1,2-环氧-1,1,2,3,3,4,4,4-八氟丁烷 | 3709-90-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 中文名称: 1,2-环氧-1,1,2,3,3,4,4,4-八氟丁烷
• 英文名称: 1,2-epoxyperfluorobutane
• 英文别名: 2,2,3-trifluoro-3-(1,1,2,2,2-pentafluoroethyl)oxirane
• CAS: 3709-90-8
• 化学式: C₄F₈O
• 分子量: 216.031
• InChiKey: ZEZAFHZIZCXHGO-UHFFFAOYSA-N

物化性质

• 沸点：
  -2.2±35.0 °C(Predicted)
• 密度：
  1.71±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,2-环氧-1,1,2,3,3,4,4,4-八氟丁烷 、 丙酮缩氨基硫脲 在 碳酸氢钠 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以72%的产率得到2-isopropylidenehydrazono-5-pentafluoroethyl-5-fluoro-4-thiazolidinone
  参考文献：
  名称：

  Synthesis and structure of reaction products obtained from 1,2-epoxyperfluorobutane and bifunctional nucleophilic reagents

  摘要：

  1,2-Epoxyperfluorobutane readily reacts with bifunctional nucleophilic reagents to provide heterocyclic compounds with a pentafluoroethyl substituent. The reaction of this epoxide with thiourea and acetone thiosemicarbazone gave rise to 2-amino-5-pentafluoroethyl-5-fluoro-4(5H)-thiazolinone and 2-iso-propylidenehydrazono-5-pentafluoroethyl-5-fluoro-4-thiazolidinone respectively. The reaction of 1,2-epoxyperfluorobutane with o-phenylenediamine and 2,3-diaminonaphthalene afforded in high yields 3-pentafluoroethyl-2(1H)-quinoxalinone and 3-(pentafluoroethyl)benzo[g]-2(1H)-quinoxalinone. The molecular and crystal structure of the obtained fluorine-containing heterocycles was established by XRD analysis.

  DOI：

  10.1134/s1070428009110219

文献信息

• Synthesis of polyfluorochloro ketones
  作者：L. A. Saloutina、A. Ya. Zapevalov、M. I. Kodess、I. P. Kolenko、L. S. German

  DOI：10.1007/bf00953182

  日期：1983.6
• Reaction with alcohols of 1-bromo(chloro)-1,2-epoxyheptafluorobutanes and 1,2-epoxyperfluorobutane. Preparation of α-bromo-, α-chloro-, and α-alkoxyhexafluorobutyric acids esters
  作者：T. I. Filyakova、A. Ya. Zapevalov、M. I. Kodess、V. I. Saloutin

  DOI：10.1134/s1070428006110157

  日期：2006.11

  1-Bromo(chloro)-1,2-epoxyheptafluorobutanes reacted with primary and secondary alcohols by two concurrent routes giving a mixture of esters of alpha-alkoxy- and alpha-bromo(chloro)-hexafluorobutyric acids with growing content of the latter on increasing the bulk of the nucleophilic agent. 1,2-Epoxyperfluorobutane under the same conditions was converted into alpha-alkoxyhexafluorobutyric acid esters. Reaction of 1-bromo- 1,2-epoxyheptafluorobutane and 1,2-epoxyperfluorobutane with potassium tert-butylate in tert-butanol resulted in tert-butyl alpha-bromohexafluorobutyrate and heptafluorobutyrate respectively due to the forced attack of the bulky nucleophile on the terminal carbon atom of the epoxy ring.
• Synthesis and properties of 2-chloroperfluorobutene oxides
  作者：L. V. Saloutina、A. Ya. Zapevalov、T. I. Filyakova、I. P. Kolenko、L. S. German

  DOI：10.1007/bf00961930

  日期：1988.6
• 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.
• 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.