6-Methyl-2-(2,2,2-trifluoroacetyl)chromen-4-one | 1257345-81-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-Methyl-2-(2,2,2-trifluoroacetyl)chromen-4-one
• 英文别名: 6-methyl-2-(2,2,2-trifluoroacetyl)chromen-4-one
• CAS: 1257345-81-5
• 化学式: C₁₂H₇F₃O₃
• 分子量: 256.181
• InChiKey: GCJNEEAYSZAUAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-Methyl-2-(2,2,2-trifluoroacetyl)chromen-4-one 在 水 作用下， 生成 6-methyl-2-(2,2,2-trifluoro-1,1-dihydroxyethyl)-4H-chromen-4-one
  参考文献：
  名称：

  Methyl 2-methoxytetrafluoropropionate as a synthetic equivalent of methyl trifluoropyruvate in the Claisen condensation. The first synthesis of 2-(trifluoroacetyl)chromones and 5-aryl-2-hydroxy-2-(trifluoromethyl)furan-3(2H)-ones

  摘要：

  2-(Trifluoroacetyl)chromones and 5-aryl-2-liydroxy-2-(trifluoromethyl)furan-3(2H)-ones were obtained in good yields via the Claisen condensation of acetophenones with methyl 2-methoxytetrafluoropropionate, followed by sulfuric acid-mediated deprotection of the reaction products. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.06.067
• 作为产物：
  描述：

  6-methyl-2-(1,2,2,2-tetrafluoro-1-methoxyethyl)chromone 在 硫酸 、 silica gel 作用下， 生成 6-Methyl-2-(2,2,2-trifluoroacetyl)chromen-4-one
  参考文献：
  名称：

  Methyl 2-methoxytetrafluoropropionate as a synthetic equivalent of methyl trifluoropyruvate in the Claisen condensation. The first synthesis of 2-(trifluoroacetyl)chromones and 5-aryl-2-hydroxy-2-(trifluoromethyl)furan-3(2H)-ones

  摘要：

  2-(Trifluoroacetyl)chromones and 5-aryl-2-liydroxy-2-(trifluoromethyl)furan-3(2H)-ones were obtained in good yields via the Claisen condensation of acetophenones with methyl 2-methoxytetrafluoropropionate, followed by sulfuric acid-mediated deprotection of the reaction products. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.06.067

文献信息

• Reactions of 2-(trifluoroacetyl)chromones with aromatic amines
  作者：Alexander V. Safrygin、Darya A. Vetyugova、Roman A. Irgashev、Vyacheslav Ya. Sosnovskikh

  DOI：10.1007/s10593-018-2218-x

  日期：2017.12

  Aromatic amines reacted with 2-(trifluoroacetyl)chromones as С- or N-nucleophiles, depending on the conditions. When the reaction was performed under solvent-free conditions at 100°С for 12–18 h, they acted as С-nucleophiles and gave bishetarylcarbinols in 21–67% yields, while in refluxing toluene the addition of primary arylamines occurred via the amino group, providing the corresponding hemiaminals

  取决于条件，芳族胺与2-（三氟乙酰基）发色酮反应为С-或N-亲核试剂。当被无溶剂条件下，在100℃С12-18小时进行反应，它们充当С亲核体，并给bishetarylcarbinols在21-67％的产率，而在回流甲苯的添加伯烷基胺的发生通过氨基，提供相应的血友病药物（80–86％）。
• Synthesis of 4-arylamino-3-(trifluoromethyl)pyridazines and pyridazino[3,4-b]quinoxalines (as by-products) from 3-aroylmethyl-2-(trifluoromethyl)quinoxalines and hydrazine hydrate
  作者：Vyacheslav Y. Sosnovskikh、Alexander V. Safrygin、Roman A. Irgashev、Marina A. Ezhikova、Mikhail I. Kodess

  DOI：10.1039/c5ra27032d

  日期：——

  4-arylamino-3-(trifluoromethyl)pyridazines were obtained in good yields via the novel reaction of 3-aroylmethyl-2-(trifluoromethyl)quinoxalines with an excess of hydrazine hydrate in refluxing n-butanol with or without acetic acid. This reaction is accompanied by the formation of side-products with the pyridazino[3,4-b]quinoxaline skeleton. The possible reaction mechanism was discussed.

  通过使3-芳酰基甲基-2-（三氟甲基）喹喔啉与过量的水合肼在回流的正丁醇中，在有或没有乙酸的情况下进行新颖的反应，以高收率获得了许多4-芳基氨基-3-（三氟甲基）哒嗪。该反应伴随有带有哒嗪并[3，4- b ]喹喔啉骨架的副产物的形成。讨论了可能的反应机理。
• Synthesis of a new class of carbinol linked bis-heterocycles via the reaction of 2-(trifluoroacetyl)chromones with indoles and pyrroles
  作者：Alexander V. Safrygin、Roman A. Irgashev、Mikhail A. Barabanov、Vyacheslav Y. Sosnovskikh

  DOI：10.1016/j.tet.2015.11.037

  日期：2016.1

  2-(Trifluoroacetyl)chromones react with indoles at 90 degrees C under solvent-free conditions to produce the target (chromon-2-yl) (indol-3-yl) (trifluoromethyl)carbinols in 69-90% yields. In a similar manner, their reactions with pyrroles under the same conditions gave (chromon-2-yl) (pyrrol-2-yl) (trifluoromethyl) carbinols in 52-95% yields. These chromone derivatives react with 60% hydrazine hydrate in refluxing ethanol to give the corresponding pyrazoles. (C) 2015 Elsevier Ltd. All rights reserved.
• Methyl 2-methoxytetrafluoropropionate as a synthetic equivalent of methyl trifluoropyruvate in the Claisen condensation. The first synthesis of 2-(trifluoroacetyl)chromones and 5-aryl-2-hydroxy-2-(trifluoromethyl)furan-3(2H)-ones
  作者：Roman A. Irgashev、Vyacheslav Ya. Sosnovskikh、Nataliya Kalinovich、Olesya Kazakova、Gerd-Volker Röschenthaler

  DOI：10.1016/j.tetlet.2009.06.067

  日期：2009.8

  2-(Trifluoroacetyl)chromones and 5-aryl-2-liydroxy-2-(trifluoromethyl)furan-3(2H)-ones were obtained in good yields via the Claisen condensation of acetophenones with methyl 2-methoxytetrafluoropropionate, followed by sulfuric acid-mediated deprotection of the reaction products. (C) 2009 Elsevier Ltd. All rights reserved.