Tag: 300.1013

Preparation of tetramethylpiperidine-1-oxoammonium salts and their use as oxidants in organic chemistry. A review was written by Merbouh, Nabyl;Bobbitt, James M.;Brueckner, Christian. And the article was included in Organic Preparations and Procedures International in 2004.COA of Formula: C11H21BF4N2O2 This article mentions the following:

The discovery of 2,2,6,6-tetramethylpiperidine-based oxoammonium salts (I; R = oxo, H, OH, NH₂, NHAc, OMe, OBz) in 1965 by Golubev et al has led to the synthesis of a number of oxoammonium-based oxidizing agents with diverse properties. However, many of the oxoammonium salts or their precursors are either not com. available or are expensive. Reports of their preparation are spread over 40 yr of literature. This review is a compilation of the most often cited and most practical procedures for their syntheses and includes exptl. details. A large body of work detailing the use of oxoammonium salts as catalytic and stoichiometric oxidants in preparative organic chem. also accumulated over the past four decades. The review of their use, however, will focus on the literature from 1990 to date, excluding the patent literature, as a number of excellent earlier reviews on select aspects of this chem. are available. The goal of this review is to allow organic chemists to prepare and study oxoammonium salts, irresp. of their list prices or com. availability. Oxoammonium salts I are derived from nitroxide free radicals (II) by a one-electron oxidation Nitroxides are generally prepared by oxidation of the corresponding amine 2,2,6,6-tetramethylpiperidine derivatives (III). The 伪-Me groups are crucial for the stabilization of the oxoammonium salts. A number of 4-substituted tetramethylpiperidine derivatives were used for the synthesis of oxoammonium salts, combined with several counter ions. Oxoammonium salts are potent but selective oxidants. They can either be prepared in situ from a nitroxide by reaction with a secondary oxidant, thus making the nitroxide a catalyst, or they can be used as stoichiometric oxidants. They are versatile oxidants in organic chem. and the mild, transition metal-free reaction conditions and the selectivity of the oxidations recommend these oxidants for wider use. Further, the option for tandem reactions will greatly increase the utility of these reagents. In the experiment, the researchers used many compounds, for example, 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate (cas: 219543-09-6COA of Formula: C11H21BF4N2O2).

4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate (cas: 219543-09-6) 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.COA of Formula: C11H21BF4N2O2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

A Practical Oxidation Experiment for Undergraduate Students: Bobbitt’s Salt as a “Green” Alternative was written by Lambert, Kyle M.;Kelly, Christopher B.;Milligan, John A.;Tilley, Leon J.;Reynolds, Robert P.;McGuire, Kellen P.;Anzalone, Luigi;Del Sesto, Kimberly E.;Walsh, Sinead. And the article was included in Journal of Chemical Education in 2022.Category: piperidines This article mentions the following:

Oxidation reactions are critical components of the synthetic toolbox taught to undergraduate students during introductory organic chem. courses. However, the oxidation reactions discussed in the undergraduate curriculum are often outdated as many organic chem. textbooks emphasize chromium-based oxidants that are no longer in regular use by practitioners, which may limit an instructor’s time to allocate to discussion of other oxidants. Further, laboratory courses have since either removed oxidation experiments or replaced them with oxidative processes not discussed in lectures, thus leading to a disconnect between the two learning settings. As part of an effort to bridge this divide and modernize the oxidation reactions discussed in our curricula, we have developed a new laboratory experiment that uses a com. available oxoammonium salt (Bobbitt’s salt) to cleanly oxidize cinnamyl alc. to cinnamaldehyde. In addition to being a safe, convenient, colorimetric and “green oxidant” suitable for use in the undergraduate teaching laboratory, the hydride-transfer mechanism allows for overlap with key course concepts presented in both introductory and advanced lecture courses. The procedure is well-suited for small and large organic I, II or advanced laboratory sections alike, and can be completed within a standard 3-4 h laboratory period. Aside from exposing students to a modern green oxidation protocol, the experiment contains expanded opportunities for interpretation of ¹H NMR, ¹³C NMR, and IR spectra. An optional addendum for advanced students involving Hammett correlations was also developed. In the experiment, the researchers used many compounds, for example, 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate (cas: 219543-09-6Category: piperidines).

4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate (cas: 219543-09-6) 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.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Oxoammonium-Mediated Allylsilane-Ether Coupling Reaction was written by Carlet, Federica;Bertarini, Greta;Broggini, Gianluigi;Pradal, Alexandre;Poli, Giovanni. And the article was included in European Journal of Organic Chemistry in 2021.SDS of cas: 219543-09-6 This article mentions the following:

A new C(sp³)-H functionalization reaction consisting of the oxidative 伪-allylation of allyl- and benzyl- Me ethers has been developed. The C-C coupling could be carried out under mild conditions thanks to the use of cheap and green oxoammonium salts. The scope of the reaction was studied over 27 examples, considering the nature of the substituents on the two coupling partners. In the experiment, the researchers used many compounds, for example, 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate (cas: 219543-09-6SDS of cas: 219543-09-6).

4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate (cas: 219543-09-6) 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 伪-glucosidase inhibitors. The former are analogs of DNJ with an improved 伪-glucosidase inhibitory profile than that of DNJ. Boisson et al.SDS of cas: 219543-09-6

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Chemo-Enzymatic Oxidative Rearrangement of Tertiary Allylic Alcohols: Synthetic Application and Integration into a Cascade Process was written by Brenna, Elisabetta;Crotti, Michele;De Pieri, Matteo;Gatti, Francesco G.;Manenti, Gabriele;Monti, Daniela. And the article was included in Advanced Synthesis & Catalysis in 2018.Recommanded Product: 219543-09-6 This article mentions the following:

A chemo-enzymic catalytic system, comprised of Bobbitt’s salt and laccase from Trametes versicolor, allowed the [1,3]-oxidative rearrangement of endocyclic allylic tertiary alcs. into the corresponding enones under an Oxygen atm. in aqueous media. The yields were in most cases quant., especially for the cyclopent-2-en-1-ol or the cyclohex-2-en-1-ol substrates without an electron withdrawing group (EWG) on the side chain. Transpositions of macrocyclic alkenols or tertiary alcs. bearing an EWG on the side chain were instead carried out in acetonitrile by using an immobilized laccase preparation Dehydro-Jasmone, dehydro-Hedione, dehydro-Muscone and other fragrance precursors were directly prepared with this procedure, while a synthetic route was developed to easily transform a cyclopentenone derivative into trans-Magnolione and dehydro-Magnolione_. The rearrangement of exocyclic allylic alcs. was tested as well, and a dynamic kinetic resolution was observed: 伪,尾-unsaturated ketones with (E)-configuration and a high diastereomeric excess were synthesized. Finally, the 2,2,6,6-tetramethyl-1-piperidinium tetrafluoroborate (TEMPO⁺BF₄^–)/laccase catalyzed oxidative rearrangement was combined with the ene-reductase/alc. dehydrogenase cascade process in a one-pot three-step synthesis of cis or trans 3-methylcyclohexan-1-ol, in both cases with a high optical purity. In the experiment, the researchers used many compounds, for example, 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate (cas: 219543-09-6Recommanded Product: 219543-09-6).

4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate (cas: 219543-09-6) 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 derivatives bearing a masked aldehyde function in the 蔚-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Recommanded Product: 219543-09-6

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Asymmetric Cross-Dehydrogenative Coupling Enabled by the Design and Application of Chiral Triazole-Containing Phosphoric Acids was written by Neel, Andrew J.;Hehn, Jorg P.;Tripet, Pascal F.;Toste, F. Dean. And the article was included in Journal of the American Chemical Society in 2013.Product Details of 219543-09-6 This article mentions the following:

Nonracemic triazolylbinaphthylphosphoric acids I [R = PhCH₂, Ph₂CH, bis(1-naphthyl)methyl, 1-naphthyl, 9-anthracenyl, 1-pyrenyl, 2,4,6-Me₃C₆H₂, 2,4,6-i-Pr₃C₆H₂, 2,4,6-(c-C₆H₁₁)₃C₆H₂, 4-t-BuC₆H₄, 3,5-t-Bu₂C₆H₃, 1-adamantyl] were prepared using azide-alkyne cycloadditions of a protected diethynylbinaphthol with azides RN₃ [R = PhCH₂, Ph₂CH, bis(1-naphthyl)methyl, 1-naphthyl, 9-anthracenyl, 1-pyrenyl, 2,4,6-Me₃C₆H₂, 2,4,6-i-Pr₃C₆H₂, 2,4,6-(c-C₆H₁₁)₃C₆H₂, 4-t-BuC₆H₄, 3,5-t-Bu₂C₆H₃, 1-adamantyl]; in the presence of I, an acetamidopiperidineoxoammonium salt, and trisodium phosphate in p-xylene, tetrahydroisoquinolinylbenzamides II [R¹ = PhCH₂, 4-MeC₆H₄CH₂, 4-MeOC₆H₄CH₂, 4-O₂NC₆H₄CH₂, 2-MeOC₆H₄CH₂, Ph, 3-MeC₆H₄, 2-MeC₆H₄, 1-naphthyl, 2-ClC₆H₄, 2-HOC₆H₄, t-Bu, cyclohexyl, (R)-MeO₂CCH(i-Pr), (S)-MeO₂CCH(i-Pr); R² = H, Me, Br, F₃C] underwent enantioselective cross-dehydrogenative coupling reactions to give tetrahydroisoquinolinoquinazolinones III [R¹ = PhCH₂, 4-MeC₆H₄CH₂, 4-MeOC₆H₄CH₂, 4-O₂NC₆H₄CH₂, 2-MeOC₆H₄CH₂, Ph, 3-MeC₆H₄, 2-MeC₆H₄, 1-naphthyl, 2-ClC₆H₄, 2-HOC₆H₄, t-Bu, cyclohexyl, (R)-MeO₂CCH(i-Pr), (S)-MeO₂CCH(i-Pr); R² = H, Me, Br, F₃C] in 38-93% yields and in 73-93% ee or in 3:1-7:1 dr. I were designed to use attractive hydrogen-bonding interactions with substrates rather than catalyst steric bulk to improve the stereoselectivity of the coupling reaction. The azides used in the preparation of I are potentially explosive and should be handled and reacted using appropriate precautions. In the experiment, the researchers used many compounds, for example, 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate (cas: 219543-09-6Product Details of 219543-09-6).

4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate (cas: 219543-09-6) 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 伪-glucosidase inhibitors. The former are analogs of DNJ with an improved 伪-glucosidase inhibitory profile than that of DNJ. Boisson et al.Product Details of 219543-09-6

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Preparation of tetramethylpiperidine-1-oxoammonium salts and their use as oxidants in organic chemistry. A review was written by Merbouh, Nabyl;Bobbitt, James M.;Brueckner, Christian. And the article was included in Organic Preparations and Procedures International in 2004.COA of Formula: C11H21BF4N2O2 This article mentions the following:

The discovery of 2,2,6,6-tetramethylpiperidine-based oxoammonium salts (I; R = oxo, H, OH, NH₂, NHAc, OMe, OBz) in 1965 by Golubev et al has led to the synthesis of a number of oxoammonium-based oxidizing agents with diverse properties. However, many of the oxoammonium salts or their precursors are either not com. available or are expensive. Reports of their preparation are spread over 40 yr of literature. This review is a compilation of the most often cited and most practical procedures for their syntheses and includes exptl. details. A large body of work detailing the use of oxoammonium salts as catalytic and stoichiometric oxidants in preparative organic chem. also accumulated over the past four decades. The review of their use, however, will focus on the literature from 1990 to date, excluding the patent literature, as a number of excellent earlier reviews on select aspects of this chem. are available. The goal of this review is to allow organic chemists to prepare and study oxoammonium salts, irresp. of their list prices or com. availability. Oxoammonium salts I are derived from nitroxide free radicals (II) by a one-electron oxidation Nitroxides are generally prepared by oxidation of the corresponding amine 2,2,6,6-tetramethylpiperidine derivatives (III). The α-Me groups are crucial for the stabilization of the oxoammonium salts. A number of 4-substituted tetramethylpiperidine derivatives were used for the synthesis of oxoammonium salts, combined with several counter ions. Oxoammonium salts are potent but selective oxidants. They can either be prepared in situ from a nitroxide by reaction with a secondary oxidant, thus making the nitroxide a catalyst, or they can be used as stoichiometric oxidants. They are versatile oxidants in organic chem. and the mild, transition metal-free reaction conditions and the selectivity of the oxidations recommend these oxidants for wider use. Further, the option for tandem reactions will greatly increase the utility of these reagents. In the experiment, the researchers used many compounds, for example, 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate (cas: 219543-09-6COA of Formula: C11H21BF4N2O2).

4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate (cas: 219543-09-6) 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.COA of Formula: C11H21BF4N2O2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

A Practical Oxidation Experiment for Undergraduate Students: Bobbitt’s Salt as a “Green” Alternative was written by Lambert, Kyle M.;Kelly, Christopher B.;Milligan, John A.;Tilley, Leon J.;Reynolds, Robert P.;McGuire, Kellen P.;Anzalone, Luigi;Del Sesto, Kimberly E.;Walsh, Sinead. And the article was included in Journal of Chemical Education in 2022.Category: piperidines This article mentions the following:

Oxidation reactions are critical components of the synthetic toolbox taught to undergraduate students during introductory organic chem. courses. However, the oxidation reactions discussed in the undergraduate curriculum are often outdated as many organic chem. textbooks emphasize chromium-based oxidants that are no longer in regular use by practitioners, which may limit an instructor’s time to allocate to discussion of other oxidants. Further, laboratory courses have since either removed oxidation experiments or replaced them with oxidative processes not discussed in lectures, thus leading to a disconnect between the two learning settings. As part of an effort to bridge this divide and modernize the oxidation reactions discussed in our curricula, we have developed a new laboratory experiment that uses a com. available oxoammonium salt (Bobbitt’s salt) to cleanly oxidize cinnamyl alc. to cinnamaldehyde. In addition to being a safe, convenient, colorimetric and “green oxidant” suitable for use in the undergraduate teaching laboratory, the hydride-transfer mechanism allows for overlap with key course concepts presented in both introductory and advanced lecture courses. The procedure is well-suited for small and large organic I, II or advanced laboratory sections alike, and can be completed within a standard 3-4 h laboratory period. Aside from exposing students to a modern green oxidation protocol, the experiment contains expanded opportunities for interpretation of ¹H NMR, ¹³C NMR, and IR spectra. An optional addendum for advanced students involving Hammett correlations was also developed. In the experiment, the researchers used many compounds, for example, 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate (cas: 219543-09-6Category: piperidines).

4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate (cas: 219543-09-6) 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.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem