6-Chloro-2-(2,2,2-trifluoroacetyl)chromen-4-one | 1257345-82-6

• 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-Chloro-2-(2,2,2-trifluoroacetyl)chromen-4-one
• 英文别名: 6-chloro-2-(2,2,2-trifluoroacetyl)chromen-4-one
• CAS: 1257345-82-6
• 化学式: C₁₁H₄ClF₃O₃
• 分子量: 276.599
• InChiKey: ZWEGEFPHMJCGNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 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-Chloro-2-(2,2,2-trifluoroacetyl)chromen-4-one 在 水 作用下， 生成 6-chloro-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-chloro-2-(1,2,2,2-tetrafluoro-1-methoxyethyl)chromone 在 硫酸 、 silica gel 作用下， 生成 6-Chloro-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

• Synthesis of 5-aryl-2-hydroxy-2-(trifluoromethyl)furan-3(2H)-ones and their reactions with aromatic 1,2-diamines, hydrazine and hydroxylamine
  作者：Alexander V. Safrygin、Roman A. Irgashev、Pavel A. Slepukhin、Gerd-Volker Röschenthaler、Vyacheslav Y. Sosnovskikh

  DOI：10.1016/j.tet.2015.09.035

  日期：2015.11

  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. These compounds react with 2,3-diaminopyridine, o-phenylenediamine and 2,3-diaminonaphthalene in refluxing acetic acid to give the corresponding quinoxaline derivatives, the regioisomeric and tautomeric composition

  通过苯乙酮的克莱森缩合用甲基2-甲氧基以良好产率得到2-（三氟甲基）呋喃酮，接着反应产物的硫酸介导的脱保护。这些化合物与2,3-二氨基吡啶反应，Ó苯二胺和在回流的乙酸，得到相应的喹喔啉衍生物2,3-二氨基萘，区域异构体和互变异构组合物，它的进行了研究。与肼和羟胺的2-（三氟甲基）呋喃酮的反应区域选择性地进行，并且以高收率得到哒嗪，吡唑和异恶唑衍生物。他们的区域化学通过X射线衍射分析确定。
• 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.