5,6,7,8-Tetrafluoro-2-ethoxycarbonyl-4H-chromen-2-one | 154678-99-6

• 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: 5,6,7,8-Tetrafluoro-2-ethoxycarbonyl-4H-chromen-2-one
• 英文别名: 2-ethoxycarbonyl-5,6,7,8-tetrafluorochromone；5,6,7,8-tetrafluoro-2-ethoxycarbonylchromone；ethyl 5,6,7,8-tetrafluoro-4-oxochromene-2-carboxylate
• CAS: 154678-99-6
• 化学式: C₁₂H₆F₄O₄
• 分子量: 290.171
• InChiKey: PWXZPZZWGOSFGB-UHFFFAOYSA-N

物化性质

• 沸点：
  349.7±42.0 °C(Predicted)
• 密度：
  1.559±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5,6,7,8-Tetrafluoro-2-ethoxycarbonyl-4H-chromen-2-one 在 盐酸 、 溶剂黄146 作用下， 反应 6.0h， 以80%的产率得到5,6,7,8-Tetrafluoro-2-carboxy-4H-chromen-2-one
  参考文献：
  名称：

  2(3)-ethoxycarbonyl-5,6,7,8-四氟色酮的合成

  摘要：

  迄今为止未知的五氟苯甲酰基丙酮酸乙酯是通过将五氟苯乙酮与草酸二乙酯缩合而制备的。该酯或其铜 (II) 螯合物以及 2-（乙氧基亚甲基）五氟苯甲酰乙酸乙酯的分子内环化得到 2- 和 3- 乙氧基羰基-5,6,7,8-四氟色酮。后者水解后脱羧得到 5,6,7,8-四氟色酮。

  DOI：

  10.1007/bf00697086
• 作为产物：
  描述：

  2',3',4',5',6'-五氟苯乙酮 在 lithium hydride 作用下， 生成 5,6,7,8-Tetrafluoro-2-ethoxycarbonyl-4H-chromen-2-one
  参考文献：
  名称：

  Novel fluorinated chromones

  摘要：

  The self-condensation of ethyl pentafluorobenzoylacetate leads to the formation of 3-pentafluorophenyl-1H-isopyrono[2,3-b]-6,7,8,9-tetrafluorochrom in 37% yield. On hydrolysis, this gave 2-pentafluorobenzoylmethyl-5,6,7,8-tetrafluorochromone. Other routes for preparing some new fluorinated chromones have been confirmed via intramolecular cyclization of ethyl pentafluorobenzoylpyruvate and also from the 2-ethoxymethylene pentafluorobenzoylacetic ester.

  DOI：

  10.1016/s0022-1139(00)80470-4

文献信息

• Synthesis of 2(3)-ethoxycarbonyl-5,6,7,8-tetrafluorochromones
  作者：V. I. Saloutin、Z. E. Skryabina、I. T. Bazyl、O. N. Chupakhin

  DOI：10.1007/bf00697086

  日期：1993.2

  The hitherto unknown ethyl pentafluorobenzoylpiruvate was prepared by condensing pentafluoroacetophenone with diethyl oxalate. Intramolecular cyclization of this ester or of its copper(II) chelate, as well as of ethyl 2-(ethoxymethylene)pentafluorobenzoylacetate affords 2- and 3-ethoxycarbonyl-5,6,7,8-tetrafluorochromones. Hydrolysis of the latter followed by decarboxylation gives 5,6,7,8-tetrafluorochromone

  迄今为止未知的五氟苯甲酰基丙酮酸乙酯是通过将五氟苯乙酮与草酸二乙酯缩合而制备的。该酯或其铜 (II) 螯合物以及 2-（乙氧基亚甲基）五氟苯甲酰乙酸乙酯的分子内环化得到 2- 和 3- 乙氧基羰基-5,6,7,8-四氟色酮。后者水解后脱羧得到 5,6,7,8-四氟色酮。
• Reactions of pentafluorobenzoylpyruvic ester and its copper(II) chelate with dinucleophiles
  作者：V.I. Saloutin、S.G. Perevalov

  DOI：10.1016/s0022-1139(99)00060-3

  日期：1999.6

  dinucleophiles — hydrazine, phenylhydrazine, hydroxylamine hydrochloride, 1,2-ethylenediamine, 1,2-phenylenediamine, 2-aminophenol — to form heterocyclic compounds. Reactions between bis(ethyl pentafluorobenzoylpyruvate)copper (II) chelate and these amine hydrochlorides also produce heterocycles. The analytical data of these compounds — elemental analysis, IR-, and NMR spectral data — are reported.

  五氟苯甲酰基丙酮酸酯与二亲核试剂（肼，苯肼，盐酸羟胺，1,2-乙二胺，1,2-苯二胺，2-氨基苯酚）反应形成杂环化合物。双（五氟苯甲酰基丙酮酸丙酮酸）铜（II）螯合物与这些胺盐酸盐之间的反应也产生杂环。报告了这些化合物的分析数据（元素分析，IR和NMR光谱数据）。
• Reactions of 2(3)-ethoxycarbonyl-5,6,7,8-tetrafluorochromones with methylamine
  作者：K. V. Shcherbakov、Ya. V. Burgart、V. I. Saloutin

  DOI：10.1007/s11172-006-0091-8

  日期：2005.9

  reacts with methylamine differently, depending on the solvent nature and the amount of the amine: in DMSO and MeCN, the fluorine atom at the C(7) atom is initially replaced and then the C(2) and/or C(9) are attacked, while in ethanol, the reaction involves the C(2) atom with opening of the pyrone ring. The reaction of 3-ethoxycarbonyl-5,6,7,8-tetrafluoro-2-methylchromone with methylamine results, regardless

  摘要 2-乙氧基羰基-5,6,7,8-四氟色酮与甲胺的反应因溶剂性质和胺的量而异：在 DMSO 和 MeCN 中，C(7) 原子上的氟原子最初被取代，然后C(2) 和/或 C(9) 受到攻击，而在乙醇中，反应涉及 C(2) 原子并打开吡喃酮环。3-乙氧羰基-5,6,7,8-四氟-2-甲基色酮与甲胺反应，无论溶剂如何，都会打开色酮环并形成中间体乙基 3-(3,4,5, 6-四氟-2-羟基苯基)-2-(1-甲基氨基)亚乙基-3-氧代丙酸酯，经过分子内环化得到5,6,7,8-四氟-3-(1-甲基-氨基)亚乙基-3 ,4-二氢-2H-苯并吡喃-2,4-二酮。
• Interaction of pentafluorobenzoylpyruvic acid and its esters with N-nucleophiles. Synthesis of 4-oxoquinoline-2-carboxylic acids
  作者：V.I. Saloutin、Z.E. Skryabina、I.T. Basyl'、P.N. Kondrat'ev、O.N. Chupakhin

  DOI：10.1016/0022-1139(94)03069-3

  日期：1994.10

  Nitrogen-substituted 4-oxoquinoline-2-carboxylic acids have been prepared by the reaction of pentafluorobenzoylpyruvic acid with isopropyl-, cyclohexyl-, phenyl- and ethanol-amine. Ammonia and triethylamine, however, were found to react with pentafluorobenzoylpyruvic acid to form only the 2-carboxy-5,6,7-8-tetrafluorochromone; such behaviour has been found in the reactions of ethyl pentafluorobenzoylpyruvate

  氮取代的4-氧代喹啉-2-羧酸是通过五氟苯甲酰基丙酮酸与异丙基，环己基，苯基和乙醇胺反应制得的。然而，发现氨和三乙胺与五氟苯甲酰基丙酮酸反应，仅形成2-羧基-5,6,7-8-四氟色酮。在五氟苯甲酰基丙酮酸乙酯与氨和环己胺的反应中发现了这种行为。
• Transcription factor modulating compounds and methods of use thereof
  申请人：Levy Stuart B.

  公开号：US20090131401A1

  公开（公告）日：2009-05-21

  Substituted benzoimidazole compounds useful as anti-infectives that decrease resistance, virulence, or growth of microbes are provided. Methods of making and using substituted benzoimidazole compounds, as well as pharmaceutical preparations thereof, in, e.g., reducing antibiotic resistance and inhibiting biofilms.

  本发明提供了可用作抗感染剂的取代苯并咪唑化合物，其可降低微生物的耐药性、毒力或生长。本发明还提供了制备和使用取代苯并咪唑化合物的方法，以及其制备的药物制剂，例如用于减少抗生素耐药性和抑制生物膜的制剂。