Day: November 21, 2022

Bailey, William F. published the artcileIntramolecular carbolithiation cascades as a route to a highly strained carbocyclic framework: competition between 5-exo-trig ring closure and proton transfer, Related Products of piperidines, the publication is Beilstein Journal of Organic Chemistry (2013), 537-543, database is CAplus and MEDLINE.

The preparation of fairly strained carbocyclic ring systems by intramol. 5-exo-trig ring closure has been well documented and the absence of proton transfers that would compromise such cyclizations is a hallmark of this chem. In an effort to explore the limitations of this approach to more highly strained systems, the preparation of a stellane (tricyclo[3.3.0.0^3,7]octane) framework by an intramol. carbolithiation cascade (tandem reaction) involving three coupled 5-exo-trig cyclization reactions of a vinyllithium group (I) derived from 2-bromo-4-vinyl-1,6-heptadiene by lithium-bromine exchange (substitution bromination) was investigated. The cascade does not afford 1-methylstellane. Rather, the cascade is terminated after two cyclizations by a proton transfer that occurs by an intermol. process catalyzed by trace amounts of endo-5-methyl-2-methylenebicyclo[2.2.1]heptane present in reaction mixtures as a consequence of inadvertent quenching of an intermediate alkyllithium during prolonged reaction times at room temperature The synthesis of the target compound I was achieved using 4-pentenoic acid 1,1-dimethylethyl ester as a starting material.

Beilstein 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

Moon, Patrick J. published the artcileDecarboxylative Benzylation of Aryl and Alkenyl Boronic Esters, Recommanded Product: (3-(3-(Ethoxycarbonyl)piperidine-1-carbonyl)phenyl)boronic acid, the publication is Angewandte Chemie, International Edition (2018), 57(17), 4612-4616, database is CAplus and MEDLINE.

The copper-catalyzed decarboxylative benzylation of aryl and alkenyl boronic esters with electron-deficient aryl acetates is reported. The oxidative coupling proceeds under mild, aerobic conditions and tolerates a host of potentially reactive electrophilic functional groups that would be problematic with traditional benzylation methods (aryl iodides and bromides, protic heteroatoms, aldehydes, Michael acceptors). A reaction pathway in which a benzylic nucleophile is generated by aryl acetate decarboxylation and in turn is intercepted by the catalyst to form diarylmethane products is supported by mechanistic studies.

Angewandte Chemie, International Edition published new progress about 1218790-81-8. 1218790-81-8 belongs to piperidines, auxiliary class Piperidine,Boronic acid and ester,Benzene,Ester,Amide,Boronic Acids,Boronic Acids,Boronic acid and ester, name is (3-(3-(Ethoxycarbonyl)piperidine-1-carbonyl)phenyl)boronic acid, and the molecular formula is C15H20BNO5, Recommanded Product: (3-(3-(Ethoxycarbonyl)piperidine-1-carbonyl)phenyl)boronic acid.

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

Potowski, Marco published the artcileTranslation of the copper/bipyridine-promoted Petasis reaction to solid phase-coupled DNA for encoded library synthesis, Recommanded Product: Piperidine-4-carboxamide, the publication is Bioorganic & Medicinal Chemistry (2020), 28(9), 115441, database is CAplus and MEDLINE.

The Petasis three-component reaction gives rise to diverse substituted α-aryl glycines from readily available amines, boronic acids and glyoxalic acid. Thus, this reaction is highly attractive for DNA-encoded small mol. screening library synthesis. The Petasis reaction is for instance promoted by a potentially DNA damaging copper(I)/bipyridine reagent system in dry organic solvents. We found that solid phase-coupled DNA strands tolerated this reagent system at elevated temperature allowing for synthesis of diverse substituted DNA-tagged α-aryl glycines from DNA-conjugated secondary amines.

Bioorganic & 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, Recommanded Product: Piperidine-4-carboxamide.

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

Babaev, E. V. published the artcileBasic techniques of working on a solid phase: From ABC of the peptide synthesis to libraries of non-natural amino acids, COA of Formula: C19H21N, the publication is Russian Journal of General Chemistry (2010), 80(12), 2572-2589, database is CAplus.

Libraries of hardly available amino acids bearing a heteroaromatic ring (2-pyrimidyl, substituted 2-pyridyl or 2-thiazolyl) at the amino group were prepared using solid-phase synthesis on various resins. The synthesized compounds are structurally similar to some known antidiabetic drugs. The paper combines features of a review (elementary introduction to the solid-phase synthesis methodol. and technique for beginners and selected methods from peptide chem.) and step-by-step exptl. protocols (tested by the authors) useful as a methodic tool. The presented protocols (immobilization and modification of amino acids, placing and removal of common protective groups) require no sophisticated equipment and may be useful as pictorial introductory tasks for students education.

Russian Journal of General Chemistry published new progress about 35661-58-6. 35661-58-6 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-((9H-Fluoren-9-yl)methyl)piperidine, and the molecular formula is C19H21N, COA of Formula: C19H21N.

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

Tanaka, Susumu published the artcileHighly Efficient Singlet Oxygen Generation and High Oxidation Resistance Enhanced by Arsole-Polymer-Based Photosensitizer: Application as a Recyclable Photooxidation Catalyst, Related Products of piperidines, the publication is Macromolecules (Washington, DC, United States) (2020), 53(6), 2006-2013, database is CAplus.

Photosensitizers have attracted considerable attention in various fields such as organic synthesis and medical care. For the development of high-performance photosensitizers, highly efficient and persistent singlet oxygen generators (¹O₂) having a high oxidation tolerance are strongly required. This study presents a detailed investigation of dithieno[3,2-b:2′,3′-d]arsole-fluorene copolymer for its ¹O₂ generation ability and application as a photooxidation catalyst in vital organic reactions. Photoirradiation of an air-saturated solution of the polymer generates ¹O₂, which was detected by ¹O₂ scavengers such as dihydronaphthoquinone and diphenylisobenzofuran. The polymer photosensitizer was completely stable in the presence of the strong oxidant ¹O₂. The photosensitizer showed the highest quantum yield of ¹O₂ generation (Φ = 0.54) in single-component main-chain type π-conjugated polymers. The quantum yield of the arsenic-free analog of the polymer-bithiophene-fluorene copolymer-was significantly lower (Φ = 0.14), suggesting that the heavy-atom effect of arsenic can improve the efficiency of intersystem crossing (ISC) from the singlet excited state to the triplet excited state of the photosensitizer. In addition, when utilized as a recyclable photocatalyst for the oxidation reaction, the photosensitizer exhibited excellent oxidation resistance without losing its recognizable catalytic activity. Finally, we demonstrated the release of ¹O₂ into the air by a film of the present polymer. Persistent ¹O₂ generation was observed on film irradiation without polymer decomposition These results suggested that the polymer exhibited excellent oxidation resistance in solution as well as in the solid state. The present mol. design concept of the photosensitizer using the main group element can facilitate the development of further functional optical materials.

Macromolecules (Washington, DC, United States) published new progress about 826-36-8. 826-36-8 belongs to piperidines, auxiliary class Natural product, name is 2,2,6,6-Tetramethylpiperidin-4-one, and the molecular formula is C12H15NO, Related Products of piperidines.

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

Borodkin, G. I. published the artcileReaction of Nitrosonium Tetrafluoroborate with Nitroxyl Radicals, Name: 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, the publication is Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii) (2003), 39(8), 1144-1150, database is CAplus.

It was established by means of multinuclear magnetic resonance method (¹H, ¹³C, ¹⁹F and ¹⁴N) that reaction of 2,2,6,6-tetramethyl-4-R-piperidin-1-oxyl radicals (R = H, OH, OMe, OCOPh, NHCOMe) with nitrosonium tetrafluoroborate gave rise to the corresponding 2,2,6,6-tetramethyl-1-oxo-4-R-piperidinium tetrafluoroborates. Linear correlations were found between the chem. shifts of atoms H⁴, C⁴ of cations and resp. σ₁-constants of substituents R and chem. shifts of C⁴ atom calculated from increments of substitution. The conformational features of the generated nitrosonium cations are considered on the grounds of vicinal coupling constants J_HH and quantum-chem. calculations by AM1 method.

Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii) 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

Bobbitt, James M. published the artcileDiscussion addendum for: preparation of 4-acetylamino-2,2,6,6-tetramethylpiperidine-1- oxoammonium tetrafluoroborate and the oxidation of geraniol to geranial (2,6-octadienal, 3,7-dimethyl-, (2e)-), Application In Synthesis of 219543-09-6, the publication is Organic Syntheses (2013), 215-228, database is CAplus.

A review. Addendum to an original article published by Bobbitt, J. M. and Merbouh, N. in Organic Synth. 2005, 82, 80. Revised preparations of I and II•BF₄^–, their solubility properties and relevance in stoichiometric alc. oxidation reactions, and examples of selective alc. oxidations of polyalcs. as well as other recent developments were discussed.

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, Application In Synthesis of 219543-09-6.

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

Bobbitt, James M. published the artcilePreparation of Some Homologous TEMPO Nitroxides and Oxoammonium Salts; Notes on the NMR Spectroscopy of Nitroxide Free Radicals; Observed Radical Nature of Oxoammonium Salt Solutions Containing Trace Amounts of Corresponding Nitroxides in an Equilibrium Relationship, Product Details of C11H21BF4N2O2, the publication is Journal of Organic Chemistry (2017), 82(18), 9279-9290, database is CAplus and MEDLINE.

Three new homologous TEMPO oxoammonium salts and three homologous nitroxide radicals have been prepared and characterized. The oxidation properties of the salts have been explored. The direct ¹³C NMR and EPR spectra of the nitroxide free radicals and the oxoammonium salts, along with TEMPO and its oxoammonium salt, have been successfully measured with little peak broadening of the NMR signals. In the spectra of all ten compounds (nitroxides and corresponding oxoammonium salts), the carbons in the 2,2,6,6-tetramethylpiperidine core do not appear, implying paramagnetic properties. This unpredicted overall paramagnetism in the oxoammonium salt solutions is explained by a redox equilibrium as shown between oxoammonium salts and trace amounts of corresponding nitroxide. This equilibrium is confirmed by electron interchange reactions between nitroxides with an N-acetyl substituent and oxoammonium salts with longer acyl side chains.

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, Product Details of C11H21BF4N2O2.

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

Gholivand, Khodayar published the artcileSynthesis, biological evaluation, QSAR study and molecular docking of novel N-(4-amino carbonylpiperazinyl) (thio)phosphoramide derivatives as cholinesterase inhibitors, Synthetic Route of 39546-32-2, the publication is Pesticide Biochemistry and Physiology (2014), 40-50, database is CAplus and MEDLINE.

Novel (thio)phosphoramidate derivatives based on piperidincarboxamide with the general formula of (NH₂-C(O)-C₅H₉N)-P(X = O,S)R₁R₂ (1-5) and (NH₂-C(O)-C₅H₉N)₂-P(O)R (6-9) were synthesized and characterized by ³¹P, ¹³C, ¹H NMR, IR spectroscopy. Furthermore, the crystal structure of compound (NH₂-C(O)-C₅H₉N)₂-P(O)(OC₆H₅) (6) was investigated. The activities of derivatives on cholinesterases (ChE) were determined using a modified Ellman’s method. Also the mixed-type mechanisms of these compounds were evaluated by Lineweaver-Burk plots. Mol. docking and quant. structure-activity relationship (QSAR) were used to understand the relationship between mol. structural features and anti-ChE activity, and to predict the binding affinity of phosphoramido-piperidinecarboxamides (PAPCAs) to ChE receptors. From mol. docking anal., noncovalent interactions especially hydrogen bonding as well as hydrophobic was found between PAPCAs and ChE. Based on the docking results, appropriate mol. structural parameters were adopted to develop a QSAR model. DFT-QSAR models for ChE enzymes demonstrated the importance of electrophilicity parameter in describing the anti-AChE and anti-BChE activities of the synthesized compounds The correlation matrix of QSAR models and docking anal. confirmed that electrophilicity descriptor can control the influence of the hydrophobic properties of P = (O, S) and C=O functional groups of PAPCA derivatives in the inhibition of human ChE enzymes.

Pesticide Biochemistry and Physiology 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, Synthetic Route of 39546-32-2.

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

Wang, Tao published the artcileA New Synthetic Route to Avibactam: Lipase Catalytic Resolution and the Simultaneous Debenzylation/Sulfation, Quality Control of 1416134-49-0, the publication is Organic Process Research & Development (2018), 22(3), 267-272, database is CAplus.

An efficient synthesis of avibactam starting from com. available ethyl-5-hydroxypicolinate was completed in ten steps and 23.9% overall yield. The synthesis features a novel lipase-catalyzed resolution, in the preparation of (2S,5S)-5-hydroxypiperidine-2-carboxylate acid, which are valuable precursors of the key intermediate Et (2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxylate. An optimized one-pot debenzylation / sulfation reaction, followed by cation exchange, gave the avibactam sodium salt on a 400.0 g scale.

Organic Process Research & Development published new progress about 1416134-49-0. 1416134-49-0 belongs to piperidines, auxiliary class Piperidine,Chiral,Amine,Benzene,Amide, name is (2S,5R)-5-((Benzyloxy)amino)piperidine-2-carboxamide, and the molecular formula is C15H21BO2, Quality Control of 1416134-49-0.

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