5-methoxycarbonyl-5-methyl-1-pyrroline N-oxide | 475672-78-7

• 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
• 英文名称: 5-methoxycarbonyl-5-methyl-1-pyrroline N-oxide
• 英文别名: Methyl 2-methyl-1-oxido-3,4-dihydropyrrol-1-ium-2-carboxylate
• CAS: 475672-78-7
• 化学式: C₇H₁₁NO₃
• 分子量: 157.169
• InChiKey: DYRWHKZXMWAOQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methoxycarbonyl-5-methyl-1-pyrroline N-oxide 在 bovine superoxide dismutase phosphate buffer 、 次黄嘌呤 、 xanthine oxidase 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  超氧化物歧化酶与铁细胞色素C：确定速率常数的自旋俘获超环氧化物的超氧化物。

  摘要：

  鉴于自旋捕集/电子顺磁共振（EPR）光谱已成为识别重要的生物产生的自由基（例如超氧化物（O 2 • -）），体外和体内模型，评估特定自旋捕集器效率的主要技术识别这种自由基至关重要。近来，含酯的硝酮的家族已经制备，这似乎对自旋明显的优点俘获ö 2 • -相比，充分研究的自旋捕获5,5-二甲基-1-吡咯啉Ñ氧化物1和5- （二乙氧基磷酰基）-5-甲基-1-吡咯啉N-氧化物2。选择自旋阱的一个重要决定因素是其与O 2 • -反应的速率常数（k app），几种不同的方法已被用来估计该k app。在本文中，O 2 • -的两种最常用的清除剂，铁细胞色素c和Cu / Zn-SOD被评估为自旋捕获该自由基的竞争性抑制剂。本文提供的数据证明，在确定O 2 • -与自旋阱的反应的k app时，SOD是优选的化合物。使用此模型，k应用为硝酮的反应1，5-叔丁氧羰基-5-甲基-1-吡咯啉Ñ氧化物3，和5-甲氧基

  DOI：

  10.1021/jo0485029
• 作为产物：
  描述：

  4-[1,3]Dioxolan-2-yl-2-methyl-2-nitro-butyric acid methyl ester 在 氯化铵 、 锌 、 盐酸 作用下， 以 乙醇 为溶剂， 生成 5-methoxycarbonyl-5-methyl-1-pyrroline N-oxide
  参考文献：
  名称：

  Esters of 5-Carboxyl-5-methyl-1-pyrroline N-Oxide:  A Family of Spin Traps for Superoxide

  摘要：

  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.

  DOI：

  10.1021/jo0350413

文献信息

• Inclusion complexes of EMPO derivatives with 2,6-di-O-methyl-β-cyclodextrin: synthesis, NMR and EPR investigations for enhanced superoxide detection
  作者：David Bardelang、Antal Rockenbauer、Hakim Karoui、Jean-Pierre Finet、Inga Biskupska、Karol Banaszak、Paul Tordo

  DOI：10.1039/b606062e

  日期：——

  The free radical trapping properties of eight 5-alkoxycarbonyl-5-methyl-1-pyrroline N-oxide (EMPO) type nitrones and those of 5,5-dimethyl-1-pyrroline N-oxide (DMPO) were evaluated for trapping of superoxide anion radicals in the presence of 2,6-di-O-methyl-β-cyclodextrin (DM-β-CD). 1H-NMR titrations were performed to determine both stoichiometries and binding constants for the diamagnetic nitrone–DM-β-CD equilibria. EPR titrations were then performed and analyzed using a two-dimensional EPR simulation program affording 1 : 1 and 1 : 2 stoichiometries for the nitroxide spin adducts with DM-β-CD and the associated binding constants after spin trapping. The nitroxide spin adducts associate more strongly with DM-β-CD than the nitrones. The ability of the nitrones to trap superoxide, the enhancement of the EPR signal intensity and the supramolecular protection by DM-β-CD against sodium L-ascorbate reduction were evaluated.

  评估了八种5-烷氧羰基-5-甲基-1-吡咯啉 N-氧化物（EMPO）型氮酮和5,5-二甲基-1-吡咯啉 N-氧化物（DMPO）在含有2,6-二-O-甲基-β-环糊精（DM-β-CD）存在下捕获超氧阴离子自由基的自由基捕获性质。通过1H-NMR滴定确定顺磁性氮酮-DM-β-CD平衡的化学计量和结合常数。然后进行EPR滴定，并使用二维EPR模拟程序进行分析，得到1:1和1:2的化学计量比以及自旋捕获后的氮氧自由基与DM-β-CD的结合常数。氮氧自由基与DM-β-CD的结合比氮酮更强。评估了氮酮捕获超氧的能力、EPR信号强度的增强以及DM-β-CD对L-抗坏血酸钠还原作用的超分子保护。