5-hydroxy-5-tridecafluorohexylimidazolidine-2,4-dione | 1373161-85-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 5-hydroxy-5-tridecafluorohexylimidazolidine-2,4-dione
• 英文别名: 5-hydroxy-5-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)imidazolidine-2,4-dione
• CAS: 1373161-85-3
• 化学式: C₉H₃F₁₃N₂O₃
• 分子量: 434.114
• InChiKey: VKTYGCGAKYLBDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  16

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 水 、 乙腈 为溶剂， 反应 0.5h， 以44.5%的产率得到2-amino-5-fluoro-5-tridecafluorohexyloxazol-4(5H)-one
  参考文献：
  名称：

  Synthesis of fluorine containing N-heterocycles using oxides of terminal perfluoroolefins and urea

  摘要：

  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.

  DOI：

  10.1016/j.jfluchem.2012.03.017

文献信息

• Synthesis of fluorine-containing allantoins, hydantoins, and oxazolones from terminal perfluoroolefin oxides and urea
  作者：L. V. Saloutina、A. Ya. Zapevalov、M. I. Kodess、V. I. Saloutin、O. N. Chupakhin

  DOI：10.1134/s1070428012030098

  日期：2012.3

  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.