84358-13-4 | Page 8 of 9 | Heterocyclic Building Blocks-piperidine

Gilbert, Audrey team published research on Tetrahedron in 2021 | 84358-13-4

Quality Control of 84358-13-4, N-BOC-piperidine-4-carboxylic acid, also known asN-Boc-isonipecotic acid , is a useful research compound. Its molecular formula is C11H19NO4 and its molecular weight is 229,28 g/mole. The purity is usually 95%.

N-Boc-isonipecotic acid is a potent antitumor agent that has been clinically shown to be effective against leukemia and lymphoma. It has potent antibacterial activity against Gram-positive bacteria such as Staphylococcus aureus and Streptococcus pyogenes. N-Boc-isonipecotic acid binds to the gyrase enzyme, which is used by these bacteria to maintain the integrity of their DNA, inhibiting protein synthesis and cell division. This drug also has anti-inflammatory properties. N-Boc-isonipecotic acid inhibits prostaglandin synthesis in cells, which may be due to its ability to inhibit the production of tumor necrosis factor α (TNFα) in macrophages., 84358-13-4.

Piperidine structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper its spicy taste. This gave the compound its name. 84358-13-4, formula is C11H19NO4, Name is 1-(tert-Butoxycarbonyl)piperidine-4-carboxylic acid. Other examples are the fire ant toxin solenopsin, the nicotine analog anabasine of tree tobacco (Nicotiana glauca), lobeline of Indian tobacco. Quality Control of 84358-13-4.

Gilbert, Audrey;Langowski, Pauline;Paquin, Jean-Francois research published 《 Synthesis of N-(2-SF₅-ethyl)amines and impact of the SF₅ substituent on their basicity and lipophilicity》, the research content is summarized as follows. The synthesis of N-(2-SF₅-ethyl)amines e.g., I is reported via the S_N2 reaction between various amines, e.g., Me (2S)-pyrrolidine-2-carboxylate and 2-(pentafluoro-λ⁶-sulfanyl)ethyl trifluoromethanesulfonate as the SF₅-containing electrophile. A total of 14 examples of SF₅-containing aliphatic amines were synthesized, with yields going from 19 to 92%. Moreover, the effect of the SF₅ substituent on the basicity and the lipophilicity of the amine was evaluated, and the SF₅ group showed to decrease both the pK_aH and the log D (pH = 7.0) values.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Ghosh, Arun K. team published research on Tetrahedron Letters in 2021 | 84358-13-4

Safety of 1-(tert-Butoxycarbonyl)piperidine-4-carboxylic acid, N-BOC-piperidine-4-carboxylic acid, also known asN-Boc-isonipecotic acid , is a useful research compound. Its molecular formula is C11H19NO4 and its molecular weight is 229,28 g/mole. The purity is usually 95%.

Ghosh, Arun K.;Shahabi, Dana research published 《 Synthesis of amide derivatives from electron deficient amines and functionalized carboxylic acids using EDC and DMAP and a catalytic amount of HOBt as the coupling reagents》, the research content is summarized as follows. A convenient protocol for amide bond formation for electron deficient amines and carboxylic acids was described. Amide coupling of aniline derivatives was investigated with a number of reagents under a variety of reaction conditions. The use of 1 equiv of EDC and 1 equiv of DMAP, catalytic amount of HOBt and DIPEA provided the best results. This method is applicable for the synthesis of a range of functionalized amide derivatives with electron deficient and unreactive amines.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Garbacz, Mateusz team published research on Organic & Biomolecular Chemistry in 2021 | 84358-13-4

84358-13-4, N-BOC-piperidine-4-carboxylic acid, also known asN-Boc-isonipecotic acid , is a useful research compound. Its molecular formula is C11H19NO4 and its molecular weight is 229,28 g/mole. The purity is usually 95%.

Piperidine the name comes from the genus name Piper, which is the Latin word for pepper. 84358-13-4, formula is C11H19NO4, Name is 1-(tert-Butoxycarbonyl)piperidine-4-carboxylic acid. Although piperidine is a common organic compound, it is best known as a representative structure element within many pharmaceuticals and alkaloids, such as natural-occurring solenopsins. SDS of cas: 84358-13-4.

Garbacz, Mateusz;Stecko, Sebastian research published 《 Synthesis of chiral branched allylamines through dual photoredox/nickel catalysis》, the research content is summarized as follows. This work describes a new approach for the preparation of allylamines, e.g., (S,E)-Et 7-((tert-butoxycarbonyl)amino)oct-5-enoate via cross-coupling of alkyl bromides, e.g., Et 4-bromobutanoate with simple 3-bromoallylamines, e.g., N-Boc (S,E)-4-bromobut-3-en-2-amine by merging the photoredox approach and Ni catalysis. The reaction proceeds under mild conditions, under blue light irradiation, and in the presence of an organic dye, 4CzIPN, as a photocatalyst. The scope of suitable reaction partners is broad, including alkyl bromides bearing reactive functionalities (e.g., esters, nitriles, aldehydes, ketones, epoxides) and N-protected allylamines, as well as N-allylated secondary and tertiary amines and heterocycles. The employment of non-racemic starting materials allows for rapid and easy construction of complex multifunctional allylamine derivatives without the loss of enantiomeric purity.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Gao, Yuanyu team published research on ChemistrySelect in 2021 | 84358-13-4

Computed Properties of 84358-13-4, N-BOC-piperidine-4-carboxylic acid, also known asN-Boc-isonipecotic acid , is a useful research compound. Its molecular formula is C11H19NO4 and its molecular weight is 229,28 g/mole. The purity is usually 95%.

Gao, Yuanyu;Liu, Yuanbai;Iqbal, Zafar;Sun, Jian;Ji, Jinbo;Zhai, Lijuan;Tang, Dong;Ji, Jingwen;He, Lili;Mu, Yangxiu;Yang, Haikang;Yang, Zhixiang research published 《 Amidine Derivatives of Avibactam: Synthesis and In Vitro β-Lactamase Inhibition Activity》, the research content is summarized as follows. Avibactam is a non-β-lactam based second generation β-lactamase inhibitor containing diazabicyclooctane (DBO) ring as β-lactam mimic. The C2 position of DBO scaffold was substituted by a number of amidine derivatives to form water soluble final compounds I [R¹ = CH₂NH₂, 4-thiazolyl, cyclohexylmethyl, 3-pyridylmethyl, etc.]. The synthesized compounds were evaluated for their antibacterial and synergistic activity in combination with an antibiotic in vitro. The compounds, were tested against ten bacterial strains alone and in combination with existing antibiotic, meropenem. All compounds didn’t showed antibacterial activity when alone (MIC, >128μM), however exhibited moderate to good synergistic activity in presence of meropenem by lowering its MIC values. Compound I [R¹ = (4-methylpiperazin-1-yl)methyl] proved most potent among other counterparts against all bacterial species with MIC from <0.29μM to 2.34μM, and showed comparable or improved activity to avibactam against eight bacterial strains. Compound I [R¹ = (4-methylpiperazin-1-yl)methyl] may prove a lead for next level in vivo and clin. studies.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Deng, Xiao-Jun team published research on Journal of Organic Chemistry in 2021 | 84358-13-4

Reference of 84358-13-4, N-BOC-piperidine-4-carboxylic acid, also known asN-Boc-isonipecotic acid , is a useful research compound. Its molecular formula is C11H19NO4 and its molecular weight is 229,28 g/mole. The purity is usually 95%.

Industrially, piperidine is produced by the hydrogenation of pyridine, usually over a molybdenum disulfide catalyst: C5H5N + 3 H2 → C5H10NH. 84358-13-4, formula is C11H19NO4, Name is 1-(tert-Butoxycarbonyl)piperidine-4-carboxylic acid. Pyridine can also be reduced to piperidine via a modified Birch reduction using sodium in ethanol. Reference of 84358-13-4.

Deng, Xiao-Jun;Liu, Hui-Xia;Zhang, Lu-Wen;Zhang, Guan-Yu;Yu, Zhi-Xiang;He, Wei research published 《 Iodoarene-Catalyzed Oxyamination of Unactivated Alkenes to Synthesize 5-Imino-2-Tetrahydrofuranyl Methanamine Derivatives》, the research content is summarized as follows. Reported here is the room-temperature metal-free iodoarene-catalyzed oxyamination of unactivated alkenes. In this process, the alkenes are difunctionalized by the oxygen atom of the amide group and the nitrogen in an exogenous HNTs₂ mol. This mild and open-air reaction provided an efficient synthesis to N-bistosyl-substituted 5-imino-2-tetrahydrofuranyl methanamine derivatives, which are important motifs in drug development and biol. studies. Mechanistic study based on experiments and d. functional theory calculations showed that this transformation proceeds via activation of the substrate alkene by an in situ generated cationic iodonium(III) intermediate, which is subsequently attacked by an oxygen atom (instead of nitrogen) of amides to form a five-membered ring intermediate. Finally, this intermediate undergoes an S_N2 reaction by NTs₂ as the nucleophile to give the oxygen and nitrogen difunctionalized 5-imino-2-tetrahydrofuranyl methanamine product. An asym. variant of the present alkene oxyamination using chiral iodoarenes as catalysts also gave promising results for some of the substrates.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Cox, Brian team published research on ACS Medicinal Chemistry Letters in 2020 | 84358-13-4

Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH2–) and one amine bridge (–NH–). 84358-13-4, formula is C11H19NO4, Name is 1-(tert-Butoxycarbonyl)piperidine-4-carboxylic acid. It is a colorless liquid with an odor described as objectionable, and typical of amines. Synthetic Route of 84358-13-4.

Cox, Brian;Duffy, James;Zdorichenko, Victor;Bellanger, Corentin;Hurcum, Jessica;Laleu, Benoit;Booker-Milburn, Kevin I.;Elliott, Luke D.;Robertson-Ralph, Michael;Swain, Christopher J.;Bishop, Stephen J.;Hallyburton, Irene;Anderson, Mark research published 《 Escaping from Flatland: Antimalarial Activity of sp³-Rich Bridged Pyrrolidine Derivatives》, the research content is summarized as follows. Synthetic photochem. to generate novel sp3-rich scaffolds and report the design, synthesis, and biol. testing of a diverse series of amides based on the 1-(amino-methyl)-2-benzyl-2-aza-bicyclo[2.1.1]hexane scaffold was utilized . Preliminary antimalarial screening of the library provided promising compounds with activity in the 1-5μM range with an enhanced hit rate. Further evaluation (solubility, drug metabolism and pharmacokinetics (DMPK), and toxicity) of a selected compound (9) suggested that this series represents an excellent opportunity for further optimization with the framework offering multiple opportunities for the addition of uniquely vectorally positioned extra functionality.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Dai, Jian-Jun team published research on Chinese Chemical Letters in 2022 | 84358-13-4

Related Products of 84358-13-4, N-BOC-piperidine-4-carboxylic acid, also known asN-Boc-isonipecotic acid , is a useful research compound. Its molecular formula is C11H19NO4 and its molecular weight is 229,28 g/mole. The purity is usually 95%.

Piperidine was first reported in 1850 by the Scottish chemist Thomas Anderson and again, independently, in 1852 by the French chemist 84358-13-4, formula is C11H19NO4, Name is 1-(tert-Butoxycarbonyl)piperidine-4-carboxylic acid. Auguste Cahours, who named it. Both of them obtained piperidine by reacting piperine with nitric acid. Related Products of 84358-13-4.

Dai, Jian-Jun;Teng, Xin-Xin;Fang, Wen;Xu, Jun;Xu, Hua-Jian research published 《 Electrochemically promoted decarboxylative borylation of alkyl N-hydroxyphthalimide esters》, the research content is summarized as follows. An electrochem. promoted decarboxylative borylation reaction is reported. The reaction proceeds under mild conditions in an undivided cell without use of transition metal- or photo-catalysts. The key feature of the reaction is the compatibility of diboron reagents with the electrochem. conditions. This reaction exhibits broad substrate scope, good functional group tolerability, and easy scalability.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Delgado, Jose A. C. team published research on Organic Letters in 2021 | 84358-13-4

Delgado, Jose A. C.;Correia, Jose T. M.;Pissinati, Emanuele F.;Paixao, Marcio W. research published 《 Biocompatible photoinduced alkylation of dehydroalanine for the synthesis of unnatural α-amino acids》, the research content is summarized as follows. A site-selective alkylation of dehydroalanine to access protected unnatural amino acids is described. The protocol is characterized by the wide nature of alkyl radicals employed, mild conditions, and functional group compatibility. This protocol is further extended to access peptides, late-stage functionalization of pharmaceuticals, and enantioenriched amino acids.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Dombrowski, Amanda W. team published research on ACS Medicinal Chemistry Letters in 2020 | 84358-13-4

Recommanded Product: 1-(tert-Butoxycarbonyl)piperidine-4-carboxylic acid, N-BOC-piperidine-4-carboxylic acid, also known asN-Boc-isonipecotic acid , is a useful research compound. Its molecular formula is C11H19NO4 and its molecular weight is 229,28 g/mole. The purity is usually 95%.

Dombrowski, Amanda W.;Gesmundo, Nathan J.;Aguirre, Ana L.;Sarris, Katerina A.;Young, Jonathon M.;Bogdan, Andrew R.;Martin, M. Cynthia;Gedeon, Shasline;Wang, Ying research published 《 Expanding the Medicinal Chemist Toolbox: Comparing Seven C(sp²)-C(sp³) Cross-Coupling Methods by Library Synthesis》, the research content is summarized as follows. Despite recent advances in the field of C(sp²)-C(sp³) cross-couplings and the accompanying increase in publications, it can be hard to determine which method is appropriate for a given reaction when using the highly functionalized intermediates prevalent in medicinal chem. Thus a study was done comparing the ability of seven methods to directly install a diverse set of alkyl groups on “drug-like” aryl structures via parallel library synthesis. Each method showed substrates that it excelled at coupling compared with the other methods. When analyzing the reactions run across all of the methods, a reaction success rate of 50% was achieved. Whereas this is promising, there are still gaps in the scope of direct C(sp²)-C(sp³) coupling methods, like tertiary group installation. The results reported herein should be used to inform future syntheses, assess reaction scope, and encourage medicinal chemists to expand their synthetic toolbox.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Duan, Shengzu team published research on Chemical Science in 2022 | 84358-13-4

Duan, Shengzu;Zi, Yujin;Wang, Lingling;Cong, Jielun;Chen, Wen;Li, Minyan;Zhang, Hongbin;Yang, Xiaodong;Walsh, Patrick J. research published 《 α-Branched amines through radical coupling with 2-azaallyl anions, redox active esters and alkenes》, the research content is summarized as follows. Herein, a unique cascade reaction that enables the preparation of α-branched amines I (R = Me, Ad, oxan-4-ylmethyl, etc.; R¹ = H, Me, Ph; R² = Ph; R¹R² = -(CH₂)₂CH(Ph)(CH₂)₂-; R³ = H, Me; R⁴ = Ph, 4-chlorophenyl, furan-3-yl, etc.) and 3-methyl-1,2,2-triphenylpentan-1-amine bearing aryl or alkyl groups at the β- or γ-positions is reported. The cascade is initiated by reduction of redox active esters II to alkyl radicals. The resulting alkyl radicals are trapped by styrene derivatives, R¹C(R²)=CHR³ leading to benzylic radicals. The persistent 2-azaallyl radicals and benzylic radicals are proposed to undergo a radical-radical coupling leading to functionalized amine products I and 3-methyl-1,2,2-triphenylpentan-1-amine. Evidence is provided that the role of the nickel catalyst is to promote formation of the alkyl radical from the redox active ester and not promote the C-C bond formation. The synthetic method introduced herein tolerates a variety of imines III and redox active esters II, allowing for efficient construction of amine building blocks.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem