2-(2-hydroxyphenyl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-1-oxyl | 626206-32-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(2-hydroxyphenyl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-1-oxyl
• 英文别名: 1-oxyl-2-(2-hydroxyphenyl)-4,4,5,5-tetramethyl-2-imidazoline；4,4,5,5-tetramethyl-2-(2-hydroxyphenyl)-imidazoline-1-oxyl
• CAS: 626206-32-4
• 化学式: C₁₃H₁₇N₂O₂
• 分子量: 233.29
• InChiKey: CJYBGFASMDIFFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 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：
  36.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-hydroxyphenyl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-1-oxyl 、 copper(II) nitrate 在 potassium methoxide 作用下， 以 甲醇 为溶剂， 以86.7%的产率得到copper(II) bis[2-[(4,4,5,5-tetramethylimidazoline-1-oxyl)-2-yl]phenolate]
  参考文献：
  名称：

  带有两个螯合酚盐取代的亚氨基亚硝基氧化物的四配位铜（II）配合物的合成，磁性和MCD光谱

  摘要：

  摘要甲醇中的硝酸铜（II）与4,4,5,5-四甲基-2-（2-羟基苯苯基）咪唑啉-1-氧基（IM2PhOH）与甲醇钾的反应制得了均化的双（亚氨基亚硝基）配合物。 [Cu（IM 2 PhO）2]（1）。对1的单晶X射线分析表明，亚氨基亚硝酸根阴离子IM2PhO-通过亚氨基N和苯氧基-O原子与CuII离子螯合，形成六元螯合环。Cu（II）离子周围的配位几何形状是扭曲的方平面多边形。两个配位平面之间的二面角为40.81°，两个配位平面分别由Cu和IM2PhO-的两个连接原子定义。磁化率和EPR谱的温度依赖性为1，表明Cu（II）和亚氨基亚硝酸根之间的磁性相互作用是铁磁性的，而两个配位的亚氨基亚硝酸盐之间存在适度的反铁磁相互作用。这些相反相互作用之间的平衡在1中达到了最低的分子双峰自旋态。配合物1的可变温度磁性圆二色性（MCD）谱还显示了两个带有大C值的负组分，这可能是由于电荷-自旋耦合IM2Ph

  DOI：

  10.1016/j.ica.2004.03.017
• 作为产物：
  描述：

  2,3-二甲基-2,3-二硝基丁烷 在 盐酸 、 氯化铵 、 lead dioxide 、 锌 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 20.33h， 生成 2-(2-hydroxyphenyl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-1-oxyl
  参考文献：
  名称：

  Novel 1-oxyl-2-substitutedphenyl-4,4,5,5-tetramethylimidazolines: Synthesis, selectively analgesic action, and QSAR analysis

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2007.02.023

文献信息

• Synthesis of 2-iminonitroxide-substituted phenols and pyridine-3-oles.
  作者：Eugene V. Tretyakov、Ilia V. Eltsov、Sergey V. Fokin、Yurii G. Shvedenkov、Galina V. Romanenko、Victor I. Ovcharenko

  DOI：10.1016/s0277-5387(03)00228-6

  日期：2003.7

  Methods for the synthesis of a new family of nitronylnitroxides, iminonitroxides, and their precursors with 2-hydroxyphenyl or 3-hydroxypyridin-2-yl substituents in the side chain have been developed. Five heterospin chelates of Cu(II) with deprotonated iminonitroxides have been isolated. Their structure and magnetic properties have been studied. In all complexes, ferromagnetic intramolecular exchange interactions take place (J similar to 40-350 cm(-1)) (C) 2003 Elsevier Science Ltd. All rights reserved.