4567-18-4

Usage

InChI:InChI=1/C7H13NO/c1-6-4-5-7(2,3)8(6)9/h4-5H2,1-3H3

Upstream product

• 3317-61-1 5,5-Dimethyl-1-pyrroline N-oxide 
• 917-64-6 methyl magnesium iodide 
• 4604-49-3 5-methyl-5-nitrohexan-2-one 
• 67-56-1 methanol 
• 7664-41-7 ammonia 
• 7758-99-8 copper(II) sulfate 
• 100962-45-6 (RS,RS)-2,5,5,2',5',5'-hexamethyl-octahydro-[2,2']bipyrrolyl-1,1'-diol 
• 106522-53-6 2,2,4a,6,6,8a-hexamethyl-(4ar,8at)-octahydro-[1,5]naphthyridine-1,5-diol 
• 100962-45-6 (R,S)-2,5,5,2',5',5'-hexamethyl-octahydro-[2,2']bipyrrolyl-1,1'-diol 

Downstream Products

• 40936-05-8 2,5,5-trimethylpyrrolidine-1-oxyl 
• 57620-51-6 2,2,5-Trimethyl-1-hydroxylpyrrolidine 
• 176236-99-0 5,8,8-trimethyl-3-phenyl-2-oxa-1-azabicyclo<3,3>oct-3-ene 
• 234445-91-1 2,5,5-Trimethyl-2-(3-oxo-3-phenylprop-1-yn-1-yl)pyrrolidin-1-yloxyl radical 
• 355019-18-0 3a,6,6-trimethyl-2-phenyl-3a,4,5,6-tetrahydropyrrolo[1,2-b]isoxazol-3-carbaldehyde 
• 79111-14-1 Sn((CH₃)3C₆H₂)3(CH₃)2C(CH₂)2C(CH₃)NO 
• 124189-85-1 2-(4-fluorophenyl)-2,5,5-trimethylpyrrolidin-1-oxyl 
• 90900-33-7 methyl 3a,4,5,6-tetrahydro-3a,6,6-trimethyl-2-phenyl-pyrrolo<1,2-b>isoxazole-3-carboxylate 
• 62539-49-5 2,5,5-Trimethyl-2-phenylpyrrolidin-1-yloxyl radical 
• 90900-50-8 hexahydro-3a,6,6-trimethyl-3-phenylpyrrolo<1,2b>-1,2,4-oxadiazol-2(3H)-one 
• 122546-94-5 3-benzoyloxy-2,5,5-trimethyl-1-pyrroline 
• 90900-34-8 3a,4,5,6-tetrahydro-3a,6,6-trimethyl-2-phenylpyrrolo<1,2-b>isoxazole-3-carbonitrile 
• 138747-68-9 2,2'-bis(5,5-dimethyl-1-pyrroline 1-oxide) 
• 20447-61-4 3,3-dimethyl-7-p-tolyl-8-thia-2,7-diaza-bicyclo[4.2.0]oct-1⁽⁶⁾-ene 8-oxide 

Relevant academic research and scientific papers

Synthesis and Magnetic Properties of (Pyrrolidin-1-oxyl)–(Nitronyl Nitroxide)/(Iminonitroxide)-Dyads

Unlike extensively studied diradicals linked by π-conjugated systems, only a few studies have investigated weakly coupled diradicals linked by an sp3 carbon atom. Herein, we prepared pyrrolidin-1-oxyl–(nitronyl nitroxide)-dyad 5 and pyrrolidin-1-oxyl–iminonitroxide-dyad 6. From the observed temperature dependence of the magnetic susceptibility, 5 and 6 were determined to be in singlet ground states with 2Jintra/kB=?35.2 K and ?13.6 K, respectively. From these results and theoretical calculations of related diradicals, the spin-polarization model counting the small spin density of the sp3 carbon atom could be used as a spin-prediction model.

Synthesis and structure of 2,2′-Bis(2,2,5-trimethyl-pyrrolidinyl)methane

Reaction of 2,5,5-trimethyl-Δ1-pyrrolidine-N-oxide with methyl lithium yields 2,2′-bis(1-hydroxy-2,2,5-trimethyl-pyrrolidinyl)methane which is reduced by Raney nickel/hydrogen to the corresponding amine. Both molecules are present in the meso-configuration in the solid state. While the hydroxylamine derivative shows intermolecular O-H...O bridge bonding no intermolecular N...H-N interaction is observed for the amine.

Electrochemical and esr spin trap studies of a new iron tetra- catecholamide complex

A new siderophore, N5,N6-thiodipropanoyl-bis[N1,N10-bis(2,3-dihydroxy benzoyl-spermidine)]-Fe (III) complex or H2LFe has been synthesised. The reaction of the reduced form of this complex with dioxygen has been investigated through electrochemical study and revealed the formation of a new species assumed to be H2O2. This species has been confirmed by esr spectroscopy using the diamagnetic compound 5-deutero-2,2,5- trimethylpyrrolidine-1-hydroxyl as spin trap. The resulting persistent radical is 5-deutero-2,2,5-trimethylpyrrolidine-1-yloxy (a(N) = 16.58 G, a(D) = 3.49 G).

2-Substituted nitrones and isomeric hydroxylamines - obtained via aluminium amalgam reduction of nitro nitriles and ketones-a new access to convenient intermediates for nitroso carbonyl compounds preparation

Substituted five-membered cyclic nitrones (pyrroline N-oxides) have been obtained in good to high yields from tertiary γ-nitro ketones and nitriles employing aluminium amalgam as a reducing agent in moist diethyl ether or THF. Attempts to obtain cyclic amino nitrones from α- or β-nitro nitriles failed and only the corresponding hydroxylamines have been isolated. Both nitrones and hydroxylamines have been used for synthesis of tertiary C-nitroso nitriles or ketones.

New 2-Substituted Pyrroline-N-oxides: An EPR Solvent Study of the Radical Spin Adducts

Ten substituted 5,5-dimethyl-1-pyrroline-N-oxides as well as the parent nitrene spin trap (DMPO) were prepared: 5,5-dimethyl-1-pyrroline-N-oxide, 2,5,5-trimethyl-1-pyrroline-N-oxide, 2-tert-butyl-5,5-dimethyl-1-pyrroline-N-oxide, 2-phenyl-5,5-dimethyl-1-pyrroline-N-oxide, 2-d5-phenyl-5,5-dimethyl-1-pyrroline-N-oxide, 2-phenyl-5,5-dimethyl-1-pyrroline-N-oxide-nitronyl-13C, 2-(4-fluorophenyl)-5,5-dimethyl-1-pyrroline-N-oxide, 2-(4-chlorophenyl)-5,5-dimethyl-1-pyrroline-N-oxide, 2-(4-tert-butylphenyl)-5,5-dimethyl-1-pyrroline-N-oxide, 2-(4-methylphenyl)-5,5-dimethyl-1-pyrroline-N-oxide and 2-(2-methylphenyl)-5,5-dimethyl-1-pyrroline-N-oxide.Analytical (i.e.EPR-grade) samples of these novel cyclic nitrones were obtained and characterized by (among other methods) 1H NMR spectroscopy.Reduction of DMPO and these various 2-substituted cyclic nitrones gave the corresponding cyclic N,N-dialkylhydroxylamines, whose structure and conformations were also analyzed by 1H NMR spectroscopy.Air oxidation of these cyclic N,N-dialkylhydroxylamines provided access to the EPR spectra of the hydrogen, methyl, tert-butyl, phenyl, d5-phenyl, nitronyl-13C-phenyl, 4-fluorophenyl, 4-chlorophenyl, 4-tert-butylphenyl, 4-methylphenyl and 2-methylphenyl cyclic aminoxyl (pyrrolidine N-oxyl nitroxide) radical spin adducts of DMPO.The 14N, 13C (where applicable) and 1H hyperfine splitting constants of these aminoxyl adducts in ten solvents of widely different polarities (e.g., hexane to water) were measured and the solvent effect on these parameters was evaluated.It was found that for the various 2-substituted DMPO-type apin adducts both the nitrogen and β-hydrogen EPR hyperfine splittings correlated linearly (r2 >/= 0.90) with typical solvent polarity parameters such as ET(30).The correlation between the nitrogen and β-hydrogen hyperfine splitting constants were even more linear (r2 >/= 0.97). - Keywords: electron paramagnetic resonance NMR 1H, 14N and 13C hyperfine splittings Spin traps Spin adducts Nitrones (1-pyrroline-N-oxides)

Mechanistic studies on the formation of aminoxyl radicals from 5,5-dimethyl-1-pyrroline-N-oxide in Fenton systems. Characterization of key precursors giving rise to background ESR signals

To assign unidentified ESR signals obtained in a Fenton system with a spin trap, 5,5-dimethyl-pyrroline-N-oxide (DMPO), fundamental reactions of DMPO have been thoroughly investigated.When the concentration of Fe(2+) in Fenton systems exceeded 1percent of that of DMPO, background ESR signals totally distinguishable from 2-hydroxy-5,5-dimethyl-1-pyrollidinyloxy (DMPO-OH) appeared, and simultaneously absorbance at 520 nm increased, which was characteristic of hydroxamic acids complexed with Fe(3+).To prove the postulated formation of hydroxamic acid as a key intermediate, DMPO was subjected to Fenton reaction or was treated with Fe(3+) in aqueous solution to produce DMPO-OH (Makino et al.Biochem.Biophy.Res.Commun. 172, 1073 (1990)), and a major product was was isolated by RPLC.Based on (1)H, (13)C NMR and MS measurements, the structure of the major product was assigned to 1-hydroxy-5,5-dimethyl-1-pyrrolid-2-one (HDMPN) having a hydroxamic acid structure.Temperature dependence of NMR spectra and careful analysis of the fragmentation patterns in MS further revealed that HDMPN was present in equilibrium with 2-hydroxy-5,5-dimethyl-1-pyrroline-N-oxide (HDMPO), a tautomer of HDMPN.It has also been shown that the oxidation of DMPO yielding HDMPN and HDMPO occurs via DMPO-OH and is driven by Fe(3+).These oxidation products (HDMPN and HDMPO) were readily converted to the corresponding ESR visible aminoxyl radicals by oxidation and .OH addition in aqueous solution, respectively, and superimposition of the ESR signals arising from these radicals accounts for the background signals observed in Fenton systems with DMPO as spin trap.

SYNTHESIS OF SOME SUBSTITUTED PYRROLINE-1-OXIDES BY CATALYTIC HYDROGENATION OF ALIPHATIC GAMMA-NITROVCARBONYL COMPOUNDS

Various pyrroline-1-oxides were prepared by the catalytic hydrogenation of appropriately substituted gamma-nitrocarbonyl compounds.Initially the reaction affords a mixture of the nitrone and the corresponding hydroxilamine, but copper(II)-catalyzed aerial oxidation readily converts the hydroxylamine to the desired cyclic nitrone.This method was found to be more convenient than the zinc-ammonium chloride reduction and the corresponding yields were comparable.

Homosolvolysis

Nitroxides, when used as solvents, promote the homolysis of a variety of weak bonds.Strong chemical evidence for the formation of free radicals is confirmed by e.s.r. studies in which the formation of free radicals has been monitored.This fission of single bonds of solute molecules dissolved in solvents with unpaired electrons is called homosolvolysis, in contrast to the common bond fission observed in polar solvents which is called heterosolvolysis.