Day: November 21, 2022

Xi, Yang published the artcilePalladium-Catalyzed Regio-, Diastereo-, and Enantioselective 1,2-Arylfluorination of Internal Enamides, Name: (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole, the publication is Angewandte Chemie, International Edition (2021), 60(5), 2699-2703, database is CAplus and MEDLINE.

We herein describe a palladium-catalyzed three-component coupling of internal enamides, arylboronic acids, and Selectfluor to access the chiral β-fluoroaminated moiety with up to 99% ee. The prefunctionalized oxazolidinone substituted alkene enables the expedient construction of two vicinal stereocenters with excellent regio-, diastereo-, and enantioselectivities. The synthetic application is exhibited by selective transformation of the product into various vicinal benzylic fluoride derivatives

Angewandte Chemie, International Edition published new progress about 138429-17-1. 138429-17-1 belongs to oxazolidine, auxiliary class BOX Ligands, name is (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole, and the molecular formula is C4H6O3, Name: (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Wu, Yongqi published the artcileIdentification of Novel Tricyclic Benzo[1,3]oxazinyloxazolidinones as Potent Antibacterial Agents with Excellent Pharmacokinetic Profiles against Drug-Resistant Pathogens, SDS of cas: 1219707-39-7, the publication is Journal of Medicinal Chemistry (2021), 64(6), 3234-3248, database is CAplus and MEDLINE.

A series of conformationally constrained novel benzo[1,3]oxazinyloxazolidinones were designed, synthesized, and evaluated on their activities against Mycobacterium tuberculosis, Gram-pos. bacteria, and Gram-neg. bacteria. The studies identified a new compound 20aa that displayed good to excellent antibacterial and antitubercular profiles against drug-resistant TB strains (MIC = 0.48-0.82μg/mL), MRSA (MIC = 0.25-0.5μg/mL), MRSE (MIC = 1μg/mL), VISA (MIC = 0.25μg/mL), and VRE (MIC = 0.25μg/mL) and some linezolid-resistant strains (MIC 1-2μg/mL). Compound 20aa was demonstrated as a promising candidate through ADME/T evaluation including microsomal stability, cytotoxicity, and inhibition of hERG and monoamine oxidase. Notably, 20aa showed excellent mouse PK profile with high plasma exposure (AUC_{0-âˆ?/sub> = 78 669 h·ng/mL), high peak plasma concentration (Cmax = 10 253 ng/mL), appropriate half-life of 3.76 h, and superior oral bioavailability (128%). The present study not only successfully provides a novel benzo[1,3]oxazinyloxazolidinone scaffold with superior druggability but also lays a good foundation for new antibacterial drug development.}

Journal of Medicinal Chemistry published new progress about 1219707-39-7. 1219707-39-7 belongs to oxazolidine, auxiliary class Other Aliphatic Heterocyclic,Oxazolidine,Chiral,Fluoride,Benzene,Amide,Alcohol,Anti-infection, name is (R)-3-(3-Fluoro-4-(1-methyl-5,6-dihydro-1,2,4-triazin-4(1H)-yl)phenyl)-5-(hydroxymethyl)oxazolidin-2-one, and the molecular formula is C8H14O4, SDS of cas: 1219707-39-7.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Kulyk-Sindler, Marija published the artcileFormylation of 2,5-unsubstituted oxazoles: preparation and characterization of 2- and 5-formyl-4-methyloxazoles, SDS of cas: 20662-83-3, the publication is Heterocycles (1994), 38(8), 1791-6, database is CAplus.

Vilsmeier formylation of 4-methyloxazole gave a mixture of 4-methyl-5-oxazolecarboxaldehyde (2) and 4-methyl-2-oxazolecarboxaldehyde (3) in a 1:1 ratio. Both aldehydes were prepared unambiguously: aldehyde 2 by oxidation of 5-hydroxymethyl-4-methyloxazole and reduction of the chloride of 4-methyl-5-oxazolecarboxylic acid and aldehyde 3 by BuLi/DMF procedure. Aldehyde 2 sublimes in a refrigerator while aldehyde 3 forms hydrate, 5-dihydroxymethyl-4-methyloxazole.

Heterocycles published new progress about 20662-83-3. 20662-83-3 belongs to oxazolidine, auxiliary class Oxazole, name is 4,5-Dimethyloxazole, and the molecular formula is C5H7NO, SDS of cas: 20662-83-3.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

St. Angelo, A. J. published the artcileChemical and instrumental analyses of warmed-over flavor in beef, Application of 4,5-Dimethyloxazole, the publication is Journal of Food Science (1987), 52(5), 1163-8, database is CAplus.

Raw, freshly cooked, stored, and recooked beef muscle samples were assessed by chem., instrumental, and sensory methods of analyses for flavor quality, with particular emphasis on warmed-over flavor (WOF). The character notes used by a trained sensory panel to describe WOF were cardboardy, rancid, stale, and metallic. Samples analyzed by direct gas chromatog. utilizing either packed of fused silica capillary columns showed that compounds usually associated with lipid oxidation reactions could be used as marker compounds to follow the development of WOF. Of the many compounds that appeared to be markers, hexanal and 2,3-octanedione as well as total volatiles showed a highly significant degree of correlation when compared to sensory scores and 2-thiobarbituric acid (TBA) numbers Many of the volatile compounds that were identified in WOF meat samples were also found in the distillates prepared for the TBA reaction.

Journal of Food Science published new progress about 20662-83-3. 20662-83-3 belongs to oxazolidine, auxiliary class Oxazole, name is 4,5-Dimethyloxazole, and the molecular formula is C8H5F3N4, Application of 4,5-Dimethyloxazole.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Collina, Simona published the artcileEfficient microwave and phosphine-free synthesis of trisubstituted olefins via Heck coupling, Application of 5-(4-Bromophenyl)oxazole, the publication is Letters in Organic Chemistry (2006), 3(1), 16-20, database is CAplus.

We describe an easy and convenient procedure for palladium-catalyzed Heck arylation of disubstituted olefins via microwave irradiation This method of synthesis produces trisubstituted olefins under phosphine-free conditions and in very short times.

Letters in Organic Chemistry published new progress about 72571-06-3. 72571-06-3 belongs to oxazolidine, auxiliary class Oxazole,Bromide,Benzene, name is 5-(4-Bromophenyl)oxazole, and the molecular formula is C9H6BrNO, Application of 5-(4-Bromophenyl)oxazole.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Takeuchi, Susumu published the artcileAsymmetric bis(alkoxycarbonylation) reaction of terminal olefins catalyzed by palladium in the presence of copper(I) triflate and a chiral bioxazoline ligand, Product Details of C14H24N2O2, the publication is Bulletin of the Chemical Society of Japan (2001), 74(5), 955-958, database is CAplus.

A palladium-catalyzed asym. bis(alkoxycarbonylation) reaction of terminal olefins in the presence of copper(I) triflate was achieved by using a chiral bioxazoline ligand, (4S,4’S)-4,4′-dibenzyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole, under normal pressure of carbon monoxide and oxygen at 25 °C to give the corresponding optically active mono-substituted succinates with enantioselectivity up to 66% ee.

Bulletin of the Chemical Society of Japan published new progress about 138429-17-1. 138429-17-1 belongs to oxazolidine, auxiliary class BOX Ligands, name is (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole, and the molecular formula is C8H6ClN, Product Details of C14H24N2O2.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Onimura, Kenjiro published the artcileAsymmetric polymerization of N-substituted maleimides with organolithium-bisoxazolines complex, Application of (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole, the publication is Polymer Bulletin (Berlin) (1997), 39(4), 437-444, database is CAplus.

Asym. anionic polymerizations of achiral N-substituted maleimide (RMI) (N-cyclohexyl, N-Ph, and N-tert-Bu) by n-butyllithium (n-BuLi) or fluorenyllithium (FlLi) complexes of chiral bisoxazoline derivatives in toluene gave optically active polymers ([α]₄₃₅²⁵ -2.9 to -8.2°). The polymers prepared with initiator of n-BuLi-2,2′-bis(4,4′-isopropyl-1,3-oxazoline) showed neg. sp. rotations (poly(RMI), [α]₄₃₅²⁵ -5.8 to -8.2°) which were greater than those ([α]₄₃₅²⁵ -2.9 to -5.9°) with other chiral 2,2′-bis(4,4′-alkyl-1,3-oxazoline) (alkyl = iso-Bu and benzyl).

Polymer Bulletin (Berlin) published new progress about 138429-17-1. 138429-17-1 belongs to oxazolidine, auxiliary class BOX Ligands, name is (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole, and the molecular formula is C14H24N2O2, Application of (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Bredereck, Hellmut published the artcileFormamide reactions. I. Imidazole syntheses with formamide, SDS of cas: 20662-83-3, the publication is Chemische Berichte (1953), 88-96, database is CAplus.

α-HO, α-halo, α-NH₂, and, under reducing conditions, α-isonitroso ketones give 4,5-disubstituted imidazoles. Boiling 10 g. acetoin with 50 cc. HCONH₂ (I) 4 h. gives 55% 4,5-dimethylimidazole, HN.CH:N.CR:CR’ (II, R = R’ = Me) (III), b₁₁ 165-75°, m. 117° (HCl salt, m. 305°). Similarly, the following II (R = R’) are prepared (R, % yield, b.p., m.p., HCl salt (a) m.p. in the order given): Et, from propionoin, 67, b₁₀ 150-60°, 82-5°, a 252-3°; Pr, 81, b₁₀ 168°, 66°, a 163°; Bu, 72, b₁₁ 197-203°, -, a 147°; iso-Bu, 61, yellow oil, b. 177-9°, a (crystallizing with 1 H₂O) m. 72°, 131° (H₂O-free); Am, 51, light yellow oil, b₉ 210-16°, a 142°; C₆H₁₃, 45, -, -, a 130°; Me₂CH (IV), -, -, 214°, a 221° (formate salt, C₉H₁₆N₂.CH₂O₂ 85% yield, m. 140°; HBr salt, m. 225°). Refluxing 4 g. sebacoin with 15 cc. I 2 h. gives 87% 4,5-octamethyleneimidazole, needles, m. 229°, HCl salt m. 270°. 1-Cyclohexadecanol-2-one, b_0.03 156°, (8 g.) refluxed 2 h. with 50 cc. I gives 91% 4,5-tetradecamethyleneimidazole, leaflets, m. 115°, HCl salt m. 241°. 1,6-Diphenylpropionoin, b_0.05 180-90°, prepared in 53% yield from 29 g. PhCH₂CH₂CO₂Et and 8 g. Na in xylene, (5 g.) and 25 cc. I 2 h. give 66% II (R = R’ = PhCH₂CH₂), m. 112°. II are also prepared from benzoins, NH₂ ketones, and halogen ketones. Refluxing 10 g. benzoin with 20 cc. I 2 h. gives 91% II (R = R’ = Ph) (V), m. 231°; 10 g. furoin and 50 cc. I 2 h. give 89% II (R = R’ = α-furyl), m. 163°; p-dimethylaminobenzoin and I give 62% II [R = 4(5)-p-Me₂NC₆H₄, R’ = 5(4)-Ph], yellowish crystals, m. 230°; and 4 g. α-hydroxybutyrophenone and 20 cc. I 3 h. give 70% II (R = Ph, R’ = Et, or R and R’ may be interchanged), m. 172°. Refluxing 5 g. PhCOCHPhNH₂ 2 h. with 30 cc. I gives 90% V. Warming 10 g. benzilmonoxime with 70 cc. I and 3 cc. HCO₂H at 70° with slow addition of 2 g. NaHSO₃ and refluxing the mixture gently 1 h. give 71% V. Refluxing 8 g. PhCOCH₃Br and 50 cc. I 2 h. gives 90% II (R = Ph, R’ = H, or R and R’ may be interchanged), m. 128°; PhCOCHBrCHMe₂ and I give 69% II (R = Ph, R’ = Me₂CH, or R and R’ may be interchanged) b₁₅ 210-15°, m. 200°. PrCOCHBrEt and I 4 h. give 49% II (R = Et, R’ = Pr, or R and R’ may be interchanged), b₂₀ 185-95°; HCl salt m. 162°. Refluxing 25 g. MeCOCHBrMe and 100 cc. I 3 h. and fractionally distilling the product give 22% 4,5-dimethyloxazole, b₇₆₀ 129-35° [H₂PtCl₆ salt m. 240° (decomposition)], and 47% III, b₁₅ 170° (HBr salt, m. 265°). m-O₂NC₆H₄COCH₂Br and I 2 h. give 72% II (R = m-O₂NC₆H₄, R’ = H, or R and R’ may be interchanged), yellow crystals, m. 224°; p-MeO analog, 62%, leaflets, m. 137°.

Chemische Berichte published new progress about 20662-83-3. 20662-83-3 belongs to oxazolidine, auxiliary class Oxazole, name is 4,5-Dimethyloxazole, and the molecular formula is C5H7NO, SDS of cas: 20662-83-3.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Adams, An published the artcileCharacterization of Model Melanoidins by the Thermal Degradation Profile, Computed Properties of 20662-83-3, the publication is Journal of Agricultural and Food Chemistry (2003), 51(15), 4338-4343, database is CAplus and MEDLINE.

Different types of model melanoidins (Maillard reaction products) were thermally degraded, with subsequent identification of the volatiles produced, to obtain and compare the thermal degradation profile of various melanoidins. At first, the volatiles produced from heated glucose/glycine standard melanoidins were compared with glucose/glutamic acid and L-(+)-ascorbic acid/glycine standard melanoidins. In the headspace of heated glucose/glycine melanoidins, mainly furans, were detected, accompanied by carbonyl compounds, pyrroles, pyrazines, pyridines, and some oxazoles. Heating of L-(+)-ascorbic acid/glycine melanoidins resulted in more N-heterocycles, while from glucose/glutamic acid melanoidins no N-heterocycles were formed. In a second part, a chem. treatment was applied to glucose/glycine melanoidins prior to the thermal degradation Acid hydrolysis was performed to cleave glycosidically linked sugar moieties from the melanoidin skeleton. Nonsol. glucose/glycine melanoidins were also subjected to an oxidation The results indicate that the thermal degradation profile is a useful tool in the characterization of different types of melanoidins.

Journal of Agricultural and Food Chemistry published new progress about 20662-83-3. 20662-83-3 belongs to oxazolidine, auxiliary class Oxazole, name is 4,5-Dimethyloxazole, and the molecular formula is C5H7NO, Computed Properties of 20662-83-3.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Li, Bijin published the artcileUnexpected Sole Enol-Form Emission of 2-(2′-Hydroxyphenyl)oxazoles for Highly Efficient Deep-Blue-Emitting Organic Electroluminescent Devices, Product Details of C9H6BrNO, the publication is Advanced Functional Materials (2017), 27(9), n/a, database is CAplus.

Considerable efforts have been devoted to the development of highly efficient blue light-emitting materials. However, deep-blue fluorescence materials that can satisfy the Commission Internationale de l’Eclairage (CIE) coordinates of (0.14, 0.08) of the National Television System Committee (NTSC) standard blue and, moreover, possess a high external quantum efficiency (EQE) over 5%, remain scarce. Here, the unusual luminescence properties of triphenylamine-bearing 2-(2′-hydroxyphenyl)oxazoles (3a-3c) and their applications in organic light-emitting diodes (OLEDs) are reported as highly efficient deep-blue emitters. The 3a-based device exhibits a high spectral stability and an excellent color purity with a narrow full-width at half-maximum of 53 nm and the CIE coordinates of (0.15, 0.08), which is very close to the NTSC standard blue. The exciton use of the device closes to 100%, exceeding the theor. limit of 25% in conventional fluorescent OLEDs. Exptl. data and theor. calculations demonstrate that 3a possesses a highly hybridized local and charge-transfer excited state character. In OLEDs, 3a exhibits a maximum luminance of 9054 cd m^-2 and an EQE up to 7.1%, which is the first example of highly efficient blue OLEDs based on the sole enol-form emission of 2-(2′-hydroxyphenyl)azoles.

Advanced Functional Materials published new progress about 72571-06-3. 72571-06-3 belongs to oxazolidine, auxiliary class Oxazole,Bromide,Benzene, name is 5-(4-Bromophenyl)oxazole, and the molecular formula is C9H6BrNO, Product Details of C9H6BrNO.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem