4-Hydroxy-6-phenyl-5-trifluoroacetyl-4-trifluoromethylhexahydropyrimidine-2-thione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-Hydroxy-6-phenyl-5-trifluoroacetyl-4-trifluoromethylhexahydropyrimidine-2-thione
• 英文别名: 2,2,2-trifluoro-1-[rel-(4R,5S,6R)-4-hydroxy-6-phenyl-2-thioxo-4-(trifluoromethyl)hexahydropyrimidin-5-yl]ethanone；2,2,2-trifluoro-1-[(4R,5S,6R)-4-hydroxy-6-phenyl-2-sulfanylidene-4-(trifluoromethyl)-1,3-diazinan-5-yl]ethanone
• 化学式: C₁₃H₁₀F₆N₂O₂S
• 分子量: 372.291
• InChiKey: KLEHINJTODMJFT-VHSKPIJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  61.36
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  六氟乙酰丙酮 、 苯甲醛 、 硫脲 在 三甲基氯硅烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-Hydroxy-6-phenyl-5-trifluoroacetyl-4-trifluoromethylhexahydropyrimidine-2-thione
  参考文献：
  名称：

  三甲基氯硅烷促进Biginelli反应中的CF 3-取代的1,3-二羰基化合物

  摘要：

  研究了三氟甲基-1,3-二酮作为Me 3 SiCl促进的Biginelli反应的反应物。建立了反应路径对α位上羰基取代基性质的依赖性。获得了一组新的含CF 3的二氢嘧啶（thi）one衍生物。合成了许多新颖的5-CF 3 CO二氢嘧啶（thi）ones。

  DOI：

  10.1016/j.jfluchem.2008.05.004

文献信息

• Biginelli condensations of fluorinated 3-oxo esters and 1,3-diketones
  作者：V.I Saloutin、Ya.V Burgart、O.G Kuzueva、C.O Kappe、O.N Chupakhin

  DOI：10.1016/s0022-1139(99)00216-x

  日期：2000.4

  Condensation of fluorinated 3-oxo esters or 1,3-diketones with benzaldehyde and (thio)urea results in the diastereoselective formation of 4-fluoroalkyl-4-hydroxy-2-oxo(thioxo)-6-phenyl-hexahydropyrimidine-5-carboxylates from which by dehydration under acidic conditions the corresponding 6-fluoroalkyl-2-oxo(thioxo)-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylates were obtained. Under the same conditions

  含氟的3-氧代酯或1,3-二酮与苯甲醛和（硫代）脲的缩合导致4-氟烷基-4-羟基-2-羟基-2-氧代（硫代）-6-苯基-六氢嘧啶-5-羧酸酯的非对映选择性形成通过在酸性条件下脱水，得到相应的6-氟烷基-2-氧代（硫代）-4-苯基-1,2,3,4-四氢嘧啶-5-羧酸酯。在相同条件下，六氟乙酰丙酮提供4,6-二羟基-4,6-二（三氟甲基）-六氢嘧啶-2-酮。描述了这些嘧啶衍生物导致稠合杂环的一些其他反应。
• ——
  作者：Ya.V. Burgart、O.G. Kuzueva、M.V. Pryadeina、C.O. Kappe、V.I. Saloutin

  DOI：10.1023/a:1012473901354

  日期：——

  Hexafluoroacetylacetone reacts with urea (thiourea) to yield respectively 4,6-bis(hydroxy)-4,6-bis(trifluoromethyl)hexahydropyrimidin-2-one(thione). The dehydration of the products and also reaction of nonsymmetrical fluoroalkyl-containing 1,3-diketones with urea (thiourea) afford substituted pyrimidines. The condensation of fluorinated 3-oxoesters and 1,3-diketones with benzaldehyde and urea (thiourea) results in 5-alkoxycarbonyl(acyl)-4-hydroxy-2-oxo(thioxo)-6-phenyl-4-fluoroalkylhexahydropyrimidines that on dehydration furnish 5-alkoxycarbonyl(acyl)-2-oxo(thioxo)-4-phenyl-6-fluoroalkyltetrahydropyrimidines. Ethyl 7-nonafluorobutyl-5-phenyl-2,3-dihydrothiazolo[3,2-a]pyrimidine-6-carboxylate hydrobromide forms in reaction of dibromoethane with ethyl ether of 2-thioxo-4-phenyl-6-nonafluorobutyltetrahydropyrimidine.
• CF3-substituted 1,3-dicarbonyl compounds in the Biginelli reaction promoted by chlorotrimethylsilane
  作者：Sergey V. Ryabukhin、Andrey S. Plaskon、Eugeniy N. Ostapchuk、Dmitriy M. Volochnyuk、Oleg V. Shishkin、Andrey A. Tolmachev

  DOI：10.1016/j.jfluchem.2008.05.004

  日期：2008.7

  Trifluoromethyl-1,3-diones were investigated as reactants in the Biginelli reaction promoted by Me3SiCl. The dependence of the reaction pathway on the nature of substituent at the α-position to the carbonyl group was established. A set of new CF3-containing dihydropyrimidine(thi)one derivatives was obtained. A number of novel 5-CF3CO dihydropyrimidine(thi)ones were synthesized.

  研究了三氟甲基-1,3-二酮作为Me 3 SiCl促进的Biginelli反应的反应物。建立了反应路径对α位上羰基取代基性质的依赖性。获得了一组新的含CF 3的二氢嘧啶（thi）one衍生物。合成了许多新颖的5-CF 3 CO二氢嘧啶（thi）ones。