Tag: M.W=150-200

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

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

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

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

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

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

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

Kumar, Jogendra published the artcileEnhancing the Extent of Enolization for α-C-H Bonds of Aliphatic Carboxylic Acid Equivalents via Ion Pair Catalysis: Application toward α-Chalcogenation, Related Products of isoquinoline, the main research area is thioether selenoether preparation regioselective; aliphatic carboxamide thiol thiolation potassium phosphate catalyst; diselenide aliphatic carboxamide selenylation potassium phosphate catalyst.

In general, the α-functionalization of carboxylic acid derivatives RCH2C(O)NHR1 [R = Me, n-Bu, Ph, 3-thienyl, etc.; R1 = pyridin-2-yl, 4-Methylpyridin-2-yl, pyrimidin-2-yl, etc.] requires either a transition metal catalyst or a stoichiometric activating agent/strong base/external additive. A transition metal free α-chalcogenation of aliphatic carboxylic acid equivalent was reported via ion pair formation using K3PO4 as a catalyst. Mild conditions, broad scope, scalability of the process, attaining bioactive glucokinase activators, and some synthetic intermediates establish merits of the strategy.

Journal of Organic Chemistry 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, Related Products of isoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Zhao, Feng published the artcileEnantioselective Synthesis of α-Aryl-β2-Amino-Esters by Cooperative Isothiourea and Broensted Acid Catalysis, Product Details of C9H10O3, the main research area is aminoarylpropanoate enantioselective preparation; enantioselective aminomethylation pentafluorophenyl arylacetate isothiourea hydrochloride catalyst; mechanism enantioselective aminomethylation pentafluorophenyl arylacetate acylisothiouronium intermediate; aminomethylation; cooperative catalysis; isothiourea; mechanistic studies; α-aryl-β-amino acid.

The synthesis of α-aryl-β2-amino esters such as (S)-Bn2NCH2CHPhCO2Me (Bn = PhCH2) through enantioselective aminomethylation of an arylacetic acid ester in high yields and enantioselectivity via cooperative isothiourea and Broensted acid catalysis is demonstrated. The scope and limitations of this process are explored (25 examples, up to 94% yield and 96:4 er), and the method was applied to the syntheses of (S)-venlafaxine hydrochloride and (S)-nakinadine B. Mechanistic studies are consistent with a C(1)-ammonium enolate pathway being followed rather than an alternative dynamic kinetic resolution process. Control studies indicate that (i) a linear effect between catalyst and product er is observed; (ii) an acyl ammonium ion can be used as a precatalyst; (iii) reversible isothiourea addition to an in situ generated iminium ion leads to an off-cycle intermediate that can be used as a productive precatalyst.

Angewandte Chemie, International Edition published new progress about Aminomethylation (stereoselective). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Product Details of C9H10O3.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Cabrera-Pardo, Jaime R. published the artcileSelective Palladium(II)-Catalyzed Carbonylation of Methylene β-C-H Bonds in Aliphatic Amines, Recommanded Product: 2-Methyl-3-(3,4-methylenedioxyphenyl)propionaldehyde, the main research area is secondary aliphatic amine palladium carbon hydrogen bond carbonylation catalyst; beta lactam disubstituted stereoselective preparation; C−H activation; aliphatic amines; carbonylation; lactams; palladium catalysis.

Palladium(II)-catalyzed C-H carbonylation reactions of methylene C-H bonds in secondary aliphatic amines lead to the formation of trans-disubstituted β-lactams in excellent yields and selectivities. The generality of the C-H carbonylation process is aided by the action of xantphos-based ligands and is important in securing good yields for the β-lactam products.

Angewandte Chemie, International Edition published new progress about C-H bond activation. 1205-17-0 belongs to class isoquinoline, name is 2-Methyl-3-(3,4-methylenedioxyphenyl)propionaldehyde, and the molecular formula is C11H12O3, Recommanded Product: 2-Methyl-3-(3,4-methylenedioxyphenyl)propionaldehyde.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem