1,3-diethyl-5-hydroxy-5-trifluoromethylimidazolidine-2,4-dione | 105480-47-5

• 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: 1,3-diethyl-5-hydroxy-5-trifluoromethylimidazolidine-2,4-dione
• 英文别名: 1,3-Diethyl-5-hydroxy-5-trifluoro-methylimidazolidine-2,4-dione；1,3-diethyl-5-hydroxy-5-(trifluoromethyl)imidazolidine-2,4-dione
• CAS: 105480-47-5
• 化学式: C₈H₁₁F₃N₂O₃
• 分子量: 240.182
• InChiKey: PTNGRHGIYMNNKQ-UHFFFAOYSA-N

物化性质

• 沸点：
  262.7±50.0 °C(Predicted)
• 密度：
  1.434±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,3-diethyl-4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-one 在 盐酸 、 尿素 作用下， 以 水 为溶剂， 以91%的产率得到1,3-diethyl-5-hydroxy-5-trifluoromethylimidazolidine-2,4-dione
  参考文献：
  名称：

  Synthesis of Fluorine-Containing Imidazolidin-2-Ones, Glycolurils, and Hydantoins Based on Perfluorodiacetyl and Ureas*

  摘要：

  The reactions of perfluorodiacetyl with urea, N,N'-dimethyl- and N,N'-diethylureas produced the cis and trans isomers of 4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-ones in 60-90% yields. The reaction of 4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-one with urea gave 1,5-bis-(trifluoro-methyl)-2,4,6,8-tetraazobicyclo[3.3.0]octane-3,7-dione in 88% yield. The analogous reaction of 1,3-di-methyl- and 1,3-diethylimidazolidin-2-ones with urea, N,N'-dimethyl- and N,N'-diethylureas led to the formation of 5-hydroxy-1,3-dimethyl(diethyl)-5-trifluoromethylimidazolidine-2,4-diones (hydantoins) in 60-87% yields. The molecular structures of cis-4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-one, trans-4,5-dihydroxy-1,3-dimethyl-4,5-bis(trifluoromethyl)imidazolidin-2-one, and 5-hydroxy-1,3-di-methyl-5-trifluoromethylimidazolidine-2,4-dione were studied by X-ray structural analysis.

  DOI：

  10.1007/s10593-014-1550-z

文献信息

• Synthesis of trifluoromethyl – containing oxo(thioxo)imidazothiazolones and thioglycolurils based on perfluorobiacetyl
  作者：L.V. Saloutina、A.Ya. Zapevalov、M.I. Kodess、I.N. Ganebnykh、V.I. Saloutin、O.N. Chupakhin

  DOI：10.1016/j.jfluchem.2018.05.015

  日期：2018.8

  olones (yield ∼50 − 16%). In contrast to it, the condensation of 4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidine-2-thione with urea under similar conditions gave mainly trifluoromethylated thioglycoluril in ∼31% yield.

  全氟联乙酰与硫脲的反应生成了4,5-二羟基-4,5-双（三氟甲基）咪唑烷-2-硫酮，主要为反式形式，收率为〜60％。首次在高温下与二甲基乙酰胺中的硫脲缩合反应中首次引入4,5-二羟基-4,5-双（三氟甲基）咪唑烷-2-硫酮（一），意外地获得了三氟甲基化的硫代（氧代）咪唑并噻唑酮（收率） 〜41-30％）。4,5-二羟基-4,5-双（三氟甲基）咪唑烷-2-硫酮（一个）与NH 4 SCN和4,5-二羟基-4,5-双（三氟甲基）咪唑烷-2-硫酮的相似反应具有N-烷基（芳基）脲和N，N'-二烷基（二芳基）脲提供了相同的硫代（氧代）咪唑并噻唑酮（收率约50-16％）。与此相反，在相似的条件下，4,5-二羟基-4,5-双（三氟甲基）咪唑烷-2-硫酮与尿素的缩合反应主要得到三氟甲基化的巯基脲，收率为31％。
• Mustafa, Mohamed El-Said; Takaoka, Akio; Ishikawa, Nobuo, Bulletin de la Societe Chimique de France, 1986, # 6, p. 944 - 954
  作者：Mustafa, Mohamed El-Said、Takaoka, Akio、Ishikawa, Nobuo

  DOI：——

  日期：——
• Trifluoropyruvic acid hydrate in heterocyclic synthesis: a facile synthesis of 5-hydroxy-5-trifluoromethylhydantoin derivatives
  作者：M. El-said Mustafa、Akio Takaoka、Nobuo Ishikawa

  DOI：10.1016/s0022-1139(00)85100-3

  日期：1986.1
• MUSTAFA, M. EL-SAID;TAKAOKA, AKIO;ISHIKAWA, NOBUO, J. FLUOR. CHEM., 1986, 30, N 4, 463-468
  作者：MUSTAFA, M. EL-SAID、TAKAOKA, AKIO、ISHIKAWA, NOBUO

  DOI：——

  日期：——
• MUSTAFA MOHAMED EL-SAID; TAKAOKA AKIO; ISHIKAWA NOBUO, BULL. SOC. CHIM. FR.,(1986) N 6, 944-954
  作者：MUSTAFA MOHAMED EL-SAID、 TAKAOKA AKIO、 ISHIKAWA NOBUO

  DOI：——

  日期：——