| 77331-80-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• CAS: 77331-80-7
• 化学式: C₇H₁₁NO₃
• 分子量: 157.169
• InChiKey: AOQQNWBAIYHQEB-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.68
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  63.27
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  5,5-二甲基-1-吡咯啉-N-氧化物 、 sodium formate 在 phosphate buffer 、 双氧水 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  Castelhano, Arlindo L.; Perkins, M. John; Griller, David, Canadian Journal of Chemistry, 1983, vol. 61, p. 298 - 299

  摘要：

  DOI：

文献信息

• Kinetics of Spin Trapping Superoxide, Hydroxyl, and Aliphatic Radicals by Cyclic Nitrones
  作者：Sara Goldstein、Gerald M. Rosen、Angelo Russo、Amram Samuni

  DOI：10.1021/jp048441i

  日期：2004.8.1

  Spin trapping coupled with electron paramagnetic resonance (EPR) spectroscopy has surfaced as one of the most specific and reliable methods for identifying free radicals in biological systems. Despite extensive studies focused on the kinetics of radical trapping by cyclic nitrones, the mechanism has not been fully elucidated. Moreover, major controversies still persist even regarding the efficiency

  自旋捕获与电子顺磁共振 (EPR) 光谱相结合已成为识别生物系统中自由基的最具体和最可靠的方法之一。尽管广泛的研究集中在环状硝酮的自由基捕获动力学，但其机制尚未完全阐明。此外，即使关于捕获反应的效率和速率常数，主要争议仍然存在。本研究使用脉冲辐解来研究 5,5-dimethyl-1-pyrroline N-oxide 1 (DMPO) 和含酯衍生物 5-tert-butoxycarbonyl-5-methyl-1-pyrroline N- 的反应。氧化物 4，与 •OH、O2•-、CO2•-、•C(OH)(CH3)2、•CH2OH 和• 。结果表明，激进的诱捕比以前意识到的要复杂得多。与 EPR 相结合的辐射化学实验表明，大约 30% 的 •OH 在 2 位添加到硝酮 1 和 4，产生相应的持久性氨氧基。剩余的 •OH 自由基形成瞬态中间体...
• Spin trapping with 5,5-dimethylpyrroline-N-oxide in aqueous solution.
  作者：YUTAKA KIRINO、TAKAAKI OHKUMA、TAKAO KWAN

  DOI：10.1248/cpb.29.29

  日期：——

  Spin trapping with 5, 5-dimethylpyrroline-N-oxide (DMPO) of various radicals was carried out in aqueous solutions and the ESR parameters for the spin adduct radicals were determined. Comparison of hyperfine coupling constants obtained in aqueous solutions and in benzene revealed that considerable solvent effect exists. For the radical obtained by the addition of a hydroxyl radical to DMPO, the hyperfine coupling constant was found to depend on the basicity of the solution. This phenomenon was analyzed in terms of the acid dissociation equilibrium of the hydroxyl proton of the adduct radical, and the pK value was determined to be 12.96.

  采用5,5-二甲基-1-吡咯啉氮氧化物（DMPO）进行自旋捕获，在水中制备了多种自由基，并测定了自旋加合物自由基的电子自旋共振（ESR）参数。比较在水中和苯中获得的超精细耦合常数，揭示了显著的溶剂效应。对于通过羟基自由基加合到DMPO上得到的自由基，其超精细耦合常数被发现依赖于溶液的碱度。这一现象基于加合物自由基中羟基质子的酸解离平衡进行了分析，并确定其pK值为12.96。
• Chemical effects of ultrasound on aqueous solutions. Formation of hydroxyl radicals and hydrogen atoms
  作者：Keisuke Makino、Magdi M. Mossoba、Peter Riesz

  DOI：10.1021/j100231a020

  日期：1983.4
• Formation of Hydroxyl Spin Adducts via Nucleophilic Addition--Oxidation to 5,5-Dimethyl-1-pyrroline N-Oxide (DMPO).
  作者：Lennart Eberson、Balin Balinov、Gunnar Hagelin、Harald Dugstad、Terje Thomassen、Benita H. Forngren、Tobias Forngren、Per Hartvig、Karin Markides、Ulrika Yngve、Mattias Ögren

  DOI：10.3891/acta.chem.scand.53-0584

  日期：——

  The formation of the hydroxyl radical spin adduct of DMPO, HO DMPO, has been studied by EPR spectroscopy under conditions where the hydroxyl radical cannot be involved. One method was the photosensitized oxidation of DMPO to its radical cation. followed by reaction of the latter with water. This procedure worked well with sensitizers Sens (quinones) having triplet states with E degrees((T)Sens*/Sens(.-))>1.7 1.8V(SCE).The second method employed nucleophilic addition of water to DMPO, followed by reaction of the intermediate hydroxylamine by mild thermal oxidants (quinones, Fe-III) with redox potentials in the range -0.5 to 0.5 V. The observation of IIO DMPO. in this reaction was dependent on the acidity of the medium, since the relatively slow rate of formation of IIO DMPO. must be compensated for by a correspondingly longer half-life, tau(1/2). This is decreased by increasing acidity, and a lower limit of tau(1/2) was estimated at 1 1.5 min. The use of buffered neutral or slightly alkaline solutions or ethyl acetate as solvent satisfied this requirement.The nucleophilic mechanism, sometimes denoted the Forrester Hepburn mechanism, was also applicable to the reaction between normal alcohols and DMPO, giving rise to RO-DMPO.. A sterically demanding alcohol (t-BuOH) or electrophilic alcohols ( 2,2,2-trifluoroethanol or 1,1,1,3,3,3-hexafluoropropan-2-ol) required photochemical activation for reaction to occur.
• Singlet Oxygen–mediated Hydroxyl Radical Production in the Presence of Phenols: Whether DMPO–·OH Formation Really Indicates Production of ·OH?¶
  作者：Jun-ichi Ueda、Keizo Takeshita、Shigenobu Matsumoto、Kinya Yazaki、Mitsuru Kawaguchi、Toshihiko Ozawa

  DOI：10.1562/0031-8655(2003)077<0165:somhrp>2.0.co;2

  日期：——

  The reaction of singlet oxygen (O-1(2)) generated by ultraviolet-A (UVA)-visible light (lambda > 330 nm) irradiation of air-saturated solutions of hematoporphyrin with phenolic compounds in the presence of a spin trap, 5,5-dimethyl-1-pyrroline-N-oxide (DMPO), gave an electron spin resonance (ESR) spectrum characteristic of the DMPO-hydroxyl radical spin adduct (DMPO-(OH)-O-.). In contrast, the ESR signal of 5,5-dimethyl-2-pyrrolidone-N-oxyl, an oxidative product of DMPO, was observed in the absence of phenolic compounds. The ESR signal of DMPO-(OH)-O-. decreased in the presence of either a (OH)-O-. scavenger or a quencher of O-1(2) and under anaerobic conditions, whereas it increased depending on the concentration of DMPO. These results indicate both O-1(2) and DMPO-mediated formation of free (OH)-O-. during the reaction. When DMPO was replaced with 5-(diethoxyphosphoryl)-5-methyl-1-pyrroline-N-oxide (DEPMPO), no DEPMPO adduct of oxygen radical species was obtained. This suggests that 102, as an oxidizing agent, reacts little with DEPMPO, in which a strong electron-withdrawing phosphoryl group increases the oxidation potential of DEPMPO compared with DMPO. A linear correlation between the amounts of DMPO-(OH)-O-. generated and the oxidation potentials of phenolic compounds was observed, suggesting that the electron-donating properties of phenolic compounds contribute to the appearance of (OH)-O-.. These observations indicate that O-1(2) reacts first with DMPO, and the resulting DMPO-O-1(2) intermediate is immediately decomposed/reduced to give (OH)-O-.. Phenolic compounds would participate in this reaction as electron donors but would not contribute to the direct conversion of O-1(2) to (OH)-O-.. Furthermore, DEPMPO did not cause the spin-trapping agent-mediated generation of (OH)-O-. like DMPO did.