3-phenyl-1-[2,3,5,6-tetrafluoro-4-(piperidin-1-yl)phenyl]prop-2-en-1-one | 125231-39-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-phenyl-1-[2,3,5,6-tetrafluoro-4-(piperidin-1-yl)phenyl]prop-2-en-1-one
• 英文别名: 3-phenyl-1-(2,3,5,6-tetrafluoro-4-piperidin-1-ylphenyl)prop-2-en-1-one
• CAS: 125231-39-2
• 化学式: C₂₀H₁₇F₄NO
• 分子量: 363.355
• InChiKey: IJOZYEKWQGIMMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-phenyl-1-[2,3,5,6-tetrafluoro-4-(piperidin-1-yl)phenyl]prop-2-en-1-one 、 邻苯二胺 在 苄基三乙基氯化铵 作用下， 以 异丙醇 为溶剂， 反应 20.0h， 以26%的产率得到2-phenyl-4-(2,3,5,6-tetrafluoro-4-piperidin-1-ylphenyl)-2,3-dihydro-1H-1,5-benzodiazepine
  参考文献：
  名称：

  Reactions of polyfluorochalcones with o- and p-phenylenediamines. Synthesis and intramolecular transformations of polyfluorinated 2,4-diaryl-2,3-dihydrobenzo-1H-1,5-diazepines

  摘要：

  Polyfluorochalcones react with o-phenylenediamine in ethanol and 2-propanol in the presence of triethylamine or benzyltriethylammonium chloride (TEBAC) affording polyfluorinated 2,4-diaryl-2,3-dihydrobenzo-1H-1,5-diazepines. Along with the latter in the presence of triethylamine Michael aza-adducts presumably formed, and at the use of TEBAC in 2-propanol products of intramolecular cyclization and rearrangement of benzo-1,5-diazepines, dihydrobenzimidazo[1,2-a]quinolines were obtained. The reactions of polyfluorochalcones with p-phenylenediamine in ethanol or DMF proceed mostly with the substitution of the para-fluorine atom in the perfluorophenyl rings.

  DOI：

  10.1134/s1070428015020207

文献信息

• Reactions of polyfluorinated chalcones with hydrazine hydrate and phenylhydrazine
  作者：K. S. Smuilovich、N. A. Orlova、E. V. Karpova、M. M. Shakirov、V. V. Shelkovnikov

  DOI：10.1007/s11172-010-0255-4

  日期：2010.7

  Polyfluorinated di-and triarylpyrazolines were synthesized by the reactions of polyfluorinated chalcones with hydrazine hydrate and phenylhydrazine, respectively. Reactions of benzyl-idenepolyfluoroacetophenones with phenylhydrazine resulted in the mixtures of isomeric 1,5-diphenyl-3-polyfluoroaryl-and 1,3-diphenyl-5-polyfluoroarylpyrazolines. Fluorescence properties of the synthesized triarylpyrazolines

  多氟二芳基吡唑啉和三芳基吡唑啉分别通过多氟查耳酮与水合肼和苯肼反应合成。苄叉多氟苯乙酮与苯肼的反应产生异构体 1,5-二苯基-3-多氟芳基和 1,3-二苯基-5-多氟芳基吡唑啉的混合物。研究了合成的三芳基吡唑啉的荧光性质。
• Reaction of polyfluorinated chalcones with guanidine
  作者：E. A. Borodina、N. A. Orlova、Yu. V. Gatilov、O. I. Sal’nikova

  DOI：10.1134/s1070428015120143

  日期：2015.12

  Reactions of polyfluorinated chalcones with guanidine in the presence of bases are accompanied by elimination of the polyfluorophenyl group. 3-(Pentafluorophenyl)-1-phenylprop-2-en-1-one and its derivatives reacted with guanidine under basic conditions to give 4-phenylpyrimidin-2-amine, polyfluorobenzenes, and Michael adducts, 3-(2-amino-4-phenylpyrimidin-5-yl)-3-(4-R-2,3,5,6-tetrafluorophenyl)-1-phenylpropan-1-ones. 1-(Pentafluorophenyl)-3-phenylprop-2-en-1-one and 1,3-bis(pentafluorophenyl)prop-2-en-1-one were converted into cinnamic acid derivatives whose reaction with guanidine afforded 2-amino-6-aryl-5,6-dihydropyrimidin-4(1H)-ones.