Month: November 2022

Richter, Heinrich published the artcileMild Metal-Free Tandem α-Alkylation/Cyclization of N-Benzyl Carbamates with Simple Olefins, Computed Properties of 219543-09-6, the publication is Angewandte Chemie, International Edition (2012), 51(34), 8656-8660, S8656/1-S8656/82, database is CAplus and MEDLINE.

Stereoselective synthesis of oxazines was achieved by metal-free tandem α-alkylation/cyclization of N-benzyl carbamates with olefins. E.g., in presence of TEMPO derivative (I) as oxidant, α-alkylation/cyclization of carbamate II (Ad = 1-adamantyl) gave a mixture of separable diastereomers 77% III and 16% IV.

Angewandte Chemie, International Edition published new progress about 219543-09-6. 219543-09-6 belongs to piperidines, auxiliary class Piperidine,Fluoride,Salt,Amine,Amide, name is 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, and the molecular formula is C11H21BF4N2O2, Computed Properties of 219543-09-6.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Biel, John H. published the artcileAntispasmodics. I. Substituted acetic acid esters of 1-alkyl-3-hydroxypiperidine, Product Details of C7H15NO, the publication is Journal of the American Chemical Society (1952), 1485-8, database is CAplus.

A modification of the method of Paul and Tchelitcheff (C.A. 40, 3757.9) for the preparation of 1-alkyl-3-hydroxypiperidines from furfural (I) or tetrahydrofurfural (II) gave consistently high yields of the alcs. The substituted acetates of the alcs. were potent acetylcholine antagonists. 3-Hydroxypyridine diphenylacetate (III) showed no spasmolytic properties. Tetrahydrofurfuryl chloride (36.0 g.), 68.0 g. Et₂NH, 90.0 g. NaI, and 150 cc. absolute EtOH heated 3 days in a citrate bottle on the steam bath, the mixture filtered, the filtrate evaporated, the residue in water acidified with dilute HCl and extracted with Et₂O, the aqueous phase saturated with KOH, and extracted with Et₂O yielded 25.4 g. N,N-diethyltetrahydrofurfurylamine (IV), b. 64-5°. Reductive aminolysis of I over Raney Ni at 70-90° yielded 71% N-ethyltetrahydrofurfurylamine (V). V (87.0 g.) or 106 g. IV in 54 cc. AcOH at 100-5° treated with 110 g. HBr during 2 h., the mixture neutralized with concentrated KOH below 30°, 350 g. KOH in 300 cc. water added, the mixture distilled, the distillate saturated with KOH and extracted with Et₂O yielded 70 g. N-ethyl-3-hydroxypiperidine (VI), b₁₅ 92-4°; benzoate m. 199-200°. 3-Hydroxypyridine (VII).HCl (39.1 g.) in 250 cc. absolute EtOH hydrogenated at 60 lb. H over 2.2 g. PtO₂ gave 9.0 g. 3-hydroxypiperidine (VIII), m. 61-3°; piperidine-HCl, m. 249-50°. VIII (3.8 g.), 2.3 g. KOH, and 5.9 g. EtI in absolute EtOH refluxed 18 h., cooled, filtered, the filtrate acidified with concentrated HCl, concentrated to dryness in vacuo, the residue dissolved in water and extracted with Et₂O and the aqueous phase saturated with KOH and extracted with Et₂O yielded 4.0 g. VI b₁₅ 93-5°. N-Methyl-3-hydroxypiperidine (IX) prepared in 70% yield from N-methyltetrahydrofurfurylamine b₁₅ 80-2°. VIII (9.0 g.), 13.1 g. 88% HCO₂H, and 8.9 g. 37% HCHO refluxed 24 h. yielded 7.0 g. IX, b₁₅ 81°. PhCH₂CN (117 g.) added during 10 min. to 44.0 g. NaNH₂ in 150 cc. C₆H₆, the mixture refluxed 