Day: January 5, 2023

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

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

Fragment Coupling and the Construction of Quaternary Carbons Using Tertiary Radicals Generated From tert-Alkyl N-Phthalimidoyl Oxalates By Visible-Light Photocatalysis was written by Lackner, Gregory L.;Quasdorf, Kyle W.;Pratsch, Gerald;Overman, Larry E.. And the article was included in Journal of Organic Chemistry in 2015.Safety of 1-Boc-4-Hydroxy-4-methylpiperidine This article mentions the following:

The coupling of tertiary carbon radicals with alkene acceptors is an underdeveloped strategy for uniting complex carbon fragments and forming new quaternary carbons. The scope and limitations of a new approach for generating nucleophilic tertiary radicals from tertiary alcs. and utilizing these intermediates in fragment coupling reactions is described. In this method, the tertiary alc. is first acylated to give the tert-alkyl N-phthalimidoyl oxalate, which in the presence of visible-light, catalytic Ru(bpy)₃(PF₆)₂, and a reductant fragments to form the corresponding tertiary carbon radical. In addition to reductive coupling with alkenes, substitution reactions of tertiary radicals with allylic and vinylic halides is described. A mechanism for the generation of tertiary carbon radicals from tert-alkyl N-phthalimidoyl oxalates is proposed that is based on earlier pioneering investigations of Okada and Barton. Deuterium labeling and competition experiments reveal that the reductive radical coupling of tert-alkyl N-phthalimidoyl oxalates with electron-deficient alkenes is terminated by hydrogen-atom transfer. In the experiment, the researchers used many compounds, for example, 1-Boc-4-Hydroxy-4-methylpiperidine (cas: 406235-30-1Safety of 1-Boc-4-Hydroxy-4-methylpiperidine).

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

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Clean six-step synthesis of a piperidino-thiomorpholine library using polymer-supported reagents was written by Habermann, Joerg;Ley, Steven V.;Scott, James S.. And the article was included in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry in 1998.SDS of cas: 33439-27-9 This article mentions the following:

Polymer-supported reagents and other solid sequestering agents, e.g., polymer-supported (dimethylamino)pyridine and Amberlyst A21, were used to generate a library of piperidinothiomorpholines, e.g., I (R = 4-Me, 4-F, 3-F₃C; R¹ = 4-MeO, H, 3-F₃C, 3,4-Cl₂), without any chromatog. purification steps. 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. 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.SDS of cas: 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

A facile, environmentally benign sulfonamide synthesis in water was written by Deng, Xiaohu;Mani, Neelakandha S.. And the article was included in Green Chemistry in 2006.Product Details of 33439-27-9 This article mentions the following:

A facile, environmentally benign synthesis of sulfonamides under dynamic pH control in aqueous media is described. This methodol. uses equimolar amounts of amino compounds and arylsulfonyl chlorides and omits the use of organic bases. Isolation of products involves only filtration after acidification. Excellent yields and purity were obtained without further purification In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Product Details 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. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.Product Details of 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem