trans/cis-dodecafluoro-3,4-epoxyhexane | 74728-99-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: trans/cis-dodecafluoro-3,4-epoxyhexane
• 英文别名: dodecafluoro-3,4-epoxyhexane；3,4-epoxydodecafluorohexane；3,4-epoxyperfluorohexane；Oxirane, 2,3-difluoro-2,3-bis(pentafluoroethyl)-；2,3-difluoro-2,3-bis(1,1,2,2,2-pentafluoroethyl)oxirane
• CAS: 74728-99-7
• 化学式: C₆F₁₂O
• 分子量: 316.046
• InChiKey: PQJIZEXSRRAPKP-UHFFFAOYSA-N

物化性质

• 沸点：
  65.1±35.0 °C(Predicted)
• 密度：
  1.75±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  2
• 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：
  13

反应信息

• 作为反应物：
  描述：

  trans/cis-dodecafluoro-3,4-epoxyhexane 在 氨 作用下， 以 乙醚 为溶剂， 生成 五氟丙胺 、 3-amino-4-iminodecafluoro-3-hexanol
  参考文献：
  名称：

  Saloutina, L. V.; Zapevalov, A. Ya.; Kodess, M. I., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 4, p. 628 - 634

  摘要：

  DOI：
• 作为产物：
  描述：

  trans-perfluoro-3-hexene 、 sodium hypochlorite 以91%的产率得到
  参考文献：
  名称：

  FILYAKOVA, T. I.;PESCHANSKIJ, N. V.;KODESS, M. I.;ZAPEVALOV, A. YA.;KOLEN+, ZH. ORGAN. XIMII, 24,(1988) N 2, 371-377

  摘要：

  DOI：

文献信息

• Synthesis of 2,3-bis(perfluoroalkyl)quinoxalines and 2,3-bis(perfluoroalkyl)-1,4-benzoxazines from oxides of internal perfluoroolefins
  作者：Lyudmila V. Saloutina、Aleksandr Ya. Zapevalov、Victor I. Saloutin、Mikhail I. Kodess、Valentina E. Kirichenko、Marina G. Pervova、Oleg N. Chupakhin

  DOI：10.1016/j.jfluchem.2005.05.001

  日期：2005.6

  The reactions of oxides of internal trans-, cis-perfluoroolefins with o-phenylenediamine and 2-aminophenol in dioxane gave 2,3-bis(perfluoroalkyl)quinoxalines and 2,3-bis(perfluoroalkyl)-2H-1,4-benzoxazin-2-ols respectively in yields of 23–67%. When N,N-dimethylacetamide was used as a solvent an anionic isomerization of the oxides into ketones, which further yielded 2-(perfluoroalkyl)benzimidazoles

  内部反式，顺式-全氟烯烃的氧化物与邻苯二胺和2-氨基苯酚在二恶烷中的反应得到2,3-双（全氟烷基）喹喔啉和2,3-双（全氟烷基）-2H-1,4-苯并恶嗪- 2-ols的产率分别为23–67％。当使用N，N-二甲基乙酰胺作为溶剂时，氧化物阴离子异构化为酮，在邻苯二胺和2-羟基N的情况下，进一步生成2-（全氟烷基）苯并咪唑在2-氨基苯酚的情况下，全氟链烷酰基苯胺成为这些反应的主要途径。在N，N-二甲基乙酰胺中的十二氟-3,4-环氧己烷与2-氨基苯酚之间的相互作用会发生导致2-五氟乙基-2-五氟丙酰基苯并恶唑烷的异常环化反应。
• Synthesis of fluorine containing glycolurils and oxazolines from oxides of internal perfluoroolefins
  作者：Lyudmila V. Saloutina、Aleksandr Ya. Zapevalov、Victor I. Saloutin、Pavel A. Slepukhin、Mikhail I. Kodess、Oleg N. Chupakhin

  DOI：10.1016/j.jfluchem.2009.06.016

  日期：2009.10

  yields. In dioxane, unexpected cyclization occurred resulting in oxazolines 7a–d in high yields. A similar reaction of oxiranes 2, 3 with urea in aqueous dioxane gave mixtures of 4,5-dihydroxy-4,5-bis(perfluoroalkyl)imidazolidine-2-ones 9b, c, glycolurils 4b, c and oxazolines 7b–d. The molecular structure of trans-isomers of oxazoline 7b and imidazolidine 9b has been established by X-ray crystallography

  内部全氟烯烃的氧化物的反应1 - 3与脲，得到2种含有取决于溶剂的性质的N-杂环化合物的新的氟的：1,5-双（全氟烷基）四氮杂[3.3.0]辛烷-3,7-二酮4a – c和2-氨基-5-氟-4,5-双（全氟烷基）-4,5-二氢恶唑-4-醇7a – d。使用极性二甲基亚砜，N，N-二甲基乙酰胺和乙腈可中等产率获得甘脲4a – c。在二恶烷中，意外的环化反应产生了高产的恶唑啉7a - d。环氧乙烷2的类似反应，3与脲在二恶烷水溶液中的混合物得到4,5-二羟基-4,5-双（全氟烷基）咪唑烷-2-酮9b，c，甘脲4b，c和恶唑啉7b - d的混合物。恶唑啉7b和咪唑烷9b的反式异构体的分子结构已经通过X射线晶体学确定。
• Zapevalov, A. Ya.; Filyakova, T. I.; Peschanskii, N. V., Journal of Organic Chemistry USSR (English Translation), 1989, vol. 25, # 3.1, p. 441 - 445
  作者：Zapevalov, A. Ya.、Filyakova, T. I.、Peschanskii, N. V.、Kodess, M. I.、Kolenko, I. P.

  DOI：——

  日期：——
• Reactions of epoxides derived from internal perfluoroolefins with o-phenylenediamine and 2-aminophenol
  作者：L. V. Saloutina、A. Ya. Zapevalov、V. I. Saloutin、M. I. Kodess、V. E. Kirichenko、M. G. Pervova、O. N. Chupakhin

  DOI：10.1134/s1070428006040130

  日期：2006.4

  The reactions of epoxy derivatives of internal perfluoroolefins with o-phenylenediamine and 2-aminophenol in dioxane gave 23-67% of the corresponding 2,3-bis(perfluoroalkyl)quinoxalines and 2,3-bis(perfluoroalkyl)-2H-1,4-benzoxazin-2-ols, respectively. When N,N-dimethylacetamide was used as a solvent, the main reaction pathway was anionic isomerization of epoxides into ketones which were then converted into 2-perfluoroalkylbenzimidazoles (in the reactions with o-phenylenediamine) or 2-hydroxy-N-perfluoroalkanoyl-anilines (in the reactions with 2-aminophenol). The reaction of 3,4-epoxydodecafluorohexane with 2-aminophenol in N,N-dimethylacetamide was accompanied by unusual cyclization to afford 2-pentafluoropropanoyl-2pentafluoroethyl-1,3-benzoxazolidine.
• Reactions of internal perfluoroolefin oxides with urea
  作者：L. V. Saloutina、A. Ya. Zapevalov、V. I. Saloutin、M. I. Kodess、P. A. Slepukhin

  DOI：10.1134/s1070428009060116

  日期：2009.6

  Internal perfluoroolefin oxides reacted with urea to give, depending on the solvent nature, two types of new fluorine-substituted nitrogen-containing heterocycles. 1,5-Bis(perfluoroalkyl)tetraazabicyclo[3.3.0]octane-3,7-diones were formed in dimethyl sulfoxide, N,N-dimethylacetamide, and acetonitrile, while the reaction in dioxane resulted in the formation of unexpected products, 2-amino-5-fluoro-4,5-bis(perfluoroalkyl)-4,5-dihydrooxazol-4-ols, existing mainly as trans isomers. trans Orientation of perfluoroalkyl substituents in these compounds was determined by analysis of F-19-F-19 spin-spin coupling constants in the F-19 NMR spectra. The molecular structure of trans-2-amino-5-fluoro-4,5-bis(trifluoromethyl)-4,5-dihydrooxazol-4-ol was studied by X-ray analysis.