Day: January 5, 2023

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

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

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

Structure and activity relationship of 2-(substituted benzoyl)-hydroxyindoles as novel CaMKII inhibitors was written by Komiya, Masafumi;Asano, Shigehiro;Koike, Nobuyuki;Koga, Erina;Igarashi, Junetsu;Nakatani, Shogo;Isobe, Yoshiaki. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2011.Product Details of 4045-22-1 This article mentions the following:

A series of novel 2-substituted-5-hydroxyindoles were synthesized and evaluated for their inhibitory activity against CaMKII. Structure and activity relationship results indicated that potent inhibitory activity could be achieved by modification at the para-position of the Ph ring of the high throughput screening hit compound I. Among the prepared compounds, we identified II as a novel CaMKII inhibitor with an activity stronger than that of KN-93, a known CaMKII inhibitor. In the experiment, the researchers used many compounds, for example, 1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1Product Details of 4045-22-1).

1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1) belongs to piperidine derivatives. The piperidine structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper its spicy taste. Industrially, piperidine is produced by the hydrogenation of pyridine, usually over a molybdenum disulfide catalyst. Pyridine can also be reduced to piperidine via a modified Birch reduction using sodium in ethanol.Product Details of 4045-22-1

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

New μ-opioid receptor agonists with a phenoxyacetic acid moiety was written by Sato, Susumu;Komoto, Teruo;Kanamaru, Yoshihiko;Kawamoto, Noriyuki;Okada, Tomomi;Kaiho, Terurnitsu;Mogi, Kinichi;Morimoto, Shinichi;Umehara, Norimitsu;Koda, Tadayuki;Miyashita, Akira;Sakamoto, Takao;Niino, Yasuhiro;Oka, Tetsuo. And the article was included in Chemical & Pharmaceutical Bulletin in 2002.Synthetic Route of C12H17NO This article mentions the following:

New μ-opioid receptor (MOR) agonists containing 4-hydroxypiperidine, piperidine and piperazine moieties were synthesized and evaluated to find a peripheral opioid analgesic. Among the synthesized compounds, I showed the highest agonist potency on the MOR in an isolated guinea-pig ileum preparation, and it also had selectivity to the human MOR expressed in Chinese hamster ovary (CHO)-K1 cells compared with the same types of δ- and κ-opioid receptors. In addition, compound I showed 10 times more potent MOR agonist activity than loperamide. Furthermore, compound I showed a peripheral analgesic activity in the rat. In the experiment, the researchers used many compounds, for example, 4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8Synthetic Route of C12H17NO).

4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8) belongs to piperidine derivatives. Piperidine is a metabolite of cadaverine, a polyamine found in the human intestine. Industrially, piperidine is produced by the hydrogenation of pyridine, usually over a molybdenum disulfide catalyst. Pyridine can also be reduced to piperidine via a modified Birch reduction using sodium in ethanol.Synthetic Route of C12H17NO

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis and in vitro evaluation of three novel radiotracers for imaging of metabotropic glutamate receptor subtype 2 in rat brain was written by Kumata, Katsushi;Yamasaki, Tomoteru;Hatori, Akiko;Zhang, Yiding;Mori, Wakana;Fujinaga, Masayuki;Xie, Lin;Okubo, Takayuki;Nengaki, Nobuki;Zhang, Ming-Rong. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2017.Product Details of 58333-75-8 This article mentions the following:

The purpose of this study was to develop three new radiotracers, 1-(cyclopropylmethyl)-4-([¹¹C/¹⁸F]substituted-phenyl)piperidin-1-yl-2-oxo-1,2-dihydropyridine-3-carbonitrile I [R = 2-O¹¹CH₃ (II), 3-O¹¹CH₃ (III), 2-OCH₂CH₂¹⁸F (IV)], and to examine their specific bindings with metabotropic glutamate receptor subtype 2 (mGluR2) in rat brain sections by using in vitro autoradiog. These compounds were found to possess potent in vitro binding affinities (K_i: 8.0-34.1 nM) for mGluR2 in rat brain homogenate. II, III, and IV were synthesized by [¹¹C/¹⁸F]alkylation of the corresponding phenol precursors with [¹¹C]methyl iodide or [¹⁸F]fluoroethyl bromide with >98% radiochem. purity and 80-130 GBq/μmol specific activity at the end of synthesis. In vitro autoradiog. indicated that these radiotracers showed heterogeneous specific bindings in mGluR2-rich brain regions, such as the cerebral cortex, striatum, hippocampus, and granular layer of the cerebellum. In the experiment, the researchers used many compounds, for example, 4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8Product Details of 58333-75-8).

4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8) belongs to piperidine derivatives. Piperidine has a role as a reagent, a protic solvent, a base, a catalyst, a plant metabolite, a human metabolite and a non-polar solvent. 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.Product Details of 58333-75-8

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Syntheses in the piperidine series. I. A facile synthesis of 4-piperidinol and the preparation of related compounds was written by Bowden, K.;Green, P. N.. And the article was included in Journal of the Chemical Society in 1952.Recommanded Product: 4045-22-1 This article mentions the following:

(ClCH₂)₂CHOH (65 g.) and 54 g. NaCN in 60 ml. H₂O, warmed 40 min. at 50-5° and kept overnight, give 6.3 g. ClCH₂CH(OH)CH₂CN and 23.3 g. (NCCH₂)₂CHOH (I). I (45 g.) in 400 ml. EtOH, hydrogenated over 10 g. Raney Ni at 50°/50 atm. (2 hrs.), gives 17.6 g. 4-piperidinol (II), b₁₀ 110-15°; chloroplatinate, m. 195° (decomposition) [Koenigs and Neumann, C.A. 9, 2254, gave 184-7° (decomposition)]; II and dilute H₂SO₄ give the sulfate, m. 272-4° (K. and N. gave 263-6°); with 4 mols. H₂O, m. 66-8°. The EtOH-insoluble matter from II yields the dipicrate, yellow, m. 238° (decomposition), of (CH₂)₅(NH₂)₂. II (3 g.) in 10 g. 47% HBr, evaporated to dryness in vacuo, the residue in 10 ml. hot EtOH evaporated in vacuo, and the product refluxed 10 min. with 5 g. PBr₃, gives 2.8 g. 4-bromopiperidinium bromide (III), m. 192-3° (decomposition); picrate, yellow, m. 162-3°; sulfate, m. 163-4°. III (2.45 g.) in 15 ml. H₂O, added to 1.54 g. BzCl in 5 ml. C₆H₆, followed dropwise with 1.27 g. Na₂CO₃ in 12.7 ml. H₂O at 5°, gives 2 g. 1-benzoyl-4-bromopiperidine, m. 67-9°. II (5 g.) in 6 ml. AcOMe, refluxed 78 hrs., gives 3 g. 1-acetyl-4-piperidinol (IV), m. 66-7°; 2.5 g. II, 1.5 AcONH₂, and 5 g. cyclohexanol, refluxed 6 hrs., give 1.5 g. IV. (ClCH₂CH₂)₂CO (4.65 g.) in 30 ml. absolute EtOH, treated dropwise (45 min.) with 6.3 g. Na₂CO₃ in 70 ml. H₂O and simultaneously with MeNH₂, and refluxed 1 hr., give 0.75 g. 4-methylpiperidone, b₁₄ 55-9°. II (5 g.) in 8 g. 90% HCO₂H, treated with 5 g. 40% aqueous HCHO, heated 8 hrs. on the steam bath, treated the next day with 10 ml. concentrated HCl, and refluxed 5 min., gives 4.3 g. 1-methyl-4-piperidinol, b₁₀ 95-6° [methiodide, m. 327° (decomposition)]. In the experiment, the researchers used many compounds, for example, 1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1Recommanded Product: 4045-22-1).

1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1) belongs to piperidine derivatives. Piperidine has a role as a reagent, a protic solvent, a base, a catalyst, a plant metabolite, a human metabolite and a non-polar solvent. Piperidine derivatives bearing a masked aldehyde function in the ε-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Recommanded Product: 4045-22-1

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

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

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