Month: November 2022

Pettenuzzo, Andrea published the artcileAn innovative and efficient route to the synthesis of metal-based glycoconjugates: proof-of-concept and potential applications, Safety of Piperidine-4-carboxamide, the publication is Dalton Transactions (2018), 47(31), 10721-10736, database is CAplus and MEDLINE.

With a view to developing more efficient strategies to the functionalization of metallodrugs with carbohydrates, the authors here report on an innovative and efficient synthetic route to generate Au(III) glycoconjugates in high yields and purity. The method is based on the initial synthesis of the Zn(II)-dithiocarbamato intermediate [Zn^II(SSC-Inp-GlcN)₂] (Inp = isonipecotic moiety; GlcN = amino-glucose) followed by the transfer of the glucoseisonipecoticdithiocarbamato ligand to the Au(III) center via transmetalation reaction between the Zn(II) intermediate and K[Au^IIIBr₄] in 1 : 2 stoichiometric ratio, yielding the corresponding glucose-functionalized Au(II)-dithiocarbamato derivative [Au^IIIBr₂(SSC-Inp-GlcN)]. No protection/deprotection of the amino-glucose scaffold and no chromatog. purification were needed. The synthetic protocol was optimized for glucose precursors bearing the amino function at either the C² or the C⁶ position, and works in the case of both α and β anomers. The application of the synthetic strategy was also successfully extended to other metal ions of biomedical interest, such as Au(I) and Pt(II), to obtain [Au^I(SSC-Inp-GlcN)(PPh₃)] and [Pt^II(SSC-Inp-GlcN)₂], resp. All compounds were fully characterized by elemental anal., mid- and far-IR, mono- and multidimensional NMR spectroscopy, and, where possible, x-ray crystallog. Results and potential applications are here discussed.

Dalton Transactions published new progress about 39546-32-2. 39546-32-2 belongs to piperidines, auxiliary class Piperidine,Amine,Amide, name is Piperidine-4-carboxamide, and the molecular formula is C6H12N2O, Safety of Piperidine-4-carboxamide.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Peraino, Nicholas J. published the artcileDiastereoselective Synthesis of γ-Lactones through Reaction of Sulfoxonium Ylides, Aldehydes, and Ketenes: Substrate Scope and Mechanistic Studies, Quality Control of 4972-31-0, the publication is European Journal of Organic Chemistry (2021), 2021(1), 151-160, database is CAplus.

In this article, we describe the synthesis of γ-lactones through the reaction of sulfoxonium ylides, aldehydes, and disubstituted ketenes [e.g., ylide precursor I.BF₄^– + benzaldehyde + isobutylphenylketene â†?II (60%, 83:17 dr)]. The one-pot sequential method provides access to γ-lactones from disubstituted ketenes, in moderate to excellent yields, and with good diastereoselectivity favoring the trans-diastereomer (dr up to 92:8). The reaction mechanism was investigated by performing labeling, crossover, and various control experiments The results of those experiments support the reaction mechanism involving betaine formation, reaction of the betaine with a ketene to form an enolate intermediate, [3,3]-sigmatropic rearrangement of an enolate intermediate, and finally, 5-exo-tet cyclization to afford the γ-lactone product.

European Journal of Organic Chemistry published new progress about 4972-31-0. 4972-31-0 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-(Phenylsulfinyl)piperidine, and the molecular formula is C11H15NOS, Quality Control of 4972-31-0.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Salama, J. Y. published the artcileSome piperidine derivatives of organophosphorus compounds, COA of Formula: C7H15NO, the publication is Muslim Scientist (1983), 12(1), 8-12, database is CAplus.

PhP(X)(OMe)OR (I; X = O, S; R = N-methyl- and N-ethyl-4-piperidinyl, N-methyl- and N-ethyl-3-piperidinyl) were prepared from PhP(X)(OMe)Cl and alkylhydroxypiperidines. I (X = S; R = N-methyl-3-piperidinyl) was active against harmful bacteria such as E. coli and B. subtilis.

Muslim Scientist published new progress about 13444-24-1. 13444-24-1 belongs to piperidines, auxiliary class Piperidine,Alcohol, name is 1-Ethylpiperidin-3-ol, and the molecular formula is C7H15NO, COA of Formula: C7H15NO.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Si, Anshupriya published the artcileSynthesis of a pentasaccharide repeating unit corresponding to the cell wall O-antigen of Escherichia coli O59 using iterative glycosylations in one pot, HPLC of Formula: 4972-31-0, the publication is Tetrahedron (2016), 72(29), 4435-4441, database is CAplus.

Synthesis of a pentasaccharide repeating unit corresponding to the cell wall O-antigen of Escherichia coli O59 has been achieved by orthogonal glycosylation and two iterative glycosylations in one pot. Synthesis of a β-D-mannosidic linkage present in the mol. has been successfully achieved with satisfactory yield by the activation of thioglycoside with a combination of 1-benzenesulfinyl piperidine (BSP) and triflic anhydride (Tf₂O). The α-D-glucosaminyl moiety was achieved in moderate yield from the α-D-mannosyl moiety by azidolysis of C-2 hydroxy group with inversion of configuration. TEMPO mediated selective oxidation of the primary hydroxyl group has been carried out at the late stage of the synthetic strategy.

Tetrahedron published new progress about 4972-31-0. 4972-31-0 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-(Phenylsulfinyl)piperidine, and the molecular formula is C38H74Cl2N2O4, HPLC of Formula: 4972-31-0.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Boehme, Horst published the artcileCleavage of aminals and of α-dialkylamino ethers by simple and mixed anhydrides, Related Products of piperidines, the publication is Justus Liebigs Annalen der Chemie (1965), 78-93, database is CAplus.

Cleavage of aminals R₂NCH₂NR₂ with (RSO₂)₂O, [(RO)₂P(O)]₂O and [(RO)₂P]₂O (Ia) affords an equimolar mixture of a dialkylmethyleneimmonium salt [R₂N: CH₂]⁺X^– of the corresponding acid, and its amide. With mixed anhydrides, the immonium salt of a stronger acid results together with an amide of the weaker one. α-Dialkylamino ethers react in the same manner giving rise to esters instead of amides. In the case of Ia the intermediate immonium salts rearrange by Michaelis-Arbuzov rearrangement into the esters of dialkylaminomethylphosphonic acids. Acetyl nitrate cleaves aminals in a different manner giving rise to a mixture of dialkyl nitramines and acetoxymethyldialkylamines. Consistently with the above scheme, mixed anhydrides are converted with MeOH or HCl to a mixture of a free stronger acid and an ester or chloride, resp., of the weaker one. All reactions were run under N and with a strict exclusion of air moisture. Into a solution of 10.2 g. (Me₂N)₂CH₂ (I) in Et₂O was added dropwise 17.4 g. (MeSO₂)₂O (II) in HCONMe₂ to yield 93% [Me₂N:CH₂]⁺MeSO₃^– (III); the mother liquor afforded MeSO₂NMe₂, m. 48-9° (CCl₄). Analogously, 18.2 g. (C₅H₁₀N)₂CH₂ (IV) (C₅H₁₀N is piperidino throughout the abstract) and 17.4 g. II afforded 72% N-methylenepiperidineimmonium methanesulfonate [C₅H₁₀N:CH₂]⁺MeSO₃^– (V) and MeSO₂NC₅H₁₀, m. 48-9° (CCl₄). An ice-cold solution of 20 g. MeSO₃H in tetrahydrofuran was treated with CH₂:C:O, the solvent evaporated, and the residue distilled to give MeSO₂OAc (VI), b_0.01 56° (air bath). Reaction of 10.2 g. I and 13.8 g. VI in Et₂O gave 87% III and AcNMe₂ from mother liquors. Analogously, 18.2 g. IV afforded 70% V and C₅H₁₀NAc, b₁₂ 100-1°, n²⁰_D 1.4804. To an ice-cold solution of 17.6 g. PhSO₂Cl in 50 cc. dioxane was added dropwise a solution of 12.2 g. BzOH and 7.9 g. pyridine in 50 cc. dioxane. Pyridine-HCl was filtered off, the solvent evaporated, and the residue crystallized from CH₂Cl₂ to give 46% hygroscopic PhSO₂OBz (VII), m. 74-6°. From 10.2 g. I and 25.2 g. VII in Et₂O, there was obtained 92% [Me₂N:CH₂]⁺PhSO₃^– (VIII) and, from the mother liquors, BzNMe₂, b₂ 100° m.p. 42°. Analogously 18.2 g. IV and 26.2 g. VII gave 77% crystalline [C₅H₁₀N:CH₂]⁺PhSO₃^– (IX) and C₅H₁₀NBz. Also, 17.1 g. piperidinomethyl butyl ether (X) and 26.2 g. VII afforded 73% IX and BzOBu. A solution of 2 g. VII in MeOH was refluxed briefly and Et₂O added to precipitate 65% PhSO₃H, m. 51°; from the mother liquor, 60% BzOMe was obtained by distillation An ethereal solution of VII was treated with gaseous HCl to give, on chilling, 90% PhSO₃H and BzCl. To an ice-cold solution of 14 g. BzCl in 50 cc. dioxane was added dropwise a solution of 14.2 g. PhSO₂H and 7.9 g. pyridine in 50 cc. dioxane. After filtering off pyridine-HCl, 48% PhS(O)OBz (XI), b_0.01 82°, was obtained. A reaction of 10.2 g. I and 24.6 g. XI in Et₂O gave 85% [Me₂N:CH₂]⁺PhSO₂^– (XII) and BzNMe₂. Analogously, 18.2 g. IV and 24.6 g. XI gave rise to 86% [C₅H₁₀N:CH₂]⁺PhSO₂^– (XIII) and C₅H₁₀NBz. Also, 17.1 g. X and 24.6 g. XI afforded 75% XIII besides BzOBu. A solution of 2 g. XI in MeOH was heated to reflux temperature, concentrated, and distilled in vacuo to yield 45% of BzOMe and 39% PhSO₂H, m. 84°. A solution of 2 g. XI in Et₂O was treated with gaseous HCl, concentrated in vacuo, and distilled to yield PhSOCl, b_0.01 73-5° and BzOH. Similarly, a solution of 14.2 g. PhSO₂H and 7.9 g. pyridine in dioxane was added dropwise to an ice-cold solution of 17.6 g. PhSO₂Cl in dioxane; the precipitated pyridine-HCl filtered off and the filtrate concentrated to give 53% PhSO₂OSOPh (XIV), m. 93-5° (CH₂Cl₂). As above, 10.2 g. I and 28.2 g. XIV in Et₂O afforded 88% VIII and PhS(O)NMe₂, b₂ 93-5°. Analogously, 18.2 g. IV and 28.2 g. XIV gave 79% IX and PhS(O)NC₅H₁₀, m. 83° (aqueous EtOH). A reaction of 17.1 g. X with 28.2 g. XIV gave rise to 87% IX, and PhS(O)OBu, b_0.01 90-5°. By refluxing a solution of 2 g. XIV in MeOH, and by subsequent precipitation with Et₂O, there was obtained 52% PhSO₃H, and PhS(O)OMe, b_0.01 75°. On treatment with gaseous HCl, a solution of 2 g. XIV in Et₂O afforded PhSO₃H and PhSOCl, b_0.01 73-5°. By the general procedure, 10.2 g. I and 29 g. tetraethyl pyrophosphate [(EtO)₂P(O)]₂O (XV) in Et₂O gave 79% [Me₂N:CH₂]⁺(EtO)₂P(O)O^– (XVI) and, from the mother liquors, 78% (EtO)₂P(O)NMe₂ (XVII), b₁₀ 93°, n²⁰_D 1.4231. Analogously, 18.2 g. IV and 29 g. XV reacted to give 80% [C₅H₁₀N:CH₂]⁺(EtO)₂P(O)O^– (XVIII) and 69% (EtO)₂P(O)NC₅H₁₀ (XIX), b_0.5 90-3°, n²⁰_D 1.4400. A reaction of 17.1 g. X and 29 g. XV afforded 75% XVIII and 66% (EtO)₂P(O)OBu (XX) b_0.5 79-80°, n²⁰_D 1.4131. By treatment of 10.2 g. I in Et₂O with 19.6 g. (EtO)₂P(O)OAc (XXI), b_0.01 57-60°, n²⁰_D 1.4128, there was formed 81% XVI and 58% AcNMe₂. Analogously, 18.2 g. IV and 19.6 g. XXI in Et₂O afforded 71% XVIII and C₅H₁₀NAc. From 17.1 g. X and 19.6 g. XXI in Et₂O, there was obtained 66% XVIII and 9.2 g. AcOBu. By the general procedure, 10.2 g. I and 25.8 g. (EtO)₂P(O)OBz (XXII), b_0.01 107-10°, n²⁰_D 1.4936, afforded in Et₂O 81% XVI and 77% BzNMe₂. Analogously, 18.2 g. IV and 25.8 g. XXII gave 78% XVIII and 85% C₅H₁₀NBz. Similarly, 17.1 g. X and 25.8 g. XXII afforded 71% XVIII and 81% BuOBz. A solution of 4.8 g. MeSO₃H in 5 cc. Et₂O was treated dropwise with a solution of 13.7 g. (EtO)₂P(O)OP(OEt)₂ (XXIII) in 20 cc. Et₂O at 20-5°. After 25 hrs. at room temperature, the mixture was distilled to yield 57% (EtO)₂POH, b_0.05 38-40°, and 80% MeS(O)₂OP(O)(OEt)₂ (XXIV), b_0.01 75°, n²⁰_D 1.4276. Treatment of 10.2 g. I with 23.2 g. XXIV in Et₂O gave 79% III and 66% XVII; 18.2 g. IV with 23.2 g. XXIV gave 68% V and 57% XIX. A mixture of 10.2 g. I and 25.8 g. [(EtO)₂P]₂O (XXV) in Et₂O reacted with evolution of heat to afford, on distillation,62% (EtO)₂PNMe₂ (XXVI), b₁₂ 46-8°, n²⁰_D 1.4260, and Me₂NCH₂P(O)(OEt)₂ (XXVII) b₁ 85°, n²⁰_D 1.4288. Analogously, 18.2 g. IV and 25.8 g. XXV in Et₂O afforded 61% (EtO)₂PNC₅H₁₀ (XXVIII), b₁ 85°, n²⁰_D 1.4465, and 64% C₅H₁₀NCH₂P(O)(OEt)₂ (XXIX), b₂ 125°, n²⁰_D 1.4558. A reaction of 17.1 g. X and 25.8 g. XXV in Et₂O also gave XXIX, b_0.3 98°, n²⁰_D 1.4563, together with (EtO)₂POBu. A solution of 15.6 g. (EtO)₂PCl in Et₂O was treated successively with 10.1 g. Et₃N and 6 g. AcOH in dry Et₂O. After 1 hr. at room temperature, the Et₃N.HCl was filtered off, and the solution of (EtO)₂POAc (XXX) was used as such in the following experiments The solution of XXX and 10.2 g. I in Et₂O treated with evolution of heat to give EtOAc and 68% Me₂NCH₂P(O)(OEt)NMe₂ (XXXI), b₁₄ 110-12°, n²⁰_D 1.4822. An analogous treatment of 18.3 g. IV with the ethereal solution of XXX gave EtOAc, and 62% C₅H₁₀NCH₂P(O)(OEt)NC₅H₁₀ (XXXII), b_0.01 125°, n²⁰_D 1.5088; XXX with 17.1 g. X furnished EtOAc and 65% C₅H₁₀NCH₂P(O)(OEt)OBu (XXXIII), b_0.01 105° n²⁰_D 1.4838. A solution of 24.2 g. (EtO)₂POBz (XXXIV), b_0.05 96°, n²⁰_D 1.4990, in Et₂O was treated with 10.2 g. I to give, on rectification, EtOBz and 55% XXXI; 24.2 g. XXXIV and 18.2 g. IV furnished EtOBz and 56% XXXII; and analogously 24.2 g. XXXIV and 17.1 g. X in Et₂O gave 61% XXXIII. A reaction of 10.2 g. I with 27.4 g. XXIII in Et₂O resulted in formation of (EtO)₃PO and 43% XXXI, b₁₀ 110°; also, 27.4 g. XXXIII and 18.2 g. IV in Et₂O gave (EtO)₃PO and 45% XXXII; and, by the same procedure, 27.4 g. XXXIII and 17.1 g. X afforded (EtO)₃PO and 47% XXXIII. A solution of AcONO₂ was prepared by adding dropwise 50 g. Ac₂O into 9 g. 68% HNO₃ at 15° and chilling to -20°. This reagent was added dropwise at -20° to a solution of 10.2 g. I in Et₂O; the reaction mixture was distilled to give 92% Me₂NCH₂OAc (XXXV), b₂₀ 40°, n²⁰_D 1.4120; the distillation residue was poured into water, extracted with CH₂Cl₂, and the solvent evaporated to yield 67% Me₂NNO₂, m. 55-6°. In an analogous experiment with 18.2 g. IV and AcONO₂ reagent, there was obtained 65% C₅H₁₀NCH₂OAc (XXXVI), b₁ 56°, n²⁰_D 1.4506, and 50% C₅H₁₀NNO₂, b₁ 90°, n²⁰_D 1.4950. A solution of 11.7 g. XXXV in MeCN was treated dropwise with a solution 17 g. AgNO₃ in MeCN, the precipitate was collected and extracted with warm MeCN; [Me₂N:CH₂]⁺NO^–₃ deposited on cooling the extract A dropwise addition, with cooling, of 16.6 (EtO)₃P to 11.7 g. XXXV furnished 85% EtOAc and 88% XXVII. Analogously, 8.3 g. XXVI and 5.9 g. XXXV afforded 68% EtOAc and 46% XXXI; and in the same manner, 16.6 g. (EtO)₃P and 15.7 g. XXXVI gave rise to 82% EtOAc and 85% XXIX. A reaction of 10.3 g. XXVIII with 7.9 g. XXXVI afforded similarly 57% EtOAc and 62% XXXII.

Justus Liebigs Annalen der Chemie published new progress about 4972-31-0. 4972-31-0 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-(Phenylsulfinyl)piperidine, and the molecular formula is C11H15NOS, Related Products of piperidines.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Kelly, Christopher B. published the artcileOxidative Esterification of Aldehydes Using a Recyclable Oxoammonium Salt, Name: 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, the publication is Organic Letters (2013), 15(9), 2222-2225, database is CAplus and MEDLINE.

A simple, high yielding, rapid route for the oxidative esterification of a wide range aldehydes to hexafluoroisopropyl (HFIP) esters using the oxoammonium salt 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate is reported. These esters can be readily transformed into a variety of other functional groups. The spent oxidant can be recovered and conveniently reoxidized to regenerate the oxoammonium salt.

Organic Letters published new progress about 219543-09-6. 219543-09-6 belongs to piperidines, auxiliary class Piperidine,Fluoride,Salt,Amine,Amide, name is 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, and the molecular formula is C11H21BF4N2O2, Name: 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Kelly, Christopher B. published the artcileOxidation of α-Trifluoromethyl Alcohols Using a Recyclable Oxoammonium Salt, Quality Control of 219543-09-6, the publication is Journal of Organic Chemistry (2012), 77(18), 8131-8141, database is CAplus and MEDLINE.

A simple, mild method for the oxidation of α-trifluoromethyl alcs. to trifluoromethyl ketones (TFMKs) using the oxoammonium salt 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate is described. Under basic conditions, oxidation proceeds rapidly and affords good to excellent yields of TFMKs, without concomitant formation of the hydrate. The byproduct of the oxidation, 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinyloxy (1c), is easily recovered and can be conveniently reoxidized to regenerate the oxoammonium salt.

Journal of Organic Chemistry published new progress about 219543-09-6. 219543-09-6 belongs to piperidines, auxiliary class Piperidine,Fluoride,Salt,Amine,Amide, name is 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, and the molecular formula is C11H21BF4N2O2, Quality Control of 219543-09-6.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Bobbitt, James M. published the artcilePreparation of 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate, and the oxidation of geraniol to geranial, SDS of cas: 219543-09-6, the publication is Organic Syntheses (2005), 80-86, database is CAplus.

The oxidation of 4-(acetylamino)-2,2,6,6-tetramethyl-1-piperidinyloxy was achieved with hydrogen tetrafluoroborate(1-)/sodium hypochlorite (NaOCl; Clorox bleach) to give the title compound, 4-(acetylamino)-2,2,6,6-tetramethyl-1-(oxo)piperidinium tetrafluoroborate. The tetrafluoroborate salt was deemed safer than the corresponding perchlorate.

Organic Syntheses published new progress about 219543-09-6. 219543-09-6 belongs to piperidines, auxiliary class Piperidine,Fluoride,Salt,Amine,Amide, name is 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, and the molecular formula is C11H21BF4N2O2, SDS of cas: 219543-09-6.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Doyle, F. P. published the artcileChemistry and pharmacology of some esters derived from basic alcohols, Safety of 1-Ethylpiperidin-3-ol, the publication is Journal of Medicinal Chemistry (1965), 8(5), 571-6, database is CAplus.

The preparation of a number of α-alkoxy-α,α-diphenylacetates derived from open-chain basic alcs. is described. Some of these compounds possess antitussive activity comparable to that of codeine phosphate and of the same order as that of their analogs which contain pyrrolidine or piperidine rings. 2-Diethylamino-1-(α-methoxy-α,α-diphenylacetoxy)propane rearranged on heating to 1-diethylamino-2-(α-methoxy-α,α-diphenylacetoxy)propane.

Journal of Medicinal Chemistry published new progress about 13444-24-1. 13444-24-1 belongs to piperidines, auxiliary class Piperidine,Alcohol, name is 1-Ethylpiperidin-3-ol, and the molecular formula is C7H15NO, Safety of 1-Ethylpiperidin-3-ol.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Dragutan, Ileana published the artcileModulation of oxidative damage by nitroxide free radicals, Formula: C11H21BF4N2O2, the publication is Free Radical Research (2007), 41(3), 303-315, database is CAplus and MEDLINE.

Piperidine nitroxides like 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) are persistent free radicals in non-acidic aqueous solutions and organic solvents that may have value as therapeutic agents in medicine. In biol. environments, they undergo mostly reduction to stable hydroxylamines but can also undergo oxidation to reactive oxoammonium compounds Reactions of the oxoammonium derivatives could have adverse consequences including chem. modification of vital macromols. and deleterious effects on cell signaling. An examination of their reactivity in aqueous solution has shown that oxoammonium compounds can oxidize almost any organic as well as many inorganic mols. found in biol. systems. Many of these reactions appear to be 1-electron transfers that reduce the oxoammonium to the corresponding nitroxide species, in contrast to a prevalence of 2-electron reductions of oxoammonium in organic solvents. Amino acids, alcs., aldehydes, phospholipids, hydrogen peroxide, other nitroxides, hydroxylamines, phenols, and certain transition metal ions and their complexes are among reductants of oxoammonium, causing conversion of this species to the paramagnetic nitroxide. On the other hand, thiols and oxoammonium yield products that cannot be detected by ESR even under conditions that would oxidize hydroxylamines to nitroxides. These products may include hindered secondary amines, sulfoxamides, and sulfonamides. Thiol oxidation products other than disulfides cannot be restored to thiols by common enzymic reduction pathways. Such products may also play a role in cell signaling events related to oxidative stress. Adverse consequences of the reactions of oxoammonium compounds may partially offset the putative beneficial effects of nitroxides in some therapeutic settings.

Free Radical Research published new progress about 219543-09-6. 219543-09-6 belongs to piperidines, auxiliary class Piperidine,Fluoride,Salt,Amine,Amide, name is 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, and the molecular formula is C11H21BF4N2O2, Formula: C11H21BF4N2O2.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem