4082-25-1

Usage

Uses

Used in Fragrance and Flavor Industry:
3-Methyl-5,6-dimethoxy-2,3-dihydro-1H-indene-1-one is used as a key ingredient in the fragrance and flavor industry for its distinctive sweet and woody scent. It contributes to the creation of various perfumes and scented products, enhancing their appeal and sensory experience.
Used in Food Industry:
In the food industry, 3-Methyl-5,6-dimethoxy-2,3-dihydro-1H-indene-1-one is used as a flavoring agent to impart a pleasant aroma and taste to a wide range of products. Its unique scent profile allows it to enhance the sensory qualities of food items, making them more enjoyable for consumers.
Used in Pharmaceutical Industry:
3-Methyl-5,6-dimethoxy-2,3-dihydro-1H-indene-1-one is used in the pharmaceutical industry for its potential medicinal applications. Its chemical properties make it a candidate for further research and development in the field of medicinal chemistry, where it may contribute to the discovery of new drugs and therapeutic agents.

Upstream product

• 91-16-7 1,2-dimethoxybenzene 
• 625-38-7 but-3-enoic acid 
• 1089665-06-4 4,5-dimethoxy-2-(prop-1-en-2-yl)benzaldehyde 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 
• 7706-60-7 3-(3,4-dimethoxy-phenyl)-crotonic acid ethyl ester 
• 67101-91-1 5-[(3,4-dimethoxyphenyl)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 90802-47-4 formamido-2-butenamide 
• 107-93-7 (E)-but-2-enoic acid 
• 27877-65-2 3-(3,4-dimethoxy-phenyl)-butyric acid 

Downstream Products

• 137542-51-9 4-Amino-5-hydroxy-6-methoxy-3-methyl-1-indanone 
• 81323-49-1 C₁₉H₂₂N₂O₄S 

Relevant academic research and scientific papers

NEW DERIVATIVES OF 18-CROWN-6 CONTAINING A METHYLINDANONE FRAGMENT IN THE RING

New derivatives of 18-crown-6 containing a methylindanone fragment in the ring have been obtained by the acylation of dibenzo-18-crown-6 with unsaturated acids in the presence of polyphosphoric acid.

A metal-free method for the facile synthesis of indanonesviathe intramolecular hydroacylation of 2-vinylbenzaldehyde

A facile method for the synthesis of indanones was developed under metal- and additive-free conditions, whereinl-proline served as an efficient and environmentally benign catalyst. Compared with previously synthesized indanones, synthesis by the transition-metal-catalyzed intramolecular hydroacylation of 2-vinylbenzaldehyde provided a more green synthetic pathway to indanone scaffolds with good to excellent yields. More importantly, it could be used to synthsize the anti-AD drug donepezil.

Meldrum's acids as acylating agents in the catalytic intramolecular Friedel-Crafts reaction

(Chemical Equation Presented) The intramolecular Friedel-Crafts acylation of aromatics with Meldrum's acid derivatives catalyzed by metal trifluoromethanesulfonates is reported. Meldrum's acids are easily prepared, functionalized, handled, and purified. The synthesis of polysubstituted 1-indanones from benzyl Meldrum's acids was investigated thoroughly, and it was shown that a variety of catalysts were effective, while accommodating a diversity of functional groups under mild conditions. The scope, limitations, and functional group tolerance (terminal alkene and alkyne, ketal, dialkyl ether, dialkyl thioether, aryl methyl ether, aryl TIPS and TBDPS ethers, nitrile- and nitro-substituted aryls, alkyl and aryl halides) for a variety of 5-benzyl (enolizable Meldrum's acids) and 5-benzyl-5-substituted Meldrum's acids (quaternized Meldrum's acids), forming 1-indanones and 2-substituted-1- indanones, respectively, are delineated. This method was further applied to the synthesis of 1-tetralones, 1-benzosuberones, and the potent acetylcholinesterase inhibitor donepezil. Rate of cyclization as a function of ring size was established for various benzocyclic ketones via competition experiments: 1-tetralones form faster than both 1-indanones and 1-benzosuberones, and 1-benzosuberones cyclize faster than 1-indanones.

Conception, characterization and correlation of new marine odorants

Via a synthetic sequence consisting of PPA-mediated Friedel-Crafts acylation of veratrol (8), Clemmensen reduction, demethylation with TMSI, Williamson ether synthesis employing 3-chloro-2-(chloromethyl)prop-1-ene and in-situ ruthenium tetroxide oxidation, numerous substituted benzo[b][1,4]dioxepinones 15-27 and 2,3-dihydro-1H-5,9-di-oxacyclohepta[f]indenones 7, 13 and 14 were prepared to study their odor-structure correlation. In the course of these studies, we discovered the extremely powerful new marine odorant 7-(3′ -methylbutyl)benzo[b][1,4]dioxepin-3-one (16). On the basis of the measured odor threshold data, an olfactophore model was constructed that rationalizes the observed odor intensities, and indicates an aliphatic hydrophobe at a distance of 6.3 A from the centre of the aromatic-ring binding site. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

1,2-substituted 2,3-dihydro-1H-5,9-dioxacyclohepta [ f ] inden -7- ones and 7-substituted benzo [ b ] [ 1,4 ] dioxepin -3-ones

The invention relates to 1,2-substituted 2,3-dihydro-1H-5,9-dioxacyclohepta[f]inden-7-ones and 7-substituted benzo[b][1,4]dioxepin-3-ones and to the use of these compounds in fragrance compositions.

α, β-Unsaturated N-Acylureas as Useful Intermediates for the Synthesis of Indanones, Chromanones and Coumarins

α,β-Unsaturated N-acylureas, viz-N-formamido-2-butenamide (I), N-formamido-3-methyl-2-butenamide (II) and N-formamido-3-phenyl-2-propenamide (III) react with aryl alkyl ethers in the presence of PPA to afford the corresponding crotonophenones and chalcones (IV) at lower temperature and 1-indanones (V) at a higher temperature.Reactions of I and II with phenols in the presence of PPA afford the 4-chromanones (VI), while III gives 3,4-dihydro-4-phenylcoumarins (VII) in excellent yields.