2-(4-nitrophenyl)-4-phenyl-1-p-tolyl-2,5-dihydro-1H-imidazole-3-oxide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-nitrophenyl)-4-phenyl-1-p-tolyl-2,5-dihydro-1H-imidazole-3-oxide
• 英文别名: 3-(4-Methylphenyl)-2-(4-nitrophenyl)-1-oxido-5-phenyl-2,4-dihydroimidazol-1-ium
• 化学式: C₂₂H₁₉N₃O₃
• 分子量: 373.411
• InChiKey: IASHOSYVIPMAHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  77.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-nitrophenyl)-4-phenyl-1-p-tolyl-2,5-dihydro-1H-imidazole-3-oxide 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 生成 3-Hydroxy-1-(4-methylphenyl)-2-(4-nitrophenyl)-4-phenylimidazolidine
  参考文献：
  名称：

  Imidazolidin-1-oles, N-2-aminoethyl nitrones and 1,2,5-oxadiazinanes. A novel ring–chain tautomerism

  摘要：

  Imidazolin-3-oxides I were reduced with NaBH4 in THF at reflux to give the corresponding 2,3,5-triarylimidazolidin-l-oles 2, which are proved to be in a ring-chain-ring tautomeric equilibrium with N-2-aminoethyl nitrones 3 and 3,5,6-triphenyl-1,2,5-oxadiazinanes 4. The ratios of the ring and chain form are determined by the substituent at the reaction centre and can be described by the equation logK(x) = p sigma(+) + logK(x=H). These are the first examples of a novel three-component ring-chain-ring tautomeric equilibrium characterized by a Hammett-type equation. The stability of the ring form was favoured by electron-withdrawing substituents. Treatment of the equilibrium mixture of 2, 3 and 4 with phenylisocyanate in refluxing toluene gives selectively the corresponding O-carbamoylated imidazolidines 5; cis-5 was shown to isomerize to trans-5 on heating. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.05.058
• 作为产物：
  描述：

  2-bromo-1-phenyl-ethanone oxime 、 对硝基苯甲醛 、 乙烷,三氯氟- 以 乙醇 为溶剂， 反应 3.33h， 生成 2-(4-nitrophenyl)-4-phenyl-1-p-tolyl-2,5-dihydro-1H-imidazole-3-oxide
  参考文献：
  名称：

  A facile stereoselective synthesis of 2-perfluoroalkyl-3a,4,5,6-tetrahydroimidazo[1,5-b]isoxazoles

  摘要：

  Methyl 2-perfluoroalkynoates 2 reacted readily with cyclic nitrones 1 via 1,3-dipolar cycloaddition at room temperature to give 2-perfluoroalkyl-3a,4,5,6-tetrahydroimidazo[1,5-b]isoxazoles 3 in good to excellent yields with high diastereoselectivity and regioselectivity. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2008.11.002

文献信息

• A facile stereoselective synthesis of 2-perfluoroalkyl-3a,4,5,6-tetrahydroimidazo[1,5-b]isoxazoles
  作者：Lei Lu、Weiguo Cao、Jie Chen、Hui Zhang、Jiaping Zhang、Huiyun Chen、Jiamei Wei、Hongmei Deng、Min Shao

  DOI：10.1016/j.jfluchem.2008.11.002

  日期：2009.3

  Methyl 2-perfluoroalkynoates 2 reacted readily with cyclic nitrones 1 via 1,3-dipolar cycloaddition at room temperature to give 2-perfluoroalkyl-3a,4,5,6-tetrahydroimidazo[1,5-b]isoxazoles 3 in good to excellent yields with high diastereoselectivity and regioselectivity. (C) 2008 Elsevier B.V. All rights reserved.
• Imidazolidin-1-oles, N-2-aminoethyl nitrones and 1,2,5-oxadiazinanes. A novel ring–chain tautomerism
  作者：Necdet Coşkun、Oktay Asutay

  DOI：10.1016/j.tetlet.2007.05.058

  日期：2007.7

  Imidazolin-3-oxides I were reduced with NaBH4 in THF at reflux to give the corresponding 2,3,5-triarylimidazolidin-l-oles 2, which are proved to be in a ring-chain-ring tautomeric equilibrium with N-2-aminoethyl nitrones 3 and 3,5,6-triphenyl-1,2,5-oxadiazinanes 4. The ratios of the ring and chain form are determined by the substituent at the reaction centre and can be described by the equation logK(x) = p sigma(+) + logK(x=H). These are the first examples of a novel three-component ring-chain-ring tautomeric equilibrium characterized by a Hammett-type equation. The stability of the ring form was favoured by electron-withdrawing substituents. Treatment of the equilibrium mixture of 2, 3 and 4 with phenylisocyanate in refluxing toluene gives selectively the corresponding O-carbamoylated imidazolidines 5; cis-5 was shown to isomerize to trans-5 on heating. (C) 2007 Elsevier Ltd. All rights reserved.