3 h., 163.0 g. bromocyclohexane in 150 cc. C₆H₆ added at a rate that maintained reflux, the mixture refluxed 8 h., cooled, 250 cc. water added, and the C₆H₆ layer distilled yielded 150 g. α-cyclohexylbenzylnitrile (X), b_0.2 mm. 128-30°, m. 56-8°. Hydrolysis of X yielded 92% phenylcyclohexylacetic acid (XI), m. 153-4°. Ph₂C(OH)CO₂H (22.8 g.) in 150 cc. AcOH at 100° hydrogenated at 60 lb. over PtO₂ yielded 12.7 g. phenylcyclohexylglycolic acid (XII), m. 161-3°. The method of Hoffmann and Schellenberg (C.A. 41, 3074g) yielded 28% phenylcyclopentylglycolic acid (XIII), m. 147-8°. VII (9.5 g.), 23.6 g. Ph₂CHCOCl (XIV), and 50 cc. pyridine refluxed 8 h., the mixture chilled, poured into 600 cc. ice water, the aqueous mixture extracted with Et₂O, the Et₂O evaporated, and the ester distilled in vacuo yielded 26.0 g. III, b_0.5 188-90°; HCl salt (XV), m. 151-2°. XV (26.0 g.) hydrogenated at 60 lb. over 0.5 g. PtO₂, the mixture filtered, the filtrate concentrated in vacuo, the residue in 300 cc. Et₂O refluxed 1 h., filtered, the solid dissolved in water, the solution saturated with KOH, extracted with Et₂O (yielding 3 g. piperidine), the Et₂O filtrate concentrated to dryness, the residue (15 g.) in 200 cc. petr. ether refluxed 1 h., filtered hot [yielding 6.6 g. Ph₂CHCO₂H (XVI), m. 146-8°], and the filtrate cooled yielded 6.0 g. Ph₂CHCO₂Et (XVII), m. 60-60.5°. XVI with LiAlH₄ yielded 77% Ph₂CHCH₂OH, m. 58-9°. XIV and excess NaOEt in absolute EtOH heated a few min. and poured into ice water yielded 80% XVII, m. 59-60°. III (5.0 g.) and 15.0 g. MeI in Et₂O let stand 2 wk in the dark yielded 2.1 g. methiodide, m. 126-8°. N-Alkyl-3-piperidyl esters. Procedure A: XIV (46.0 g.), 25.8 g. VI, and 100 cc. pyridine refluxed 4 h., poured into 800 cc. ice water, the aqueous phase extracted with Et₂O and the extracts evaporated yielded 52.0 g. N-ethyl-3-piperidyl diphenylacetate-HCl. Procedure B: Ph₂C(OH)CO₂H (47.0 g.), 30.5 g. N-ethyl-3-chloropiperidine, and 130 cc. iso-PrOH refluxed 72 h., the solvent removed in vacuo, the residue poured into 200 cc. ice water, acidified with concentrated HCl, extracted with Et₂O, the aqueous layer made alk. with 12 g. NaOH and extracted with Et₂O yielded 49.0 g. N-ethyl-3-piperidyl benzilate-HCl (XVIII), m. 189-90°. Procedure C: The Et ester of XII (21.0 g.), 17.0 g. IX, 0.3 g. Na, and 100 cc. xylene heated at 165° in an oil bath (water and xylene slowly distilled) during 16 h., water, IX, and xylene removed in vacuo, the residue in water acidified with HCl, the aqueous layer extracted with Et₂O, made alk. with KOH, and extracted with Et₂O yielded 3.6 g. N-methyl-3-piperidyl 1-phenylcyclohexylcarboxylate HCl salt, m. 215-16°. XVIII (3.76 g.), and 16.0 g. KOH in alc. refluxed 24 h. yielded 1.2 g. VI, b₁₂ 86-8°; benzoate-HCl, m. 198-9°. Other RCO₂R’ (R’ = 1-ethyl-3-piperidyl) prepared are (R, b.p./mm., salt, and its m.p. given): Ph₂CH, 191-2°/0.18, HCl, 195-6° (MeBr salt, m. 168-9°); Ph(C₆H₁₁)CH, 172-4°/0.55, HCl, 214-16° (MeBr salt, m. 126-7°); Ph₂COH, 207-8°/0.50, HCl, 187-8° (MeBr salt, m. 179-80°); Ph(C₆H₁₁)COH, 166-7°/0.5, HCl, 215-17°; 9-fluorene, -, HCl 226-7°;9-xanthene, -, HCl, 226-7°. Ph₂CHCO₂R (R = 1-methyl-3-piperidyl) b_0.16 173-5° (HCl salt, m. 193-4°).

Journal of the American Chemical Society published new progress about 13444-24-1. 13444-24-1 belongs to piperidines, auxiliary class Piperidine,Alcohol, name is 1-Ethylpiperidin-3-ol, and the molecular formula is C7H15NO, Product Details of C7H15NO.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Steiner, Gerd published the artcileTricyclic epines. Novel (E)- and (Z)-11H-dibenz[b,e]azepines as potential central nervous system agents. Variation of the basic side chain, Name: (1-Methylpiperidin-3-yl)methanamine, the publication is Journal of Medicinal Chemistry (1986), 29(10), 1877-88, database is CAplus and MEDLINE.

Dibenzazepinylideneacetonitriles I (R = alkylamino, aminoalkoxy; R¹ = H, Me, Cl; R² = H, Cl) were prepared and their pharmacol. activities were determined The introduction of the cyanomethylene group into the 11-position of the 11H-dibenz[b,e]azepine framework was carried out by a Wittig-Horner reaction under mild conditions. The (E),(Z) isomers were separated by fractional crystallization, assignment being achieved by X-ray anal. I (R = 4-methyl-1-piperazinyl, R¹ = R² = H; R¹ = 3-Me 3-Cl, R² = H; R¹ = H, R² = 8-Cl) show neuroleptic activity 2-7 times that of clozapine. The screening included tests for sedative and anticholinergic activity in mice, apomorphine and tryptamine antagonism in rats, and muscle-relaxing activity in rabbits. The divergence in the activity profile in the case of the separated (E),(Z) isomers has been observed as an interesting new aspect: the (Z) isomers show a significantly higher sedative and muscle-relaxant activity, whereas the (E) isomers possess a higher anticholinergic efficacy and somewhat greater apomorphine antagonism. Broad changes in the basic side chain were made in order to investigate structure-activity relationships. The important geometrical parameters for the mols., obtained by X-ray anal., were compared with the corresponding features in dopamine agonists and antagonists.

Journal of Medicinal Chemistry published new progress about 14613-37-7. 14613-37-7 belongs to piperidines, auxiliary class Piperidine,Amine, name is (1-Methylpiperidin-3-yl)methanamine, and the molecular formula is C25H23NO4, Name: (1-Methylpiperidin-3-yl)methanamine.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Tresse, Cedric published the artcileTotal synthesis of tiacumicin B: study of the challenging β-selective glycosylations, Recommanded Product: 1-(Phenylsulfinyl)piperidine, the publication is Chemistry – A European Journal (2021), 27(16), 5230-5239, database is CAplus and MEDLINE.

We give a full account of the total synthesis of tiacumicin B (Tcn-B), a natural glycosylated macrolide with remarkable antibiotic properties. Our strategy is based on our experience with the synthesis of the tiacumicin B aglycon and on unique 1,2-cis-glycosylation steps. We used sulfoxide anomeric leaving-groups in combination with a remote 3-O-picoloyl group on the donors that allowed highly β-selective rhamnosylation and noviosylation that rely on H-bond-mediated aglycon delivery. The rhamnosylated C1-C3 fragment was anchored to the C4-C19 aglycon fragment by a Suzuki-Miyaura cross-coupling. Ring-size-selective Shiina macrolactonization provided a semi-glycosylated aglycon that was engaged directly in the noviolysation step with a virtually total β-selectivity. Finally, a novel deprotection method was devised for the removal of a 2-naphthylmethyl ether on a phenol, and efficient removal of all the protecting groups provided synthetic tiacumicin B.

Chemistry – A European Journal published new progress about 4972-31-0. 4972-31-0 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-(Phenylsulfinyl)piperidine, and the molecular formula is C12H16O3, Recommanded Product: 1-(Phenylsulfinyl)piperidine.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Bevan, Thomas W. published the artcileA colorful azulene-based protecting group for carboxylic acids, SDS of cas: 35661-58-6, the publication is Tetrahedron (2018), 74(24), 2942-2955, database is CAplus.

An intensely blue-colored protecting group for carboxylic acids has been developed. The protecting group is introduced through Steglich esterification that couples 6-(2-hydroxyethyl)azulene (AzulE) and the carboxylic acid substrate RC(O)OH (R = cyclohexyl, (E,E)-CH₃CH=CH-CH=CH, ([(9H-fluoren-9-ylmethoxy)carbonyl]amino)methyl, etc.). Deprotection is effected under basic conditions by the addition of the amidine base DBU, whereupon cleavage occurs, accompanied by a color change. A two-step deprotection methodol. comprising activation with oxalyl chloride and deprotection with a very mild base was developed for use with base-sensitive substrates. The AzulE esters I were found to be compatible with other commonly employed protecting groups – silyl ethers, MOM acetals – by studying their orthogonal and concomitant deprotections. The stability of the new protecting group towards various synthetic processes – oxidation, reduction, cross-coupling, olefination and treatment with base – provided the basis of a versatility profile. This indicated that AzulE esters are sensitive to strongly oxidizing and basic agents while being compatible with reducing conditions and selected other reactions. The convenience of a highly colored protecting group for tracking material (and avoiding loss of compound) through laboratory processes warrants further investigation of this and/or related species.

Tetrahedron published new progress about 35661-58-6. 35661-58-6 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-((9H-Fluoren-9-yl)methyl)piperidine, and the molecular formula is C19H21N, SDS of cas: 35661-58-6.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Mathison, Ian W. published the artcileNew compounds. N,N-dimethyl-[3-(1-alkylpiperidy)]carbamates, potential cholinesterase inhibitors, COA of Formula: C7H15NO, the publication is Journal of Pharmaceutical Sciences (1973), 62(1), 158-60, database is CAplus and MEDLINE.

Ten 1-alkylpiperidinyl carbamates [I, R = Me, Et, Me(CH2), n = 2-8] were prepared by condensation of 1-alkyl-3-hydroxypiperidines with Me2NCOCl or by treatment of the hydroxy compound with Cl2CO followed by Me2NH.

Journal of Pharmaceutical Sciences published new progress about 13444-24-1. 13444-24-1 belongs to piperidines, auxiliary class Piperidine,Alcohol, name is 1-Ethylpiperidin-3-ol, and the molecular formula is C7H15NO, COA of Formula: C7H15NO.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Lefebvre, Carole-Anne published the artcileSynthesis of novel substituted pyrimidine derivatives bearing a sulfamide group and their in vitro cancer growth inhibition activity, COA of Formula: C6H12N2O, the publication is Bioorganic & Medicinal Chemistry Letters (2017), 27(2), 299-302, database is CAplus and MEDLINE.

The synthesis of two series of novel substituted pyrimidine derivatives bearing a sulfamide group have been described and their in vitro cancer growth inhibition activities have been evaluated against three human tumor cell lines (HT-29, M21, and MCF7). In general, growth inhibition activity has been enhanced by the introduction of a bulky substituent on the aromatic ring with the best compound having GI₅₀ < 6 μM for all the human tumor cell lines. The MCF7 selective compounds were evaluated on four addnl. human invasive breast ductal carcinoma cell lines (MDA-MB-231, MDA-MB-468, SKBR3, and T47D) and were selective against T47D cell line in all cases except one, suggesting a potential antiestrogen activity.

Bioorganic & Medicinal Chemistry Letters published new progress about 39546-32-2. 39546-32-2 belongs to piperidines, auxiliary class Piperidine,Amine,Amide, name is Piperidine-4-carboxamide, and the molecular formula is C6H12N2O, COA of Formula: C6H12N2O.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Wallace, Michael D. published the artcileRed Algal Molecules – Synthesis of Methyl Neo-β-carrabioside and Its S-Linked Variant via Two Synthetic Routes: A Late Stage Ring Closure and Using a 3,6-Anhydro-D-galactosyl Donor, SDS of cas: 4972-31-0, the publication is Journal of Organic Chemistry (2020), 85(24), 16182-16195, database is CAplus and MEDLINE.

Me neo-β-carrabioside has been synthesized for the first time, employing either a late stage ring closure to install the required 3,6-anhydro-bridge or a suitable 3,6-anhydro-galactosyl donor to form the unfavored 1,2-cis-equatorial α-linkage. Using the late stage ring closure approach, an S-linked analog of Me neo-β-carrabioside was also realized. These compounds have applications in the identification and characterization of marine bacterial exo-α-3,6-anhydro-D-galactosidases that have specific activity on red algal neo-carrageenan oligosaccharides, such as those found in both family 127 and 129 of the glycoside hydrolases. In addition a biochem. assay using the synthesized Me neo-β-carrabioside and the marine bacterial exo-α-3,6-anhydro-D-galactosidase ZgGH129 demonstrates that the min. substrate unit for the enzyme is neo-β-carrabiose.

Journal of Organic Chemistry published new progress about 4972-31-0. 4972-31-0 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-(Phenylsulfinyl)piperidine, and the molecular formula is C24H12, SDS of cas: 4972-31-0.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Cunha, Anna C. published the artcileChemistry and anti-herpes simplex virus type 1 evaluation of 4-substituted-1H-1,2,3-triazole-nitroxyl-linked hybrids, Product Details of C9H17NO, the publication is Molecular Diversity (2021), 25(4), 2035-2043, database is CAplus and MEDLINE.

Abstract: HSV disease is distributed worldwide. Anti-herpesvirus drugs are a problem in clin. settings, particularly in immunocompromised individuals undergoing herpes simplex virus type 1 infection. In this work, 4-substituted-1,2,3-1H-1,2,3-triazole linked nitroxyl radical derived from TEMPOL were synthesized, and their ability to inhibit the in vitro replication of HSV-1 was evaluated. The nitroxide derivatives were characterized by IR spectroscopy and elemental anal., and three of them had their crystal structures determined by single-crystal X-ray diffraction. Four hybrid mols. showed important anti-HSV-1 activity with IC₅₀ values ranged from 0.80 to 1.32μM. In particular, one of the nitroxide derivatives was more active than Acyclovir (IC₅₀ = 0.99μM). All compounds tested were more selective inhibitors than the reference antiviral drug. Among them, two compounds were 4.5 (IC₅₀ 0.80μM; selectivity index CC₅₀/IC₅₀ 3886) and 7.7 times (IC₅₀ 1.10μM; selectivity index CC₅₀/IC₅₀ 6698) more selective than acyclovir (IC₅₀ 0.99μM; selectivity index CC₅₀/IC₅₀: 869). These nitroxide derivatives may be elected as leading compounds due to their antiherpetic activities and good selectivity.

Molecular Diversity published new progress about 826-36-8. 826-36-8 belongs to piperidines, auxiliary class Natural product, name is 2,2,6,6-Tetramethylpiperidin-4-one, and the molecular formula is C9H17NO, Product Details of C9H17NO.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Peng, Chuan published the artcileLow temperature co-pyrolysis of food waste with PVC-derived char: Products distributions, char properties and mechanism of bio-oil upgrading, Recommanded Product: 2,2,6,6-Tetramethylpiperidin-4-one, the publication is Energy (Oxford, United Kingdom) (2021), 119670, database is CAplus.

The main components of municipal solid waste (MSW) include food waste (FW) and polyvinyl chloride (PVC), which present an opportunity to convert energy or value-added products through low-temperature synergetic pyrolysis. In this study, the characteristics of char and bio-oil derived from MSW, FW and PVC feedstocks via pyrolysis at relatively low temperatures (200-300 °C) for 60 min were investigated. The results revealed that the transformation of PVC to HCl gas production started at a temperature of > 200 °C. The oxygenated carbon groups on the char surface were decomposed at elevated reaction temperatures The relative mol. mass of bio-oil derived from FW increased when PVC-derived char was used as a catalyst at 250 °C. In addition, active functional groups and pore structures were formed through synergistic pyrolysis. This work provides information regarding the possible route underlying the network of char and bio-oil production from the synergistic conversion of FW and PVC-derived char.

Energy (Oxford, United Kingdom) published new progress about 826-36-8. 826-36-8 belongs to piperidines, auxiliary class Natural product, name is 2,2,6,6-Tetramethylpiperidin-4-one, and the molecular formula is C9H17NO, Recommanded Product: 2,2,6,6-Tetramethylpiperidin-4-one.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem