1-oxyl-2-(4-nitrophenyl)-4,4,5,5-tetramethyl-2-imidazoline | 172301-95-0

• 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-oxyl-2-(4-nitrophenyl)-4,4,5,5-tetramethyl-2-imidazoline
• 英文别名: 2-(4'-nitrophenyl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazolyl-1-oxyl
• CAS: 172301-95-0
• 化学式: C₁₃H₁₆N₃O₃
• 分子量: 262.288
• InChiKey: RSZFXZYUUHKKGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  62.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-oxyl-2-(4-nitrophenyl)-4,4,5,5-tetramethyl-2-imidazoline 在 盐酸羟胺 、 sodium methylate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 24.5h， 生成 1-(acetyloxy)-4,4,5,5-tetramethyl-2-(4-nitrophenyl)-4,5-dihydro-1H-imidazole
  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
• 作为产物：
  描述：

  2-(4-硝基苯基)-4,4,5,5-四甲基咪唑啉-3-氧化物-1-氧基 在 2,3,5,6-四氟-7,7',8,8'-四氰二甲基对苯醌 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以62%的产率得到1-oxyl-2-(4-nitrophenyl)-4,4,5,5-tetramethyl-2-imidazoline
  参考文献：
  名称：

  Deoxygenation Reaction of Phenyl Nitronyl Nitroxides with the Strong Acceptors TCNQF4 and TCNQ

  摘要：

  某些苯基硝酰基亚硝基衍生物与 TCNQF4 或 TCNQ 等强受体在适当的溶剂中发生反应，通过与受体的反常脱氧反应，以选择性的方式得到相应的亚胺亚硝基衍生物。

  DOI：

  10.1039/a904049h

文献信息

• Substituent effects on the reaction of 2-(substituted phenyl)-4,5-dihydro-4,4,5,5-tetramethylimidazol-1-oxyl 3-oxides with nitric oxide: an experimental and MNDO study
  作者：Osamu Shimomura、Kazuhisa Abe、Minoru Hirota

  DOI：10.1039/p29880000795

  日期：——

  constants of the oxygen transfer reaction of 2-(substituted phenyl)-4,5-dihydro-4,4,5,5-tetramethylimidazol-1-oxyl 3-oxides with nitric oxide have been measured by using liquid chromatography (h.p.l.c.). The Hammett ρ value (–0.37) indicates that electron-donating substituents favour the reaction. This can be explained by a mechanism which includes electron transfer to nitric oxide and can be rationalised by

  使用液相色谱法测定了2-（取代的苯基）-4,5-二氢-4,4,5,5-四甲基咪唑-1-氧基3-氧化物与一氧化氮的氧转移反应的相对速率常数（ hplc）。哈米特ρ值（–0.37）表明给电子取代基有利于反应。这可以通过包括电子转移到一氧化氮的机制来解释，并且可以通过半经验MNDO方法计算出的硝酰氧的前沿轨道能量和电子密度来合理化。
• Deoxygenation Reaction of Phenyl Nitronyl Nitroxides with the Strong Acceptors TCNQF4 and TCNQ
  作者：Shin'ichi Nakatsuji、Atsushi Takai、Takeo Ojima、Hiroyuki Anzai

  DOI：10.1039/a904049h

  日期：——

  The reaction of certain phenyl nitronyl nitroxide derivatives with strong acceptors such as TCNQF4 or TCNQ in appropriate solvents give the corresponding imine nitroxide derivatives by an anomalous deoxygenation reaction with acceptors in a selective manner.

  某些苯基硝酰基亚硝基衍生物与 TCNQF4 或 TCNQ 等强受体在适当的溶剂中发生反应，通过与受体的反常脱氧反应，以选择性的方式得到相应的亚胺亚硝基衍生物。
• Oshio, Hiroki; Watanabe, Takashi; Ohto, Akihiro, Inorganic Chemistry, 1996, vol. 35, # 2, p. 472 - 479
  作者：Oshio, Hiroki、Watanabe, Takashi、Ohto, Akihiro、Ito, Tasuku、Masuda, Hideki

  DOI：——

  日期：——
• 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.
• Novel 1-oxyl-2-substitutedphenyl-4,4,5,5-tetramethylimidazolines: Synthesis, selectively analgesic action, and QSAR analysis
  作者：Ming Zhao、Zheng Li、Li Peng、Yu-Rong Tang、Chao Wang、Ziding Zhang、Shiqi Peng

  DOI：10.1016/j.bmc.2007.02.023

  日期：2007.4

  Based on the knowledge that imidazoline can result in analgesic action due to its selective binding with the prostacyclin receptor, 20 1-oxyl-2-substitutedphenyl-4,4,5,5-tetramethylimidazolines (3a-t) were prepared in moderate yields. At 0.13 mmol/kg dose, their in vivo analgesic activities were evaluated after the mice were administered at 30, 60, 90, and 150 min. Compared with the pain threshold (12.27 +/- 9.56-17.71 +/- 7.00%) of normal saline (NS) receiving mice, the pain threshold (23.42 +/- 8.14% to 102.58 +/- 10.66%) of 3a-t receiving mice increases significantly. Considering a prostacyclin receptor targeting analgesic agent usually had bleeding action and to appraise the bleeding risk, the in vivo tail bleeding time of 1.30 mmol/kg 3a-t receiving mice was found to be ranged from 116.3 +/- 8.2 s to 120.3 +/- 9.2 s, which was substantially equal to that (117.8 +/- 8.4 s to 119.0 +/- 8.6 s) of NS receiving mice. Based on the possibility of imidazoline acting as vasodilator, the in vitro vasorelaxations of 3a-t were tested using the rat aortic strip model. When the aortic strip contracted by noradrenaline (NE, final concentration 10(-7) mol/l) was treated with 3a-t (final concentration 5 x 10(-4) mol/l), only lower percentage inhibitions (6.55 +/- 5.70-37.40 +/- 4.07%) were recorded, implying that the vasorelaxation of 3a-t was neglectable. By selecting appropriate molecular descriptors generated from e-dragon server, the QSAR model of the analgesic activities of 3a-t was constructed using the multiple linear regression method. The established QSAR model showed reasonable accuracy and thus it is promising to be used for screening new 1-oxyl-2-substitutedphenyl-4,4,5,5-tetramethylimidazoline derivatives as analgesic agents. (c) 2007 Elsevier Ltd. All rights reserved.