2-phenyl-5,5-dimethyl-1-pyrroline N-oxide (nitronyl-13C) | 156351-49-4

• 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-phenyl-5,5-dimethyl-1-pyrroline N-oxide (nitronyl-13C)
• 英文别名: 2-Phenyl-5,5-dimethyl-1-pyrroline-N-oxide-nitronyl-13C；2,2-dimethyl-1-oxido-5-phenyl-(513C)3,4-dihydropyrrol-1-ium
• CAS: 156351-49-4
• 化学式: C₁₂H₁₅NO
• 分子量: 190.246
• InChiKey: WNWSBJPGOXENQE-KHWBWMQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  28.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  phenylcarbonyloxy radical 、 2-phenyl-5,5-dimethyl-1-pyrroline N-oxide (nitronyl-13C) 以 苯 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of a Novel Nitrone, 2-Phenyl-5,5-dimethyl-1-pyrroline N-Oxide (nitronyl-13C), for Enhanced Radical Addend Recognition and Spin Adduct Persistence

  摘要：

  Synthesis and spin trapping chemistry of the new C-13-labeled cyclic nitrone, 2-phenyl-5,5-dimethyl-1-pyrroline N-oxide (nitronyl-C-13), is described. A total of 15 carbon- and oxygen-centered radical adducts were prepared and their electron paramagnetic resonance (EPR) spectral parameters examined in organic as well as aqueous solutions. All the radical spin adducts derived from the novel nitrone displayed a well-resolved triplet of doublets in the EPR spectra. The alpha-C-13 hyperfine splitting is a good indicator for the chemical structure of the added radical and varies from around 3.2 to 6.2 G. Free radicals are spin trapped at rates that are quite comparable to those observed with C-phenyl-N-tert-butylnitrone (PBN). The main advantage, however, is the enhanced persistence of its radical spin adducts. For this reason the title nitrone holds promise as a biological spin trapping agent because spin adduct decay during metabolism or isolation often governs the success or failure of a given experiment.

  DOI：

  10.1021/ja00088a009
• 作为产物：
  描述：

  1-phenyl-2-propen-1-al-1-13C 在 苄基三甲基氢氧化铵 、 溶剂黄146 、 锌 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 24.0h， 生成 2-phenyl-5,5-dimethyl-1-pyrroline N-oxide (nitronyl-13C)
  参考文献：
  名称：

  Synthesis of a Novel Nitrone, 2-Phenyl-5,5-dimethyl-1-pyrroline N-Oxide (nitronyl-13C), for Enhanced Radical Addend Recognition and Spin Adduct Persistence

  摘要：

  Synthesis and spin trapping chemistry of the new C-13-labeled cyclic nitrone, 2-phenyl-5,5-dimethyl-1-pyrroline N-oxide (nitronyl-C-13), is described. A total of 15 carbon- and oxygen-centered radical adducts were prepared and their electron paramagnetic resonance (EPR) spectral parameters examined in organic as well as aqueous solutions. All the radical spin adducts derived from the novel nitrone displayed a well-resolved triplet of doublets in the EPR spectra. The alpha-C-13 hyperfine splitting is a good indicator for the chemical structure of the added radical and varies from around 3.2 to 6.2 G. Free radicals are spin trapped at rates that are quite comparable to those observed with C-phenyl-N-tert-butylnitrone (PBN). The main advantage, however, is the enhanced persistence of its radical spin adducts. For this reason the title nitrone holds promise as a biological spin trapping agent because spin adduct decay during metabolism or isolation often governs the success or failure of a given experiment.

  DOI：

  10.1021/ja00088a009

文献信息

• New 2-substituted pyrroline-N-oxides: An EPR solvent study of the radical spin adducts
  作者：Edward G. Janzen、Yong-Kang Zhang、D. Lawrence Haire

  DOI：10.1002/mrc.1260321203

  日期：1994.12

  water) were measured and the solvent effect on these parameters was evaluated. It was found that for the various 2‐substituted DMPO‐type spin adducts both the nitrogen and β‐hydrogen EPR hyperfine splittings correlated linearly (r2 ⩾ 0.90) with typical solvent polarity parameters such as ET(30). The correlation between the nitrogen and β‐hydrogen hyperfine splitting constants were even more linear (r2

  制备了 10 个取代的 5,5-二甲基-1-吡咯啉-N-氧化物以及母体氮烯自旋阱（DMPO）：5,5-二甲基-1-吡咯啉-N-氧化物、2,5,5-三甲基-1-吡咯啉-N-氧化物、2-叔丁基-5,5-二甲基-1-吡咯啉-N-氧化物、2-苯基-5,5-二甲基-1-吡咯啉-N-氧化物、2-d5 -苯基-5,5-二甲基-1-吡咯啉-N-氧化物, 2-苯基-5,5-二甲基-1-吡咯啉-N-氧化物-硝酰基-13 C, 2-(4-氟苯基)-5, 5-二甲基-1-吡咯啉-N-氧化物、2-(4-氯苯基)-5,5-二甲基-1-吡咯啉-N-氧化物、2-(4-叔丁基苯基)-5,5-二甲基- 1-吡咯啉-N-氧化物、2-(4-甲基苯基-5,5-二甲基-1-吡咯啉-N-氧化物)和2-(2-甲基苯基)-5,5-二甲基-1-吡咯啉-N-氧化物。获得了这些新型环状硝酮的分析（即 EPR 级）样品，并通过（除其他方法外）1H