Category: 104-01-8

Suzuki, Hirotsugu published the artcileRhodium-catalysed decarbonylative C(sp2)-H alkylation of indolines with alkyl carboxylic acids and carboxylic anhydrides under redox-neutral conditions, HPLC of Formula: 104-01-8, the main research area is pyrimidinyl indoline preparation; indoline carboxylic acid decarbonylative alkylation catalyst rhodium; anhydride carboxylic indoline decarbonylative alkylation catalyst rhodium.

A rhodium-catalyzed decarbonylative C(sp2)-H alkylation method for indolines was developed. This reaction facilitated the use of alkyl carboxylic acids and their anhydrides as a cheap, abundant and non-toxic alkyl source under redox-neutral conditions, featuring the introduction of a primary alkyl chain, which cannot be addressed by previous radical-mediated decarboxylative reaction. Through a mechanistic investigation, revealed that an initially formed C-7 acylated indoline was transformed into the corresponding alkylated indoline I [R1 = H, 2-Me, 3-Me, 2-Ph; R2 = 4-Me, 5-Me, 5-MeO, etc.; R3 = Me, i-Bu, cyclohexyl, etc.] via a decarbonylation process.

Organic & Biomolecular Chemistry published new progress about Alkylation (decarbonylative). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, HPLC of Formula: 104-01-8.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Yu, Haiyang published the artcileRhodium(I)-Catalyzed C2-Selective Decarbonylative C-H Alkylation of Indoles with Alkyl Carboxylic Acids and Anhydrides, Category: isoquinoline, the main research area is pyrimidyl alkylated indole preparation regioselective rhodium catalyst; indole alkyl carboxylic acid anhydride decarbonylative alkylation.

A Rh(I)-catalyzed chelation-assisted C2-selective C-H decarbonylative alkylation of indoles with readily available, cheap, safe and structurally diverse alkyl carboxylic acids or anhydrides has been developed. A wide variety of primary and secondary alkyl carboxylic acids and differently substituted indoles are compatible with this transformation, allowing facile synthesis of various C2-alkylated indoles with high efficiency and broad tolerance of diverse functional groups. The reaction proceeds in the absence of any external oxidant, and the presence of readily installable and removable N-pyrimidyl directing group is critical for catalysis. The process is convenient and scalable, and avoids the use of a dried solvent and an inert atm. Moreover, selective C7-alkylation and C2, C7-dialkylation have also been achieved by slightly modifying the reaction conditions.

Asian Journal of Organic Chemistry published new progress about Alkylation (decarbonylative). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Category: isoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Young, Claire M. published the artcileEvaluating aryl esters as bench-stable C(1)-ammonium enolate precursors in catalytic, enantioselective Michael addition-lactonizations, Product Details of C9H10O3, the main research area is keto ester preparation enantioselective diastereoselective; trifluoromethyl enone trichlorophenyl ester Michael lactonization methanolysis isothiourea catalyst; dihydropyranone preparation enantioselective diastereoselective; trichlorophenyl ester trifluoromethyl enone Michael addition lactonization isothiourea catalyst.

An evaluation of a range of aryl, alkyl and vinyl esters as prospective C(1)-ammonium enolate precursors in enantioselective Michael addition-lactonization processes with (E)-trifluoromethylenones using isothiourea catalysis was reported. Electron deficient aryl esters were required for reactivity, with 2,4,6-trichlorophenyl esters providing optimal product yields. Catalyst screening showed that tetramisole was the most effective isothiourea catalyst, giving the desired dihydropyranone products I [Ar = Ph, 4-MeC6H4, 4-F3CC6H4; Ar1 = Ph] in excellent yield and stereoselectivity (up to 90 : 10 dr and 98 : 2 er). The scope and limitations of this process were evaluated, with a range of keto ester products II [Ar1 = Ph, 2-furyl, 4-MeC6H4, 3-MeOC6H4, 4-BrC6H4] being generated after ring-opening with MeOH to give stereodefined dihydropyranones with excellent stereocontrol (10 examples, typically ∼90 : 10 dr and >95 : 5 er).

Organic & Biomolecular Chemistry published new progress about Diastereoselective synthesis. 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

Filatov, Vadim E. published the artcilecis-Diastereoselective Synthesis of Spirooxindolo-β-Lactams by Staudinger Cycloaddition with TsCl as Activating Co-reagent, Computed Properties of 104-01-8, the main research area is spirooxindolo beta lactam preparation cis diastereoselective Staudinger cycloaddition TsCl.

A convenient and versatile one-pot method for synthesis of 1,3-bis-aryl spirooxindolo-β-lactams from isatin Schiff bases and substituted phenylacetic acids using ketene-imine cycloaddition reaction with TsCl for a ketene generation has been developed. The reaction procedure does not require absolute solvents and unstable starting reagents. The studied reactions lead to cis-diastereoselective β-lactam formation for all tested phenylacetic acids except 4-MeOC6H4CH2COOH. An increase of trans-diastereomers yields with increasing temperature and solvent polarity was demonstrated.

ACS Omega published new progress about Diastereoselective synthesis. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Computed Properties of 104-01-8.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Shimbo, Daisuke published the artcileN-Alkenylation of hydroxamic acid derivatives with ethynyl benziodoxolone to synthesize cis-enamides through vinyl benziodoxolones, Application In Synthesis of 104-01-8, the main research area is methoxyamide vinyl benziodoxolone preparation diastereoselective; alkyl hydroxamic acid ethynyl benziodoxolone acetonitrile complex alkenylation.

The stereoselective synthesis of cis-β-N-alkoxyamidevinyl benziodoxolones (cis-β-N-RO-amide-VBXs) I (R = 4-iodophenyl, cyclopropyl, pyridin-3-yl, etc.) from O-alkyl hydroxamic acids RC(O)NHOCH3 in the presence of an ethynyl benziodoxolone-acetonitrile complex (EBX-MeCN) is reported herein. The reaction was performed under mild conditions including an aqueous solvent, a mild base, and room temperature The reaction tolerated various O-alkyl hydroxamic acids derived from carboxylic acids, such as amino acids, pharmaceuticals, and natural products. Vinyl dideuterated cis-β-N-MeO-amide-VBXs, e.g., II, were also synthesized using deuterium oxide as the deuterium source. Valine-derived cis-β-N-MeO-amide-VBX was stereospecifically derivatized to hydroxamic acid-derived cis-enamides, e.g., III, without the loss of stereoselectivity or reduction in the deuterium/hydrogen ratio.

Organic & Biomolecular Chemistry published new progress about Alkenylation, stereoselective. 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

Grotjahn, Sascha published the artcilePhotosubstitution in Dicyanobenzene-based Photocatalysts, SDS of cas: 104-01-8, the main research area is photosubstitution cyano group dicyanobenzene photocatalysts; dicyanobenzene photocatalysts photosubstitution.

We report the photosubstitution of one cyano group in dicyanobenzene-based photocatalysts and thermally activated delayed fluorescence (TADF) emitters. The reaction is a general degradation pathway for some widely used organic photocatalysts such as 4CzIPN and suggests that the active photocatalyst in many reactions is likely different from 4CzIPN. On the contrary, photosubstitution is a facile route to diverse highly reducing photocatalysts and blue TADF emitters.

Organic Letters published new progress about Benzylation (decarboxylative). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, SDS of cas: 104-01-8.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Wu, Xiaofan published the artcileAsymmetric Synthesis of a Key Dextromethorphan Intermediate and Its Analogues Enabled by a New Cyclohexylamine Oxidase: Enzyme Discovery, Reaction Development, and Mechanistic Insight, HPLC of Formula: 104-01-8, the main research area is cyclohexylamine oxidase dextromethorphan intermediate asym synthesis.

(S)-1-(4-Methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline [(S)-1-(4-methoxybenzyl)-OHIQ, (S)-1a] is a key synthetic intermediate in the industrial production of dextromethorphan, one of the most widely used over-the-counter antitussives. We report here that a new cyclohexylamine oxidase discovered by genome mining, named CHAOCCH12-C2, was able to completely deracemize 100 mM 1a under Turner’s deracemization conditions to afford (S)-1a in 80% isolated yield and 99% ee at a semipreparative scale (0.4 mmol). When this biocatalytic reaction was scaled up to a gram scale (5.8 mmol), without reaction optimization (S)-1a was still isolated in 67% yield and 96% ee. The relatively higher kcat determined for CHAOCCH12-C2 was rationalized as one major factor rendering this enzyme capable of oxidizing 1a effectively at elevated substrate concentrations Protein sequence alignment, anal. of our co-crystal structure of CHAOCCH12-C2 complexed with the product 1-(4-methoxybenzyl)-3,4,5,6,7,8-hexahydroisoquinoline [1-(4-methoxybenzyl)-HHIQ, 2a], and the structure-guided mutagenesis study together indicated L295 is one of the critical residues for this efficient enzymic oxidation process and supported the presence of two cavities as well as a catalytically important “”aromatic cage”” formed by F342, Y433, and FAD. The synthetic applicability of CHAOCCH12-C2 was further underscored by the stereoselective synthesis of various enantioenriched 1-benzyl-OHIQ derivatives of potential pharmaceutical importance at a semipreparative scale.

Journal of Organic Chemistry published new progress about Biochemical reaction kinetics. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, HPLC of Formula: 104-01-8.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Kang, Yang published the artcileTwo-Step Synthesis of π-Expanded Maleimides from 3,4-Diphenylfuran-2(5H)-ones, Recommanded Product: 4-Methoxyphenylacetic acid, the main research area is primary amine diphenylfuranone photoinduced dehydrogenative annulation light fluorescent; pi expanded maleimide preparation.

An efficient two-step synthesis of π-expanded maleimide derivatives was reported, which proceeded via a photoinduced dehydrogenative annulation of 3,4-diphenylfuran-2(5H)-ones in EtOH at room temperature for 5 h under an argon atm., followed by interaction with primary amine in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene and O2. The synthesis of highly conjugated maleimides demonstrated that 3,4-diphenylfuran-2(5H)-ones were useful precursors for synthesis of π-expanded lactones and π-expanded maleimides with no need of a transition-metal catalyst. Addnl., the fluorescent properties of the highly conjugated maleimides were characterized and were found to possess high fluorescence quantum yields in dichloromethane solution

Journal of Organic Chemistry published new progress about Cyclization (dehydrogenative). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Recommanded Product: 4-Methoxyphenylacetic acid.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Maeta, Naoya published the artcileProbing Intramolecular Electron Transfer in Redox Tag Processes, Related Products of isoquinoline, the main research area is intramol electron transfer photocatalytic cycloaddition double bond metathesis.

Herein, we show that redox tag-guided intermol. formal [2 + 2] cycloaddition can be used as a probe to investigate intramol. single-electron transfer (SET) mechanisms. The efficacy of intramol. SET can be evaluated in association with concomitant carbon-carbon bond formation and/or cleavage, leading to cycloaddition or cross-metathesis. Exptl. and theor. results suggest that the intramol. SET is under both thermodn. and kinetic control and can also occur through bonds, not only through space.

Organic Letters published new progress about [2+2] Cycloaddition reaction. 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

Hong, Seung Youn published the artcileStereodefined Access to Lactams via Olefin Difunctionalization: Iridium Nitrenoids as a Motif of LUMO-Controlled Dipoles, Product Details of C9H10O3, the main research area is lactam stereodefined synthesis olefin difunctionalization iridium nitrenoid dipole.

Reported herein is a general platform of a stereodefined access to γ-lactams via Cp*Ir-catalyzed olefin difunctionalization, where in situ generated Ir-nitrenoid is utilized as a key motif of 1,3-dipoles to enable amido transfer in a syn-selective manner. Computational studies suggested that the stereodefined process can be attributed to the proposed working mode of concerted [3+2] cyclization. Frontier MO (FMO) anal. implied that a low-lying LUMO (LUMO) of the Ir-imido fragment engages in the olefin interaction. Mechanistic understanding on the nitrene transfer process led us to develop mild catalytic protocols of stereoselective difunctionalization of alkenyl dioxazolones to furnish α-(haloalkyl)- or (oxyalkyl)lactam products which are of high synthetic and medicinal utility. Product stereochem. (threo and erythro) was found to be designated by the olefin geometry (E/Z) of substrates.

Journal of the American Chemical Society published new progress about [3+2] Cycloaddition reaction. 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