3-Methyl-4H-[1]-6,7,8,9-tetrafluorobenzopyrano[3,4-d]isoxazole-4-one | 209736-46-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-Methyl-4H-[1]-6,7,8,9-tetrafluorobenzopyrano[3,4-d]isoxazole-4-one
• 英文别名: 6,7,8,9-Tetrafluoro-3-methyl-4H-benzopyrano<3,4-d>isoxazol-4-one；3-Methyl-6,7,8,9-tetrafluoro-1H-benzopyrano[3,4-d]isoxazol-4-one；3-Methyl-5,6,7,8-tetrafluoro-4H-benzopyrano[3,4-d]isoxazol-4-one；Isoxazolo[4,5-c]coumarin, 6,7,8,9-tetrafluoro-3-methyl-；6,7,8,9-tetrafluoro-3-methylchromeno[3,4-d][1,2]oxazol-4-one
• CAS: 209736-46-9
• 化学式: C₁₁H₃F₄NO₃
• 分子量: 273.143
• InChiKey: YTVAZUCTZGIHIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-Methyl-4H-[1]-6,7,8,9-tetrafluorobenzopyrano[3,4-d]isoxazole-4-one 在 2-氨基苯硫醇 作用下， 以 苯 为溶剂， 反应 5.0h， 以36%的产率得到3-acetimidoyl-5,6,7,8-tetrafluoro-4-hydroxy-2H-chromen-2-one
  参考文献：
  名称：

  4-羟基-5,6,7,8-四氟香豆素衍生物与S-亲核试剂的反应

  摘要：

  与反应ø -氨基苯硫酚，4 -羟基-（3 -（亚氨基）乙酰基）-5,6,7,8-四氟香豆素在C-7原子处产生S取代的产物。由于杂环开环，7-取代的5,6,8-三氟香豆素形成苯并噻唑；3-乙氧基羰基-2-甲基-5,6,7,8-四氟色酮经历酸裂解反应生成2-（2-羟基-3,4,5,6-四氟苯基）苯并噻唑。在碱性条件下，S-取代的香豆素分解为苯乙酮。在酸性介质中，4-羟基-3-亚氨基乙酰基-5,6,8-三氟-7-（2-氨基苯硫基）香豆素得到7-（2-氨基苯硫基）-2-甲基-5,6,8-三氟色酮。从7-（2-氨基苯硫基）-4-羟基-5,6,8-的缩合分离出4-羟基-5,6-二氟-2-H-吡喃并[6,5-a]吩噻嗪-2-one。 NaH存在下的三氟香豆素。

  DOI：

  10.1016/s0022-1139(99)00210-9
• 作为产物：
  描述：

  乙基5,6,7,8-四氟-2-甲基-4-氧代-4H-苯并吡喃-3-羧酸酯 在 tetrasulfane 、 盐酸羟胺 、 水 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 3.5h， 生成 3-Methyl-4H-[1]-6,7,8,9-tetrafluorobenzopyrano[3,4-d]isoxazole-4-one
  参考文献：
  名称：

  Interaction of 3-ethoxycarbonyl(carboxy)-substituted 5,6,7,8-tetrafluorochromones with N-nucleophiles: synthesis of fluorocoumarins

  摘要：

  Polyfluorobenzopyranopyrazoles (isoxazoles) have been prepared via cyclization of 5-tetrafluorophenyl-4-ethoxycarbonyl(carboxy)pyrazoles (isoxazoles) produced by the reaction of 3-ethoxycarbonyl-2-methyl- and 3-carboxy-substituted 5,6,7,8-tetrafluorochromone with hydrazine(hydroxylamine). It has been found that 3-ethoxycarbonyl-2-methyl-5,6,7,8-tetrafluorochromone forms the corresponding 2-ethylidenamino-substituted 1,3-keto esters with ammonia and benzylamine, from which 3-ethylidenamino-4-oxy-5,6,7,8-tetrafluorocoumarins were readily obtained. In contrast to the non-fluorinated analogues, 3-ethoxycarbonyl-2-methyl-5,6,7,8-tetrafluorocoumarins were found to undergo acyl-lactone transformation into coumarin structures under acidic conditions. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-1139(98)00350-9

文献信息

• Bazyl'; Kisil'; Sharapko, Russian Journal of Organic Chemistry, 1998, vol. 34, # 3, p. 363 - 368
  作者：Bazyl'、Kisil'、Sharapko、Burgart、Saloutin、Chupakhin

  DOI：——

  日期：——
• Saloutin; Bazyl'; Skryabina, Russian Journal of Organic Chemistry, 1997, vol. 33, # 8, p. 1167 - 1175
  作者：Saloutin、Bazyl'、Skryabina、Kisil'

  DOI：——

  日期：——
• Bazyl'; Kisil'; Burgart, Russian Journal of Organic Chemistry, 2000, vol. 36, # 6, p. 904 - 909
  作者：Bazyl'、Kisil'、Burgart、Saloutin

  DOI：——

  日期：——
• Reactions of 4-hydroxy-5,6,7,8-tetrafluorocoumarin derivatives with S-nucleophiles
  作者：I.T Bazyl′、S.P Kisil′、Ya.V Burgart、V.I Saloutin

  DOI：10.1016/s0022-1139(99)00210-9

  日期：2000.4

  In the reactions with o-aminothiophenol, 4-hydroxy-(3-(imino)acetyl)-5,6,7,8-tetrafluorocoumarins give products of S-substitution at the C-7 atom. 7-Substituted 5,6,8-trifluorocoumarins form benzothiazole as a result of heterocyclic ring opening; 3-ethoxycarbonyl-2-methyl-5,6,7,8-tetrafluorochromone undergoes acid splitting to 2-(2-hydroxy-3,4,5,6-tetrafluorophenyl)benzothiazole. Under alkaline conditions

  与反应ø -氨基苯硫酚，4 -羟基-（3 -（亚氨基）乙酰基）-5,6,7,8-四氟香豆素在C-7原子处产生S取代的产物。由于杂环开环，7-取代的5,6,8-三氟香豆素形成苯并噻唑；3-乙氧基羰基-2-甲基-5,6,7,8-四氟色酮经历酸裂解反应生成2-（2-羟基-3,4,5,6-四氟苯基）苯并噻唑。在碱性条件下，S-取代的香豆素分解为苯乙酮。在酸性介质中，4-羟基-3-亚氨基乙酰基-5,6,8-三氟-7-（2-氨基苯硫基）香豆素得到7-（2-氨基苯硫基）-2-甲基-5,6,8-三氟色酮。从7-（2-氨基苯硫基）-4-羟基-5,6,8-的缩合分离出4-羟基-5,6-二氟-2-H-吡喃并[6,5-a]吩噻嗪-2-one。 NaH存在下的三氟香豆素。
• Interaction of 3-ethoxycarbonyl(carboxy)-substituted 5,6,7,8-tetrafluorochromones with N-nucleophiles: synthesis of fluorocoumarins
  作者：V.I. Saloutin、Z.E. Skryabina、I.T. Bazyl'、S.P. Kisil'

  DOI：10.1016/s0022-1139(98)00350-9

  日期：1999.2

  Polyfluorobenzopyranopyrazoles (isoxazoles) have been prepared via cyclization of 5-tetrafluorophenyl-4-ethoxycarbonyl(carboxy)pyrazoles (isoxazoles) produced by the reaction of 3-ethoxycarbonyl-2-methyl- and 3-carboxy-substituted 5,6,7,8-tetrafluorochromone with hydrazine(hydroxylamine). It has been found that 3-ethoxycarbonyl-2-methyl-5,6,7,8-tetrafluorochromone forms the corresponding 2-ethylidenamino-substituted 1,3-keto esters with ammonia and benzylamine, from which 3-ethylidenamino-4-oxy-5,6,7,8-tetrafluorocoumarins were readily obtained. In contrast to the non-fluorinated analogues, 3-ethoxycarbonyl-2-methyl-5,6,7,8-tetrafluorocoumarins were found to undergo acyl-lactone transformation into coumarin structures under acidic conditions. (C) 1999 Elsevier Science S.A. All rights reserved.