2-methyl-2-nitro-5-oxopentanoic acid ethyl ester | 98426-90-5

• 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: 2-methyl-2-nitro-5-oxopentanoic acid ethyl ester
• 英文别名: 2-methyl-2-nitro-5-oxo-valeric acid ethyl ester；2-Methyl-2-nitro-5-oxo-valeriansaeure-aethylester；Ethyl 2-methyl-2-nitro-5-oxopentanoate；ethyl 2-methyl-2-nitro-5-oxopentanoate
• CAS: 98426-90-5
• 化学式: C₈H₁₃NO₅
• 分子量: 203.195
• InChiKey: CMNQHURLJCIQTO-UHFFFAOYSA-N

物化性质

• 沸点：
  107 °C(Press: 0.5 Torr)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2-溴丙酸乙酯 在 间苯三酚 、 三乙胺 、 sodium nitrite 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 2-methyl-2-nitro-5-oxopentanoic acid ethyl ester
  参考文献：
  名称：

  Inclusion complexes of EMPO derivatives with 2,6-di-O-methyl-β-cyclodextrin: synthesis, NMR and EPR investigations for enhanced superoxide detection

  摘要：

  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。

  DOI：

  10.1039/b606062e

文献信息

• Highly Efficient Ytterbium Triflate Catalyzed Michael Additions of α-Nitroesters in Water
  作者：Erik Keller、Ben Feringa

  DOI：10.1055/s-1997-5761

  日期：1997.7

  Michael additions of alpha-nitroesters with enones and alpha,beta-unsaturated aldehydes result in quantitative conversions to the corresponding 1,4-adducts by performing the reactions in water in the presence of ytterbium triflate as water-tolerant Lewis acid.

  通过在三氟甲磺酸镱作为耐水路易斯酸的存在下在水中进行反应，α-硝基酯与烯酮和 α，β-不饱和醛的迈克尔加成导致定量转化为相应的 1,4-加合物。
• Synthetic Studies on <i>N</i>-Alkoxyamines: A Mild and Broadly Applicable Route Starting from Nitroxide Radicals and Aldehydes
  作者：Kai-Uwe Schoening、Walter Fischer、Stefan Hauck、Alexander Dichtl、Michael Kuepfert

  DOI：10.1021/jo802403j

  日期：2009.2.20

  A broad variety of 2,2,6,6-tetramethylpiperidine-based N-alkoxyamines were prepared in a newly found reaction. By means of a copper-catalyzed fragmentation reaction of aldehyde peroxides in the presence of TEMPO or TEMPO derivatives, N-alkoxyamines were obtained in moderate to good yields.
• 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.
• Spin trapping experiments with different carbamoyl-substituted EMPO derivatives
  作者：Klaus Stolze、Natascha Rohr-Udilova、Andreas Hofinger、Thomas Rosenau

  DOI：10.1016/j.bmc.2008.07.057

  日期：2008.9

  The spin trapping behavior of five carbamoyl-substituted EMPO derivatives, 5-aminocarbonyl-5-methylpyrroline N-oxide (CAMPO (AMPO)), 5-aminocarbonyl-5-ethyl-pyrroline N-oxide (CAEPO), 5-aminocarbonyl-5-propyl-pyrroline N-oxide (CAPPO), 5-aminocarbonyl-5-n-butyl-pyrroline N-oxide (CABPO), and 5-aminocarbonyl-5-n-pentyl-pyrroline N-oxide (CAPtPO), toward different oxygen-and carbon-centered radicals is described, the stabilities of the superoxide adducts ranging from about 8 to 17 min. (C) 2008 Elsevier Ltd. All rights reserved.
• Bonnett et al., Journal of the Chemical Society, 1959, p. 2087,2092
  作者：Bonnett et al.

  DOI：——

  日期：——