4-methyl-4-nitro-[2,2-²H₂]-pentanal | 845623-21-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methyl-4-nitro-[2,2-²H₂]-pentanal
• 英文别名: 2,2-Dideuterio-4-methyl-4-nitropentanal
• CAS: 845623-21-4
• 化学式: C₆H₁₁NO₃
• 分子量: 147.142
• InChiKey: YDVAFDALOGXWTO-SMZGMGDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methyl-4-nitro-[2,2-²H₂]-pentanal 在 溶剂黄146 、 锌 作用下， 以 乙醇 为溶剂， 以21%的产率得到5,5-dimethyl-[3,3-²H₂]-1-pyrroline N-oxide
  参考文献：
  名称：

  Assignment of the EPR Spectrum of 5,5-Dimethyl-1-pyrroline N-Oxide (DMPO) Superoxide Spin Adduct

  摘要：

  [GRAPHICS]Spin trapping consists of using a nitrone or a nitroso compound to "trap" an unstable free radical as a long-lived nitroxide that can be characterized by electron paramagnetic resonance (EPR) spectroscopy. The formation of DMPO-OOH, the spin adduct resulting from trapping superoxide (O-2(.-)) with 5,5-dimethyl-1-pyrroline N-oxide (DMPO), has been exploited to detect the generation of superoxide in a wide variety of biological and chemical systems. The 12-line EPR spectrum of DMPO-OOH has been either reported or mentioned in more than a thousand papers. It has been interpreted as resulting from the following couplings: A(N) similar or equal to 1.42 mT, A(Hbeta) similar or equal to 1.134 mT, and A(Hgamma) (1H) similar or equal to 0.125 mT. However, the DMPO-OOH EPR spectrum has an asymmetry that cannot be reproduced when the spectrum is calculated considering a single species. Recently, it was proposed that the 0.125 mT splitting was misassigned and actually results from the superimposition of two individual EPR spectra associated with different conformers of DMPO-OOH. We have prepared 5,5-dimethyl-[3,3-H-2(2)]-1-pyrroline N-oxide (DMPO-d(2)), and we showed that the EPR spectrum of the corresponding superoxide spin adduct is composed of only six lines, in agreement with the assignment of the 0.125 mT splitting to a gamma-splitting from a hydrogen atom bonded to carbon 3 of DMPO. This result was supported by DFT calculations including water solvation, and the asymmetry of the DMPO-OOH EPR spectrum was nicely reproduced assuming a chemical exchange between two conformers.

  DOI：

  10.1021/jo048518z
• 作为产物：
  描述：

  4-甲基-4-硝基戊醛 在 吡啶 、 重水 作用下， 反应 30.0h， 以23%的产率得到4-methyl-4-nitro-[2,2-²H₂]-pentanal
  参考文献：
  名称：

  Assignment of the EPR Spectrum of 5,5-Dimethyl-1-pyrroline N-Oxide (DMPO) Superoxide Spin Adduct

  摘要：

  [GRAPHICS]Spin trapping consists of using a nitrone or a nitroso compound to "trap" an unstable free radical as a long-lived nitroxide that can be characterized by electron paramagnetic resonance (EPR) spectroscopy. The formation of DMPO-OOH, the spin adduct resulting from trapping superoxide (O-2(.-)) with 5,5-dimethyl-1-pyrroline N-oxide (DMPO), has been exploited to detect the generation of superoxide in a wide variety of biological and chemical systems. The 12-line EPR spectrum of DMPO-OOH has been either reported or mentioned in more than a thousand papers. It has been interpreted as resulting from the following couplings: A(N) similar or equal to 1.42 mT, A(Hbeta) similar or equal to 1.134 mT, and A(Hgamma) (1H) similar or equal to 0.125 mT. However, the DMPO-OOH EPR spectrum has an asymmetry that cannot be reproduced when the spectrum is calculated considering a single species. Recently, it was proposed that the 0.125 mT splitting was misassigned and actually results from the superimposition of two individual EPR spectra associated with different conformers of DMPO-OOH. We have prepared 5,5-dimethyl-[3,3-H-2(2)]-1-pyrroline N-oxide (DMPO-d(2)), and we showed that the EPR spectrum of the corresponding superoxide spin adduct is composed of only six lines, in agreement with the assignment of the 0.125 mT splitting to a gamma-splitting from a hydrogen atom bonded to carbon 3 of DMPO. This result was supported by DFT calculations including water solvation, and the asymmetry of the DMPO-OOH EPR spectrum was nicely reproduced assuming a chemical exchange between two conformers.

  DOI：

  10.1021/jo048518z

文献信息

• Assignment of the EPR Spectrum of 5,5-Dimethyl-1-pyrroline <i>N</i>-Oxide (DMPO) Superoxide Spin Adduct
  作者：Jean-Louis Clément、Nicolas Ferré、Didier Siri、Hakim Karoui、Antal Rockenbauer、Paul Tordo

  DOI：10.1021/jo048518z

  日期：2005.2.1

  [GRAPHICS]Spin trapping consists of using a nitrone or a nitroso compound to "trap" an unstable free radical as a long-lived nitroxide that can be characterized by electron paramagnetic resonance (EPR) spectroscopy. The formation of DMPO-OOH, the spin adduct resulting from trapping superoxide (O-2(.-)) with 5,5-dimethyl-1-pyrroline N-oxide (DMPO), has been exploited to detect the generation of superoxide in a wide variety of biological and chemical systems. The 12-line EPR spectrum of DMPO-OOH has been either reported or mentioned in more than a thousand papers. It has been interpreted as resulting from the following couplings: A(N) similar or equal to 1.42 mT, A(Hbeta) similar or equal to 1.134 mT, and A(Hgamma) (1H) similar or equal to 0.125 mT. However, the DMPO-OOH EPR spectrum has an asymmetry that cannot be reproduced when the spectrum is calculated considering a single species. Recently, it was proposed that the 0.125 mT splitting was misassigned and actually results from the superimposition of two individual EPR spectra associated with different conformers of DMPO-OOH. We have prepared 5,5-dimethyl-[3,3-H-2(2)]-1-pyrroline N-oxide (DMPO-d(2)), and we showed that the EPR spectrum of the corresponding superoxide spin adduct is composed of only six lines, in agreement with the assignment of the 0.125 mT splitting to a gamma-splitting from a hydrogen atom bonded to carbon 3 of DMPO. This result was supported by DFT calculations including water solvation, and the asymmetry of the DMPO-OOH EPR spectrum was nicely reproduced assuming a chemical exchange between two conformers.