3-Pentafluoroethyl-quinoxalin-2-ol | 89995-28-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-Pentafluoroethyl-quinoxalin-2-ol
• 英文别名: 2(1H)-Quinoxalinone, 3-(pentafluoroethyl)-；3-(1,1,2,2,2-pentafluoroethyl)-1H-quinoxalin-2-one
• CAS: 89995-28-8
• 化学式: C₁₀H₅F₅N₂O
• 分子量: 264.155
• InChiKey: OGIPRRXQYMYUMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,3,4,4,4-五氟-2-氧代丁酸甲酯 、 邻苯二胺 反应 0.5h， 以77%的产率得到3-Pentafluoroethyl-quinoxalin-2-ol
  参考文献：
  名称：

  Reaction of methyl esters of fluorine-containing ?-keto acids with amines

  摘要：

  DOI：

  10.1007/bf00954715

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 and structure of reaction products obtained from 1,2-epoxyperfluorobutane and bifunctional nucleophilic reagents
  作者：T. I. Filyakova、M. I. Kodess、P. A. Slepukhin、A. Ya. Zapevalov

  DOI：10.1134/s1070428009110219

  日期：2009.11

  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.
• 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.
• SALOUTIN, V. I.;PITERSKIX, I. A.;PASHKEVICH, K. I.;KODESS, M. I., IZV. AN CCCP. CEP. XIM., 1983, N 11, 2568-2575
  作者：SALOUTIN, V. I.、PITERSKIX, I. A.、PASHKEVICH, K. I.、KODESS, M. I.

  DOI：——

  日期：——
• Reaction of methyl esters of fluorine-containing ?-keto acids with amines
  作者：V. I. Saloutin、I. A. Piterskikh、K. I. Pashkevich、M. I. Kodess

  DOI：10.1007/bf00954715

  日期：1983.11