1-phenyl-6-oxyl-5,5,7,7-tetramethyltetrahydroimidazo[1,5-b][1,2,4]oxadiazol-2-one | 103741-13-5

• 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: 1-phenyl-6-oxyl-5,5,7,7-tetramethyltetrahydroimidazo[1,5-b][1,2,4]oxadiazol-2-one
• CAS: 103741-13-5
• 化学式: C₁₄H₁₈N₃O₃
• 分子量: 276.315
• InChiKey: QEOWOYANGVRAOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-phenyl-6-oxyl-5,5,7,7-tetramethyltetrahydroimidazo[1,5-b][1,2,4]oxadiazol-2-one 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以90%的产率得到4-phenyl-amino-2,2,5,5-tetramethyl-3-imidazoline-1-oxyl
  参考文献：
  名称：

  3-咪唑啉氮氧化物杂环am衍生物的合成及某些性质

  摘要：

  2,2,5,5-四甲基-3-咪唑啉-3-氧化物-1-氧基与异氰酸酯的相互作用导致恶二唑烷环加成物平稳转化为am-4-R-氨基-2,2,5,5 -四甲基-3-咪唑啉-1-氧基用亲核试剂处理时。该反应被用于合成一些含有各种官能团的顺磁性which，这些顺磁性am可用作具有pH敏感的ESR光谱的自旋标记。讨论了恶二唑烷转化为transformation的机理以及合成的auto的互变异构平衡。

  DOI：

  10.1016/s0040-4020(01)81558-1
• 作为产物：
  描述：

  2,2,5,5-tetramethyl-3-imidazoline-3-oxide-1-oxyl 、 异氰酸苯酯 以65%的产率得到1-phenyl-6-oxyl-5,5,7,7-tetramethyltetrahydroimidazo[1,5-b][1,2,4]oxadiazol-2-one
  参考文献：
  名称：

  A stable nitroxide - 2,2,5,5-tetramethyl-3-imidazoline-3-oxide-1-oxyl - a reagent for spin labeling via 1,3-dipolar cycloaddition

  摘要：

  DOI：

  10.1016/s0040-4039(00)94955-4

文献信息

• Synthesis and some properties of heterocyclic amidine derivatives of 3-imidazoline nitroxides
  作者：Tatyana A. Berezina、Vladimir A. Reznikov、Leonid B. Volodarsky

  DOI：10.1016/s0040-4020(01)81558-1

  日期：1993.1

  smoothly transformed into amidines - 4-R-amino-2,2,5,5-tetramethyl-3-imidazoline-1-oxyles when treated with nucleophilic reagents. This reaction was applied to the synthesis of some paramagnetic amidines containing various functional groups which may be used as spin labels having a pH-sensitive ESR spectrum. The mechanism of transformation of oxadiazolidines into amidines and the tautomeric equilibrium

  2,2,5,5-四甲基-3-咪唑啉-3-氧化物-1-氧基与异氰酸酯的相互作用导致恶二唑烷环加成物平稳转化为am-4-R-氨基-2,2,5,5 -四甲基-3-咪唑啉-1-氧基用亲核试剂处理时。该反应被用于合成一些含有各种官能团的顺磁性which，这些顺磁性am可用作具有pH敏感的ESR光谱的自旋标记。讨论了恶二唑烷转化为transformation的机理以及合成的auto的互变异构平衡。
• Studies toward the Synthesis of 4-(2-R-ethyl)amino-2,2,5,5-tetramethyl-3-imidazoline 1-Oxyls. Nucleophilic Substitution of Bromide in the <i>N</i>-Alkyl Chain of the 1,2,4-Oxadiazol-2-one Precursor
  作者：Julya F. Polienko、Thomas Schanding、Yury V. Gatilov、Igor A. Grigor'ev、Maxim A. Voinov

  DOI：10.1021/jo701803a

  日期：2008.1.1

  [GRAPHICS]A synthetic approach to access the new nitroxides of the amidine type exhibiting pH-dependent EPR spectra through substitution of a halide in the exo-N-halogenoalkyl chain of 1-(2-bromoethyl)-6-oxyl-5,5,7,7-tetramethyltetrahydroimidazo[1,5-b][1,2,4]oxadiazol-2-one is reported. In this approach, an oxycarbonyl moiety of the oxadiazolone heterocycle plays the role of a "protecting group" for the amidine functionality. A nucleophilic cleavage of the oxadiazolone heterocycle under mild nonbasic conditions, applicable to substrates bearing substituents vulnerable to attack by strong basic nucleophiles, is elaborated. The approach allows for the new amidine nitroxides bearing various functional groups (e.g., such as CN, N-3, NH2, COOEt) to be synthesized. A series of nitroxides obtained through the Staudinger/intermolecular aza-Wittig reaction of the azido derivative is also described. The nitroxides synthesized here were found to have pfl-dependent two-component EPR spectra indicative of a slow, on the EPR time scale, R-center dot reversible arrow (RH+)-H-center dot chemical exchange, and pK(a) values ranging from 2.8 to 12.5 units. The guanidine derivatives synthesized in this work show the highest pK(a) values (pK(a) = 10.2 and 12.5, respectively) ever reported for the nitroxide pH-probes of a "basic type".
• A stable nitroxide - 2,2,5,5-tetramethyl-3-imidazoline-3-oxide-1-oxyl - a reagent for spin labeling via 1,3-dipolar cycloaddition
  作者：L.B. Volodarsky、V.V. Martin、T.F. Leluch

  DOI：10.1016/s0040-4039(00)94955-4

  日期：1985.1