31P-labeled pyrroline N-oxides:: Synthesis of 5-diethylphosphono-5-methyl-1-pyrroline N-oxide (DEPMPO) by oxidation of diethyl (2-methylpyrrolidin-2-yl)phosphonate

被引：0

作者：

Barbati, S

Clément, JL

Fréjaville, C

Bouteiller, JC

Tordo, P

Michel, JC

Yadan, JC

机构：

[1] Univ Aix Marseille 1, Ctr St Jerome, Lab SREP, CNRS,UMR Chim Biol & Radicaux Libres 6517, F-13397 Marseille 20, France

[2] Oxis Int SA, Res Ctr, F-94385 Bonneuil Sur Marne, France

来源：

SYNTHESIS-STUTTGART | 1999年 / 12期

关键词：

aminophosphorylation; secondary amines; oxidations; nitrones; heterocycles; spin label; phosphorus; additions;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of DEPMPO from diethyl (2-methylpyrrolidin-2-yl)phosphonate (3), prepared by the addition of diethyl phosphite to 2-methylpyrroline, was carried out using different oxidation reagents: H2O2, m-CPBA, Oxone, 2-phenylsulfonyl-3-phenyloxaziridine (PSPO), dimethyldioxirane (DMD) and N-methylmorpholine N-oxide with catalytic amounts of tetrapropylammonium perruthenate (NMO/TPAP). The highest yield of DEPMPO (>80%) was obtained using two equivalents of PSPO or DMD. Different compounds involved in the oxidation of 3 have been isolated and characterized.

引用

页码：2036 / 2040

页数：5

共 44 条

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Chalier, F
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JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2002, (12): : 2110 - 2117
[3] Characterization of the high-resolution ESR spectra of superoxide radical adducts of 5-(diethoxyphosphoryl)-5-methyl-1-pyrroline N-oxide (DEPMPO) and 5,5-dimethyl-1-pyrroline N-oxide (DMPO).: Analysis of conformational exchange
Dikalov, S
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FREE RADICAL RESEARCH, 2005, 39 (08) : 825 - 836
[4] Characterization of the high resolution ESR spectra of the methoxyl radical adducts of 5-(diethoxyphosphoryl)-5-methyl-1-pyrroline N-oxide (DEPMPO)
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FREE RADICAL RESEARCH, 2003, 37 (07) : 705 - 712
[5] ELECTRON-PARAMAGNETIC-RESONANCE (EPR) STUDY OF THE DECOMPOSITION OF PEROXYNITROUS ACID USING 5-DIETHOXYPHOSPHORYL-5-METHYL-1-PYRROLINE N-OXIDE (DEPMPO)
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FASEB JOURNAL, 1995, 9 (03): : A31 - A31
[6] New perspectives on the cardioprotective phosphonate effect of the spin trap 5-(diethoxyphosphoryl)-5-methyl-1-pyrroline N-oxide:: An hemodynamic and 31P NMR study in rat hearts
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FREE RADICAL BIOLOGY AND MEDICINE, 1999, 27 (1-2) : 34 - 41
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Kamibayashi, Masato
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Kameda, Hiroaki
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Ozawa, Toshihiko
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FREE RADICAL RESEARCH, 2006, 40 (11) : 1166 - 1172
[8] Synthesis of 5,5-dimethyl-1-pyrroline-N-oxide-2-14C
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JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2000, 43 (11): : 1107 - 1111
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Journal of Labelled Compounds and Radiopharmaceuticals, 2000, 43 (11) : 1107 - 1111
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Shioji, K
Tsukimoto, S
Tanaka, H
Okuma, K
CHEMISTRY LETTERS, 2003, 32 (07) : 604 - 605

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