Month: November 2022

Buckley, Aoife M. published the artcileDirhodium Carboxylate Catalysts from 2-Fenchyloxy or 2-Menthyloxy Arylacetic Acids: Enantioselective C-H Insertion, Aromatic Addition and Oxonium Ylide Formation/Rearrangement, Synthetic Route of 104-01-8, the main research area is dirhodium carboxylate preparation; arylacetic acid diazocarbonyl compound addition reaction; tetrahydrothiopyran preparation enantioselective diastereoselective; diazooxosulfone carbon hydrogen insertion rhodium catalyst; Aromatic Addition; Carbenoids; C−H Insertion; Diazo Compounds; Rhodium Catalysis.

A new class of dirhodium carboxylate catalysts I (Ar = Ph, naphthalen-2-yl, 4-bromophenyl, etc.; R = 1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl, menthyl) have been designed and synthesized from 2-fenchyloxy or 2-menthyloxy arylacetic acids ArC(OR)COOH which display excellent enantioselectivity across a range of transformations of α-diazocarbonyl compds ArC(=N2)C(O)Ot-Bu. The catalysts were successfully applied to enantioselective C-H insertion reactions of aryldiazoacetates and α-diazo-β-oxosulfones R1(CH2)4S(O)OC(=N2)C(O)R2 (R1 = Ph, octyl, 4-fluorophenyl, etc.; R2 = Me, Bn, Ph) and Me 2-((cyclohexylethyl)sulfonyl)-2-diazoacetate affording the resp. products II and Me (1R,4aS,8aR)-octahydro-1H-isothiochromene-1-carboxylate 2,2-dioxide in up to 93% ee with excellent trans diastereoselectivity in most cases. Furthermore, efficient desymmetrization in an intramol. C-H insertion was achieved. In addition, these catalysts prove highly enantioselective for intramol. aromatic addition with up to 88% ee, and Me 2-diazo-3-(2-allyloxyphenyl)-3-oxopropionate formation and rearrangement with up to 74% ee.

ChemCatChem published new progress about Diastereoselective synthesis. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Synthetic Route of 104-01-8.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Li, Zhen published the artcileLigand-Enabled C-H Hydroxylation with Aqueous H2O2 at Room Temperature, Safety of 4-Methoxyphenylacetic acid, the main research area is benzoic phenylacetic acid hydroxylation hydrogen peroxide carboxyl pyridone ligand; carbon hydrogen bond activation palladium catalyst.

With the large number of Pd(II)-catalyzed C-H activation reactions of native substrates developed in the past decade, the development of catalysts to enable the use of green oxidants under safe and practical conditions has become an increasingly important challenge. Notably, the compatibility of Pd(II) catalysts with sustainable aqueous H2O2 has been a long-standing challenge in catalysis including Wacker-type oxidations Authors report herein a bifunctional bidentate carboxyl-pyridone (CarboxPyridone) ligand that enables room-temperature Pd-catalyzed C-H hydroxylation of a broad range of benzoic and phenylacetic acids with an industry-compatible oxidant, aqueous hydrogen peroxide (35% H2O2). The scalability of this methodol. is demonstrated by a 1000 mmol scale reaction of ibuprofen (206 g) using only a 1 mol % Pd catalyst loading. The utility of this protocol is further illustrated through derivatization of the products and synthesis of polyfluorinated natural product coumestan and pterocarpene from phenol intermediates prepared using this methodol.

Journal of the American Chemical Society published new progress about C-H bond activation. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Safety of 4-Methoxyphenylacetic acid.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Tanaka, Tsukushi published the artcileChemoselective Catalytic α-Oxidation of Carboxylic Acids: Iron/Alkali Metal Cooperative Redox Active Catalysis, Related Products of isoquinoline, the main research area is tetramethyl piperidinyl oxy arylacetic acid preparation chemoselective; carboxylic acid piperidinyloxy tetramethyl enolization iron catalyst.

Chemoselective catalytic activation of carboxylic acid for a 1e- radical process is described. The α-oxidation of a variety of carboxylic acids HOC(O)CH2R (R = 4-methylphenyl, 2H-1,3-benzodioxol-5-yl, thiophen-3-yl, etc.), which preferentially undergo undesired decarboxylation under radical conditions, proceeded efficiently under the optimized conditions. Chemoselective enolization of carboxylic acid was also achieved even in the presence of more acidic carbonyls. Extensive mechanistic studies revealed that the cooperative actions of iron species and alkali metal ions derived from 4 Å mol. sieves substantially facilitated the enolization. For the first time, catalytic enolization of unprotected carboxylic acid was achieved without external addition of stoichiometric amounts of Bronsted base. The formed redox-active heterobimetallic enediolate efficiently coupled with free radical TEMPO, providing synthetically useful α-hydroxy and keto acid derivatives R3OC(O)CH(OR2)R (R2 = 2,2,6,6-tetramethylpiperidin-1-yl, 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-yl, 2,2,6,6-tetramethyl-4-(prop-2-yn-1-yloxy)piperidin-1-yl, 2,2,6,6-tetramethyl-4-(methylcarbonylamino)piperidin-1-yl; R3 = H, Me).

Journal of the American Chemical Society published new progress about Aromatic esters Role: SPN (Synthetic Preparation), PREP (Preparation). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Related Products of isoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Pu, Xiang published the artcileDoubly stereoconvergent construction of vicinal all-carbon quaternary and tertiary stereocenters by Cu/Mg-catalyzed propargylic substitution, Recommanded Product: 1-Methylurea, the main research area is alkyl acetyl benzyl phenyl pentynoate preparation diastereoselective enantioselective; propargyl carbonate keto ester propargylic substitution copper magnesium catalyst.

Here a doubly stereoconvergent, Cu/Mg-catalyzed asym. propargylic substitution reaction to convert simple starting materials to products with vicinal tertiary and all-carbon quaternary stereocenters in high yields and excellent diastereo- and enantioselectivities was reported. Both the nucleophiles and the electrophiles employed in this transformation were racemic. This reaction uses earth abundant metal catalysts, operates under ambient conditions and demonstrated broad substrate scope. The products of this reaction were functional group rich and synthetically versatile. Key to the success of this development was the devise of a Cu/Mg dual catalytic system and the identification of a bulky tridentate pyridinebisimidazoline (PyBim) ligand.

Nature Communications published new progress about Diastereoselective synthesis. 598-50-5 belongs to class isoquinoline, name is 1-Methylurea, and the molecular formula is C2H6N2O, Recommanded Product: 1-Methylurea.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Nugent, Thomas C. published the artcileNoncovalent Bifunctional Organocatalysts: Powerful Tools for Contiguous Quaternary-Tertiary Stereogenic Carbon Formation, Scope, and Origin of Enantioselectivity, COA of Formula: C11H12O3, the main research area is Michael product Mannich reaction products stereoselective crystal structure.

Relying on the assembly of com. available catalyst building blocks, highly stereocontrolled quaternary carbon (all carbon substituted) formation has been achieved with unmatched substrate diversity. For example, the in situ assembly of a tricomponent catalyst system allows α-branched aldehyde addition to nitroalkene or maleimide electrophiles (Michael products), while addition to an α-iminoester affords Mannich reaction products. Very good yields are observed and for fifteen of the eighteen examples 96-99 % ee is observed Using racemic α-branched aldehydes, two contiguous (quaternary-tertiary) stereogenic centers can be formed in high diastereo- and enantiomeric excess (eight examples) via an efficient in situ dynamic kinetic resolution, solving a known shortcoming for maleimide electrophiles in particular. The method is of practical value, requiring only 1.2 equiv of the aldehyde, a 5.0 mol % loading of each catalyst component, for example, O-tBu-L-threonine (O-tBu-L-Thr), sulfamide, DMAP or O-tBu-L-Thr, KOH, and room temperature reactions. As a highlight, the first demonstration of ethylisovaleraldehyde (7) addition is disclosed, providing the most congested quaternary stereogenic carbon containing succinimide product (8) known to date. Finally, mechanistic insight, via DFT calculations, support a noncovalent assembly of the catalyst components into a bifunctional catalyst, correctly predict two levels of product stereoselectivity, and suggest the origin of the tricomponent catalyst system’s exceptionality: an alternative hydrogen bond motif for the donor-acceptor pair than currently suggested for non-assembled catalysts.

Chemistry – A European Journal published new progress about Crystal structure. 1205-17-0 belongs to class isoquinoline, name is 2-Methyl-3-(3,4-methylenedioxyphenyl)propionaldehyde, and the molecular formula is C11H12O3, COA of Formula: C11H12O3.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Cai, Mengke published the artcileEvaluation of antimicrobial activity of Pterocarpus extracts, Application In Synthesis of 104-01-8, the main research area is Pterocarpus Populus Coriolus Gloeophyllum extract antimicrobial.

Pterocarpus is one of the most widely used timber resources on the market. But the utilization rate has been low. In order to improve the utilization of Pterocarpus processing residue, as well as explore the reason of its good decay-resistance. In this study, the antifungal mechanism of Peterocarpes spp., aqueous extracts and ethanol extracts of three Pterocarpus species were studied. The antimicrobial active factors were analyzed by gas chromatog.-mass spectrometry. Italian poplar (Populus euramevicana cv. I-214) wood was immersed in the extracts and then inoculated with both Coriolus versicolor and Gloeophyllum trabeum. The antimicrobial properties of the extracts were studied, and the mechanism underlying these properties were analyzed using gas chromatog.-mass spectrometry. The results showed that the yield of ethanol extracts from the three Pterocarpus species was significantly higher than that of aqueous extracts Pterocarpus soyauxii and Pterocarpus macarocarpus produced the highest yield of ethanol extracts (28.59%) and aqueous extracts (14.31%), resp. With increasing concentrations, the antimicrobial activities of aqueous extracts of Pterocarpus angolensis and Pterocarpus macarocarpus gradually increased, while the antimicrobial activity of other extracts remained constant Gas chromatog.-mass spectrometry anal. identified a considerable number of phenols, ketones, amines, and aromatic compounds in all extracts, which is consistent with their antimicrobial activity and suggests synergism among the chems.

Industrial Crops and Products published new progress about Amines Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Application In Synthesis of 104-01-8.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

White, Nicholas A. published the artcilePhosphoramidates as Steering Elements for Highly Selective Access to Complementary Imidazo[1,2-a]pyrimidine Isomers, Application of 4-Methoxy-N-methylaniline, the main research area is imidazopyrimidine isomer preparation; phosphoryl aminoimidazole ethoxy acrylamide condensation; aminobenzimidazole diethyl chlorophosphate phosphorylation.

Selective N-phosphorylation of aminoimidazoles results in a key steering element that controls isomeric selectivity in the condensation of β-ethoxy acrylamides and aminoimidazoles to furnish imidazo[1,2-a]pyrimidines is reported. Conditions that provide highly selective (99:1) phosphorylation at the endo- or exocyclic nitrogen are identified. Either the 2-amino or 4-amino isomer of the (benzo)imidazo[1,2-a]pyrimidine products could be isolated in 64-95% yield. Mass spectrometric anal. and computational studies give insight into the mechanism of this exceptionally selective transformation.

Organic Letters published new progress about Benzimidazoles Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (amino). 5961-59-1 belongs to class isoquinoline, name is 4-Methoxy-N-methylaniline, and the molecular formula is C8H11NO, Application of 4-Methoxy-N-methylaniline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Hamel, Jean-Denys published the artcileHighly regioselective gold-catalyzed formal hydration of propargylic gem-difluorides, Formula: C11H12O3, the main research area is difluoroketone preparation regioselective; propargylic gem difluoride hydration gold catalyst.

Herein, a highly regioselective gold-catalyzed formal hydration of propargylic gem-difluorides was reported. Not only does this transformation provide access to versatile fluorinated building blocks that were difficult or hardly possible to access beforehand, but it also represents a rare case of a highly regioselective gold-catalyzed hydroalkoxylation of internal alkynes and puts forward the utility of the difluoromethylene unit as a directing group in catalysis.

Organic & Biomolecular Chemistry published new progress about Haloketones Role: SPN (Synthetic Preparation), PREP (Preparation). 1205-17-0 belongs to class isoquinoline, name is 2-Methyl-3-(3,4-methylenedioxyphenyl)propionaldehyde, and the molecular formula is C11H12O3, Formula: C11H12O3.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Tang, Jinghua published the artcileChemoselective Cross-Coupling between Two Different and Unactivated C(aryl)-O Bonds Enabled by Chromium Catalysis, SDS of cas: 86-51-1, the main research area is aryl methyl ether imino aryl ester chromium cross coupling; biaryl preparation.

We report here the first example of cross-coupling between two different and unactivated C(aryl)-O bonds with chromium catalysis. The combination of a low-cost Cr(II) salt, 4,4′-di-tert-butyl-2,2′-dipyridyl (dtbpy) as the ligand, and magnesium as the reductant shows high reactivity in promoting the reductive cross-coupling of aryl Me ether derivatives with aryl esters by cleavage and coupling of two different C(aryl)-O bonds under mild conditions. The formation of active low-valent Cr species by reduction of CrCl2 with Mg can be considered, which prefers to initially activate the C(aryl)-O bond of Ph Me ether with the chelation help of dtbpy and an o-imine auxiliary. The subsequent consecutive reduction, second C(aryl)-O activation, and reductive elimination allow for the achievement of selective cross-coupling of C(aryl)-O/C(aryl)-O bonds.

Journal of the American Chemical Society published new progress about Aromatic esters Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 86-51-1 belongs to class isoquinoline, name is 2,3-Dimethoxybenzaldehyde, and the molecular formula is C9H10O3, SDS of cas: 86-51-1.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Ruan, Mengyao published the artcileElectrochemical two-electron oxygen reduction reaction (ORR) induced aerobic oxidation of α-diazoesters, Synthetic Route of 104-01-8, the main research area is ketoester preparation electrochem green chem; diazoester oxygen reduction reaction aerobic oxidation.

The recent progress in the oxidation of α-diazoesters R1C(=N2)C(O)OR2 (R1 = Ph, 2-naphthyl, benzo[d][1,3]dioxol-5-yl, etc.; R2 = Me, cyclohexyl, (tetrahydrofuran-2-yl)methyl, etc.) to α-ketoesters R1C(O)C(O)OR2 by in situ generated hydrogen peroxide via a two-electron oxygen reduction approach was described. A diverse collection of valuable α-ketoester products was obtained with moderate to high yields under an exogenous-oxidant-free and metal catalyst-free electrochem. conditions.

Chemical Communications (Cambridge, United Kingdom) published new progress about Electrochemical oxidation (aerobic). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Synthetic Route of 104-01-8.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem