Category: 25504-47-6

Klein, K. P.; Reimschuessel, H. K. published the artcile< Polyimide from 4-carboxy-2-piperidone-poly[1,3-(2,6-dioxopiperidinediyl)ethylene]>, Electric Literature of 25504-47-6, the main research area is polyimide carboxypiperidone; piperidone carboxy polyimide; hydrocyanation itaconate ester; cyanomethylsuccinate dimethyl hydrogenation.

A polyimide (I) [84128-67-6] soluble in HCO2H, m-cresol, CF3CH2OH, and H2SO4 was prepared by heating 4-carboxy-2-piperidone (II) [24537-50-6] at 220-235°. I had Mark-Houwink constants K and α 4.2 × 10-4 and 0.647, resp., in m-cresol and glass transition temperature 130-135°. II was prepared by hydrocyanation of di-Me itaconate  [617-52-7], reduction-cyclization of the di-Me (cyanomethyl)succinate  [24537-51-7] to 4-(carbomethoxy)-2-piperidone  [25504-47-6], and hydrolysis.

Macromolecular Syntheses published new progress about Polyimides Role: SPN (Synthetic Preparation), PREP (Preparation). 25504-47-6 belongs to class piperidines, and the molecular formula is C7H11NO3, Electric Literature of 25504-47-6.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Mazur, Robert H. published the artcile< Resolution and configuration of 1-(3-hydroxy-3-phenylpropyl)-4-ethoxycarbonyl-4-phenylpiperidine>, SDS of cas: 25504-47-6, the main research area is .

The title carbinol, Ph(EtO2C)C5H8NCH2CH2CH(OR)Ph (I, R = H) (II), was prepared for pharmacol. evalution since it should exhibit greater stability than the corresponding ketone (III), a Mannich base with analgesic properties, and its resolution could lead to a separation of analgesic and respiratory depressant activities. III HCl salt (12.0 g.) in 48 ml. 50% alc. and 1.2 g. NaOH in 72 ml. alc. stirred 10 min. at 20° with 1.1 g. NaBH4, diluted with CHCl3, the washed and dried CHCl3 extract distilled, and the crystalline residue, m. 89-91°, in 60 ml. Me2CHOH treated with 6.6 ml. 6.8N HCl in Me2CHOH gave 96% material, recrystallized from Me2CHOH to give dl-II HCl salt, m. 198-9°. II (3.7 g.) in 40 ml. C5H5N and 10 ml. Ac2O heated on a steam bath briefly and kept 16 hrs. at 20°, excess Ac2O decomposed with H2O, the solution taken up in Et2O, and the product on evaporation treated with 1.3 g. maleic acid in Et2O gave 94% product, recrystallized to give I (R = Ac) H maleate salt (IV), m. 137-9°. Similarly, 3.7 g. II and 3.9 g. (EtCO)2O yielded I (R = EtCO) H maleate salt (V), m. 142-3°. II (3.7 g.) in 20 ml. C5H5N kept 3 hrs. with 3.5 ml. l-menthoxyacetyl chloride with occasional swirling, the clear cold solution (ice bath) treated with 2 ml. H2O and diluted with Et2O, the product from evaporation of the washed and dried Et2O extract taken up in 15 ml. EtOAc and heated with 1.4 g. maleic acid, the filtered solution concentrated, and the residue treated with 50 ml. dry Et 2O yielded 93% salt, m. 79-86°, [α]D -30°, crystallized (50 g.) from 150 ml. alc. and 2.5 ml. to give 9.2 g. material, m. 137-9°, recrystallized from 18 ml. alc. and 450 ml. Et2O to yield 33% I (R = menthoxyacetyl) l,l-hydrogen maleate (VI), m. 139-40°, [α]D -50° (1% MeOH). The optically pure VI (6.8 g.) in 70 ml. MeOH hydrolyzed with 2.8 g. KOH in 35 ml. 80% MeOH 15 min. at 20° and the solution diluted with 200 ml. H2O gave the free base (3.7 g., m. 83-4°), recrystallized from dilute MeOH to yield l-II, m. 86.0-6.5°, [α]D -21°, acidified (1.1 g.) in 5 ml. Me2CHOH with 1 ml. 6.8N HCl in Me2CHOH to give 0.9 g. salt, m. 187-8°, crystallized from 5 ml. Me2CHOH to yield 67% l-II HCl salt, m. 187-8°, [α]D -23°. l-II (1.1 g.) kept 16 hrs. at 20° in 10 ml. C5H5N and 5 ml. Ac2O, excess Ac2O decomposed with 5 ml. H2O, taken up in Et2O and the washed and dried Et2O layer added to 0.4 g. maleic acid in 0.8 ml. MeOH and 10 ml. Et2O, filtered from 1.5 g. product, m. 141-2°, and crystallized from 5 ml. alc. and 75 ml. Et2O yielded 87% l-IV, m. 142-3°, [α]D -22°. Similarly, use of (EtCO)2O gave 80% l-V, m. 143-4°, [α]D -23°. Acylation of 35.0 g. II with 22.1 g. d-menthoxyacetyl chloride yielded, after fractional crystallization, 49% optically pure I (R = menthoxyacetyl) d,d-hydrogen maleate (VII), m. 138.0-8.5°, [α]D 50°, hydrolyzed (13.6 g.) to give 5.2 g. d-II HCl salt, m. 186-7°, [α]D 25°. l-II (1.9 g.) acetylated, the oily ester taken up in 100 ml. dry C6H6 and refluxed 5 hrs. with BrCN, C6H6 removed, the residue refluxed 5 hrs. with 0.8 g. LiAlH4 in 100 ml. dry tetrahydrofuran, excess LiAlH4 destroyed with EtOAc, the mixture treated with dilute HCl and Et2O, the residue on evaporation of the Et2O layer heated 2 hrs. on a steam bath with 1.0 ml. α-C10H7NCO, excess reagent destroyed with 90% aqueous Me2CO, the residue on evaporation taken up in ligroine (b. 60-80°) and chromatographed over 20 g. silica gel, the column washed with 500 ml. 1:1 C6H6-ligroine and eluted with C6H6, and the fraction crystallized from ligroine gave 0.8 g. needles, m. 113-15°, recrystallized from ligroine to give l-α-C10H7NHCO2CHPhEt, m. 116-17°, [α]D -31.5°, also produced by conversion of l-HOCHPhEt (VII) to the urethan. A duplicate experiment using 3.7 g. racemic base gave dl-α-C10H7NHCO2CHPhEt, m. 102-3° (ligroine). VII had the S configuration and l-II was S-1-(3-hydroxy-3-phenylpropyl)-4-ethoxycarbonyl-4-phenylpiperidine. The analgesic potencies in mice are listed (morphine = 1): dl-II HCl, 14; dl-IV, 8; dl-V 14; l-II HCl, 25; l-IV, 11; l-V, 14; d-II, HCl, 7. An increase in analgesic activity was accompanied by an approximately corresponding increase in respiratory depression.

Journal of Organic Chemistry published new progress about Analgesics. 25504-47-6 belongs to class piperidines, and the molecular formula is C7H11NO3, SDS of cas: 25504-47-6.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Wagener, Tobias; Lueckemeier, Lukas; Daniliuc, Constantin G.; Glorius, Frank published the artcile< Interrupted pyridine hydrogenation: Asymmetric synthesis of δ-lactams>, Related Products of 25504-47-6, the main research area is delta lactam preparation oxazolidinone substituted pyridine interrupted hydrogenation; asymmetric catalysis; heterogeneous catalysis; hydrogenation; lactams; nitrogen heterocycles.

Metal-catalyzed hydrogenation is an effective method to transform readily available arenes into saturated motifs, however, current hydrogenation strategies are limited to the formation of C-H and N-H bonds. The stepwise addition of hydrogen yields reactive unsaturated intermediates that are rapidly reduced. In contrast, the interruption of complete hydrogenation by further functionalization of unsaturated intermediates offers great potential for increasing chem. complexity in a single reaction step. Overcoming the tenet of full reduction in arene hydrogenation has been seldom demonstrated. In this work the authors report the synthesis of sought-after, enantioenriched δ-lactams from oxazolidinone-substituted pyridines and water by an interrupted hydrogenation mechanism.

Angewandte Chemie, International Edition published new progress about Hydrogenation. 25504-47-6 belongs to class piperidines, and the molecular formula is C7H11NO3, Related Products of 25504-47-6.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Zacharie, Boulos; Abbott, Shaun D.; Baigent, Christopher B.; Doyle, Christopher; Yalagala, Ravi Shekar published the artcile< An Efficient Two-Step Preparation of α-, β-, γ- or δ-Amino Acids from 2-Pyrazinones, 2-Hydroxypyrimidines or 2-Pyridones Respectively>, Electric Literature of 25504-47-6, the main research area is amino acid alpha beta gamma preparation pyrazinone hydroxypyrimidine pyridone.

A practical and efficient two-step procedure is reported for the preparation of a variety of α-, β-, γ- and δ-amino acids from 2-pyridone, 2-pyrazinone or 2-hydroxypyrimidine and derivatives The procedure is amenable to scale-up and in most cases no chromatog. purification of the product is required. This approach is useful, especially in the synthesis of amino acids or deuterated amino acids that are not obtained by other methods.

European Journal of Organic Chemistry published new progress about Amino acids Role: SPN (Synthetic Preparation), PREP (Preparation). 25504-47-6 belongs to class piperidines, and the molecular formula is C7H11NO3, Electric Literature of 25504-47-6.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Chen, Yilin; Du, Jianbo; Zuo, Zhiwei published the artcile< Selective C-C Bond Scission of Ketones via Visible-Light-Mediated Cerium Catalysis>, Application of C7H11NO3, the main research area is hydrazine regioselective preparation photochem; ketone DIAD photochem carbon bond cleavage cerium catalyst.

A general catalytic manifold for selective C-C bond scission of ketones via exploitation of ligand-to-metal charge transfer (LMCT) excitation mode was reported. Through a cooperative utilization of Lewis acid catalysis and LMCT catalysis, the C-C bond of ketones could be selectively and effectively cleaved, enabling installation of different functionalities at each carbon of cleaved C-C bond through a sequential and orthogonal manner. This reaction manifold served as a photocatalytic alternative to Norrish type I reaction with combination of visible light and inexpensive cerium salts. Under operationally simple conditions, a wide range of acyclic and cyclic ketones, from simple strained cyclobutanones to complex androsterone with less strained cyclopentanone moiety, could be successfully transformed into versatile chem. building blocks.

Chem published new progress about Bond cleavage catalysts (C-C, regioselective). 25504-47-6 belongs to class piperidines, and the molecular formula is C7H11NO3, Application of C7H11NO3.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Takahashi, Torizo; Kariyone, Kazuo published the artcile< Studies on insecticides. V. Synthesis of 2-piperidone derivatives>, Formula: C7H11NO3, the main research area is .

Distillation of 3-methyl-2(1H)-pyridone after hydrogenation gave two fractions: 3-methyl-2-piperidone, b8 128-31°, and 1,3-dimethylpiperidine (I); picrate m. 105°. NaNO2 (6.5 g.) in 30 ml. H2O added dropwise to 8.0 g. 2-amino-4-ethylpyridine in 120 ml. 10% HCl, the mixture stirred 0.5 hr., refluxed 3 hrs., and evaporated to dryness in vacuo, the residue dissolved in H2O, and the solution neutralized, extracted with CHCl3, dried, and concentrated in vacuo gave 5.5 g. 4-ethyl-2(1H)-pyridone (II). A solution containing 9.0 g. isonicotinic acid 1-oxide in 50 ml. MeOH and 1 g. H2SO4 refluxed 5 hrs., concentrated, diluted with 20 ml. H2O, neutralized, extracted with CHCl3, dried, and evaporated to dryness gave Me isonicotinate 1-oxide (III), m. 121° (acetone); picrate derivative m. 107° (EtOH). Hydrogenation of II and III yielded 4-ethyl-2-piperidone and Me 2-oxoisonipecotate, resp. Acetylation of 4-ethylpyridine 1-oxide gave 4-(1-hydroxyethyl)pyridine, m. 63°. III refluxed with Ac2O and concentrated in vacuo, the residue dissolved in H2O, and the solution neutralized and extracted with CHCl3 gave a 4-carbomethoxy-2(1H)-pyridone, m. 210° (acetone).

Chem. & Pharm. Bull. (Tokyo) published new progress about Insecticides. 25504-47-6 belongs to class piperidines, and the molecular formula is C7H11NO3, Formula: C7H11NO3.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Wagener, Tobias; Lueckemeier, Lukas; Daniliuc, Constantin G.; Glorius, Frank published the artcile< Interrupted pyridine hydrogenation: Asymmetric synthesis of δ-lactams>, COA of Formula: C7H11NO3, the main research area is delta lactam preparation oxazolidinone substituted pyridine interrupted hydrogenation; asymmetric catalysis; heterogeneous catalysis; hydrogenation; lactams; nitrogen heterocycles.

Metal-catalyzed hydrogenation is an effective method to transform readily available arenes into saturated motifs, however, current hydrogenation strategies are limited to the formation of C-H and N-H bonds. The stepwise addition of hydrogen yields reactive unsaturated intermediates that are rapidly reduced. In contrast, the interruption of complete hydrogenation by further functionalization of unsaturated intermediates offers great potential for increasing chem. complexity in a single reaction step. Overcoming the tenet of full reduction in arene hydrogenation has been seldom demonstrated. In this work the authors report the synthesis of sought-after, enantioenriched δ-lactams from oxazolidinone-substituted pyridines and water by an interrupted hydrogenation mechanism.

Angewandte Chemie, International Edition published new progress about Hydrogenation. 25504-47-6 belongs to class piperidines, and the molecular formula is C7H11NO3, COA of Formula: C7H11NO3.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Zacharie, Boulos; Abbott, Shaun D.; Baigent, Christopher B.; Doyle, Christopher; Yalagala, Ravi Shekar published the artcile< An Efficient Two-Step Preparation of α-, β-, γ- or δ-Amino Acids from 2-Pyrazinones, 2-Hydroxypyrimidines or 2-Pyridones Respectively>, SDS of cas: 25504-47-6, the main research area is amino acid alpha beta gamma preparation pyrazinone hydroxypyrimidine pyridone.

A practical and efficient two-step procedure is reported for the preparation of a variety of α-, β-, γ- and δ-amino acids from 2-pyridone, 2-pyrazinone or 2-hydroxypyrimidine and derivatives The procedure is amenable to scale-up and in most cases no chromatog. purification of the product is required. This approach is useful, especially in the synthesis of amino acids or deuterated amino acids that are not obtained by other methods.

European Journal of Organic Chemistry published new progress about Amino acids Role: SPN (Synthetic Preparation), PREP (Preparation). 25504-47-6 belongs to class piperidines, and the molecular formula is C7H11NO3, SDS of cas: 25504-47-6.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Chen, Yilin; Du, Jianbo; Zuo, Zhiwei published the artcile< Selective C-C Bond Scission of Ketones via Visible-Light-Mediated Cerium Catalysis>, Synthetic Route of 25504-47-6, the main research area is hydrazine regioselective preparation photochem; ketone DIAD photochem carbon bond cleavage cerium catalyst.

A general catalytic manifold for selective C-C bond scission of ketones via exploitation of ligand-to-metal charge transfer (LMCT) excitation mode was reported. Through a cooperative utilization of Lewis acid catalysis and LMCT catalysis, the C-C bond of ketones could be selectively and effectively cleaved, enabling installation of different functionalities at each carbon of cleaved C-C bond through a sequential and orthogonal manner. This reaction manifold served as a photocatalytic alternative to Norrish type I reaction with combination of visible light and inexpensive cerium salts. Under operationally simple conditions, a wide range of acyclic and cyclic ketones, from simple strained cyclobutanones to complex androsterone with less strained cyclopentanone moiety, could be successfully transformed into versatile chem. building blocks.

Chem published new progress about Bond cleavage catalysts (C-C, regioselective). 25504-47-6 belongs to class piperidines, and the molecular formula is C7H11NO3, Synthetic Route of 25504-47-6.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Wagener, Tobias; Lueckemeier, Lukas; Daniliuc, Constantin G.; Glorius, Frank published the artcile< Interrupted pyridine hydrogenation: Asymmetric synthesis of δ-lactams>, SDS of cas: 25504-47-6, the main research area is delta lactam preparation oxazolidinone substituted pyridine interrupted hydrogenation; asymmetric catalysis; heterogeneous catalysis; hydrogenation; lactams; nitrogen heterocycles.

Metal-catalyzed hydrogenation is an effective method to transform readily available arenes into saturated motifs, however, current hydrogenation strategies are limited to the formation of C-H and N-H bonds. The stepwise addition of hydrogen yields reactive unsaturated intermediates that are rapidly reduced. In contrast, the interruption of complete hydrogenation by further functionalization of unsaturated intermediates offers great potential for increasing chem. complexity in a single reaction step. Overcoming the tenet of full reduction in arene hydrogenation has been seldom demonstrated. In this work the authors report the synthesis of sought-after, enantioenriched δ-lactams from oxazolidinone-substituted pyridines and water by an interrupted hydrogenation mechanism.

Angewandte Chemie, International Editionpublished new progress about Hydrogenation. 25504-47-6 belongs to class piperidines, and the molecular formula is C7H11NO3, SDS of cas: 25504-47-6.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem