Tag: 200-300

Red-Light-Mediated Barton-McCombie Reaction was written by Ogura, Akihiro;Ichii, Naoki;Shibata, Kouhei;Takao, Ken-ichi. And the article was included in Bulletin of the Chemical Society of Japan in 2020.SDS of cas: 33439-27-9 This article mentions the following:

A red-light-mediated Barton-McCombie reaction is described, in which chlorophyll a is used as a photocatalyst and tris(trimethylsilyl)silane or Hantzsch ester is used as the hydrogen source. The reaction can be performed with a set of easily available equipment and reagents, and a variety of linear and cyclic xanthates could be applied. In contrast to the traditional conditions, the reaction does not involve toxic organotin or an explosive radical initiator. The reaction mechanism was analyzed both by experiments and computation, and it was suggested that the radical chain mechanism initiated by excitation of complex followed by charge transfer is likely to be operative. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9SDS of cas: 33439-27-9).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. The piperidine ring can be found not only in more than half of the currently known structures of alkaloids, but also in many natural or synthetic compounds with interesting biological activities. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.SDS of cas: 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Hindered dialkyl ether synthesis with electrogenerated carbocations was written by Xiang, Jinbao;Shang, Ming;Kawamata, Yu;Lundberg, Helena;Reisberg, Solomon H.;Chen, Miao;Mykhailiuk, Pavel;Beutner, Gregory;Collins, Michael R.;Davies, Alyn;Del Bel, Matthew;Gallego, Gary M.;Spangler, Jillian E.;Starr, Jeremy;Yang, Shouliang;Blackmond, Donna G.;Baran, Phil S.. And the article was included in Nature (London, United Kingdom) in 2019.Quality Control of Benzyl 3-hydroxypiperidine-1-carboxylate This article mentions the following:

Hindered ethers are of high value for various applications; however, they remain an underexplored area of chem. space because they are difficult to synthesize via conventional reactions. Such motifs are highly coveted in medicinal chem., because extensive substitution about the ether bond prevents unwanted metabolic processes that can lead to rapid degradation in vivo. Here we report a simple route towards the synthesis of hindered ethers, in which electrochem. oxidation is used to liberate high-energy carbocations from simple carboxylic acids. These reactive carbocation intermediates, which are generated with low electrochem. potentials, capture an alc. donor under non-acidic conditions; this enables the formation of a range of ethers (more than 80 have been prepared here) that would otherwise be difficult to access. The carbocations can also be intercepted by simple nucleophiles, leading to the formation of hindered alcs. and even alkyl fluorides. This method was evaluated for its ability to circumvent the synthetic bottlenecks encountered in the preparation of 12 chem. scaffolds, leading to higher yields of the required products, in addition to substantial reductions in the number of steps and the amount of labor required to prepare them. The use of mol. probes and the results of kinetic studies support the proposed mechanism and the role of additives under the conditions examined The reaction manifold that we report here demonstrates the power of electrochem. to access highly reactive intermediates under mild conditions and, in turn, the substantial improvements in efficiency that can be achieved with these otherwise-inaccessible intermediates. In the experiment, the researchers used many compounds, for example, Benzyl 3-hydroxypiperidine-1-carboxylate (cas: 95798-22-4Quality Control of Benzyl 3-hydroxypiperidine-1-carboxylate).

Benzyl 3-hydroxypiperidine-1-carboxylate (cas: 95798-22-4) belongs to piperidine derivatives. Piperidine and its derivatives have become increasingly popular in many synthetic schemes. The piperidine and polyhydroxylated indolizidine derivatives have shown to be promising α-glucosidase inhibitors. The former are analogs of DNJ with an improved α-glucosidase inhibitory profile than that of DNJ. Boisson et al.Quality Control of Benzyl 3-hydroxypiperidine-1-carboxylate

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Site-Specific Alkene Hydromethylation via Protonolysis of Titanacyclobutanes was written by Law, James A.;Bartfield, Noah M.;Frederich, James H.. And the article was included in Angewandte Chemie, International Edition in 2021.Application In Synthesis of 1-Tosylpiperidin-4-one This article mentions the following:

Me groups are ubiquitous in biol. active mols. Thus, new tactics to introduce this alkyl fragment into polyfunctional structures are of significant interest. With this goal in mind, a direct method for the Markovnikov hydromethylation of alkenes is reported. This method exploits the degenerate metathesis reaction between the titanium methylidene unveiled from Cp₂Ti(μ-Cl)(μ-CH₂)AlMe₂ (Tebbe’s reagent) and unactivated alkenes. Protonolysis of the resulting titanacyclobutanes in situ effects hydromethylation in a chemo-, regio-, and site-selective manner. The broad utility of this method is demonstrated across a series of mono- and di-substituted alkenes containing pendant alcs., ethers, amides, carbamates, and basic amines. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Application In Synthesis of 1-Tosylpiperidin-4-one).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. Piperidine is a saturated organic heteromonocyclic parent, an azacycloalkane, a secondary amine and a member of piperidines. The piperidine and polyhydroxylated indolizidine derivatives have shown to be promising α-glucosidase inhibitors. The former are analogs of DNJ with an improved α-glucosidase inhibitory profile than that of DNJ. Boisson et al.Application In Synthesis of 1-Tosylpiperidin-4-one

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Chiral amino-amides as solution phase and immobilized ligands for the catalytic asymmetric alkylation of aromatic aldehydes was written by Lesma, Giordano;Danieli, Bruno;Passarella, Daniele;Sacchetti, Alessandro;Silvani, Alessandra. And the article was included in Letters in Organic Chemistry in 2006.Formula: C12H15NO3S This article mentions the following:

Novel chiral amino-amide 9-keto-bispidines are investigated as ligands in the addition reaction of diethylzinc to aromatic aldehydes. The ligands are easily obtained by a single-step procedure starting from com. available products. Selected ligands were also supported onto different insoluble resins in order to test their activity as heterogeneous catalysts. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Formula: C12H15NO3S).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. Piperidine is a metabolite of cadaverine, a polyamine found in the human intestine. Fluorinated piperidines are also the subject of continued interest in medicinal chemistry, for example in the synthesis of selective dipeptidyl peptidase II (DPP II) inhibitors. Piperidine derivatives are also used in solid-phase peptide synthesis (SPPS) and many degradation reactions.Formula: C12H15NO3S

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Modular Photocatalytic Synthesis of α-Trialkyl-α-Tertiary Amines was written by Henry Blackwell, J.;Harris, Georgia R.;Smith, Milo A.;Gaunt, Matthew J.. And the article was included in Journal of the American Chemical Society.Category: piperidines This article mentions the following:

Here, authors report an operationally straightforward, multicomponent protocol for the synthesis of a range of functionally and structurally diverse α-trialkyl-α-tertiary amines, which makes use of three readily available components: dialkyl ketones, benzylamines, and alkenes. The strategy relies on the of use visible-light-mediated photocatalysis with readily available Ir(III) complexes to bring about single-electron reduction of an all-alkyl ketimine species to an α-amino radical intermediate; the α-amino radical undergoes Giese-type addition with a variety of alkenes to forge the α-trialkyl-α-tertiary amine center. The mechanism of this process is believed to proceed through an overall redox neutral pathway that involves photocatalytic redox-relay of the imine, generated from the starting amine-ketone condensation, through to an imine-derived product. This is possible because the presence of a benzylic amine component in the intermediate scaffold drives a 1,5-hydrogen atom transfer step after the Giese addition to form a stable benzylic α-amino radical, which is able to close the photocatalytic cycle. Authors believe this transformation will provide convenient access to previously unexplored α-trialkyl-α-tertiary amine scaffolds that should be of considerable interest to practitioners of synthetic and medicinal chem. in academic and industrial institutions. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Category: piperidines).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives.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. The piperidine and polyhydroxylated indolizidine derivatives have shown to be promising α-glucosidase inhibitors. The former are analogs of DNJ with an improved α-glucosidase inhibitory profile than that of DNJ. Boisson et al.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Efficient and modular synthesis of new structurally diverse functionalized [n]paracyclophanes by a ring-distortion strategy was written by Krieger, Jean-Philippe;Ricci, Gino;Lesuisse, Dominique;Meyer, Christophe;Cossy, Janine. And the article was included in Angewandte Chemie, International Edition in 2014.Recommanded Product: 1-Tosylpiperidin-4-one This article mentions the following:

With the goal of synthesizing new [n]paracyclophanes, the expansion of the scope of a strategy originally disclosed by Winterfeldt et al., was investigated. This approach involves sequential Diels-Alder/retro-Diels-Alder reactions, the applications of which were constrained so far to steroid derivatives An efficient access to new functionalized [9]-, [10]-, and [16]paracyclophanes, including original cage architectures, was developed from readily available building blocks using thermal electrocyclization and a cycloaddition/cycloreversion sequence as the key steps. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Recommanded Product: 1-Tosylpiperidin-4-one).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. Piperidine and its derivatives have become increasingly popular in many synthetic schemes. The piperidine and polyhydroxylated indolizidine derivatives have shown to be promising α-glucosidase inhibitors. The former are analogs of DNJ with an improved α-glucosidase inhibitory profile than that of DNJ. Boisson et al.Recommanded Product: 1-Tosylpiperidin-4-one

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Reactions with arenesulfonyl azides of some indoles with oxygen- and nitrogen-containing substituents was written by Bailey, A. Sydney;Birch, Christopher M.;Illingworth, David;Willmott, Janet C.. And the article was included in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) in 1978.Application In Synthesis of 1-Tosylpiperidin-4-one This article mentions the following:

The pyridoindole I (X = NSO₂C₆H₄Me-4) with 4-RC₆H₄SO₂N₃ (II, R = O₂N) gave 34% spiro compound III. Pyranoindole I (X = O) with II (R = Cl) gave 89% spiro compound IV. Me 1,3-dimethylindole-2-carboxylate with II (R = O₂N) in pyridine was kepy 4 wk at 80° to give Me 1,3-dimethyl-2-(p-nitrophenylsulfonylimino)indoline-3-carboxylate by CO₂Me migration. Me 1,3-dimethyl-2-indoleacetate with II (R = O₂N, Cl) gave the resp. 2-(carbomethoxymethylene)-3-(benzenesulfonamido)indoline derivatives In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Application In Synthesis of 1-Tosylpiperidin-4-one).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. Piperidine and its derivatives have become increasingly popular in many synthetic schemes. Piperidine prefers a chair conformation, similar to cyclohexane. Unlike cyclohexane, piperidine has two distinguishable chair conformations: one with the N–H bond in an axial position, and the other in an equatorial position.Application In Synthesis of 1-Tosylpiperidin-4-one

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Preparation of Indolenines via Nucleophilic Aromatic Substitution was written by Huber, Florian;Roesslein, Joel;Gademann, Karl. And the article was included in Organic Letters in 2019.Electric Literature of C13H16N2 This article mentions the following:

An unusual aromatic substitution to access indolenines is described. 2-(2-Methoxyphenyl)acetonitrile derivatives are reacted with various alkyl and aryl Li reagents to furnish the corresponding indolenine products, constituents of natural products, and cyanine dyes such as indocyanine green. This new method was used to synthesize 41 indolenines with large functional group tolerance, and selected examples were further converted to the corresponding indolenine dyes. Key experiments provide insight into the mechanism of this nucleophilic aromatic substitution. In the experiment, the researchers used many compounds, for example, 1-Benzylpiperidine-4-carbonitrile (cas: 62718-31-4Electric Literature of C13H16N2).

1-Benzylpiperidine-4-carbonitrile (cas: 62718-31-4) belongs to piperidine derivatives. Piperidine is a saturated organic heteromonocyclic parent, an azacycloalkane, a secondary amine and a member of piperidines. The piperidine and polyhydroxylated indolizidine derivatives have shown to be promising α-glucosidase inhibitors. The former are analogs of DNJ with an improved α-glucosidase inhibitory profile than that of DNJ. Boisson et al.Electric Literature of C13H16N2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Design, synthesis and characterization of PROTACs targeting the androgen receptor in prostate and lung cancer models was written by Gockel, Lukas M.;Pfeifer, Vladlena;Baltes, Fabian;Bachmaier, Rafael D.;Wagner, Karl G.;Bendas, Gerd;Guetschow, Michael;Sosic, Izidor;Steinebach, Christian. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 2022.Formula: C10H20ClNO2 This article mentions the following:

Three subgroups of enzalutamide-based PROTACs was presented in which only the exit vector was modified. By recruiting cereblon, the potent degradation of AR in lung cancer cells was demonstrated. Furthermore, the initial evaluation enabled the design of an optimized PROTAC with a rigid linker that degraded AR with a DC₅₀ value in the nanomolar range. These results provide novel AR-directed PROTACs and a clear rationale for further investigating AR involvement in lung cancer models. In the experiment, the researchers used many compounds, for example, tert-Butyl piperidine-4-carboxylate hydrochloride (cas: 892493-65-1Formula: C10H20ClNO2).

tert-Butyl piperidine-4-carboxylate hydrochloride (cas: 892493-65-1) belongs to piperidine derivatives. The piperidine ring can be found not only in more than half of the currently known structures of alkaloids, but also in many natural or synthetic compounds with interesting biological activities. Fluorinated piperidines are also the subject of continued interest in medicinal chemistry, for example in the synthesis of selective dipeptidyl peptidase II (DPP II) inhibitors. Piperidine derivatives are also used in solid-phase peptide synthesis (SPPS) and many degradation reactions.Formula: C10H20ClNO2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Direct and enantioselective α-allylation of ketones via singly occupied molecular orbital (SOMO) catalysis was written by Mastracchio, Anthony;Warkentin, Alexander A.;Walji, Abbas M.;MacMillan, David W. C.. And the article was included in Proceedings of the National Academy of Sciences of the United States of America in 2010.Category: piperidines This article mentions the following:

The first enantioselective organocatalytic α-allylation of cyclic ketones was accomplished via singly occupied MO catalysis. Geometrically constrained radical cations, forged from the one-electron oxidation of transiently generated enamines, readily undergo allylic alkylation with a variety of com. available allylsilanes. A reasonable latitude in both the ketone and allylsilane components is readily accommodated in this new transformation. Moreover, three new oxidatively stable imidazolidinone catalysts have been developed that allow cyclic ketones to successfully participate in this transformation. The new catalyst platform has also been exploited in the first catalytic enantioselective α-oxoalkylation and α-arylalkylation of ketones. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Category: piperidines).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. The piperidine structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper its spicy taste. Several piperidine alkaloids isolated from natural herbs, were found to exhibit antiproliferation and antimetastatic effects on various types of cancers both in vitro and in vivo for example Piperine, Evodiamine, Matrine, Berberine and Tetrandine.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem