| 387334-35-2

• 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: 387334-35-2
• 化学式: C₈H₁₄NO₅
• 分子量: 204.203
• InChiKey: YJIUJFOTHHVDFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  60
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-methyl-2-nitro-5-oxopentanoic acid ethyl ester 在 二乙烯三胺五醋酸 、 氯化铵 、 对甲苯磺酸 、 2,6-蒽二酚 、 还原型辅酶II(NADPH)四钠盐 、 锌 作用下， 以 phosphate buffer 、 乙醇 、 苯 为溶剂， 反应 27.05h， 生成
  参考文献：
  名称：

  5-Carboxy-5-methyl-1-pyrroline N-oxide: a spin trap for the hydroxyl radical

  摘要：

  实时体内原位检测羟基自由基（HO˙）一直是生物学中自由基研究的一大挑战。虽然我们已经能够将这种自由基识别为HO˙的第二标志物，但发现5-羧基-5-甲基-1-吡咯啉N-氧化物2能够特异性地捕捉HO˙而牺牲超氧阴离子（O2˙−），为研究开辟了新的途径。特别是，硝酮2将使我们能够实时检测来自低剂量辐射的动物肿瘤中的HO˙。

  DOI：

  10.1039/b101945g

文献信息

• Synthesis and characterization of 5-hydroxymethyl-5-methyl-pyrroline N-oxide and its derivatives
  作者：Klaus Stolze、Natascha Rohr-Udilova、Anjan Patel、Thomas Rosenau

  DOI：10.1016/j.bmc.2010.11.052

  日期：2011.1

  Synthesis and spin trapping behavior of three novel DMPO derivatives, namely 5-hydroxymethyl-5-methyl-pyrroline N-oxide (HMMPO), 5-(2-furanyl)-oxymethyl-5-methyl-pyrroline N-oxide (FMMPO), and 5-(2-pyranyl)-oxymethyl-5-methyl-pyrroline N-oxide (PMMPO) towards different oxygen- and carbon-centered radicals are described. The stabilizing effect of a series of cyclodextrins on the superoxide adducts was

  三种新型DMPO衍生物（5-羟甲基-5-甲基-吡咯啉N-氧化物（HMMPO），5-（2-呋喃基）-氧甲基-5-甲基-吡咯啉N-氧化物（FMMPO），和5-（2-吡喃基）-氧甲基-5-甲基-吡咯啉N-氧化物（PMMPO）对不同的以氧和碳为中心的基团进行了描述。测试了一系列环糊精对超氧化物加合物的稳定作用。
• Reactivity of Superoxide Radical Anion with Cyclic Nitrones:  Role of Intramolecular H-Bond and Electrostatic Effects
  作者：Frederick A. Villamena、Shijing Xia、John K. Merle、Robert Lauricella、Beatrice Tuccio、Christopher M. Hadad、Jay L. Zweier

  DOI：10.1021/ja0702622

  日期：2007.7.1

  kinetics were employed to predict the reactivity of functionalized spin traps with superoxide radical anion (O2*-). Functional groups provide versatility and can potentially improve spin-trap reactivity, adduct stability, and target specificity. The effect of functional group substitution at the C-5 position of pyrroline N-oxides on spin-trap reactivity toward O2*- was computationally rationalized at

  使用电子顺磁共振 (EPR) 光谱进行生物自由基检测的常用环状硝酮自旋陷阱存在局限性。由于缺乏系统和合理的设计方法，使用 EPR 光谱学设计用于生物自由基检测和识别的新自旋陷阱一直是一项重大挑战。在这项工作中，密度泛函理论 (DFT) 计算和停流动力学被用来预测功能化自旋陷阱与超氧自由基阴离子 (O2*-) 的反应性。官能团提供多功能性，并有可能提高自旋陷阱反应性、加合物稳定性和目标特异性。在 PCM/B3LYP/6-31+G(d,p)//B3LYP/6 计算上合理化了吡咯啉 N-氧化物 C-5 位置的官能团取代对 O2*- 的自旋陷阱反应性的影响-31G(d) 和 PCM/mPW1K/6-31+G(d,p) 理论水平。发现计算出的 O2*- 与模型硝酮反应的自由能和速率常数与使用停流和 EPR 光谱方法通过实验获得的速率常数相关。讨论了对 O2* 亲核性质的新见解 - 添加到硝酮以及 O2*
• Esters of 5-Carboxyl-5-methyl-1-pyrroline <i>N</i>-Oxide:  A Family of Spin Traps for Superoxide
  作者：Pei Tsai、Kazuhiro Ichikawa、Colin Mailer、Sovitj Pou、Howard J. Halpern、Bruce H. Robinson、Robert Nielsen、Gerald M. Rosen

  DOI：10.1021/jo0350413

  日期：2003.10.1

  Apparent rate constants, at acidic pH and neutral pH for the reaction of a family of ester-containing 5-carboxyl-5-methyl-1-pyrroline N-oxides with superoxide (O-2(.-)) were estimated, using ferricytochrome c as a competitive inhibitor. It was of interest to note that the rate constants were similar among the different nitrones and not that significantly different from that found for 5-(diethoxyphosphoryl)-5-dimethyl-1-pyrroline N-oxide. At acidic pH, the rate constant for spin trapping O-2(.-) was 3-fold greater than that at physiological pH. Subsequent experiments determined the half-life of aminoxyls, derived from the reaction of these nitrones with O-2(.-). The EPR spectra were modeled by using a global analysis method. The results clearly demonstrated that EPR spectra of all the aminoxyls were inconsistent with a model that included a single gamma-hydrogen splitting. A better interpretation modeled them as two diastereomers with identical nitrogen splittings and slightly different beta-hydrogen splittings. Detailed line width analyses slightly favored an equal line width-unequal population ratio for the two diastereomers.