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。
• 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.
• 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：——