2-(4-cyanophenyl)-4,4,5,5-tetramethyl-4,5-dihydro-1-H-imidazole-3-oxide-1-oxyl | 117566-85-5

• 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: 2-(4-cyanophenyl)-4,4,5,5-tetramethyl-4,5-dihydro-1-H-imidazole-3-oxide-1-oxyl
• 英文别名: 2-(4'-cyanophenyl)-4,4,5,5-tetramethyl-2-imidazoline-3-oxide-1-oxyl；2-(4-cyanophenyl)-4,4,5,5-tetramethylimidazoline-3-oxide-1-oxyl；NIT-p-NCC6H4
• CAS: 117566-85-5
• 化学式: C₁₄H₁₆N₃O₂
• 分子量: 258.3
• InChiKey: WECBTBCSISKMOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.03
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  73.0
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(4-cyanophenyl)-4,4,5,5-tetramethyl-4,5-dihydro-1-H-imidazole-3-oxide-1-oxyl 在 nitric oxide 作用下， 以 正己烷 、 氯仿 为溶剂， 生成
  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：

  4,4,5,5-tetramethylimidazolin-1-oxyl-3-oxide 、 4-碘氰基苯 在 四(三苯基膦)钯 、 sodium t-butanolate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以81%的产率得到2-(4-cyanophenyl)-4,4,5,5-tetramethyl-4,5-dihydro-1-H-imidazole-3-oxide-1-oxyl
  参考文献：
  名称：

  Environmentally Benign Strategy for Arylation of Nitronyl Nitroxide Using a Non-Transition Metal Nucleophile

  摘要：

  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.

  DOI：

  10.1021/acs.orglett.9b04655

文献信息

• Heterospin complexes of fluorinated dinuclear CuII and MnII triketonates with nitroxides
  作者：V. I. Ovcharenko、S. V. Fokin、G. V. Romanenko、A. S. Bogomyakov、D. S. Yachevskii、D. L. Chizhov、V. N. Charushin、O. N. Chupakhin

  DOI：10.1007/s11172-010-0219-8

  日期：2010.6

  Dinuclear heterospin complexes of CuII and MnII 1,1,1,7,7,7-hexafluoroheptane-2,4,6-trionates ([Cu2L2] and [Mn2L2], respectively) with nitronyl nitroxides 2-R-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazole-3-oxide 1-oxyls (NIT-R, R = H, Me, Et, m-C5H4N, m-NCC6H4, p-NCC6H4, PzMe) and the diradical NIT-Pz-(CH2)4-Pz-NIT (Pz is 1,4-pyrazolylene) were synthesized and structurally characterized. In the complexes under study, the CuII atom tends to have the square-pyramidal coordination environment, and the MnII atom is in an octahedral environment. The magnetochemical investigation of the compounds in the temperature range of 2–300 K showed that the antiferromagnetic exchange coupling dominates in the [Cu2L2] molecules, whereas this coupling in [Mn2L2] is manifested in the experimental plot μeff(T) at T < 100 K. The magnetic properties of the heterospin complexes of [Cu2L2] with NIT-R are also determined by the intramatrix antiferromagnetic exchange coupling. For the complexes of [Mn2L2] with NIT-R, the coordination mode of the nitroxide plays a decisive role.

  CuII 和 MnII 1,1,1,7,7,7-六氟庚烷-2,4,6-三元酸酯（分别为 [Cu2L2] 和 [Mn2L2]）与硝基硝基氧 2-R-4,4 的双核异旋配合物， 5,5-四甲基-4,5-二氢-1H-咪唑-3-氧化物1-氧基（NIT-R，R = H，Me，Et，m-C5H4N，m-NCC6H4，p-NCC6H4，PzMe）和合成了双自由基NIT-Pz-(CH2)4-Pz-NIT（Pz是1,4-亚吡唑基）并进行了结构表征。在所研究的配合物中，CuII原子倾向于具有方锥体配位环境，并且MnII原子处于八面体环境中。在 2–300 K 温度范围内对化合物的磁化学研究表明，反铁磁交换耦合在 [Cu2L2] 分子中占主导地位，而 [Mn2L2] 中的这种耦合在 T < 100 时的实验曲线 μeff(T) 中得到体现K. [Cu2L2] 与 NIT-R 的异旋复合物的磁性也由基质内反铁磁交换耦合决定。对于[Mn2L2]与NIT-R的配合物，硝基氧的配位方式起着决定性的作用。
• Molecular magnets based on M(hfac) 2 and spin-labeled nitrile
  作者：O.V. Koreneva、G.V. Romanenko、Yu.G. Shvedenkov、V.N. Ikorskii、V.I. Ovcharenko

  DOI：10.1016/s0277-5387(03)00229-8

  日期：2003.7

  Syntheses, structure, and magnetic properties of [Cu(hfac)(2)](2)L, Cu(hfac)(2)L, and [M(hfac)(2)](3)L2, where M = Mn, Co, are described. Special attention is paid to the unusual structure of the two polymorphs of Cu(hfac)2L and to the magnetic properties of [M(hfac)(2)](3)L-2 . 0.5C(7)H(16), for which a magnetic phase transition to the ferromagnetic state has been found. (C) 2003 Elsevier Science Ltd. All rights reserved.