Tag: 200-300

Umpolung Difunctionalization of Carbonyls via Visible-light Photoredox Catalytic Radical-Carbanion Relay was written by Wang, Shun;Cheng, Bei-Yi;Srsen, Matea;Koenig, Burkhard. And the article was included in Journal of the American Chemical Society in 2020.SDS of cas: 33439-27-9 This article mentions the following:

The combination of photoredox catalysis with the Wolff-Kishner (WK) reaction allows the difunctionalization of carbonyl groups by a radical-carbanion relay sequence (photo-Wolff-Kishner reaction). Photoredox initiated radical addition to N-sulfonylhydrazones yields α-functionalized carbanions following WK-type mechanism. With sulfur-centered radicals, the carbanions were further functionalized by reaction with electrophiles including CO₂ and aldehydes to gave phenylthio aryl acetic acids R¹C(SR²)(CO₂H)R³ [R¹ = 4-MeC₆H₃, 2-thienyl, Bn, etc.; R² = Ph, cyclohexyl, CH₂CH₂Ph, etc.; R³ = H, Me, cyclopropyl, etc.] and phenylthio aryl ethanols (R³)(R⁴)C(SPh)CH(OH)R⁵ [R³ = H, Me; R⁴ = Ph, 2-thienyl, 4-PhC₆H₄; R⁵ = H, Et, Ph, etc.], whereas CF₃ radical addition furnished a wide range of gem-difluoroalkenes R⁶R⁷C=CF₂ [R⁶ = Ph, CH₂C(O)NHPh, 4-PhC₆H₄CH₂; R⁷ = H, Me, Bn, etc.; R⁶R⁷ = CH₂N(Ts)CH₂, CH₂CH₂N(Ts)CH₂CH₂, CH₂CH₂N(Boc)CH₂CH₂, CH₂CH₂CH(t-Bu)CH₂CH₂, (CH₂)₁₁] through β-fluoride elimination of the generated α-CF₃ carbanions. More than 80 substrate examples demonstrated the broad applicability of this reaction sequence. A series of investigations including radical inhibition, deuterium labeling, fluorescence quenching, cyclic voltammetry and control experiments support the proposed radical-carbanion relay mechanism. 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 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.SDS of cas: 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Heteroatom-Directed Alkylcyanation of Alkynes was written by Nakao, Yoshiaki;Yada, Akira;Hiyama, Tamejiro. And the article was included in Journal of the American Chemical Society in 2010.HPLC of Formula: 62718-31-4 This article mentions the following:

Alkanenitriles having a heteroatom such as nitrogen, oxygen, and sulfur at the γ-position add across alkynes stereo- and regioselectively by nickel/Lewis acid catalysis to give highly substituted acrylonitriles. The heteroatom functionalities likely coordinate to the nickel center to make oxidative addition of the C-CN bonds of the alkyl cyanides kinetically favorable, forming a five-membered nickelacycle intermediate and, thus, preventing β-hydride elimination to allow the alkylcyanation reaction. 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 has a role as a reagent, a protic solvent, a base, a catalyst, a plant metabolite, a human metabolite and a non-polar solvent. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.HPLC of Formula: 62718-31-4

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Heterocycle-derived β-S-enals as bifunctional linchpins for the catalytic synthesis of saturated heterocycles was written by Niu, Jingze;Willis, Michael C.. And the article was included in Organic Chemistry Frontiers in 2016.Application of 33439-27-9 This article mentions the following:

We demonstrated how heterocycle-derived β-S-enals can be employed as bifunctional substrates in a cascade of two rhodium-catalyzed C-C bond forming reactions to deliver substituted heterocyclic products. A single rhodium-catalyst, generated in situ from a com. salt and ligand combination, was used to promote both an initial alkene or alkyne hydroacylation reaction, and then a Suzuki-type cross-coupling, resulting in a three-component assembly of the targeted heterocycles. Substrates based on N-, O- and S-heterocycles were included, as were a range of alkenes, alkynes and boronic acid derivatives 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. Piperidine is a saturated organic heteromonocyclic parent, an azacycloalkane, a secondary amine and a member of piperidines. Piperidine derivatives bearing a masked aldehyde function in the ε-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Application of 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis of hetero-aryl-piperazines and hetero-aryl-bipiperidines with a restricted side chain and their affinities for 5-HT_1A receptor was written by Yoo, Kyung Ho;Choi, Hyun Sik;Kim, Dong Chan;Shin, Kye Jung;Kim, Dong Jin;Song, Yun Seon;Jin, Changbae. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 2003.Reference of 33439-27-9 This article mentions the following:

Heteroarylpiperazine and heteroarylbipiperidine derivatives, bearing a 4-piperidine ring instead of an alkylamino side chain to give the semi-rigidity, were prepared and evaluated for their abilities to displace [³H]-8-OH-DPAT binding to the rat hippocampal synaptic membranes. These compounds showed low to moderate affinities for 5-HT_1A receptor, with Ki values ranging from 6912 nM to 232 nM. Of these compounds, I and II exhibited the best affinities for 5-HT_1A receptor with Ki values of 232 nM and 338 nM, resp. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Reference of 33439-27-9).

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 bearing a masked aldehyde function in the ε-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Reference of 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Au-Catalyzed Formation of Functionalized Quinolines from 2-Alkynyl Arylazide Derivatives was written by Gronnier, Colombe;Boissonnat, Guillaume;Gagosz, Fabien. And the article was included in Organic Letters in 2013.SDS of cas: 33439-27-9 This article mentions the following:

A new method for converting 2-alkynyl arylazide derivatives into functionalized polysubstituted quinolines following a gold-catalyzed 1,3-acetoxy shift/cyclization/1,2-group shift sequence has been developed (e.g., I → II). This transformation proceeds under mild reaction conditions, is efficient, and tolerates a large variety of functional groups. 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. 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

Design and synthesis of 4-(heterocyclic substituted amino)-1H-pyrazole-3-carboxamide derivatives and their potent activity against acute myeloid leukemia (AML) was written by Zhi, Yanle;Wang, Zhijie;Yao, Chao;Li, Baoquan;Heng, Hao;Cai, Jiongheng;Xiang, Li;Wang, Yue;Lu, Tao;Lu, Shuai. And the article was included in International Journal of Molecular Sciences in 2019.Synthetic Route of C9H19N3O2 This article mentions the following:

Fms-like receptor tyrosine kinase 3 (FLT3) has been emerging as an attractive target for the treatment of acute myeloid leukemia (AML). By modifying the structure of FN-1501, a potent FLT3 inhibitor, 24 novel 1H-pyrazole-3-carboxamide derivatives I [R = Ph, pyridin-4-yl, 1-(tert-butoxycarbonyl)piperidine-4-yl, piperidin-4-yl] and II [R¹ = H, (morpholin-4-yl)carbonyl, (4-methylpiperazin-1-yl)carbonyl, piperazin-1-yl, etc.; R² = H, 4-methyl-1,4-diazepan-1-yl; X = CH, N; R³ = thieno[2,3-d]pyrimidin-4-yl, 7H-pyrrolo[2,3-d]pyrimidin-4-yl, etc.] were designed and synthesized. Compound II [R¹ = piperazin-1-yl, R² = H, X = CH, R³ = 7-thia-9,11-diazatricyclo[6.4.0.0(2,6)]dodeca-1(8),2(6),9,11-tetraen-12-yl (III)] showed strong activity against FLT3 (IC⁵⁰: 0.089 nM) and CDK2/4 (IC⁵⁰: 0.719/0.770 nM), which is more efficient than FN-1501(FLT3, IC⁵⁰: 2.33 nM; CDK2/4, IC⁵⁰: 1.02/0.39 nM). Compound III also showed excellent inhibitory activity against a variety of FLT3 mutants (IC⁵⁰ >5 nM), and potent anti-proliferative effect within the nanomolar range on acute myeloid leukemia (MV4-11, IC⁵⁰: 1.22 nM). In addition, compound III significantly inhibited the proliferation of most human cell lines of NCI60 (GI⁵⁰ < 1μ M for most cell lines). Taken together, these results demonstrated the potential of III as a novel compound for further development into a kinase inhibitor applied in cancer therapeutics. In the experiment, the researchers used many compounds, for example, tert-Butyl 4-aminopiperazine-1-carboxylate (cas: 118753-66-5Synthetic Route of C9H19N3O2).

tert-Butyl 4-aminopiperazine-1-carboxylate (cas: 118753-66-5) 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.Synthetic Route of C9H19N3O2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Expedient Access to 2,3-Dihydropyridines from Unsaturated Oximes by Rh(III)-Catalyzed C-H Activation was written by Romanov-Michailidis, Fedor;Sedillo, Kassandra F.;Neely, Jamie M.;Rovis, Tomislav. And the article was included in Journal of the American Chemical Society in 2015.Quality Control of 1-Tosylpiperidin-4-one This article mentions the following:

α,β-Unsaturated oxime pivalates are proposed to undergo reversible C(sp²)-H insertion with cationic Rh(III) complexes to furnish five-membered metallacycles. In the presence of 1,1-disubstituted olefins, these species participate in irreversible migratory insertion to give, after reductive elimination, 2,3-dihydropyridine products in good yields. Catalytic hydrogenation can then be used to convert these mols. into piperidines, which are important structural components of numerous pharmaceuticals. Thus, e.g., heterocyclization of unsaturated oxime pivalate I with alkene II in presence of [Rh(MeCN)₃(C₅Me₄CF₃)](SbF₆)₂ afforded dihydropyridine III (99%). In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Quality Control 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. 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.Quality Control of 1-Tosylpiperidin-4-one

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

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

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