2-methyl-5-methoxy-6,7,8-trifluoro-3-ethoxycarbonyl-4H-1,4-dihydrobenzopyran-4-one | 358353-03-4

• 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: 2-methyl-5-methoxy-6,7,8-trifluoro-3-ethoxycarbonyl-4H-1,4-dihydrobenzopyran-4-one
• 英文别名: 3-Ethoxycarbonyl-2-methyl-5-methoxy-6,7,8-trifluoro-4H-1,4-dihydrobenzopyran-4-one；2-methyl-5-methoxy-6,7,8-trifluoro-3-ethoxycarbonylchromone；ethyl 6,7,8-trifluoro-5-methoxy-2-methyl-4-oxochromene-3-carboxylate
• CAS: 358353-03-4
• 化学式: C₁₄H₁₁F₃O₅
• 分子量: 316.234
• InChiKey: MBJVDKUJZURCIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-methyl-5-methoxy-6,7,8-trifluoro-3-ethoxycarbonyl-4H-1,4-dihydrobenzopyran-4-one 在 ammonium hydroxide 、 硫酸 作用下， 以 水 为溶剂， 反应 2.25h， 生成 3-Acetyl-4-hydroxy-5-methoxy-6,7,8-trifluoro-2H-1,2-dihydrobenzopyran-2-one
  参考文献：
  名称：

  摘要：

  For the first time were obtained ethyl 2-(2-methoxy-3,4,5,6-tetrafluorobenzoyl)-3-oxobutanoate and ethyl 2-pentafluorobenzoyl-3-oxobutanoate and their copper chelates. The compounds were prepared by acylation of ethyl acetoacetate with 2-methoxy-3,4,5,6-tetrafluoro- and pentafluorobenzoyl chlorides. Cyclization of these beta,beta(1)-dioxoesters afforded substituted chromones. 2-Methyl-5-methoxy-6,7,8-trifluoro-3-ethoxycarbonylchromone hydrolyzes depending on reaction conditions either to 5-hydroxy-2-methyl-6,7,8-trifluorochromone or to 5-hydroxy-2-methyl-6,7,8-trifluorochromone-3-carboxylic acid. Reaction with morpholine provided 7-substituted product, and with aqueous ammonia as a result of rearrangement forms 3-acetimidoyl-4-hydroxy-5-methoxy-6,7,8-trifluorocoumarin. Hydrolysis of the latter yields 3-acetyl-4-hydroxy-5-methoxy-6,7,8-trifluorocoumarin.

  DOI：

  10.1023/a:1013479323203
• 作为产物：
  描述：

  2-methoxy-3,4,5,6-tetrafluorobenzoyl chloride 在 magnesium ethylate 作用下， 生成 2-methyl-5-methoxy-6,7,8-trifluoro-3-ethoxycarbonyl-4H-1,4-dihydrobenzopyran-4-one
  参考文献：
  名称：

  Fluoroaryl containing β,β′-dioxoesters in the synthesis of fluorobenzopyran-4(2)-ones

  摘要：

  Fluoroaryl containing beta, beta'-dioxoesters and their copper(II) chelates have been prepared by acylation of ethyl acetoacetate with 2,6-dimethoxy-3,4,5-trifluorobenzoyl, 2-methoxy-3,4,5,6-tetrafluorobenzoyl and pentafluorobenzoyl chlorides. Cyclization of these beta,beta'-dioxoesters leads to formation of substituted fluorochromones. Depending on conditions, 2-methyl-5-methoxy-6,7,8-trifluoro-3-ethoxycarbonylchromone hydrolyzed to 5-hydroxy-2-methyl-6,7,8-trifluorochromone or 5-hydroxy-2-methyl-6,7,8-trifluorochromone-3-carboxylic acid. The same chromone reacts with morpholine to form a seven-substituted product and ammonium hydroxide to give 3-iminoacetyl-4-hydroxy-5-methoxy-6,7,8-trifluorocoumarin. Hydrolysis of the latter affords 3-acetyl-4-hydroxy-5-methoxy-6,7,8-trifluorocoumarin Ethyl-2-(2,6-dimethoxy-3,4,5-trifluorobenzoyl)-3-oxobutanoates undergoes ketone-splitting to 1-(2,6-dimethoxy-3,4,5-trifluorophenyl)-1.3-butandione. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(01)00346-3

文献信息

• Fluoroaryl containing β,β′-dioxoesters in the synthesis of fluorobenzopyran-4(2)-ones
  作者：S.P Kisil’、Ya.V Burgart、V.I Saloutin、O.N Chupakhin

  DOI：10.1016/s0022-1139(01)00346-3

  日期：2001.5

  Fluoroaryl containing beta, beta'-dioxoesters and their copper(II) chelates have been prepared by acylation of ethyl acetoacetate with 2,6-dimethoxy-3,4,5-trifluorobenzoyl, 2-methoxy-3,4,5,6-tetrafluorobenzoyl and pentafluorobenzoyl chlorides. Cyclization of these beta,beta'-dioxoesters leads to formation of substituted fluorochromones. Depending on conditions, 2-methyl-5-methoxy-6,7,8-trifluoro-3-ethoxycarbonylchromone hydrolyzed to 5-hydroxy-2-methyl-6,7,8-trifluorochromone or 5-hydroxy-2-methyl-6,7,8-trifluorochromone-3-carboxylic acid. The same chromone reacts with morpholine to form a seven-substituted product and ammonium hydroxide to give 3-iminoacetyl-4-hydroxy-5-methoxy-6,7,8-trifluorocoumarin. Hydrolysis of the latter affords 3-acetyl-4-hydroxy-5-methoxy-6,7,8-trifluorocoumarin Ethyl-2-(2,6-dimethoxy-3,4,5-trifluorobenzoyl)-3-oxobutanoates undergoes ketone-splitting to 1-(2,6-dimethoxy-3,4,5-trifluorophenyl)-1.3-butandione. (C) 2001 Elsevier Science B.V. All rights reserved.
• ——
  作者：S. P. Kisil'、Ya. V. Burgart、V. I. Saloutin

  DOI：10.1023/a:1013479323203

  日期：——

  For the first time were obtained ethyl 2-(2-methoxy-3,4,5,6-tetrafluorobenzoyl)-3-oxobutanoate and ethyl 2-pentafluorobenzoyl-3-oxobutanoate and their copper chelates. The compounds were prepared by acylation of ethyl acetoacetate with 2-methoxy-3,4,5,6-tetrafluoro- and pentafluorobenzoyl chlorides. Cyclization of these beta,beta(1)-dioxoesters afforded substituted chromones. 2-Methyl-5-methoxy-6,7,8-trifluoro-3-ethoxycarbonylchromone hydrolyzes depending on reaction conditions either to 5-hydroxy-2-methyl-6,7,8-trifluorochromone or to 5-hydroxy-2-methyl-6,7,8-trifluorochromone-3-carboxylic acid. Reaction with morpholine provided 7-substituted product, and with aqueous ammonia as a result of rearrangement forms 3-acetimidoyl-4-hydroxy-5-methoxy-6,7,8-trifluorocoumarin. Hydrolysis of the latter yields 3-acetyl-4-hydroxy-5-methoxy-6,7,8-trifluorocoumarin.