Tag: M.W=300-350

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

Kim, Myeong Jin published the artcileOxoammonium salt-mediated oxidative nitriles synthesis from aldehydes with ammonium acetate, Quality Control of 219543-09-6, the publication is Tetrahedron Letters (2017), 58(50), 4695-4698, database is CAplus.

An efficient and scalable route for the synthesis of nitriles I [R = n-heptyl, cyclohexyl, 4-MeOC₆H₄, 2-thienyl, etc.] was developed by oxoammonium salt (4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate) mediated oxidative conversion of aldehydes with ammonium acetate (NH₄OAc). A variety of aliphatic aldehydes as well as benzaldehydes were converted into the corresponding nitriles in high yields. The nitroxyl radical which was the reduced species of the used oxoammonium salt was recovered by simple acid-base extraction for the recycling.

Tetrahedron 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, Quality Control of 219543-09-6.

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

Miller, Shelli A. published the artcileProbing the Effect of Counterions on the Oxidation of Alcohols Using Oxoammonium Salts, Computed Properties of 219543-09-6, the publication is European Journal of Organic Chemistry (2020), 2020(1), 108-112, database is CAplus.

The effect of varying the counterion in the oxoammonium salt mediated oxidation of alcs. has been probed. Computational and exptl. results suggest that the counterion is non-innocent in oxoammonium salt mediated oxidations and the outcome of the reaction is related, at least in part, to the ability of the hydrogen-bond accepting nature of the anion.

European 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, Computed Properties of 219543-09-6.

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

Millimaci, Alexandra M. published the artcileMetal Free Amino-Oxidation of Electron Rich Alkenes Mediated by an Oxoammonium Salt, Computed Properties of 219543-09-6, the publication is Israel Journal of Chemistry (2021), 61(5-6), 322-326, database is CAplus.

4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium tetrafluoroborate (Bobbitt′s salt) effectively activates electron rich alkenes and promotes the addition of anilines. This transformation provides a direct, transition metal free method for amino-oxidation of alkenes under mild conditions. The relative stereochem. of the amino-oxidation is influenced by solvent effects, with both the syn and anti amino-oxidation products being accessible from identical starting materials.

Israel Journal of 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, Computed Properties of 219543-09-6.

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

Garg, Komal published the artcileStriking differences in properties of geometric isomers of [Ir(tpy)(ppy)H]⁺: Experimental and computational studies of their hydricities, interaction with CO₂, and photochemistry, Recommanded Product: 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, the publication is Angewandte Chemie, International Edition (2015), 54(47), 14128-14132, database is CAplus and MEDLINE.

We prepared two geometric isomers of [Ir(tpy)(ppy)H]⁺, previously proposed as a key intermediate in the photochem. reduction of CO₂ to CO, and characterized their notably different ground- and excited-state interactions with CO₂ and their hydricities using exptl. and computational methods. Only one isomer, C-trans-[Ir(tpy)(ppy)H]⁺, reacts with CO₂ to generate the formato complex in the ground state, consistent with its calculated hydricity. Under photocatalytic conditions in CH₃CN/TEOA, a common reactive C-trans-[Ir(tpy)(ppy)]⁰ species, irresp. of the starting isomer or monodentate ligand (such as hydride or Cl), reacts with CO₂ and produces CO with the same catalytic efficiency.

Angewandte Chemie, International Edition 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, Recommanded Product: 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate.

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

Kelso, Geoffrey F. published the artcileA Mitochondria-Targeted Macrocyclic Mn(II) Superoxide Dismutase Mimetic, Computed Properties of 219543-09-6, the publication is Chemistry & Biology (Oxford, United Kingdom) (2012), 19(10), 1237-1246, database is CAplus and MEDLINE.

Superoxide (O₂^l-) is the proximal mitochondrial reactive oxygen species underlying pathol. and redox signaling. This central role prioritizes development of a mitochondria-targeted reagent selective for controlling O₂l^–. We have conjugated a mitochondria-targeting triphenylphosphonium (TPP) cation to a O₂l^–-selective pentaaza macrocyclic Mn(II) superoxide dismutase (SOD) mimetic to make MitoSOD, a mitochondria-targeted SOD mimetic. MitoSOD showed rapid and extensive membrane potential-dependent uptake into mitochondria without loss of Mn and retained SOD activity. Pulse radiolysis measurements confirmed that MitoSOD was a very effective catalytic SOD mimetic. MitoSOD also catalyzes the ascorbate-dependent reduction of O₂l^–. The combination of mitochondrial uptake and O₂l^– scavenging by MitoSOD decreased inactivation of the matrix enzyme aconitase caused by O₂l^–. MitoSOD is an effective mitochondria-targeted macrocyclic SOD mimetic that selectively protects mitochondria from O₂l^– damage.

Chemistry & Biology (Oxford, United Kingdom) 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, Computed Properties of 219543-09-6.

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

Zhao, Xuna published the artcileIn Situ Generated TEMPO Oxoammonium Salt Mediated Tandem Cyclization of β-Oxoamides with Amine Hydrochlorides for the Synthesis of Pyrrolin-4-ones, Computed Properties of 219543-09-6, the publication is Journal of Organic Chemistry (2017), 82(12), 6125-6132, database is CAplus and MEDLINE.

In the presence of TEMPO (via its in situ-generated oxoammonium salt), acetoacetamides MeCOCH₂CONHR (R = Ph, 4-MeOC₆H₄, 3-MeOC₆H₄, 2-MeOC₆H₄, 4-MeC₆H₄, 2-MeC₆H₄, 2,4-Me₂C₆H₃, 4-ClC₆H₄, 3-ClC₆H₄, 2-ClC₆H₄, 4-EtO₂CC₆H₄, PhCH₂, t-Bu) underwent chemoselective oxidative cyclocondensations with amine hydrochlorides R¹NH₂·HCl (R¹ = Ph, 4-MeOC₆H₄, 4-MeC₆H₄, 3-MeC₆H₄, 2-MeC₆H₄, 4-ClC₆H₄, 3-ClC₆H₄, HCCCH₂, PhCH₂, n-Pr, H) or ammonium chloride in DMF to yield oxopyrroledicarboxamides I (R = Ph, 4-MeOC₆H₄, 3-MeOC₆H₄, 2-MeOC₆H₄, 4-MeC₆H₄, 2-MeC₆H₄, 2,4-Me₂C₆H₃, 4-ClC₆H₄, 3-ClC₆H₄, 2-ClC₆H₄, 4-EtO₂CC₆H₄, PhCH₂, t-Bu; R¹ = Ph, 4-MeOC₆H₄, 4-MeC₆H₄, 3-MeC₆H₄, 2-MeC₆H₄, 4-ClC₆H₄, 3-ClC₆H₄, HCCCH₂, PhCH₂, n-Pr, H) in 48-82% yields. Detailed mechanistic studies disclosed that TEMPO oxoammonium salt generated in situ was crucial for the transformation involving the formation of enaminone precursors in situ by condensation of the β-oxoamides with amines, followed by sequential oxidative coupling with β-oxoamides, intramol. cyclization, and 1,2-alkyl migration steps.

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 C7H10O4, Computed Properties of 219543-09-6.

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

Fang, Li published the artcileA Metal-Free Oxidative Cross-Dehydrogenative Coupling of N-Aryl Tetrahydroisoquinolines and 2-Methylazaarenes Using a Recyclable Oxoammonium Salt as Oxidant in Aqueous Media, Related Products of piperidines, the publication is European Journal of Organic Chemistry (2016), 2016(21), 3559-3567, database is CAplus.

A metal-free oxidative cross-dehydrogenative coupling of N-aryl tetrahydroisoquinolines and 2-methylazaarenes in water under mild conditions was developed. 4-Acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate was employed as a mild oxidant that can be recovered and reused directly. The reaction proceeds through formation of an iminium ion in situ followed by condensation with various nucleophiles, providing the desired products in moderate to good yields.

European 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, Related Products of piperidines.

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

Kelly, Christopher B. published the artcileAccess to nitriles from aldehydes mediated by an oxoammonium salt, Name: 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, the publication is Angewandte Chemie, International Edition (2015), 54(14), 4241-4245, database is CAplus and MEDLINE.

A scalable, high yielding, rapid route to access an array of nitriles from aldehydes mediated by an oxoammonium salt (4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate) and hexamethyldisilazane (HMDS) as an ammonia surrogate has been developed. The reaction likely involves two distinct chem. transformations: reversible silyl-imine formation between HMDS and an aldehyde, followed by oxidation mediated by the oxoammonium salt and desilylation to furnish a nitrile. The spent oxidant can be easily recovered and used to regenerate the oxoammonium salt oxidant.

Angewandte Chemie, International Edition 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