Month: December 2022

Singh, Sanjay published the artcileDevelopment of Transition-Metal-Free Lewis Acid-Initiated Double Arylation of Aldehyde: A Facile Approach Towards the Total Synthesis of Anti-Breast-Cancer Agent, Recommanded Product: 1,2-Dimethoxybenzene, the publication is Chemistry – A European Journal (2022), 28(14), e202104545, database is CAplus and MEDLINE.

This work describes a mild and robust double hydroarylation strategy for the synthesis of sym. /unsym. diaryl- and triarylmethanes in excellent yields using Lambert salt (0.2-1.0 mol%). Despite the anticipated challenges associated with controlling selective product formation, unsym. diaryl- and triarylmethanes products are obtained unprecedentedly. A highly efficient gram scale reaction has also been reported (TON for sym. product=475 and for unsym. product=390). The synthetic utility of the methodol. is demonstrated by the preparation of several unexplored diaryl- and triarylmethane-based biol. relevant mols., such as arundine, vibrindole A, turbomycin B, and certain anti-inflammatory agents. A total synthesis of an anti-breast-cancer agent is also demonstrated. Control experiments, Hammett anal., HRMS and GC-MS studies reveal the reaction intermediates and reaction mechanism.

Chemistry – A European Journal published new progress about 91-16-7. 91-16-7 belongs to ethers-buliding-blocks, auxiliary class Benzene,Ether,Inhibitor,Inhibitor,Inhibitor, name is 1,2-Dimethoxybenzene, and the molecular formula is C13H18BBrO3, Recommanded Product: 1,2-Dimethoxybenzene.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Kurnia, Dessy Yulyani published the artcileTotal synthesis of xylapeptide B [Cyclo-( L-Leu-L-Pro-N-Me-Phe-L-Val-D-Ala )], Application of (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, the publication is Journal of Heterocyclic Chemistry (2022), 59(1), 131-136, database is CAplus.

Xylapeptide B is a cyclopentapeptide isolated from Xylaria sp. derived from the Chinese medicinal plant Sophora tonkinensis. Xylapeptide B was successfully synthesized by a combination of solid- and solution-phase, using the Fmoc (Fmoc = 9-fluorenylmethoxycarbonyl) strategy, and 2-chlorotrityl chloride resin. The coupling reagent used is a combination of HBTU/HOBt to assist in the formation of amide bonds. D-Ala was chosen as the C-terminal because it has a small residue and can facilitate the cyclization process. Linear peptide was cleaved from the resin using a dilute acid concentration of 20% TFA in DCM because the peptide has no protecting group at the side chain. Crude linear peptide was purified by semi-preparative RP-HPLC using 0%-100% ACN eluent for 35 min and obtained a pure mass of 22.4 mg (18.83%). Cyclization was carried out in solution phase using HBTU (3 equivalent) and DIPEA (1% volume/volume) in diluted concentration (1.25 mM) for 72 h at room temperature The cyclization stage was monitored by thin-layer chromatog. (TLC). Crude xylapeptide B was purified by semi-preparative RP-HPLC using 30%-80% ACN eluent for 40 min, to result in 6 mg (8.91%) of the desired xylapeptide B. All synthesized products were characterized by HR-TOFMS, ¹H-, and ¹³C-NMR.

Journal of Heterocyclic Chemistry published new progress about 77128-73-5. 77128-73-5 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, and the molecular formula is C25H23NO4, Application of (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Mugford, Paul F. published the artcileUnexpected Subtilisin-Catalyzed Hydrolysis of a Sulfinamide Bond in Preference to a Carboxamide Bond in N-Acyl Sulfinamides, Name: 2-Methoxyacetamide, the publication is Journal of the American Chemical Society (2005), 127(18), 6536-6537, database is CAplus and MEDLINE.

Subtilisin Carlsberg-catalyzed hydrolysis of N-chloroacetyl p-toluenesulfinamide favored cleavage of the sulfinamide (S(O)-N) bond with a minor amount (âˆ?5%) of the expected carboxamide (C(O)-N) bond. The sulfinamide hydrolysis was enantioselective (E âˆ?17) and yielded remaining starting material enriched in the R-enantiomer and achiral product, sulfinic acid and chloroacetamide, as confirmed by mass spectra and NMR. In contrast, the related subtilisin BPN’ and E favored the carboxamide hydrolysis. Hydrolysis of the pseudo-sym. N-p-toluoyl p-toluenesulfinamide, which contains a sulfinamide and a carboxamide in similar steric and electronic environments, gave only sulfinamide cleavage (>10:1) for subtilisin Carlsberg, showing that sulfinamide cleavage is the preferred path even when a similar carboxamide is available.

Journal of the American Chemical Society published new progress about 16332-06-2. 16332-06-2 belongs to ethers-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Ether, name is 2-Methoxyacetamide, and the molecular formula is C3H7NO2, Name: 2-Methoxyacetamide.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Pancrazzi, Francesco published the artcileOxidative Dearomatization of Phenols and Polycyclic Aromatics with Hydrogen Peroxide Triggered by Heterogeneous Sulfonic Acids, Application In Synthesis of 93-04-9, the publication is European Journal of Organic Chemistry (2021), 2021(39), 5407-5414, database is CAplus.

Authors report herein a method for the oxidative dearomatization of phenols and bare polycyclic arenes into the corresponding quinoid derivatives using hydrogen peroxide. The reaction is catalyzed by sulfonic acids and best results were achieved using heterogenized species. The best results using phenols were achieved using a hybrid material, namely a perfluorinated polymer functionalized with sulfonic acid groups supported on silica. The dearomatization of polycyclic aromatic hydrocarbons performed better using the polymeric acid catalyst. These methods operate under mild conditions, using mild and benign oxidants and thus minimizing the formation of waste.

European Journal of Organic Chemistry published new progress about 93-04-9. 93-04-9 belongs to ethers-buliding-blocks, auxiliary class Naphthalene,Ether, name is 2-Methoxynaphthalene, and the molecular formula is C11H10O, Application In Synthesis of 93-04-9.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Blank, Benoit published the artcileAn efficient method for the selective iridium-catalyzed monoalkylation of (hetero)aromatic amines with primary alcohols, Computed Properties of 52818-63-0, the publication is Advanced Synthesis & Catalysis (2008), 350(5), 749-758, database is CAplus.

An efficient multi-gram scale synthesis protocol of a variety of P,N ligands is described. The synthesis is achieved in a two-step reaction. First, the amine is deprotonated and subsequently the chlorophosphine is added to yield the corresponding P,N ligand. Deprotonation of the amine is normally achieved with BuLi at low temperature, but for the preparation of ligands with a 2,2′-dipyridylamino backbone and phosphines with a high steric demand KH has to be employed in combination with reaction temperatures of 110°C for the salt metathesis step. The reaction of two equivalent of a selected P,N ligand with one equivalent of the iridium complex [IrCl(cod)]₂ (cod = 1,5-cyclooctadiene) affords P,N ligand-coordinated iridium complexes in quant. yield. X-Ray single crystal structure anal. of one of these complexes reveals a monomeric five-coordinated structure in the solid state. The iridium complexes were used to form catalysts for the N-alkylation of aromatic amines with alcs. The catalyst system was optimized by studying 8 different P,N ligands, 9 different solvents and 14 different bases. Systematic variation of the substrate to base and the amine to alc. ratios as well as the catalyst loading led to optimized catalytic reaction conditions. The substrate scope of the developed catalytic protocol was shown by synthesizing 20 different amines of which 12 could be obtained in isolated yields higher than 90%. A new efficient catalyst system for the selective monoalkylation of primary aromatic and heteroaromatic amines with primary aromatic, heteroaromatic as well as aliphatic alcs. has been established. The reaction proceeds with rather moderate catalyst loadings.

Advanced Synthesis & Catalysis published new progress about 52818-63-0. 52818-63-0 belongs to ethers-buliding-blocks, auxiliary class Pyridine,Amine,Benzene,Ether, name is N-(4-Methoxybenzyl)pyridin-2-amine, and the molecular formula is C13H14N2O, Computed Properties of 52818-63-0.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Frisell, Wilhelm R. published the artcileThe binding sites of sarcosine oxidase, Safety of 2-Methoxyacetamide, the publication is Journal of Biological Chemistry (1955), 275-85, database is CAplus.

cf. C.A. 48, 7680h. Methoxyacetate and acetate inhibit the oxidative demethylation of sarcosine by liver mitochondria competitively and to a comyarative degree. When the carboxylate group of either inhibitor is replaced by a less polar substituent, the order of inhibitory activity is COO^– > CHO â‰?CH₂OH > CONH₂. Substitution in the terminal Me group decreased the inhibition in the order: Me > CH₂F > CH₂Cl > CH₂Br > CH₂I. In the methoxyacetate series, binding is proportional to the nucleophilic character of the β-position: N > O > S > CH₂. It is deduced that the carboxylate group is bound to the active surface by an NH₄, guanidinium, or other electrophilic substituent, and that the Me group is bound by a hydrocarbon moiety. In addition to these primary sites there is a 3rd site, electrophilic in nature, which binds N, O, or S. From the comparable activity of methoxyacetate and acetate it is deduced that the carboxylate- and Me-binding sites comprise contiguous corners of a square pattern in which the O, N, and S binding site is a 3rd corner. In fitting such a surface, methoxyacetate and sarcosine assume their most compact or square configuration. MeOCH₂CO₂Et with concentrated NH₄OH yielded the amide, m. 97-9° (uncorrected). HSCH₂CO₂Et treated with MeI in alc. NaOMe and the product hydrolyzed with NaOH yielded S-methylthioglycolic acid, b₂₀ 119-20°.

Journal of Biological Chemistry published new progress about 16332-06-2. 16332-06-2 belongs to ethers-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Ether, name is 2-Methoxyacetamide, and the molecular formula is C3H7NO2, Safety of 2-Methoxyacetamide.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Divya, R. published the artcileSynthesis, experimental and computational characterizations of 8,9-dimethoxybenzo[b]naphtho[2,3-d] thiophene (DBNT) crystals for electro-mechano utilities, Recommanded Product: 1,2-Dimethoxybenzene, the publication is Inorganic Chemistry Communications (2022), 109249, database is CAplus.

Single crystals of organic nonlinear optical material, 8,9-Dimethoxybenzo[b]naphtho[2,3-d] thiophene (DBNT) are need to grow as the titled crystals have thiophene, since thiophenes are having potential bio activity and industrial uses. The entitled specimen is well-grown by solution growth method and reported for the first time for computational and exptl. study. Characterization of the crystals is made using single crystal x-ray diffraction and compared for the elucidation of structure of DBNT for bond parameters. The titled compound is having the chem. formula C₁₈H₁₄O₂S. From the structure, the planar rings are properly identified. The crystal system of DBNT is monoclinic in nature and the space group is P2₁/n. The lattice constants are 13.0063 Å, 5.9632 Å and 18.3802 Å and β is 104.020° which is determined by XRD anal. The nonlinear optical – NLO characteristics of this material is analyzed and is used for opto-electronic gadgets and filters because of its nonlinearities and in exptl. frequency doubling circuits. The composition of elements present in the grown specimen of DBNT crystal was theor. and exptl. analyzed. The morphol. effect of DBNT is analyzed and reported for the surfaces of crystal with magnifications and the dielec. behavior was studied properly for all polarizations and reported for entitled crystalline DBNT material, in mechano use by preloading data as coated DBNT. The dielec. and crystalline nature of the specimen is by elec. correlation and the thin film influx refers the proper grown confirmation of the DBNT and encompasses the filter usage exclusively of opto-electronic way.

Inorganic Chemistry Communications published new progress about 91-16-7. 91-16-7 belongs to ethers-buliding-blocks, auxiliary class Benzene,Ether,Inhibitor,Inhibitor,Inhibitor, name is 1,2-Dimethoxybenzene, and the molecular formula is C8H10O2, Recommanded Product: 1,2-Dimethoxybenzene.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Sheng, Yuanyuan published the artcileEthanol organosolv lignin from different agricultural residues: Toward basic structural units and antioxidant activity, Category: ethers-buliding-blocks, the publication is Food Chemistry (2022), 131895, database is CAplus and MEDLINE.

The growing interest in the substitution of synthetic food antioxidants by natural ones has fostered research on vegetable sources and the screening of raw materials for identifying new antioxidants. Special attention is focused on their extraction from inexpensive or residual sources from agricultural industries. Herein, the antioxidant activities of lignin obtained from 4 residual sources were investigated. The obtained lignin samples were characterized by different anal. techniques evaluating their chem. structure, phenolic content, thermal behavior and mol. weight The antioxidant activity of the analyzed lignins was evaluated by the DPPH assay, the radical ABTS assay, and trivalent iron reduction method. It was found t that lignin antioxidants could scavenge free radicals and reduce oxidants. The high correlation between antioxidant capacity and its total phenol content indicated that phenolic hydroxyl groups were the main contributors to these lignins antioxidant activity.

Food Chemistry published new progress about 134-96-3. 134-96-3 belongs to ethers-buliding-blocks, auxiliary class Immunology/Inflammation,COX,Natural product, name is 4-Hydroxy-3,5-dimethoxybenzaldehyde, and the molecular formula is C19H14Cl2, Category: ethers-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Zhou, Jun published the artcileVisible light-initiated aerobic oxidation of amines to imines over TiO₂ microspheres with TEMPO⁺PF₆^–, Recommanded Product: (2-Methoxyphenyl)methanamine, the publication is Sustainable Energy & Fuels (2022), 6(3), 894-902, database is CAplus.

Semiconductor photocatalysis holds great promise to drive vital chem. reactions utilizing sunlight. Amongst semiconductors, TiO₂-related materials are one of the most viable to achieve enhanced photocatalytic performances because of their intrinsic merits. Here TiO₂ microspheres assembled from nanocrystals with a distinct hierarchical architecture and a high sp. surface area were fabricated using a simple template-free solvothermal process. Assembling amines on TiO₂ microspheres initiated by visible light can lead to a surface complex that captures visible light for further oxidation of amines. Moreover, the selective oxidation of amines could be boosted by fully exploring the surface polarity of TiO₂ microspheres with more polar 2,2,6,6-tetramethylpiperidine-1-oxoammonium hexafluorophosphate (TEMPO⁺PF₆^–) instead of (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO) as the redox mediator. As such, cooperative photocatalysis with TEMPO⁺PF₆^– was framed over TiO₂ microspheres to initiate the efficient and selective aerobic oxidation of benzyl amines into imines. Significantly, the activity of TEMPO⁺PF₆^– surpassed that of TEMPO in aiding the visible light-initiated selective oxidation of amines over TiO₂ microspheres, reaching more than about 3 times in some cases. This work suggests that the surface properties of a semiconductor could be maneuvered to enable coupling with a suitable redox mediator to ameliorate selective organic conversions in an unprecedented manner.

Sustainable Energy & Fuels published new progress about 6850-57-3. 6850-57-3 belongs to ethers-buliding-blocks, auxiliary class Amine,Benzene,Ether, name is (2-Methoxyphenyl)methanamine, and the molecular formula is C7H10O4, Recommanded Product: (2-Methoxyphenyl)methanamine.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Li, Xia published the artcileBlue light-powered hydroxynaphthoic acid-titanium dioxide photocatalysis for the selective aerobic oxidation of amines, COA of Formula: C8H11NO, the publication is Journal of Colloid and Interface Science (2021), 534-543, database is CAplus and MEDLINE.

Solar photocatalysis is the key to resolve many environmental challenges but is usually hard to achieve over a metal oxide semiconductor. Therefore, assembling π-conjugated mols. onto semiconductors becomes an efficient approach to solar conversion via ligand-to-metal charge transfer. Here, a rational design of ligands for titanium dioxide (TiO₂) is presented to produce robust visible light photocatalysts. Three hydroxynaphthoic acids (HNAs) were selected as ligands by extending an extra benzene ring of salicylic acid (SA) at 3,4 or 4,5 or 5,6 positions. These ligands could regulate the performance of TiO₂ in which 2-hydroxy-1-naphthoic acid (2H1NA) endows the best outcome. In detail, blue light-powered cooperative photocatalysis of 2H1NA-TiO₂ with 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO, 5 mol%) inaugurates the expeditious formation of imines by oxidation of amines with atm. oxygen (O₂). Interestingly, the increase of the O₂ pressure from 1 atm to 0.4 MPa promoted the selective oxidation of benzylamine but thereafter declined with a further boost to 0.6 MPa. Notably, an electron transfer between the oxidatively quenched 2H1NA-TiO₂ and TEMPO is established, offering a new pathway for environmental applications. This work presents a strategy in designing cutting-edge visible light photocatalysts via altering semiconductors with surface ligands.

Journal of Colloid and Interface Science published new progress about 6850-57-3. 6850-57-3 belongs to ethers-buliding-blocks, auxiliary class Amine,Benzene,Ether, name is (2-Methoxyphenyl)methanamine, and the molecular formula is C8H11NO, COA of Formula: C8H11NO.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem