2-amino-5-fluoro-5-tridecafluorohexyloxazol-4(5H)-one | 1373161-96-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 2-amino-5-fluoro-5-tridecafluorohexyloxazol-4(5H)-one
• 英文别名: 2-amino-5-fluoro-5-tridecafluorohexyloxazole-4-one
• CAS: 1373161-96-6
• 化学式: C₉H₂F₁₄N₂O₂
• 分子量: 436.105
• InChiKey: QRQBEFLWYRSEDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  64.68
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1,2-epoxy-1,1,2,3,3,4,4,5,5,6,6,7,7,8,8,8-hexadecafluorooctane 、 尿素 以 乙腈 为溶剂， 反应 0.25h， 以82%的产率得到2-amino-5-fluoro-5-tridecafluorohexyloxazol-4(5H)-one
  参考文献：
  名称：

  Synthesis of fluorine-containing allantoins, hydantoins, and oxazolones from terminal perfluoroolefin oxides and urea

  摘要：

  1,2-Epoxyoctafluorobutane reacted with urea in DMSO and aqueous DMSO, dioxane, and acetonitrile to give 40-42% of 5-hydroxy-5-pentafluoroethylimidazolidine-2,4-dione. 5-Hydroxy-5-tridecafluorohexylimidazolidine-2,4-dione was formed in 54% yield in analogous reaction of 1,2-epoxytridecafluorooctane with urea in aqueous DMSO. The reactions of 1,2-epoxyoctafluorobutane and 1,2-epoxytridecafluorooctane with urea in anhydrous dioxane and acetonitrile unexpectedly afforded heterocyclization products, 2-amino-5-fluoro-5-perfluoroalkyloxazol-4(5H)-ones (yield 11-82%). Fluorine-containing allantoin, 5-tridecafluorohexyl-5-ureidoimidazolidine-2,4-dione (yield 19%), and N-(1-hydroxy-2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoroheptyl)-urea (yield 46%) were synthesized for the first time by reaction of 1,2-epoxytridecafluoroctane with urea in DMSO and aqueous DMSO.

  DOI：

  10.1134/s1070428012030098

文献信息

• Synthesis of fluorine containing N-heterocycles using oxides of terminal perfluoroolefins and urea
  作者：Lyudmila V. Saloutina、Aleksandr Ya. Zapevalov、Mikhail I. Kodess、Pavel A. Slepukhin、Victor I. Saloutin、Oleg N. Chupakhin

  DOI：10.1016/j.jfluchem.2012.03.017

  日期：2012.7

  The reaction of octafluoro-1,2-epoxybutane (1) with urea in Me2SO, aqueous Me2SO, aqueous dioxane, aqueous acetonitrile and of hexadecafluoro-1,2-epoxyoctane (2) with urea in aqueous Me2SO gave perfluoroalkylhydantoins - 5-hydroxy-5-pentafluoroethylimidazolidine-2,4-dione (4a) (yield 40-42%) and 5-hydroxy-5-tridecafluorohexylimidazolidine-2,4-dione (4b) (yield 54%), respectively. Use of dioxane and acetonitrile in the reaction of oxiranes 1, 2 with urea led to unexpected heterocyclic products - perfluoroalkyloxazoles 7a, b (yield 11-82%). Perfluoroalkyl containing allantoin - 5-tridecafluorohexyl-5-ureidoimidazolidine-2,4-dione (3b) (yield 19%) and polyfluoroalkyl containing urea-(2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoro-1-hydroxyheptyl)urea (6b) (yield 46%) have been first obtained by the reaction of oxirane 2 with urea in Me2SO and aqueous Me2SO, respectively.The molecular and crystal structure of hydantoin 4a has been studied by X-ray crystallography. (C) 2012 Elsevier B.V. All rights reserved.