Heterocyclic Building Blocks-piperidine

Synthetic Route of C9H17NOOn March 24, 2020, Tanaka, Susumu; Enoki, Toshiaki; Imoto, Hiroaki; Ooyama, Yousuke; Ohshita, Joji; Kato, Takuji; Naka, Kensuke published an article in Macromolecules (Washington, DC, United States). The article was 《Highly Efficient Singlet Oxygen Generation and High Oxidation Resistance Enhanced by Arsole-Polymer-Based Photosensitizer: Application as a Recyclable Photooxidation Catalyst》. The article mentions the following:

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. In the experimental materials used by the author, we found Triacetonamine(cas: 826-36-8Synthetic Route of C9H17NO)

Triacetonamine(cas: 826-36-8) is a member of piperidine. Piperidine-containing compounds are also frequently employed in synthesis as ligands or auxiliaries. Accordingly, many efforts have been devoted to the development of novel methods for the synthesis of these compounds over the years.Synthetic Route of C9H17NO

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Ishag, Abd Elaziz Sulieman Ahmed; Abdelbagi, Azhari Omer; Hammad, Ahmed Mohammed Ali; Elsheikh, Elsiddig Ahmed Elmustafa; Hur, Jang-Hyun published an article on February 28 ,2019. The article was titled 《Photodegradation of chlorpyrifos, malathion, and dimethoate by sunlight in the Sudan》, and you may find the article in Environmental Earth Sciences.Application In Synthesis of Triacetonamine The information in the text is summarized as follows:

The potential of sunlight photolysis in remediation of pesticide-polluted soils in Sudan was studied. Chlorpyrifos, malathion and dimethoate, common pollutants, were exposed to sunlight over glass and soil surfaces with periodic samples drawn for GC and GC-MS anal. Photo-degradation followed a biphasic model. Alpha half-lives of direct photolysis over glass surface range between 1.99 and 9.36 days while the range in soil surfaces is 1.88-10.77 days. Resp. values for indirect photolysis with βcarotene are 0.96-2.40 days whereas for benzophenone are 0.38-2.37 days (not including malathion as starting material was completely lost after 3 days). Values for soil β-carotene sensitized photolysis are 0.85-4.02 days while resp. values for soil benzophenone sensitized photolysis are 0.88-3.74 days. Metrol. factors did not have a significant impact on photolysis rates. No photoproducts detected in direct photolysis. However, many photoproducts were detected on the indirect sets. Photo-degradation efficiency can be ordered as; benzophenone > β-carotene > direct exposure. In the experiment, the researchers used many compounds, for example, Triacetonamine(cas: 826-36-8Application In Synthesis of Triacetonamine)

Triacetonamine(cas: 826-36-8) is a member of piperidine. Piperidine is a key saturated heterocyclic scaffold found in several of the top-selling small molecule pharmaceuticals and natural alkaloids, with a diverse range of biological activities. Hence, continuous efforts have been made to develop convenient methods to prepare piperidine derivatives.Application In Synthesis of Triacetonamine

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Liao, Chenzhong; Nicklaus, Marc C. published their research in Journal of Chemical Information and Modeling on December 31 ,2009. The article was titled 《Comparison of Nine Programs Predicting pKa Values of Pharmaceutical Substances》.Reference of Methyl 1-methylpiperidine-3-carboxylate The article contains the following contents:

Knowledge of the possible ionization states of a pharmaceutical substance, embodied in the pKa values (logarithm of the acid dissociation constant), is vital for understanding many properties essential to drug development. We compare nine com. available or free programs for predicting ionization constants Eight of these programs are based on empirical methods: ACD/pKa DB 12.0, ADME Boxes 4.9, ADMET Predictor 3.0, Epik 1.6, Marvin 5.1.4, Pallas pKalc Net 2.0, Pipeline Pilot 5.0, and SPARC 4.2; one program is based on a quantum chem. method: Jaguar 7.5. We compared their performances by applying them to 197 pharmaceutical substances with 261 carefully determined and highly reliable exptl. pKa values from a literature source. The programs ADME Boxes 4.9, ACD/pKa DB 12.0, and SPARC 4.2 ranked as the top three with mean absolute deviations of 0.389, 0.478, and 0.651 and r2 values of 0.944, 0.908, and 0.894, resp. ACD/pKa DB 12.0 predicted all sites, whereas ADME Boxes 4.9 and SPARC 4.2 failed to predict 5 and 18 sites, resp. The performance of the quantum chem.-based program Jaguar 7.5 was not as expected, with a mean absolute deviation of 1.283 and an r2 value of 0.579, indicating the potential for further development of this type of approach to pKa prediction. In the part of experimental materials, we found many familiar compounds, such as Methyl 1-methylpiperidine-3-carboxylate(cas: 1690-72-8Reference of Methyl 1-methylpiperidine-3-carboxylate)

Methyl 1-methylpiperidine-3-carboxylate(cas: 1690-72-8) is a member of piperidine. Piperidine-containing compounds are also frequently employed in synthesis as ligands or auxiliaries. Accordingly, many efforts have been devoted to the development of novel methods for the synthesis of these compounds over the years.Reference of Methyl 1-methylpiperidine-3-carboxylate

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Liu, Li; Li, Yuxin; Pang, Yaqian; Lan, Yeqing; Zhou, Lixiang published their research in Chemical Engineering Journal (Amsterdam, Netherlands) on December 1 ,2020. The article was titled 《Activation of peroxymonosulfate with CuCo2O4@kaolin for efficient degradation of phenacetin》.Quality Control of Triacetonamine The article contains the following contents:

CuCo2O4@kaolin was successfully synthesized by a sol-gel method and used as a heterogeneous catalyst to activate peroxymonosulfate (PMS) for the degradation of phenacetin (PNT). The results demonstrated that 10 mg/L PNT was completely decomposed by 1 mM PMS activated with 0.1 g/L CuCo2O4@kaolin within 15 min at initial pH 7. CuCo2O4@kaolin exhibited the best excellent catalytic performance among the tested catalysts, and the pseudo-first-order rate constants of PNT degradation were CuCo2O4@kaolin (0.40 min-1) > CuCo2O4 (0.22 min-1) > Co3O4@kaolin (0.10 min-1) > CuO@kaolin (0.08 min-1) > kaolin (0.02 min-1). CuCo2O4@kaolin also possessed superior stability, and the degradation efficiency of PNT declined from 100% in the first round to 80% in the fourth round. Nevertheless, a simple calcinating treatment (20 min) after the third round could restore its catalytic activity substantially and 95% removal of PNT was realized, 15% higher compared to without treatment. ·OH, SO4·-, and 1O2 were the reactive oxygen species driving the PNT degradation Based on the results mentioned above, characterizations of CuCo2O4@kaolin, and intermediates of PNT degradation, the possible pathways and underlying mechanisms of the PNT degradation in the CuCo2O4@kaolin/PMS system were deduced. CuCo2O4@kaolin/PMS had a universal degradation potential toward various organic pollutants, and the degradation efficiencies of sulfisoxazole, p-nitrophenol, chloramphenicol, and 2,4,6-Trichlorophenol reached 95-100% within 5-45 min. Thus, this work provides a novel and efficient PMS activator through an eco-friendly synthetic route, and it may be put into practice to degrade organic matter in wastewater.Triacetonamine(cas: 826-36-8Quality Control of Triacetonamine) was used in this study.

Triacetonamine(cas: 826-36-8) is a member of piperidine. Piperidine-containing compounds are also frequently employed in synthesis as ligands or auxiliaries. Accordingly, many efforts have been devoted to the development of novel methods for the synthesis of these compounds over the years.Quality Control of Triacetonamine

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

The author of 《One-pot synthesis of novel tert-butyl-4-substituted phenyl-1H-1,2,3-triazolo piperazine/piperidine carboxylates, potential GPR119 agonists》 were Bashetti, Nagaraju; Shanmukha Kumar, J. V.; Seelam, Naresh Varma; Prasanna, B.; Mintz, Akiva; Damuka, Naresh; Devanathan, Sriram; Solingapuram Sai, Kiran Kumar. And the article was published in Bioorganic & Medicinal Chemistry Letters in 2019. Reference of tert-Butyl 4-hydroxypiperidine-1-carboxylate The author mentioned the following in the article:

We have synthesized a new series of 1,2,3-triazolo piperazine and piperidine carboxylate derivatives using a simple and one-pot click chem. with significantly reduced reaction times (∼5 min) and enhanced reaction yields (∼95-98%). The fourteen novel compounds thus synthesized were tested for ability to target GPR119, a G-protein coupled target receptor that plays critical role in regulation of type-2 diabetes mellitus. Four analogs demonstrated similar or better EC50 values over previously reported AR231453 activity towards GPR119. The experimental process involved the reaction of tert-Butyl 4-hydroxypiperidine-1-carboxylate(cas: 109384-19-2Reference of tert-Butyl 4-hydroxypiperidine-1-carboxylate)

tert-Butyl 4-hydroxypiperidine-1-carboxylate(cas:109384-19-2) is a 4-hydroxypyridine with a boc protecting group used in the preparation of neurologically active agents and other pharmaceutical compounds.Reference of tert-Butyl 4-hydroxypiperidine-1-carboxylate

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

《Photocatalytic α-Tertiary Amine Synthesis via C-H Alkylation of Unmasked Primary Amines》 was written by Ryder, Alison S. H.; Cunningham, William B.; Ballantyne, George; Mules, Tom; Kinsella, Anna G.; Turner-Dore, Jacob; Alder, Catherine M.; Edwards, Lee J.; McKay, Blandine S. J.; Grayson, Matthew N.; Cresswell, Alexander J.. Product Details of 87120-72-7 And the article was included in Angewandte Chemie, International Edition in 2020. The article conveys some information:

A practical, catalytic entry to α,α,α-trisubstituted (α-tertiary) primary amines by C-H functionalization has long been recognized as a critical gap in the synthetic toolbox. The authors report a simple and scalable solution to this problem that does not require any in situ protection of the amino group and proceeds with 100% atom-economy. The authors’ strategy, which uses an organic photocatalyst in combination with azide ion as a hydrogen atom transfer (HAT) catalyst, provides a direct synthesis of α-tertiary amines, or their corresponding γ-lactams. The authors anticipate that this methodol. will inspire new retrosynthetic disconnections for substituted amine derivatives in organic synthesis, and particularly for challenging α-tertiary primary amines. In the part of experimental materials, we found many familiar compounds, such as tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7Product Details of 87120-72-7)

tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7) belongs to anime. Acylation is one of the most important reactions of primary and secondary amines; a hydrogen atom is replaced by an acyl group (a group derived from an acid, such as RCOOH or RSO3H, by removal of ―OH, such as RC(=O)―, RS(O)2―, and so on). Reagents may be acid chlorides (RCOC1, RSO2C1), anhydrides ((RCO)2O), or even esters (RCOOR′); the products are amides of the corresponding acids.Product Details of 87120-72-7

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Blackwell, J. Henry; Kumar, Roopender; Gaunt, Matthew J. published their research in Journal of the American Chemical Society in 2021. The article was titled 《Visible-Light-Mediated Carbonyl Alkylative Amination to All-Alkyl α-Tertiary Amino Acid Derivatives》.Product Details of 87120-72-7 The article contains the following contents:

The all-alkyl α-tertiary amino acid scaffold represents an important structural feature in many biol. and pharmaceutically relevant mols. Syntheses of this class of mol., however, often involve multiple steps and require activating auxiliary groups on the nitrogen atom or tailored building blocks. A straightforward, single-step, and modular methodol. for the synthesis of all-alkyl α-tertiary amino esters was reported. This new strategy uses visible light and a silane reductant to bring about a carbonyl alkylative amination reaction that combines a wide range of primary amines, α-ketoesters, and alkyl iodides to form functionally diverse all-alkyl α-tertiary amino esters. Bronsted acid-mediated in situ condensation of primary amine and α-ketoester delivers the corresponding ketiminium species, which undergoes rapid 1,2-addition of an alkyl radical (generated from an alkyl iodide by the action of visible light and silane reductant) to form an aminium radical cation. Upon a polarity-matched and irreversible hydrogen atom transfer from electron rich silane, the electrophilic aminium radical cation is converted to an all-alkyl α-tertiary amino ester product. The benign nature of this process allows for broad scope in all three components and generates structurally and functionally diverse suite of α-tertiary amino esters that will likely have widespread use in academic and industrial settings. In the part of experimental materials, we found many familiar compounds, such as tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7Product Details of 87120-72-7)

tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7) belongs to anime.Typically the presence of an amine functional group is deduced by a combination of techniques, including mass spectrometry as well as NMR and IR spectroscopies. 1H NMR signals for amines disappear upon treatment of the sample with D2O. In their infrared spectrum primary amines exhibit two N-H bands, whereas secondary amines exhibit only one.Product Details of 87120-72-7

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Kostrzewa, Tomasz; Wolosewicz, Karol; Jamrozik, Marek; Drzezdzon, Joanna; Sieminska, Julia; Jacewicz, Dagmara; Gorska-Ponikowska, Magdalena; Kolaczkowski, Marcin; Lazny, Ryszard; Kuban-Jankowska, Alicja published their research in International Journal of Molecular Sciences in 2021. The article was titled 《Curcumin and Its New Derivatives: Correlation between Cytotoxicity against Breast Cancer Cell Lines, Degradation of PTP1B Phosphatase and ROS Generation》.Electric Literature of C6H11NO The article contains the following contents:

Breast cancer is the most common cancer of women-it affects more than 2 million women worldwide. PTP1B phosphatase can be one of the possible targets for new drugs in breast cancer therapy. In this paper, we present new curcumin derivatives featuring a 4-piperidone ring as PTP1B inhibitors and ROS inducers. We performed cytotoxicity anal. for twelve curcumin derivatives against breast cancer MCF-7 and MDA-MB-231 cell lines and the human keratinocyte HaCaT cell line. Furthermore, because curcumin is a known antioxidant, we assessed antioxidant effects in its derivatives For the most potent cytotoxic compounds, we determined intracellular ROS and PTP1B phosphatase levels. Moreover, for curcumin and its derivatives, we performed real-time microscopy to observe the photosensitizing effect. Finally, computational anal. was performed for the curcumin derivatives with an inhibitory effect against PTP1B phosphatase to assess the potential binding mode of new inhibitors within the allosteric site of the enzyme. We observed that two tested compounds are better anticancer agents than curcumin. Moreover, we suggest that blocking the -OH group in phenolic compounds causes an increase in the cytotoxicity effect, even at a low concentration Furthermore, due to this modification, a higher level of ROS is induced, which correlates with a lower level of PTP1B. The results came from multiple reactions, including the reaction of 1-Methyl-4-piperidone(cas: 1445-73-4Electric Literature of C6H11NO)

1-Methyl-4-piperidone(cas: 1445-73-4) is a member of piperidine. Piperidine is a key saturated heterocyclic scaffold found in several of the top-selling small molecule pharmaceuticals and natural alkaloids, with a diverse range of biological activities. Hence, continuous efforts have been made to develop convenient methods to prepare piperidine derivatives.Electric Literature of C6H11NO

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Berger, Kathleen J.; Driscoll, Julia L.; Yuan, Mingbin; Dherange, Balu D.; Gutierrez, Osvaldo; Levin, Mark D. published their research in Journal of the American Chemical Society in 2021. The article was titled 《Direct Deamination of Primary Amines via Isodiazene Intermediates》.Name: tert-Butyl 4-aminopiperidine-1-carboxylate The article contains the following contents:

A reaction that selectively deaminated primary amines and anilines under mild conditions and with remarkable functional group tolerance including a range of pharmaceutical compounds, amino acids, amino sugars, and natural products was reported. An anomeric amide reagent was uniquely capable of facilitating the reaction through the intermediacy of an unprecedented monosubstituted isodiazene intermediate. In addition to dramatically simplifying deamination compared to existing protocols, this approach enabled strategic applications of iminium and amine-directed chemistries as traceless methods. Mechanistic and computational studies supported the intermedicacy of a primary isodiazene which exhibited an unexpected divergence from previously studied secondary isodiazenes, leading to cage-escaping, free radical species that engage in a chain, hydrogen-atom transfer process involving aliphatic and diazenyl radical intermediates. In the experimental materials used by the author, we found tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7Name: tert-Butyl 4-aminopiperidine-1-carboxylate)

tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7) belongs to anime. Many important products require amines as part of their syntheses. Methylamine is utilized in the production of the analgesic meperidine (trade name Demerol) and the photographic developer Metol (trademark), and dimethylamine is used in the synthesis of the antihistamine diphenhydramine (trade name Benadryl), the solvent dimethylformamide (DMF), and the rocket propellant 1,1-dimethylhydrazine. The synthesis of the insect repellent N,N-diethyl-m-toluamide (DEET) incorporates diethylamine while that of the synthetic fibre Kevlar requires aromatic amines.Name: tert-Butyl 4-aminopiperidine-1-carboxylate

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

In 2022,Nakagawa, Masanari; Matsuki, Yuki; Nagao, Kazunori; Ohmiya, Hirohisa published an article in Journal of the American Chemical Society. The title of the article was 《A Triple Photoredox/Cobalt/Bronsted Acid Catalysis Enabling Markovnikov Hydroalkoxylation of Unactivated Alkenes》.Application of 109384-19-2 The author mentioned the following in the article:

Authors demonstrate Markovnikov hydroalkoxylation of unactivated alkenes using alcs. through a triple catalysis consisting of photoredox, cobalt, and Bronsted acid catalysts under visible light irradiation The triple catalysis realizes three key elementary steps in a single catalytic cycle: (1) Co(III) hydride generation by photochem. reduction of Co(II) followed by protonation, (2) metal hydride hydrogen atom transfer (MHAT) of alkenes by Co(III) hydride, and (3) oxidation of the alkyl Co(III) complex to alkyl Co(IV). The precise control of protons and electrons by the three catalysts allows the elimination of strong acids and external reductants/oxidants that are required in the conventional methods. After reading the article, we found that the author used tert-Butyl 4-hydroxypiperidine-1-carboxylate(cas: 109384-19-2Application of 109384-19-2)

tert-Butyl 4-hydroxypiperidine-1-carboxylate(cas:109384-19-2) is a 4-hydroxypyridine with a boc protecting group used in the preparation of neurologically active agents and other pharmaceutical compounds.Application of 109384-19-2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem