1-oxyl-2-(4-methylphenyl)-3-oxo-4,4,5,5-tetramethyl-2-imidazoline | 117566-78-6

• 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-methylphenyl)-3-oxo-4,4,5,5-tetramethyl-2-imidazoline
• 英文别名: 2-(4'-methylphenyl)-4,4,5,5-tetramethylimidazolidine-3-oxide-1-oxyl；2-(4-methylphenyl)-4,4,5,5-tetramethylimidazoline-3-oxide-1-oxyl；α-o-Tolylnitronylnitroxid；2-(4-methylphenyl)-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide radical
• CAS: 117566-78-6
• 化学式: C₁₄H₁₉N₂O₂
• 分子量: 247.317
• InChiKey: SDYFMHMSGYIGGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 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：
  33
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-oxyl-2-(4-methylphenyl)-3-oxo-4,4,5,5-tetramethyl-2-imidazoline 在 nitric oxide 作用下， 以 正己烷 、 氯仿 为溶剂， 生成 1-oxyl-2-(4-methylphenyl)-4,4,5,5-tetramethyl-2-imidazoline
  参考文献：
  名称：

  取代基对2-（取代苯基）-4,5-二氢-4,4,5,5-四甲基咪唑-1-氧基3-氧化物与一氧化氮反应的影响：一项实验和MNDO研究

  摘要：

  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。

  DOI：

  10.1039/p29880000795
• 作为产物：
  描述：

  1,3-dihydroxyl-2-(4'-methylphen-1'-yl)-4,4,5,5-tetramethylimidazolidine 在 lead dioxide 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以80%的产率得到1-oxyl-2-(4-methylphenyl)-3-oxo-4,4,5,5-tetramethyl-2-imidazoline
  参考文献：
  名称：

  作为自由基清除剂的新型2-取代硝酰基硝基氧化合物：合成，生物学评估和结构-活性关系。

  摘要：

  为了开发具有增强的自由基清除剂性能的更有效的小分子，我们设计并合成了一系列硝酰基硝基氧衍生物4a-h。基于Ach诱导的血管舒张测定法发现了前导化合物4f。基于该支架的进一步化学修饰提供了一系列新的2-取代的苯基亚硝酰基硝基氧化物衍生物6a-s。基于PC12细胞存活测定法，新合成的化合物6a-s具有改善的自由基清除剂的活性。就NO，H（2）O（2）和OH的清除能力而言，化合物6g，n，o和s是一些最有效的化合物。2-取代的苯基亚硝基硝基氮氧化物具有较高的自由基清除活性，带有给电子基团（EDG）。相比之下，吸电子基团（EWG）引入芳环导致其自由基清除活性急剧下降。这些结果表明，芳香环的给电子基团（EDG）可能是影响这些化合物清除自由基行为的重要因素，清除自由基的能力很大程度上取决于苯环的位置和电子性质。取代基。新型的2-取代的硝酰基氮氧化物的增强的自由基清除能力可能是对抗ROS（活性氧）/ R

  DOI：

  10.1016/j.bmc.2006.04.016

文献信息

• Supramolecular interactions and magnetism of metal–radical chains †
  作者：Andrea Caneschi、Dante Gatteschi、Nikolia Lalioti、Claudio Sangregorio、Roberta Sessoli

  DOI：10.1039/b004244g

  日期：——

  The combination of organic imidazoline-1-oxyl-3-oxide radicals as building blocks with metal ions can yield 1-D magnetic chains in various conformations, depending on the metal ion and the 2 substituent of the radicals.

  将有机咪唑啉-1-氧代-3-氧化物自由基作为构建模块与金属离子相结合，可产生各种构象的一维磁链，具体取决于金属离子和自由基的 2 个取代基。
• 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.
• Environmentally Benign Strategy for Arylation of Nitronyl Nitroxide Using a Non-Transition Metal Nucleophile
  作者：Shuichi Suzuki、Fumiya Nakamura、Takeshi Naota

  DOI：10.1021/acs.orglett.9b04655

  日期：2020.2.21

  We have developed a method for the arylation of nitronyl nitroxide without using its transition metal complex as a nucleophile. Various nitronyl nitroxide-substituted ff-electronic compounds can be obtained from the parent nitronyl nitroxide and the corresponding aryl iodides using a combination of zero-valent palladium catalysts and a 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl ligand in the presence of sodium tert-butoxide. The utility of the method has been demonstrated by the direct synthesis of open-shell compounds with giant pi-electronic systems, such as 10P.
• Synthesis and Magnetism of Rare Earth Binuclear Complexes with Bridging Nitronyl Nitroxides
  作者：Zong-Hui Jiang、Wei Zhang、Dai-Zheng Liao、Zhen-Wei Huan、Bai-Wang Sun、Geng-Lin Wang

  DOI：10.1080/00945719608005132

  日期：1996.9

  Sir compounds of the general formula [Ln(pfpr)(8)](2)(NITphMe). nH(2)O, where Ln = Nd, Gd, Dy, Ho, Er, Y, pfpr = pentafluoropropionate, NITphMe = 2-(4-methylphenyl)-4,4,5,5-tetramethyl-4,5-dihydro-1H- imidazolyl-1-oxyl-3-oxide, and n = 4 (for Nd, Gd); 2 (for Dy); 6 (for Ho); 0 (for Er); 5 (for Y), have been synthesized. These complexes were characterized by elemental analyses, DR, electronic spectra and molar conductances. The variable temperature (4-300 K) magnetic susceptibility of the complex [Gd(pfpr)(8)](2)(NITphMe). 4H(2)O was determined. The observed susceptibility data were fit to those from the theoretical magnetic equation by the least-squares method. The exchange integral, J, was found to be equal to 0.263 cm(-1). This indicates weak ferromagnetic spin-exchange interaction between the radical and the gadolinium(III) ion.
• Sun, Bai-Wang; Zhao, Qi-Hua; Liao, Dai-Zheng, Canadian Journal of Chemistry, 2000, vol. 78, # 3, p. 322 - 327
  作者：Sun, Bai-Wang、Zhao, Qi-Hua、Liao, Dai-Zheng、Jiang, Zong-Hui、Yan, Shi-Ping、Wang, Geng-Lin、Yao, Xin-Kai、Wang, Hong-Gen

  DOI：——

  日期：——