也与2-聚氟烷基铬酮发生反应，生成相应的2,6-二取代的4-聚氟烷基嘧啶。
• A Novel Redox Reaction between 8-Aza-5,7-dimethyl-2-trifluoromethylchromone and Alkyl Mercaptoacetates. Facile Synthesis of CF₃-Containing 2-Pyridone Derivatives
  作者：Vyacheslav Ya. Sosnovskikh、Mikhail A. Barabanov、Boris I. Usachev

  DOI：10.1021/jo049117m

  日期：2004.11.1

  8-Aza-5,7-dimethyl-2-trifluoromethylchromone reacts with alkyl mercaptoacetates in the presence of triethylamine to give pyrido derivatives of 2-oxa-7-thiabicyclo[3.2.1]octane, which undergo the reductive ring opening to alkyl 2-[3-(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)-3-oxo-1-(trifluoromethyl)propyl]sulfanyl}acetates.The latter can be also obtained directly from 8-aza-5,7-dimethyl-2-trifluoromethylchromone

  8-Aza-5,7-二甲基-2-三氟甲基色酮在三乙胺的存在下与巯基乙酸烷基酯反应，生成2-oxa-7-硫代双环[3.2.1]辛烷的吡啶基衍生物，该衍生物经还原性开环反应成烷基2 -[[3-（4,6-二甲基-2-氧代-1,2-二氢吡啶基-3-基）-3-氧代-1-（三氟甲基）丙基]硫烷基}乙酸酯。后者也可以直接从8-氮杂5,7-二甲基-2-三氟甲基色酮，表现为被掩盖的α，β-不饱和酮，4,6-二甲基-3-（4,4,4-三氟丁-2-烯酰基）吡啶-2（ 1 H）-一。该化合物是由3-乙酰基-4,6-二甲基-2-吡啶酮独立合成的，并对其合成潜力进行了研究。已经以良好至中等的产率制备了多种包含CF 3基团的2-吡啶酮衍生物。
• A Novel Redox Reaction between 8-Aza-5,7-dimethyl-2-trifluoromethylchromone and Alkyl Mercaptoacetates
  作者：Vyacheslav Ya. Sosnovskikh、Mikhail A. Barabanov、Boris I. Usachev

  DOI：10.1021/ol034766q

  日期：2003.7.1

  [reaction: see text] 8-Aza-5,7-dimethyl-2-trifluoromethylchromone reacts with alkyl mercaptoacetates to give pyrido derivatives of 2-oxa-7-thiabicyclo[3.2.1]octane, which undergo the reductive ring-opening to sulfanyl acetates. The latter compounds are useful CF(3)-containing building blocks for the preparation of a variety of 2-pyridone derivatives.

  [反应：请参见文本] 8-Aza-5,7-二甲基-2-三氟甲基色酮与巯基乙酸烷基酯反应生成2-oxa-7-噻二环[3.2.1]辛烷的吡啶衍生物，其还原性开环为乙酸硫烷基酯。后面的化合物是用于制备各种2-吡啶酮衍生物的有用的含CF（3）的结构单元。
• 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.
• ——
  作者：V. Ya. Sosnovskikh、M. A. Barabanov、B. I. Usachev

  DOI：10.1023/a:1026000619881

  日期：——

  On treatment with ammonia, primary amines, and pyrrolidine, 5,7-dimethyl-2-trifluoromethyl-8-azachromone undergoes ring opening to give beta-aminovinyl ketones. The reactions with morpholine and piperidine proceed as addition to give 2-morpholino- and 2-piperidino-8-azachromanones. With ethylene diamine, diethylenetriamines, hydrazine hydrate, and hydroxylamine, this compound reacts similarly to 2-polyfluoroalkylchromones, yielding CF3-containing dihydrodiazepines, pyrazoles, and isoxazoles,with a 2-pyridone substituent.