Category: piperidines

Indoline derivatives. Synthesis and factor Xa (FXa) inhibitory activities was written by Noguchi, Tetsuji;Tanaka, Naoki;Nishimata, Toyoki;Goto, Riki;Hayakawa, Miho;Sugidachi, Atsuhiro;Ogawa, Taketoshi;Asai, Fumitoshi;Matsui, Yumi;Fujimoto, Koichi. And the article was included in Chemical & Pharmaceutical Bulletin in 2006.Formula: C7H13NO2 This article mentions the following:

A series of bisamidine derivatives each having a ring structure in the center of the mol. was synthesized and their Factor Xa (FXa) inhibitory activities were evaluated. Among them, some indoline derivatives showed potent inhibitory activities in vitro. In particular, compound (I) having an (R)-configuration at the 2-position of the indoline ring exhibited the most potent FXa inhibitory activity in vitro, more potent than DX-9065a. Furthermore, I exhibited more potent anticoagulant activity than DX-9065a. The authors also succeeded in obtaining an x-ray crystal structure of FXa bound with I. In the experiment, the researchers used many compounds, for example, 1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1Formula: C7H13NO2).

1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1) 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. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.Formula: C7H13NO2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Visible-light photoredox synthesis of internal alkynes containing quaternary carbons was written by Gao, Chang;Li, Jingjing;Yu, Jipan;Yang, Haijun;Fu, Hua. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2016.Application of 406235-30-1 This article mentions the following:

A novel and efficient visible-light photoredox method for the synthesis of internal alkynes RCCAr (R = tert-Bu, 1-methylcyclohexyl, 1-methylcycloheptyl, etc.; Ar = C₆H₅, thiophen-2-yl, naphthalen-1-yl, etc.) containing quaternary carbons has been developed via coupling reactions of N-phthalimidoyl oxalates of tert-alcs. I with 1-(2-(arylsulfonyl)ethynyl)benzenes ArCCS(O)₂C₆H₅. The reactions proceeded well at room temperature with good functional group tolerability. In the experiment, the researchers used many compounds, for example, 1-Boc-4-Hydroxy-4-methylpiperidine (cas: 406235-30-1Application of 406235-30-1).

1-Boc-4-Hydroxy-4-methylpiperidine (cas: 406235-30-1) 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. 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.Application of 406235-30-1

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

C-H Insertion via Ruthenium Catalyzed gem-Hydrogenation of 1,3-Enynes was written by Peil, Sebastian;Gutierrez Gonzalez, Alejandro;Leutzsch, Markus;Fuerstner, Alois. And the article was included in Journal of the American Chemical Society in 2022.Electric Literature of C12H15NO3S This article mentions the following:

Gem-Hydrogenation of an internal alkyne with the aid of [Cp*RuCl]₄ as the precatalyst is a highly unorthodox transformation, in which one C atom of the triple bond is transformed into a methylene group, whereas the second C atom gets converted into a ruthenium carbene. In the case of 1,3-enynes bearing a propargylic steering substituent as the substrates, the reaction occurs regioselectively, giving rise to vinyl carbene complexes that adopt interconverting η¹/η³-binding modes in solution; a prototypical example of such a reactive intermediate was characterized in detail by spectroscopic means. Although both forms are similarly stable, only the η³-vinyl carbene proved kinetically competent to insert into primary, secondary, or tertiary C-H bonds on the steering group itself or another suitably placed ether, acetal, orthoester, or (sulfon)amide substituent. The ensuing net hydrogenative C-H insertion reaction is highly enabling in that it gives ready access to spirocyclic as well as bridged ring systems of immediate relevance as building blocks for medicinal chem. Moreover, the reaction scales well and lends itself to the formation of partly or fully deuterated isotopologues. Labeling experiments in combination with PHIP NMR spectroscopy (PHIP = parahydrogen induced polarization) confirmed that the reactions are indeed triggered by gem-hydrogenation, whereas kinetic data provided valuable insights into the very nature of the turnover-limiting transition state of the actual C-H insertion step. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Electric Literature of 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. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.Electric Literature of C12H15NO3S

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Tertiary Amine Mediated Tandem Cross-Rauhut-Currier/Acetalization Reactions: Access to Functionalized Spiro-3,4-Dihydropyrans was written by Yao, Weijun;Wu, Yihua;Wang, Gang;Zhang, Yiping;Ma, Cheng. And the article was included in Angewandte Chemie, International Edition in 2009.Synthetic Route of C12H15NO3S This article mentions the following:

Spiro-3,4-dihydropyrans, e.g. I (R¹ = Ph,, R² = Me, Et; R¹ = 4-FC₆H₄, 4-MeC₆H₄, R² = Me; R¹ = 3-O₂NC₆H₄, 4-MeOC₆H₄, 2-furyl, N-tosylindol-3-yl, R² = Et), were prepared by DBU-mediated cross-Rauhut-Currier/acetalization of cyclic β-haloenals, e.g. II, with β,γ-unsaturated α-ketoesters, e.g. (E)-R¹CH:CHCOCO₂R², followed by oxidation In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Synthetic Route of C12H15NO3S).

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. Piperidine derivatives are being utilized in different ways as anticancer, antiviral, antimalarial, antimicrobial, antifungal, antihypertension, analgesic, anti-inflammatory, anti-Alzheimer, antipsychotic and/or anticoagulant agents.Synthetic Route of C12H15NO3S

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

p-Trifluoromethyl- and p-pentafluorothio-substituted curcuminoids of the 2,6-di[(E)-benzylidene)]cycloalkanone type: syntheses and activities against Leishmania major and Toxoplasma gondii parasites was written by Al Nasr, Ibrahim S.;Hanachi, Riadh;Said, Ridha B.;Rahali, Seyfeddine;Tangour, Bahoueddine;Abdelwahab, Siddig I.;Farasani, Abdullah;M. E. Taha, Manal;Bidwai, Anil;Koko, Waleed S.;Khan, Tariq A.;Schobert, Rainer;Biersack, Bernhard. And the article was included in Bioorganic Chemistry in 2021.Application of 33439-27-9 This article mentions the following:

A series of the title curcuminoids I (X = NH, NTs, S, CH₂, etc.; R = CF₃, SF₅) with structural variance in the heteroatom of the cycloalkanone and the p-substituents of the Ph rings were tested for their activities against Leishmania major and Toxoplasma gondii parasites. The majority of them showed high activities against both parasite forms with EC₅₀ values in the sub-micromolar concentration range. The compound I (X = NH; R = SF₅) was not just noticeable antiparasitic, but also exhibited a considerable selectivity for L. major promastigotes over normal Vero cells. While derivatives differing only in the p-Ph substituents being CF₃ or SF₅ showed similar antiparasitic activities, the cyclic ketone hub was more decisive both for the anti-parasitic activities and the selectivities for the parasites vs. normal cells. QSAR calculations confirmed the observed structure-activity relations and suggested structural variations for a further improvement of the antiparasitic activity. Docking studies based on DFT calculations revealed L. major pteridine reductase 1 as a likely mol. target protein of the title compounds In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Application of 33439-27-9).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. The piperidine moiety constitutes an important building block for the synthesis of a variety of bioactive natural products, alkaloids and other drugs. 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 of 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis of α-enaminones from cyclic ketones and anilines using oxoammonium salt as an oxygen transfer reagent was written by Xu, Biping;Shang, Yaping;Jie, Xiaoming;Zhang, Xiaofeng;Kan, Jian;Yedage, Subhash Laxman;Su, Weiping. And the article was included in Green Chemistry in 2020.Safety of 1-Tosylpiperidin-4-one This article mentions the following:

A convenient and straightforward transformation of cyclic ketones with anilines at room temperature was developed using oxoammonium salt TEMPO^+PF6- as an oxidant. This method enabled the synthesis of a broad range of α-enaminones. The ¹⁸O-labeling experiment demonstrated that oxoammonium salt served as the oxygen transfer reagent. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Safety of 1-Tosylpiperidin-4-one).

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. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.Safety of 1-Tosylpiperidin-4-one

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Copper-Mediated Radical-Polar Crossover Enables Photocatalytic Oxidative Functionalization of Sterically Bulky Alkenes was written by Reed, Nicholas L.;Lutovsky, Grace A.;Yoon, Tehshik P.. And the article was included in Journal of the American Chemical Society in 2021.Electric Literature of C12H15NO3S This article mentions the following:

Oxidative heterofunctionalization reactions are among the most attractive methods for the conversion of alkenes and heteroat. nucleophiles into complex saturated heterocycles. However, the state-of-the-art transition-metal-catalyzed methods to effect oxidative heterofunctionalizations are typically limited to unhindered olefins, and different nucleophilic partners generally require quite different reaction conditions. Herein, we show that Cu(II)-mediated radical-polar crossover allows for highly efficient and exceptionally mild photocatalytic oxidative heterofunctionalization reactions between bulky tri- and tetrasubstituted alkenes and a wide variety of nucleophilic partners. Moreover, we demonstrate that the broad scope of this transformation arises from photocatalytic alkene activation and thus complements existing transition-metal-catalyzed methods for oxidative heterofunctionalization. More broadly, these results further demonstrate that Cu(II) salts are ideal terminal oxidants for photoredox applications and that the combination of photocatalytic substrate activation and Cu(II)-mediated radical oxidation can address long-standing challenges in catalytic oxidation chem. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Electric Literature of C12H15NO3S).

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.Electric Literature of C12H15NO3S

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Microwave-promoted amination of 3-bromoisoxazoles was written by Moore, Jane E.;Spinks, Daniel;Harrity, Joseph P. A.. And the article was included in Tetrahedron Letters in 2004.Recommanded Product: 58333-75-8 This article mentions the following:

Amination of 3-bromoisoxazoles, by a nucleophilic aromatic substitution reaction, is described. 3-Bromoisoxazoles were found to be inert to substitution under thermal conditions, however, the employment of phosphazene bases under microwave irradiation facilitated the amination process and allowed 3-aminoisoxazoles, e.g., I, to be isolated in moderate yields. In the experiment, the researchers used many compounds, for example, 4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8Recommanded Product: 58333-75-8).

4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8) 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. 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.Recommanded Product: 58333-75-8

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Nontraditional Fragment Couplings of Alcohols and Carboxylic Acids: C(sp³)-C(sp³) Cross-Coupling via Radical Sorting was written by Sakai, Holt A.;MacMillan, David W. C.. And the article was included in Journal of the American Chemical Society in 2022.Related Products of 406235-30-1 This article mentions the following:

In this report, the C(sp³)-C(sp³) cross-coupling of alcs. and carboxylic acids through the dual combination of N-heterocyclic carbene (NHC)-mediated deoxygenation and hypervalent iodine-mediated decarboxylation were described. This mild and practical Ni-catalyzed radical-coupling protocol was employed to prepare a wide array of alkyl-alkyl cross-coupled products, including highly congested quaternary carbon centers from the corresponding tertiary alcs. or tertiary carboxylic acids. Synthetic applications of this methodol. to alc. C1-alkylation and formal homologation, as well as to the late-stage functionalization of drugs, natural products, and biomols. were demonstrated. In the experiment, the researchers used many compounds, for example, 1-Boc-4-Hydroxy-4-methylpiperidine (cas: 406235-30-1Related Products of 406235-30-1).

1-Boc-4-Hydroxy-4-methylpiperidine (cas: 406235-30-1) 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.Related Products of 406235-30-1

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Substitution of α-azido ethers with Grignard reagents and its use in combinatorial chemistry was written by Baruah, Mukulesh;Bols, Mikael. And the article was included in Journal of the Chemical Society, Perkin Transactions 1 in 2002.COA of Formula: C7H13NO2 This article mentions the following:

α-Azidobenzyl ethers reacted with alkyl or aryl Grignard reagents in toluene to produce α-alkylbenzyl or diarylmethyl ethers in 82-94% yield. α-Azidobenzyl ethers also reacted with multicomponent Grignard reagents to produce libraries of α-alkylbenzyl ethers. In the experiment, the researchers used many compounds, for example, 1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1COA of Formula: C7H13NO2).

1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1) 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. 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.COA of Formula: C7H13NO2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem