1-(3,4,5-trifluoro-2,6-dimethoxybenzoyl)butane-1,3-dione | 308368-90-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3,4,5-trifluoro-2,6-dimethoxybenzoyl)butane-1,3-dione
• 英文别名: 1-(2,6-Dimethoxy-3,4,5-trifluorophenyl)-butan-1,3-dione；1-(3,4,5-Trifluoro-2,6-dimethoxyphenyl)butane-1,3-dione
• CAS: 308368-90-3
• 化学式: C₁₂H₁₁F₃O₄
• 分子量: 276.212
• InChiKey: IHBMJDUZGPXMOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(3,4,5-trifluoro-2,6-dimethoxybenzoyl)butane-1,3-dione 在 氢溴酸 作用下， 反应 3.0h， 以40%的产率得到5-Hydroxy-2-methyl-6,7,8-trifluoro-4H-1,4-dihydrobenzopyran-4-one
  参考文献：
  名称：

  Synthesis of ethyl 3-oxo-2-(3,4,5-trifluoro-2,6-dimethoxybenzoyl)butyrate

  摘要：

  Ethyl acetoacetate was acylated with 3,4,5-trifluoro-2,6-dimethoxybenzoyl chloride to give, for the first time, ethyl 3-oxo-2-(3,4,5-trifluoro-2,6-dimethoxybenzoyl)butyrate and its copper chelate. The title compound was used for the synthesis of 6,7,8-trifluoro-5-hydroxy-2-methylchromone, 1-(3,4,5-trifluoro-2,6-dimethoxyphenyl)butane-1,3-dione, and its copper chelate.

  DOI：

  10.1007/bf02494900
• 作为产物：
  描述：

  2,6-Dimethoxy-3,4,5-trifluorobenzoyl chloride 在 氢溴酸 、 magnesium ethylate 作用下， 反应 76.25h， 生成 1-(3,4,5-trifluoro-2,6-dimethoxybenzoyl)butane-1,3-dione
  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