59743-69-0

Usage

Uses

Used in Pharmaceutical Applications:
4,7-DIMETHOXY-2-METHYL-INDAN-1-ONE is used as a building block in the synthesis of various organic compounds for pharmaceutical purposes, due to its unique chemical structure and potential to be modified for specific therapeutic effects.
Used in Research and Development:
In the field of organic chemistry and drug design, 4,7-DIMETHOXY-2-METHYL-INDAN-1-ONE is utilized for research and development, allowing scientists to explore its properties and potential applications further.

Upstream product

• 93-02-7 2,5-dimethoxybenzaldehyde 
• 848610-51-5 5-(2,5-dimethoxybenzyl)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 848610-82-2 5-(2,5-dimethoxybenzyl)-2,2,5-trimethyl-1,3-dioxane-4,6-dione 
• 78572-86-8 4,7-dihydroxy-2-methyl-indan-1-one 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 78591-52-3 (+/-)-demethoxyeleutherin 
• 78572-88-0 3-acetonyl-2-acetyl-1,4-dimethoxybenzene 
• 78572-89-1 2-(1-hydroxyethyl)-3-(2-hydroxypropyl)-1,4-dimethoxybenzene 

Relevant academic research and scientific papers

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.

Pyranonaphthoquinone Antibiotics. Part 1. Syntheses of 9-Demethoxyeleutherins and 9-Deoxynanaomycin A Methyl Ester.

The syntheses of 9-demethoxyeleutherins and 9-deoxynanaomycin A methyl ester starting from indan-1-one derivatives are described.Lemieux-Johnson oxidation of the indene (15) derived from 4,7-dimethoxy-2-methylindan-1-one (14) afforded the diketone (16).The diol (17) obtained by lithium aluminium hydride reduction of (16) was treated with hydrochloric acid to give a ca. 1:2 mixture of cis-5,8-dimethoxy-1,3-dimethylisochroman (18) and the trans-isomer (19).Treatment of (16) with hydrogen bromide in acetic acid followed by catalytic reduction gave exclusively the cis-isochroman (18).Oxidative demethylation of the isochromans (18) and (19) afforded the quinones (22) and (23), benzannelation of which in two steps yielded 9-demethoxyeleutherin (24) and 9-demethoxyisoeleutherin (25) respectively.The same oxidation of the indene (32) derived from 4,7-dimethoxyindan-1-one (28) afforded the keto-aldehyde (33), which was treated with methoxycarbonylmethylenetriphenylphosphorane to give the conjugated ester (34).Reductive cyclisation of (34) with sodium borohydride afforded a ca. 1:3.5 mixture of cis-5,8-dimethoxy-3-methoxycarbonylmethyl-1-methylisochroman (35) and the trans-isomer (36).Oxidative demethylation of (36) followed by benzannelation produced 9-deoxynanaomycin A methyl ester (39).