Month: February 2023

Ethynyl epoxides as synthons for 1,3-diketones and furans was written by Eichinger, Karl;Berbalk, Hans;Machat, Eduard;Wimmer, Johann. And the article was included in Journal of Chemical Research, Synopses in 1983.Safety of 1-Tosylpiperidin-4-one This article mentions the following:

Substituent effects were examined in the reaction of ethynyl epoxides I [X = CH₂, CHMe, CHPh; R = Ph; X = CPh₂, R = Me, Ph, 3,4-(MeO)₂C₆H₃, 4-O₂NC₆H₄] with HCO₂H to give 1,3-diketones II and of I [X = CH₂, CHMe, CHPh, SO₂, NSO₂C₆H₃Me-p, NCO₂Et, CPh₂, R = Ph; X = CPh₂, R = Ph, 4-MeOC₆H₄, 3,4-(MeO)₂C₆H₃, 4-O₂NC₆H₄, 2,4-(O₂N)₂C₆H₃, Me] to give the corresponding furans III. The yields of furans were not markedly dependent on the nature of the substituents, whereas significant yields of 1,3-diketones were obtained only when R is moderately electron-withdrawing or -releasing. E.g., refluxing I (X = Ph₂, R = Ph) (IV) with 95% aqueous HCO₂H for 30 min gave 76% III (X = CPh₂, R = Ph), whereas similar treatment of I [X = CPh₂, R = 3,4-(MeO)₂C₆H₃] gave only 6% III [X = CPh₂, R = 3,4-(MeO)₂C₆H₃]. Treatment of IV with HgSO₄ in refluxing Me₂CO-aqueous H₂SO₄ gave 79% II (X = CPh₂, R = Ph). 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.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. 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.Safety of 1-Tosylpiperidin-4-one

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis of 5-Azaindoles via a Cycloaddition Reaction between Nitriles and Donor-Acceptor Cyclopropanes was written by Abd Rabo Moustafa, Mahmoud M.;Pagenkopf, Brian L.. And the article was included in Organic Letters in 2010.HPLC of Formula: 33439-27-9 This article mentions the following:

A new method for the synthesis of 5-azaindole derivatives, e.g. I, is reported. A [3+2] dipolar cycloaddition between nitriles and a 3,4-cyclopropanopiperidine II followed by SeO₂ oxidation affords the target compounds in moderate to excellent yields. The divergent nature and cost effectiveness of this method makes it very suitable for combinatorial applications in the pharmaceutical industry. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9HPLC of Formula: 33439-27-9).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. Piperidine and its derivatives have become increasingly popular in many synthetic schemes. 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.HPLC of Formula: 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Iron-Catalyzed Radical Activation Mechanism for Denitrogenative Rearrangement Over C(sp³)-H Amination was written by Roy, Satyajit;Das, Sandip Kumar;Khatua, Hillol;Das, Subrata;Singh, Krishna Nand;Chattopadhyay, Buddhadeb. And the article was included in Angewandte Chemie, International Edition in 2021.COA of Formula: C12H15NO3S This article mentions the following:

An iron-catalyzed denitrogenative rearrangement of 1,2,3,4-tetrazole is developed over the competitive C(sp³)-H amination. This catalytic rearrangement reaction follows an unprecedented metalloradical activation mechanism. Employing the developed method, a wide number of complex-N-heterocyclic product classes have been accessed. The synthetic utility of this radical activation method is showcased with the short synthesis of a bioactive mol. Collectively, this discovery underlines the progress of radical activation strategy that should find wide application in the perspective of medicinal chem., drug discovery and natural product synthesis research. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9COA of Formula: C12H15NO3S).

1-Tosylpiperidin-4-one (cas: 33439-27-9) 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.COA of Formula: C12H15NO3S

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Developing Antagonists for the Met-HGF/SF Protein-Protein Interaction Using a Fragment-Based Approach was written by Winter, Anja;Sigurdardottir, Anna G.;DiCara, Danielle;Valenti, Giovanni;Blundell, Tom L.;Gherardi, Ermanno. And the article was included in Molecular Cancer Therapeutics in 2016.Electric Literature of C12H17NO This article mentions the following:

In many cancers, aberrant activation of the Met receptor tyrosine kinase leads to dissociation of cells from the primary tumor, causing metastasis. Accordingly, Met is a high-profile target for the development of cancer therapies, and progress has been made through development of small mol. kinase inhibitors and antibodies. However, both approaches pose significant challenges with respect to either target specificity (kinase inhibitors) or the cost involved in treating large patient cohorts (antibodies). Here, we use a fragment-based approach in order to target the protein-protein interaction (PPI) between the α-chain of hepatocyte growth factor/scatter factor (HGF/SF; the NK1 fragment) and its high-affinity binding site located on the Met Sema domain. Surface plasmon resonance was used for initial fragment library screening and hits were developed into larger compounds using substructure (similarity) searches. We identified compounds able to interfere with NK1 binding to Met, disrupt Met signaling, and inhibit tumorsphere generation and cell migration. Using mol. docking, we concluded that some of these compounds inhibit the PPI directly, whereas others act indirectly. Our results indicate that chem. fragments can efficiently target the HGF/SF-Met interface and may be used as building blocks for generating biol. active lead compounds This strategy may have broad application for the development of a new class of Met inhibitors, namely receptor antagonists, and in general for the development of small mol. PPI inhibitors of key therapeutic targets when structural information is not available. Mol Cancer Ther; 15(1); 3-14. ©2015 AACR. In the experiment, the researchers used many compounds, for example, 4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8Electric Literature of C12H17NO).

4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8) 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.Electric Literature of C12H17NO

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis of Nitriles from Aldoximes and Primary Amides Using XtalFluor-E was written by Keita, Massaba;Vandamme, Mathilde;Paquin, Jean-Francois. And the article was included in Synthesis in 2015.HPLC of Formula: 62718-31-4 This article mentions the following:

The dehydration reaction of aldoximes and amides for the synthesis of nitriles using [Et₂NSF₂]BF₄ (XtalFluor-E) is described. Overall, the reaction proceeds rapidly (normally <1 h) at room temperature in an environmentally benign solvent (EtOAc) with only a slight excess of the dehydrating agent (1.1 equiv). A broad scope of nitriles can be prepared, including chiral nonracemic ones. In addition, in a number of cases, further purification of the nitrile after the workup was not required. In the experiment, the researchers used many compounds, for example, 1-Benzylpiperidine-4-carbonitrile (cas: 62718-31-4HPLC of Formula: 62718-31-4).

1-Benzylpiperidine-4-carbonitrile (cas: 62718-31-4) belongs to piperidine derivatives. Piperidine and its derivatives have become increasingly popular in many synthetic schemes. 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.HPLC of Formula: 62718-31-4

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

6-Tosyl-4,5,6,7-Tetrahydrothieno[2,3-c]Pyridine-3-Carboxamide Analogues: Synthesis, Characterization, MO Calculation, and Antibacterial Activity was written by Doshi, Hiren;Thakkar, Sampark;Khirsariya, Prashant;Thakur, Mukund Chandra;Ray, Arabinda. And the article was included in Applied Biochemistry and Biotechnology in 2015.Computed Properties of C12H15NO3S This article mentions the following:

A series of 6-tosyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide I (R¹ = H, OH; R² = R³ = H, Cl, OCH₃; R⁴ = H, Cl, OCH₃, OH) analogs are synthesized. These are tested for their antibacterial activity against Bacillus subtilis (abbreviated as BS), Staphylococcus aureus (abbreviated as SA), and Escherichia coli (abbreviated as EC). The synthesized compounds are able to inhibit the growth of the SA and EC. None of the compounds are effective against BS. All valence MO (abbreviated as MO) calculations with PM⁶ have been carried out for the mols. for which bioactivity data are available. Ciprofloxacin is taken as the standard antibiotics to compare activity with the mols. synthesized. It has been attempted to correlate the activity of the mols. with their electronic structure. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Computed Properties of C12H15NO3S).

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. 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.Computed Properties of C12H15NO3S

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Direct Synthesis of Indoles from Azoarenes and Ketones with Bis(neopentylglycolato)diboron Using 4,4′-Bipyridyl as an Organocatalyst was written by Misal Castro, Luis C.;Sultan, Ibrahim;Nishi, Kohei;Tsurugi, Hayato;Mashima, Kazushi. And the article was included in Journal of Organic Chemistry in 2021.Synthetic Route of C12H15NO3S This article mentions the following:

Multifunctionalized indole derivatives were prepared by reducing azoarenes in the presence of ketones and bis(neopentylglycolato)diboron (B₂nep₂) with a catalytic amount of 4,4′-bipyridyl under neutral reaction conditions, where 4,4′-bipyridyl acted as an organocatalyst to activate the B-B bond of B₂nep₂ and form N,N’-diboryl-1,2-diarylhydrazines as a key intermediate. Further reaction of N,N’-diboryl-1,2-diarylhydrazines with ketones afforded N-vinyl-1,2-diarylhydrazines, which rearranged to the corresponding indoles via the Fischer indole mechanism. This organocatalytic system was applied to diverse alkyl cyclic ketones, dialkyl, and alkyl/aryl ketones, including heteroatoms. Me alkyl ketones gave the corresponding 2-methyl-3-substituted indoles in a regioselective manner. This protocol allowed us to expand the preparation of indoles having high compatibility with not only electron-donating and electron-withdrawing groups but also N- and O-protecting functional groups. 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 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.Synthetic Route of C12H15NO3S

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Flexible Routes to Thiophenes was written by Jullien, Helene;Quiclet-Sire, Beatrice;Tetart, Thomas;Zard, Samir Z.. And the article was included in Organic Letters in 2014.Synthetic Route of C12H15NO3S This article mentions the following:

Three convergent routes to thiophenes are described, hinging on the radical addition of α-xanthyl ketones to Et vinyl sulfide or to vinyl pivalate. The latter route ultimately proved to be the most versatile and efficient (61-94%). 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. 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. 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.Synthetic Route of C12H15NO3S

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Convergent and stereoselective method for the synthesis of acyclic α-chloroenamides was written by Surgenor, Richard R.;Grote, Andrea C.;McGeough, Catherine;Narayanan, Arjun;Wang, Wenyu;Collier, Philip N.. And the article was included in Journal of Organic Chemistry in 2020.Quality Control of 1-(Methylsulfonyl)piperidin-4-amine hydrochloride This article mentions the following:

A direct, stereocontrolled synthesis of acyclic α-chloroenamides is presented. Our methodol. showed good yields and substrate scope. Mechanistic insights are provided that account for the high levels of stereoselectivity reported. Subsequent synthetic manipulation of the α-chloroenamides provides direct entry to polyfunctionalized acyclic enamides, compounds of wide use in organic chem. and the pharmaceutical industry. In the experiment, the researchers used many compounds, for example, 1-(Methylsulfonyl)piperidin-4-amine hydrochloride (cas: 651057-01-1Quality Control of 1-(Methylsulfonyl)piperidin-4-amine hydrochloride).

1-(Methylsulfonyl)piperidin-4-amine hydrochloride (cas: 651057-01-1) belongs to piperidine derivatives. Piperidine is a metabolite of cadaverine, a polyamine found in the human intestine. 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.Quality Control of 1-(Methylsulfonyl)piperidin-4-amine hydrochloride

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Alcohols as Alkylating Agents: Photoredox-Catalyzed Conjugate Alkylation via In Situ Deoxygenation was written by Wang, Johnny Z.;Sakai, Holt A.;MacMillan, David W. C.. And the article was included in Angewandte Chemie, International Edition in 2022.Recommanded Product: 1-Boc-4-Hydroxy-4-methylpiperidine This article mentions the following:

Herein, an operationally convenient, N-heterocyclic carbene (NHC)-mediated deoxygenative Giese-type addition of alc.-derived alkyl radicals to electron-deficient alkenes under mild photocatalytic conditions was described. The fragment coupling accommodated a broad range of primary, secondary, and tertiary alc. partners, as well as structurally varied Michael acceptors containing traditionally reactive sites, such as electrophilic or oxidizable moieties. The late-stage diversification of densely functionalized mol. architectures, including drugs and biomols. was demonstrated, and this protocol with metallaphotoredox cross-coupling for step-economic access to sp³-rich complexity was telescoped. In the experiment, the researchers used many compounds, for example, 1-Boc-4-Hydroxy-4-methylpiperidine (cas: 406235-30-1Recommanded Product: 1-Boc-4-Hydroxy-4-methylpiperidine).

1-Boc-4-Hydroxy-4-methylpiperidine (cas: 406235-30-1) belongs to piperidine derivatives. Piperidine is a saturated organic heteromonocyclic parent, an azacycloalkane, a secondary amine and a member of piperidines. 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.Recommanded Product: 1-Boc-4-Hydroxy-4-methylpiperidine

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem