Day: November 21, 2022

Miller, Shelli A. published the artcileOxidation of terminal diols using an oxoammonium salt: a systematic study, Formula: C11H21BF4N2O2, the publication is Organic & Biomolecular Chemistry (2017), 15(13), 2817-2822, database is CAplus and MEDLINE.

A systematic study of the oxidation of a range of terminal diols is reported, employing the oxoammonium salt 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (4-NHAc-TEMPO⁺ BF₄^–) as the oxidant. For substrates bearing a hydrocarbon chain of seven carbon atoms or more, the sole product is the dialdehyde. A series of post-oxidation reactions have been performed showing that the product mixture resulting from the oxidation step can be taken on directly to a subsequent transformation. For diols containing four to six carbon atoms, the lactone product is the major product upon oxidation In the case of 1,2-ethanediol and 1,3-propanediol, when using a 1 : 0.5 stoichiometric ratio of substrate to oxidant, the corresponding monoaldehyde is formed which reacts rapidly with further diol to yield the acetal product. This is of particular synthetic value given both the difficulty of their preparation using other approaches and also their potential application in further reaction chem.

Organic & Biomolecular 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, Formula: C11H21BF4N2O2.

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

Merbouh, Nabyl published the artcileOxoammonium salts. Part 8: Oxidations in base: oxidation of O-1 unprotected monosaccharides to lactones using 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate, HPLC of Formula: 219543-09-6, the publication is Tetrahedron Letters (2001), 42(50), 8793-8796, database is CAplus.

The oxidant, 4-acetylamino-2,2,6,6-tetramethylpiperidine-oxoammonium tetrafluoroborate in pyridine/CH₂Cl₂, is reported to be an excellent reagent for the conversion of hemiacetals to lactones. Specifically, the conversion of 1-O unprotected sugars to their corresponding aldonolactones is achieved in high yields. The basic reaction conditions partially overcome some disadvantages reported for oxoammonium-type oxidants, namely the inability to run the reaction in the presence of acid-labile groups and in the presence of β-oxygens.

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, HPLC of Formula: 219543-09-6.

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

Merbouh, Nabyl published the artcileOxoammonium Salts. 9. Oxidative Dimerization of Polyfunctional Primary Alcohols to Esters. An Interesting β Oxygen Effect, Application of 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, the publication is Journal of Organic Chemistry (2004), 69(15), 5116-5119, database is CAplus and MEDLINE.

The use of the oxidant 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate in combination with pyridine for the oxidative, dimeric esterification of primary alcs. is described. The ester is the predominant product of the reaction with alcs. containing a β oxygen. In the absence of a β oxygen, the corresponding aldehyde is found in appreciable amounts, but a concentration effect can be observed In the absence of pyridine, little ester is formed, and no appreciable reaction takes place with β-oxygenated compounds δ Lactones have been prepared from diethylene glycol and 2,2′-thiodiethanol, without sulfur oxidation

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, Application of 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate.

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

Merbouh, Nabyl published the artcilePreparation of tetramethylpiperidine-1-oxoammonium salts and their use as oxidants in organic chemistry. A review, SDS of cas: 219543-09-6, the publication is Organic Preparations and Procedures International (2004), 36(1), 3-31, database is CAplus.

A review. The discovery of 2,2,6,6-tetramethylpiperidine-based oxoammonium salts (I; R = oxo, H, OH, NH₂, NHAc, OMe, OBz) in 1965 by Golubev et al has led to the synthesis of a number of oxoammonium-based oxidizing agents with diverse properties. However, many of the oxoammonium salts or their precursors are either not com. available or are expensive. Reports of their preparation are spread over 40 yr of literature. This review is a compilation of the most often cited and most practical procedures for their syntheses and includes exptl. details. A large body of work detailing the use of oxoammonium salts as catalytic and stoichiometric oxidants in preparative organic chem. also accumulated over the past four decades. The review of their use, however, will focus on the literature from 1990 to date, excluding the patent literature, as a number of excellent earlier reviews on select aspects of this chem. are available. The goal of this review is to allow organic chemists to prepare and study oxoammonium salts, irresp. of their list prices or com. availability. Oxoammonium salts I are derived from nitroxide free radicals (II) by a one-electron oxidation Nitroxides are generally prepared by oxidation of the corresponding amine 2,2,6,6-tetramethylpiperidine derivatives (III). The α-Me groups are crucial for the stabilization of the oxoammonium salts. A number of 4-substituted tetramethylpiperidine derivatives were used for the synthesis of oxoammonium salts, combined with several counter ions. Oxoammonium salts are potent but selective oxidants. They can either be prepared in situ from a nitroxide by reaction with a secondary oxidant, thus making the nitroxide a catalyst, or they can be used as stoichiometric oxidants. They are versatile oxidants in organic chem. and the mild, transition metal-free reaction conditions and the selectivity of the oxidations recommend these oxidants for wider use. Further, the option for tandem reactions will greatly increase the utility of these reagents.

Organic Preparations and Procedures International 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

Lambert, Kyle M. published the artcileFacile Oxidation of Primary Amines to Nitriles Using an Oxoammonium Salt, Computed Properties of 219543-09-6, the publication is Organic Letters (2014), 16(24), 6484-6487, database is CAplus and MEDLINE.

The oxidation of primary amines using a stoichiometric quantity of 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (1) in CH₂Cl₂-pyridine solvent at room temperature or at gentle reflux affords nitriles in good yield under mild conditions. The mechanism of the oxidation, which has been investigated computationally, involves a hydride transfer from the amine to the oxygen atom of 1 as the rate-limiting step.

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, Computed Properties of 219543-09-6.

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

Tanzer, Maria C. published the artcilePhosphoproteome profiling uncovers a key role for CDKs in TNF signaling, Computed Properties of 1702809-17-3, the publication is Nature Communications (2021), 12(1), 6053, database is CAplus and MEDLINE.

Abstract: Tumor necrosis factor (TNF) is one of the few cytokines successfully targeted by therapies against inflammatory diseases. However, blocking this well studied and pleiotropic ligand can cause dramatic side-effects. Here, we reason that a systems-level proteomic anal. of TNF signaling could dissect its diverse functions and offer a base for developing more targeted therapies. Therefore, we combine phosphoproteomics time course experiments with subcellular localization and kinase inhibitor anal. to identify functional modules of protein phosphorylation. The majority of regulated phosphorylation events can be assigned to an upstream kinase by inhibiting master kinases. Spatial proteomics reveals phosphorylation-dependent translocations of hundreds of proteins upon TNF stimulation. Phosphoproteome anal. of TNF-induced apoptosis and necroptosis uncovers a key role for transcriptional cyclin-dependent kinase activity to promote cytokine production and prevent excessive cell death downstream of the TNF signaling receptor. This resource of TNF-induced pathways and sites can be explored at http://tnfviewer.biochem.mpg.de/.

Nature Communications published new progress about 1702809-17-3. 1702809-17-3 belongs to piperidines, auxiliary class Cell Cycle,CDK, name is (R,E)-N-(4-(3-((5-Chloro-4-(1H-indol-3-yl)pyrimidin-2-yl)amino)piperidine-1-carbonyl)phenyl)-4-(dimethylamino)but-2-enamide, and the molecular formula is C4H5NS2, Computed Properties of 1702809-17-3.

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

Dahlbom, Richard published the artcileN- Alkyl – 3 – piperidyl phenothiazine – 10 – carboxylates, Category: piperidines, the publication is Acta Chemica Scandinavica (1961), 2043-6, database is CAplus.

cf. Biel, et al., CA 48, 694a; Schmitt, et al., CA 52, 1172d. From phenothiazine-10-carbonyl chlorides were prepared the title compounds, potential spasmolytic agents. 2-Methylphenothiazine (42.4 g.) in 750 ml. PhMe with 330 ml. 10% by volume COCl₂-PhMe was refluxed 4 hrs. at 90°, 50 ml. EtOH added to the cold product, and the solvent evaporated in vacuo to give 54 g. 2-methylphenothiazine-10-carbonyl chloride, m. 122-2.5° (AcOEt). 2-Ethyl- (I) and 2-methoxyphenothiazine-10-carbonyl chloride (II) were similarly prepared I did not crystallize. II (88% yield) m. 94-5° (MeOH). In the modified method for the preparation of 2-chlorophenothiazine-10-carbonyl chloride (III) from 46.5 g. 2-chlorophenothiazine (IV), heating 6 hrs. at 140° was followed by addition of 130 ml. more COCl₂ solution and heating 8 hrs. at 140°. Filtration, after the addition of C₆H₆ to the crude III, removed IV as a residue. Evaporation of C₆H₆ gave 35.0 g. III, m. 100-1° (AcOEt). AlCl₃ (200 g.) was added to 131 g. phenothiazine-10-carbonyl chloride (V) stirred in 800 ml. CS₂, the mixture refluxed to dissolve V, and to the cold product added 54.9 g. AcCl in portions. Heating to 30° started a vigorous reaction and after 1 hr. the mixture was refluxed 3 hrs. The cold lower layer from the product was poured on 1 kg. ice and 25 ml. 10N HCl to precipitate 150 g. 2-acetyl derivative of V, m. 120-2° (AcOEt), giving with KOH in EtOH 2-acetylphenothiazine. The appropriate 2-substituted V (0.05 mole), 0.05 mole N-methyl- (VI) or N-ethyl3-hydroxypiperidine (VII), 0.075 mole NEt₃, and 50 ml. PhMe were refluxed (4 hrs. with VI, 8 hrs. with VII), the Et₃NHCl filtered off from the cold product, the PhMe solution washed (H₂O), and then extracted (N HCl). VIII.HCl separated, was dissolved in H₂O, and the solution combined with the aqueous acidic extract before being made alk. (Na₂CO₃) to precipitate VIII. VIII was converted into VIII.HCl by HCl in Et₂O or was quaternized (CA 49, 4659c). Thus, the following VIII and derivatives were prepared [R, R’, nature of derivative, recrystallizing solvent, % yield, and m.p. (the salts decomposed) given]: H, Me, free base, petr. ether, 72, 88-90°; H, Me, HCl, MeOH-Et₂O (IX), -, 230-2°; H, Me, MeBr, MeOH, 86, 273-4°; H, Et, HCl, EtOH-Et₂O (X), 55, 222-3°; H, Et. MeBr, X, 67, 232-3°; H, Et, EtI, X, 71, 220-1°; Me, Me, HCl, X, 92, 242-4°; Me, Et, HCl, X, 69, 223.-4°; Et, Me, HCl, MeOH, 80, 240-2°; Et, Et, HCl, X, 57, 202-3°; MeO, Me, HCl, IX, 80, 242-4°; MeO, Et, HCl, IX, 66, 230-1°; Cl, Me, HCl, IX, 77, 235-7°; Cl, Et, HCl, X, 64, 220-2°; Ac, Me, free base, EtOH, 80, 112-14°; Ac, Me, HCl, EtOH, -, 236-8°; Ac, Et, HCl, X, 49, 188-9°.

Acta Chemica Scandinavica 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, Category: piperidines.

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

Miller, Shelli A. published the artcileCatalytic Oxidation of Alcohols Using a 2,2,6,6-Tetramethylpiperidine-N-hydroxyammonium Cation, Category: piperidines, the publication is European Journal of Organic Chemistry (2019), 2019(6), 1413-1417, database is CAplus.

The oxidation of alcs. to aldehydes, ketones, and carboxylic acids is reported using 2,2,6,6-tetramethylpiperidine-4-acetamido-hydroxyammonium tetrafluoroborate as a catalyst in conjunction with sodium hypochlorite pentahydrate as a terminal oxidant. The reaction is generally complete within 30-120 min using an acetonitrile/water mix as the solvent, and no additives are required. Product yields are good to excellent and of particular note is that the methodol. can be used to access aryl α-trifluoromethyl ketones.

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, Category: piperidines.

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

Kung, Pei-Pei published the artcileCharacterization of Specific N-α-Acetyltransferase 50 (Naa50) Inhibitors Identified Using a DNA Encoded Library, Related Products of piperidines, the publication is ACS Medicinal Chemistry Letters (2020), 11(6), 1175-1184, database is CAplus and MEDLINE.

Two novel compounds were identified as Naa50 binders/inhibitors using DNA-encoded technol. screening. Biophys. and biochem. data as well as cocrystal structures were obtained for both compounds (3a and 4a) to understand their mechanism of action. These data were also used to rationalize the binding affinity differences observed between the two compounds and a MLGP peptide-containing substrate. Cellular target engagement experiments further confirm the Naa50 binding of 4a and demonstrate its selectivity toward related enzymes (Naa10 and Naa60). Addnl. analogs of inhibitor 4a were also evaluated to study the binding mode observed in the cocrystal structures.

ACS Medicinal Chemistry Letters published new progress about 72002-30-3. 72002-30-3 belongs to piperidines, auxiliary class Piperidine,Chiral,Carboxylic acid,Amide, name is (R)-6-Oxopiperidine-2-carboxylic acid, and the molecular formula is C6H9NO3, Related Products of piperidines.

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

Galambos, Janos published the artcileDiscovery of 4-amino-3-arylsulfoquinolines, a novel non-acetylenic chemotype of metabotropic glutamate 5 (mGlu₅) receptor negative allosteric modulators, Product Details of C6H12N2O, the publication is European Journal of Medicinal Chemistry (2017), 240-254, database is CAplus and MEDLINE.

Neg. allosteric modulators of metabotropic glutamate receptor 5 (mGlu₅) showed efficacy in a number of animal models of different CNS diseases including anxiety and depression. Virtually all of the compounds which reached the clinic belong to the same chemotype having an acetylenic linker that connects (hetero)cyclic moieties. Searching for new chemotypes we identified a morpholino-sulfoquinoline derivative (1) by screening our corporate compound deck. The HTS hit showed reasonable affinity and selectivity towards mGlu₅ receptors, however, its inferior metabolic stability prevented its testing in vivo. In a chem. program we aimed to improve the affinity, physicochem. properties and metabolic stability exploring three regions of the hit. Systematic variation of different amines at position 4 (region I) led to the identification of 4-methyl-piperidinyl analogs. Substituents of the quinoline core (region II) and the phenylsulfonyl moiety (region III) were mapped by parallel synthesis. Evaluation of both morpholino- and 4-methyl-piperidinyl-sulfoquinoline libraries of about 270 derivatives revealed beneficial substituent combinations in regions II and III. Blood levels of optimized 4-methyl-piperidinyl-sulfoquinolines, however, were still insufficient for robust in vivo efficacy. Finally, introducing 4-hydoxymethyl-piperidinyl substituent to region I resulted in new sulfoquinolines with greatly improved solubility and reasonable affinity coupled with affordable metabolic stability. The most promising analogs (24 and 25) showed high blood levels and demonstrated significant efficacy in the exptl. model of anxiety.

European Journal of Medicinal Chemistry 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, Product Details of C6H12N2O.

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