1-oxyl-2-(4-bromophenyl)-3-oxo-4,4,5,5-tetramethyl-2-imidazoline | 117566-82-2

• 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-bromophenyl)-3-oxo-4,4,5,5-tetramethyl-2-imidazoline
• 英文别名: 2-(4'-bromophenyl)-4,4,5,5-tetramethylimidazolidine-3-oxide-1-oxyl；2-(4'-bromophenyl)-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide；NITPhBr
• CAS: 117566-82-2
• 化学式: C₁₃H₁₆BrN₂O₂
• 分子量: 312.186
• InChiKey: PMAZYCNXXFRSMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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-bromophenyl)-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-bromophenyl)-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：

  2,3-二甲基-2,3-二硝基丁烷 在 sodium periodate 、 氯化铵 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 生成 1-oxyl-2-(4-bromophenyl)-3-oxo-4,4,5,5-tetramethyl-2-imidazoline
  参考文献：
  名称：

  硝酰基氮氧自由基配位铜(II)配合物的合成、晶体结构和磁性

  摘要：

  为硝酰基氮氧自由基 NIT-Ph-4-Br 和 Cu II (hfac) 2 (H 2 O) 2 构建单元构建的配位化合物 (NIT-Ph-4-Br = 2-(4-bromo-phenyl)-4 ,4,5,5-四甲基咪唑啉-1-oxyl-3-oxide, hfac = hexafluoroacetylacetonato) 成功合成。单晶 X 射线衍射分析表明配合物 {(NIT-Ph-4-Br) 2 [Cu(hfac) 2 ] 3 } 具有中心对称的五自旋结构，由两个桥接的三个 Cu(II) 离子组成。氮氧化物配体，它们由两种类型的铜原子组成，一种具有严重的 Jahn-Teller 扭曲 (4 + 2) 八面体配位 (Cu oct ) 和 hfac 的转位，另一种具有方锥五配位 (Cu pyr ) 底部有三个 hfac 氧原子和 N-O 氧原子，顶部有一个 hfac 氧原子。铜离子的不同几何

  DOI：

  10.1007/s11243-019-00370-y

文献信息

• Novel 2-substituted nitronyl nitroxides as free radical scavengers: Synthesis, biological evaluation and structure–activity relationship
  作者：Yihui Wu、Lanrong Bi、Wei Bi、Zeng Li、Ming Zhao、Chao Wang、Jingfang Ju、Shiqi Peng

  DOI：10.1016/j.bmc.2006.04.016

  日期：2006.8

  nitroxide derivatives 4a-h. A lead compound 4f was discovered based on Ach-induced vascorelaxation assay. Further chemical modification based on this scaffold provided a new series of 2-substituted phenylnitronyl nitroxide derivatives 6a-s. The newly synthesized compounds 6a-s possess improved radical scavenger's activity based on PC12 cell survival assay. Compounds 6g,n,o, and s are some of the most

  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
• Synthesis, Crystal Structures, and Magnetic Properties of a Cobalt Complex With Nitronyl Nitroxide Radical
  作者：Chen-Xi Zhang、Hai-Wen Chen、Wen-Min Wang、Yu-Ying Zhang

  DOI：10.1080/15533174.2011.613885

  日期：2012.4.1

  A cobalt complex with nitronyl nitroxide, Co(hfac)2(NITPh-p-Br)2 (hfac = hexafluoroacetylacetonate; NITPh-p-Br = 2-(4′- bromophenyl)-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide), was synthesized. The complex has been investigated by X-ray crystal diffraction and magnetic susceptibility measurements. The crystal structure consists of Radical-Co-Radical tri-spin units, in which the central Co(II) ion

  一种与硝酰基硝基氧Co（hfac）2（NITPh-p-Br）2（hfac =六氟乙酰丙酮; NITPh-p-Br = 2-（4'-溴苯基）-4,4,5,5-四甲基咪唑啉-合成了1-氧化1-3-氧化物）。通过X射线晶体衍射和磁化率测量研究了该配合物。晶体结构由自由基-共-自由基三自旋单元组成，其中中心Co（II）离子由来自两个hfac的四个氧原子和来自NITPh-p-Br的两个氧原子配位。此外，调光结构[Co（hfac）2（NITPh-p-Br）2 ] 2通过来自hfac配体的CH基团的氢原子和来自另一个hafc配体的CF基团的氟原子之间的氢键相互作用形成α。磁化率测量表明，Co（II）离子与自由基的直接键合氮氧化物基团发生反铁磁性相互作用。
• Synthesis, Crystal Structures, and Magnetic Properties of a Cobalt Complex with Nitronyl Nitroxide Radical
  作者：Chen-Xi Zhang、Hai-Wen Chen、Wen-Min Wang、Yu-Ying Zhang

  DOI：10.1080/15533174.2012.680093

  日期：2013.2.1

  A cobalt complex with nitronyl nitroxide, Co(hfac)2(NITPh-p-Br)2 (hfac = hexafluoroacetylacetonate; NITPh-p-Br = 2-(4/-bromophenyl)-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide) was synthesized. The complex has been investigated by X-ray crystal diffraction and magnetic susceptibility measurements. The crystal structure consists of Radical-Co-Radical tri-spin units, in which the central Co(II) ion

  一种与硝酸亚硝酰基钴（hfac）2（NITPh-p-Br）2（hfac =六氟乙酰丙酮; NITPh-p-Br = 2-（4- / -溴苯基）-4,4,5,5-四甲基咪唑啉-合成了（1-氧-3-氧化物）。通过X射线晶体衍射和磁化率测量研究了该配合物。晶体结构由自由基-共-自由基三自旋单元组成，其中中心Co（II）离子由来自两个hfac的四个氧原子和来自NITPh-p-Br的两个氧原子配位。此外，调光结构[Co（hfac）2（NITPh-p-Br）2 ] 2通过来自hfac配体的CH基团的氢原子和来自另一个hafc配体的CF基团的氟原子之间的氢键相互作用形成C 1。磁化率测量表明，Co（II）离子与自由基的直接键合氮氧化物基团发生反铁磁性相互作用。
• 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.
• Crystal structures and magnetic properties of two complexes synthesized from manganese and halogenophenyl-substituted nitronyl nitroxide
  作者：Chen-Xi Zhang、Xiang-Yu Zhao、Na-Na Sun、Yan-Ling Guo、Yuying Zhang

  DOI：10.1016/j.ica.2010.12.019

  日期：2011.2

  One-dimensional complex (1), [Mn(hfac)(2)(NITPhF)](2) and one binuclear radical complex (2), [Mn(hfac)(2)(NITPhBr)](infinity) have been synthesized. Here hfac stands for hexafluoroacetylacetonate, NITPhF for 2-(4'-fluorophenyl)-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide, and NITPhBr for 2-(4'-bromophenyl)-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide). All the two precursors were prepared and characterized by single-crystal X-ray diffraction analysis, IR, and magnetic analysis. In complex 1, the NITPhF radical acts as a bridge ligand linking two Mn(II) ions through the oxygen atom of the N-O group to form cyclic dimer. The dimers further connect two oxygen atoms of uncoordinated nitroxides of two adjacent radicals and yield one-dimensional chain sections. Instead in complex 2, the Mn(II) ions are bridged by the NITPhBr radicals through their N-O groups giving infinite one-dimensional chains. Magnetic susceptibility measurements indicate that both complex 1 and 2 behave ferrimagnetically. The Mn(II) ions interact antiferromagnetically with the direct bonding nitroxide group of the radicals alt(h)ough the structures of two complexes are different. The magnetic behaviors can be satisfactorily explained on the basis of the structural data. (C) 2010 Elsevier B.V. All rights reserved.