5,5-difluoro-1,3-dimethylbarbituric acid | 135664-29-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5,5-difluoro-1,3-dimethylbarbituric acid
• 英文别名: 1,3-dimethyl-5,5-difluorobarbituric acid；5,5-Difluoro-1,3-dimethyl-1,3-diazinane-2,4,6-trione
• CAS: 135664-29-8
• 化学式: C₆H₆F₂N₂O₃
• 分子量: 192.122
• InChiKey: GMIBZFOZYQRKMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,3-二甲基巴比妥酸 在 N-fluorobis<(trifluoromethyl)sulfonyl>imide 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以95%的产率得到5,5-difluoro-1,3-dimethylbarbituric acid
  参考文献：
  名称：

  N-fluorobis[(trifluoromethyl)sulfonyl]imide: an efficient reagent for the .alpha.-fluorination of functionalized carbonyl compounds

  摘要：

  The N-fluorobis[(trifluoromethyl)sulfonyl]imide (1) has been used in the electrophilic fluorination of the lithium enolate of esters, amides, and ketones. The corresponding alpha-fluorocarbonyl compounds have been obtained in good yields. The alpha-fluorination of beta-diesters, beta-diamides, beta-keto esters, and beta-diketones has been performed either on the neutral compounds or on the metal enolates. In this way some geminal azafluoro, chlorofluoro, fluorooxy compounds have been prepared in nearly quantitative yields. Also some alpha-keto esters and acids have been selectively monofluorinated in the beta-position by simple treatment of the neutral compound with 1.

  DOI：

  10.1021/jo00016a022

文献信息

• Direct fluorination of 1,3-dicarbonyl compounds
  作者：Richard D. Chambers、Martin P. Greenhall、John Hutchinson

  DOI：10.1039/c39950000021

  日期：——

  1,3-Dicarbonyls, such as 1,3-diketones and 1,3-ketoesters, react directly with elemental fluorine at room temperature to give the corresponding 2-fluoro- and, in some cases, 2,2-difluoro-compounds in high yield.

  1,3-二酮类化合物，如1,3-二酮和1,3-酮酯，能在室温下与元素氟直接反应，生成对应的2-氟化合物，在某些情况下，还能生成2,2-二氟化合物，反应产率很高。
• N-fluorobis[(trifluoromethyl)sulfonyl]imide: an efficient reagent for the .alpha.-fluorination of functionalized carbonyl compounds
  作者：Giuseppe Resnati、Darryl D. DesMarteau

  DOI：10.1021/jo00016a022

  日期：1991.8

  The N-fluorobis[(trifluoromethyl)sulfonyl]imide (1) has been used in the electrophilic fluorination of the lithium enolate of esters, amides, and ketones. The corresponding alpha-fluorocarbonyl compounds have been obtained in good yields. The alpha-fluorination of beta-diesters, beta-diamides, beta-keto esters, and beta-diketones has been performed either on the neutral compounds or on the metal enolates. In this way some geminal azafluoro, chlorofluoro, fluorooxy compounds have been prepared in nearly quantitative yields. Also some alpha-keto esters and acids have been selectively monofluorinated in the beta-position by simple treatment of the neutral compound with 1.