1,4,4,5,5-pentamethyl-2-(4-nitrophenyl)-4,5-dihydro-1H-imidazole 3-oxide | 735279-05-7

• 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: 1,4,4,5,5-pentamethyl-2-(4-nitrophenyl)-4,5-dihydro-1H-imidazole 3-oxide
• 英文别名: 1,4,4,5,5-Pentamethyl-2-(4-nitrophenyl)-3-oxidoimidazol-3-ium
• CAS: 735279-05-7
• 化学式: C₁₄H₁₉N₃O₃
• 分子量: 277.323
• InChiKey: YRJIHYKWZPGMKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  77.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯丙炔酸甲酯 、 1,4,4,5,5-pentamethyl-2-(4-nitrophenyl)-4,5-dihydro-1H-imidazole 3-oxide 60.0~70.0 ℃ 、133.32 Pa 条件下， 以76%的产率得到methyl 1,2,2,3,3-pentamethyl-6-phenyl-7a-(4-nitrophenyl)-1,2,3,7a-tetrahydroimidazo[1,2-b]isoxazole-7-carboxylate
  参考文献：
  名称：

  4,5-二氢-1 H-咪唑3-氧化物与炔烃的1,3-偶极环加成反应

  摘要：

  显示在杂环的1和2位带有不同取代基的4,5-二氢-1 H-咪唑3-氧化物可与各种受体取代的炔烃反应形成相应的环加合物-1,2,3,7a衍生物-四氢咪唑并[1,2- b ]异恶唑。揭示了该过程的高区域选择性，这是由氮原子与硝酮基团的缀合所规定的。

  DOI：

  10.1002/jhet.5570430206
• 作为产物：
  描述：

  1-oxyl-2-(4-nitrophenyl)-4,4,5,5-tetramethyl-2-imidazoline 在 sodium hydroxide 、 盐酸羟胺 、 sodium methylate 作用下， 以 甲醇 、 乙醚 、 氯仿 为溶剂， 反应 72.67h， 生成 1,4,4,5,5-pentamethyl-2-(4-nitrophenyl)-4,5-dihydro-1H-imidazole 3-oxide
  参考文献：
  名称：

  Aminonitrone-N-hydroxyaminoimine tautomeric equilibrium in the series of 1-hydroxy-2-imidazolines

  摘要：

  A series of 2-substituted 1-hydroxy-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazoles have been synthesized. Various effects on the state of the aminonitrone-N-hydroxyaminoimine tautomeric equilibrium, including solvent effects and substituent effect in the 2 position of heterocycle, have been studied. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2004.02.028

文献信息

• The model of 1,3-dipolar cycloaddition reaction of 4,5-dihydro-1H-imidazole 3-oxide derivatives with alkynes
  作者：Sergey A. Popov、Galina V. Romanenko、Vladimir A. Reznikov

  DOI：10.1016/j.molstruc.2007.02.015

  日期：2008.1

  solvents and different structural factors on the rate of 1,3-dipolar cycloaddition reaction of the 4,5-dihydro-1 H -imidazole 3-oxide derivatives with alkynes have been studied. Nitrones and alkynes have been ranged by their relative activity in this reaction. Using the DFT calculation with the triple zets basis set, the energy profile of the reaction has been plotted, and the structures and energy characteristics

  摘要 研究了溶剂和不同结构因素对4,5-二氢-1H-咪唑3-氧化物衍生物与炔烃的1,3-偶极环加成反应速率的影响。硝酮和炔烃根据它们在该反应中的相对活性而定。使用具有三重 zets 基组的 DFT 计算，绘制了反应的能量分布图，并确定了过渡态的结构和能量特性。这种反应的机制已被证明是协调一致的和异步的。已经证明了用于详细研究硝酮的 1,3-偶极环加成的计算方法的有效性。
• Aminonitrone-N-hydroxyaminoimine tautomeric equilibrium in the series of 1-hydroxy-2-imidazolines
  作者：Sergey A. Popov、Rodion V. Andreev、Galina V. Romanenko、Viktor I. Ovcharenko、Vladimir A. Reznikov

  DOI：10.1016/j.molstruc.2004.02.028

  日期：2004.7

  A series of 2-substituted 1-hydroxy-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazoles have been synthesized. Various effects on the state of the aminonitrone-N-hydroxyaminoimine tautomeric equilibrium, including solvent effects and substituent effect in the 2 position of heterocycle, have been studied. (C) 2004 Elsevier B.V. All rights reserved.
• 1,3-Dipolar cycloaddition reaction of 4,5-dihydro-1<i>H</i>-imidazole 3-oxides with alkynes
  作者：Sergey A. Popov、Nikita V. Chukanov、Galina V. Romanenko、Tatjana V. Rybalova、Yuri V. Gatilov、Vladimir A. Reznikov

  DOI：10.1002/jhet.5570430206

  日期：2006.3

  4,5-Dihydro-1H-imidazole 3-oxides bearing different substituents at positions 1 and 2 of the heterocycle were shown to react with a wide range of acceptor-substituted alkynes forming corrsponding cycloadducts - derivatives of 1,2,3,7a-tetrahydroimidazo[1,2-b]isoxazole. High regioselectivity of this process stipulated by conjugation of the nitrogen atom with the nitrone group was revealed.

  显示在杂环的1和2位带有不同取代基的4,5-二氢-1 H-咪唑3-氧化物可与各种受体取代的炔烃反应形成相应的环加合物-1,2,3,7a衍生物-四氢咪唑并[1,2- b ]异恶唑。揭示了该过程的高区域选择性，这是由氮原子与硝酮基团的缀合所规定的。