13185-18-7

Usage

Uses

Used in Fragrance Industry:
8-Methoxy-3,4-dihydronaphthalen-1(2H)-one is used as a fixative and fragrance ingredient for its long-lasting and stable scent. It is particularly valued in the creation of perfumes, colognes, and other scented products due to its ability to enhance and prolong the aroma of these products.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 8-Methoxy-3,4-dihydronaphthalen-1(2H)-one serves as a key intermediate in the synthesis of various organic compounds and pharmaceuticals. Its chemical properties make it a versatile building block for developing new drugs and medicinal agents.
Used in Chemical Industry:
8-Methoxy-3,4-dihydronaphthalen-1(2H)-one is also utilized in the chemical industry for its aromatic and stabilizing properties. It contributes to the development of a wide range of chemical products, enhancing their performance and quality.

InChI:InChI=1/C11H12O2/c1-13-10-7-3-5-8-4-2-6-9(12)11(8)10/h3,5,7H,2,4,6H2,1H3

Upstream product

• 5356-83-2 ethoxydimethylvinylsilane 
• 88430-97-1 N,N-diethyl-2-methoxy-6-methylbenzamide 
• 77259-96-2 5-Brom-8-methoxy-1,2,3,4-tetrahydro-1-naphthalinon 
• 79383-44-1 methyl 2-methyl-6-methoxybenzoate 
• 292638-85-8 acrylic acid methyl ester 
• 7695-47-8 8-hydroxy-1,2,3,4-tetrahydro-1-naphthalenone 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 24743-11-1 4-(m-methoxyphenyl)butanoic acid 
• 57816-01-0 ethyl 4-(3'-methoxyphenyl)butyrate 
• 824-98-6 m-methoxybenzyl chloride 
• 1292823-28-9 4-(toluene-p-sulfonoxy)-8-methoxy-1-tetralone 
• 766-85-8 3-methoxy-1-iodobenzene 
• 137744-81-1 (E)-4-(m-methoxyphenyl)but-3-enoic acid 

Downstream Products

• 535935-61-6 8-methoxy-1,2,3,4-tetrahydro-1-naphthalenamine 
• 117661-46-8 9-methoxy-2-nitro-naphto<1,2-b>furan 
• 77260-14-1 N-(2,4-Dinitro-phenyl)-N'-[8-methoxy-3,4-dihydro-2H-naphthalen-(1E)-ylidene]-hydrazine 
• 5656-61-1 4,5-dihydro-3H-naphtho<1,8-bc>furan 
• 133601-13-5 8-hydroxymethyl-1,2,3,4-tetrahydro-1-naphthalenone 
• 77260-16-3 N-[8-Bromo-5-methoxy-4a-methyl-4,4a,9,10-tetrahydro-3H-phenanthren-(2E)-ylidene]-N'-(2,4-dinitro-phenyl)-hydrazine 

Relevant academic research and scientific papers

Free energy perturbation studies on binding of the inhibitor 5,6- dihydrobenzo[h]cinnolin-3(2H)one-2-acetic acid and its methoxylated analogs to aldose reductase

Free energy perturbation simulations have been employed to rationalize the binding differences between a benzocinnolinone carboxylic acid inhibitor of aldose reductase and its methoxylated analogs in four selected substitution sites. The calculated free energy differences are in qualitative agreement with the experimental results. The balance between the cost for desolvation and the gain in enzyme binding correctly predicts and rationalizes the different inhibitory activities of each methoxylated compound. The implications for perturbations occurring at the interface between protein residues and water molecules present at the active site are discussed.

Discovery of Chromane-6-Sulfonamide Derivative as a Potent, Selective, and Orally Available Novel Retinoic Acid Receptor-Related Orphan Receptor γt Inverse Agonist

Interleukin-17 (IL-17) is a proinflammatory cytokine that plays a dominant role in inflammation, autoimmunity, and host defense. RORγt is a key transcription factor mediating T helper 17 (Th17) cell differentiation and IL-17 production, which is able to activate CD8+ T cells and elicit antitumor efficacy. A series of sulfonamide derivatives as novel RORγt inverse agonists were designed and synthesized. Using GSK2981278 (phase II) as a starting point, we engineered structural modifications that significantly improved the activity and pharmacokinetic profile. In animal studies, oral administration of compound d3 showed a robust and dose-dependent inhibition of the IL-17A cytokine expression in a mouse imiquimod-induced skin inflammation model. Docking analysis of the binding mode revealed that the compound d3 occupied the active pocket suitably. Thus, compound d3 was selected as a clinical compound for the treatment of Th17-driven autoimmune diseases.

A class of 2, 3 - dihydro - 1H - indenyl -4 - sulfonamide ROR γ regulator and its use (by machine translation)

The invention relates to a structure of formula (I) compound of formula or a stereoisomer thereof, tautomers or its pharmaceutically acceptable salt or solvate or prodrug, its preparation method, a pharmaceutical composition containing these modulators and their use in the treatment ROR γ-mediated inflammatory, metabolic and autoimmune disorders. (by machine translation)

Revisiting secondary interactions in neighboring group participation, exemplified by reactivity changes of iminylium intermediates

Neighboring group participation is defined as the action of a substituent to stabilize a transition state or an intermediate by forming a bond or a partial bond with the reaction center. In addition to the primary interaction with the nearest neighboring group, secondary interactions involving another neighboring group(s) could also occur in principle. Here, we revisit this issue by examining the influence of secondary interactions on the stability and reactivity of the putative iminylium cation intermediates, formed by N-O bond cleavage of 1-tetralone oxime systems. A direct observation of a peri-bromo-iminylium intermediate in solution supported the involvement of iminylium cations and the stabilizing effect of secondary interactions arising from a distal tandem substituent. Both experimental and computational findings support the idea that secondary interactions of a tandem-neighboring group on the primary peri-heteroatom (Br, Cl, and O(Me))-iminylium bonding interaction, i.e., a weak halogen bonding interaction (ester (nitro) oxygen-halogen bonding) and an unprecedented hydrogen bonding interaction between a nitro oxygen atom and a CH3O hydrogen atom, are crucial determinants of the reaction pathway, leading to either overwhelmingly selective syn-migration of the oxime functionality or covalent bond formation under acid-catalyzed Beckmann rearrangement conditions.

An Expeditious Synthesis of 8-Methoxy-1-tetralone

8-Methoxy-1-tetralone was synthesized in a concise and efficient manner involving a sequential palladium-mediated cross-coupling reaction (Heck), catalytic hydrogenation, and intramolecular acylation mediated by Eaton's reagent or Lewis acids. The pivotal step in the synthesis was the use of a bromine substituent at the benzenoid C4 position of the intermediate methyl 4-arylbutyric ester to ensure cyclization ortho to the methoxy moiety and obviate cyclization at the para position to the thermodynamically preferred 6-methoxy-1-tetralone, the sole product obtained in the absence of this blocking group.

Hydrogen Bonded Phenol-Quinolines with Highly Controlled Proton-Transfer Coordinate

A series of polycyclic phenols with intramolecular hydrogen bonds (IMHB) to quinolines was synthesized by Friedl?nder annulation of cycloalkanone-functionalized anisoles with 2-aminobenzaldehyde. The prepared compounds represent the first series of IMHB phenols in which the substitution and conjugation patterns between the phenols and the hydrogen bond acceptors are kept constant, and in which comparable electronic interaction between the two subunits is thus ensured. The distance and relative orientation between the phenolic OH and the quinolone nitrogen atom is controlled by 1,3-cycloalkadienes of different ring sizes to which the phenol and quinoline subunits are formally annulated.1H δ(OH) chemical shift and X-ray crystal structure characterization support the conclusion that the size and conformational preference of the 1,3-cycloalkadiene rings control the H-bond geometry and strength. As a result, the oxygen to nitrogen distances differ by as much as 0.30 ? across the series.

A facile and regioselective synthesis of 1-tetralones via silver-catalyzed ring expansion

A regioselective synthesis of 1-tetralones via silver-catalyzed ring expansion is described. A variety of 1-tetralones are furnished under mild reaction conditions from tertiary cyclobutanols regardless of the electronic properties and steric hindrance of substituents, providing a new and practical method to access diverse 1-tetralone building blocks. Preliminary experimental and DFT studies revealed that a radical-mediated sequence of C-C bond cleavage/C-C bond formation is involved.

Transformation of 5-methoxy-1-tetralone into 8-methoxy-1-tetralone

The transformation of 1-hydroxy-5-methoxtetralin into 4-hydroxy-8-methoxy- 1-tetralone was accomplished in three steps (benzoylation, oxidation and alkaline hydrolysis). Treatment of the corresponding ketotosylate with sodium iodide and zinc dust in dimet

Synthetic methods for the preparation of ARQ 501 (β-Lapachone) human blood metabolites

ARQ 501 (3,4-dihydro-2,2-dimethyl-2H-naphthol[1,2-b] pyran-5,6-dione), a synthetic version of β-Lapachone, is a promising anti-cancer agent currently in multiple Phase II clinical trials. Promising anti-cancer activity was observed in Phase I and Phase II trials. Metabolism by red blood cells of drugs is an understudied area of research and the metabolites arising from oxidative ring opening (M2 and M3), decarbonylation/ring contraction (M5), and decarbonylation/oxidation (M4 and M6) of ARQ 501 offer a unique opportunity to provide insight into these metabolic processes. Since these metabolites were not detected in in vitro incubations of ARQ 501 with liver microsomes and were structurally diverse, confirmation by chemical synthesis was considered essential. In this report, we disclose the synthetic routes employed and the characterization of the reference standards for these blood metabolites as well as additional postulated structures, which were not confirmed as metabolites.