4593-38-8

Usage

Chemical Properties

white to light yellow crystal powder

InChI:InChI=1/C10H10O/c1-7-2-4-9-8(6-7)3-5-10(9)11/h2,4,6H,3,5H2,1H3

Upstream product

• 22422-21-5 4'-methyl-3-chloropropiophenone 
• 618084-94-9 2,2-dimethyl-5-(3-methylbenzyl)-1,3-dioxane-4,6-dione 
• 33333-00-5 5,5-ethylenedithio-7a-methyl-2,3,5,6,7,7a-hexahydro-1H-inden-1-one 
• 103040-39-7 3-(3-methylphenyl)propionyl chloride 
• 3751-48-2 3-(3-methylphenyl)propanoic acid 

Downstream Products

• 528-44-9 1,2,4-benzene tricarboxylic acid 
• 511533-14-5 1-(2',4'-dichlorophenyl)-6-methyl-1,4-dihydroindeno[1,2-c]pyrazole-3-carboxylic acid 
• 923036-60-6 1-(2,4-dichloro-phenyl)-6-methyl-1,4-dihydro-indeno[1,2-c]pyrazole-3-carbonyl chloride 
• 511533-26-9 ethyl 1-(2',4'-dichlorophenyl)-6-methyl-1,4-dihydroindeno[1,2-c]pyrazole-3-carboxylate 
• 511532-96-0 gp1a 
• 168902-79-2 5-methyl-1-aminoindane 
• 1160053-91-7 5-methyl-2-(4-nitrobenzyl)-2,3-dihydro-1H-inden-1-one 
• 1620645-86-4 2-[[3-acetyl-1-(o-tolylmethyl)-4H-pyridin-4-yl]methyl]-5-methyl-indan-1-one 

Relevant academic research and scientific papers

Non-conventional methodologies in the synthesis of 1-indanones

1-Indanones have been successfully prepared by means of three different non-conventional techniques, namely microwaves, high-intensity ultrasound and a Q-tube reactor. A library of differently substituted 1-indanones has been prepared via one-pot intramolecular Friedel-Crafts acylation and their efficiency and "greenness" have been compared.

SUBSTITUTED FLUOROETHYL UREAS AS ALPHA 2 ADRENERGIC AGENTS

Therapeutic compounds, and methods, compositions, and medicaments related thereto are disclosed herein.

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.

Indanylidenes. 1. Design and synthesis of (E)-2-(4,6-difluoro-1-indanylidene)acetamide, a potent, centrally acting muscle relaxant with antiinflammatory and analgesic activity

The design of rigid cyclic analogues derived from cinnamamide 1, (E)-N-cyclopropyl-3-(3-fluorophenyl)prop-2-enamide, and β-methylcinnamamide 2, (E)-N-cyclopropyl-3-(3-fluorophenyl)but-2-enamide, has led to the discovery of the potent, centrally acting muscle relaxant (E)-2-(4,6-difluoro-1-indanylidene)acetamide, 17. Compound 17 also possesses potent antiinflammatory and analgesic activity. This paper describes the synthesis and the muscle relaxant, antiinflammatory, and analgesic structure-activity relationships of 17 and 67 of its analogues. Compound 17 has been taken into phase I clinical trials.

Convenient Access to Polysubstituted 1-Indanones by Sc(OTf) 3-Catalyzed Intramolecular Friedel-Crafts Acylation of Benzyl Meldrum's Acid Derivatives

(Matrix presented) The intramolecular Friedel-Crafts acylation of benzyl Meldrum's acids is catalyzed by Sc(OTf)3 under mild reaction conditions. Several polysubstituted 1-indanones have been prepared.

Electron-transfer-induced tautomerization in methylindanones: Electronic control of the tunneling rate for enolization

The radical cations generated from 4-methyl- and 4,7-dimethylindanone, as well as their deuterated isotopomers, isolated in Argon matrices, were found to undergo enolization to the corresponding enol radical cations at rates that differ by orders of magnitude. It is shown by quantum chemical calculations that the effect of the remote methyl group in the 4-position is of purely electronic nature in that it stabilizes the unreactive π-radical relative to the reactive σ-radical state of the 7-methylindanone radical cation. The observed kinetic behavior of the two compounds can be reproduced satisfactorily on the basis of calculated heigth and width of the thermal barrier for enolization, using the Bell model for quantum mechanical tunneling. High-level calculations on the methylacrolein radical cation show that barriers for enolization in radical cations are overestimated by B3LYP/6-31G*.

An expeditious preparation of all enantiopure diastereoisomers of aromatic A-ring analogues of strigolactones, germination stimulants for seeds of the parasitic weeds Striga and Orobanche

An expeditious manner to prepare all enantiopure diastereomers of aromatic A-ring strigolactone analogues is described. The racemic diastereoisomers of 8-methyl GR 24 and of its regioisomer 6-methyl GR 24 were prepared and separated, and subsequently chro

Integrated chemical process: One-pot aromatization of cyclic enones by the double elimination methodology

A variety of aromatic hydrocarbons bearing multiple alkyl substituents are accessible with perfect regiocontrol in a one-pot reaction starting from cyclo-hexenones and their aromatic analogues [Eq. (1)]. The present methodology can be further extended to the synthesis of polycyclic aromatic hydrocarbons. The drawbacks encountered in the Friedel-Crafts reaction are resolved since the reaction proceeds under basic conditions.

Synthesis and Na+/H+ exchange inhibitory activity of indanylideneacetylguanidines

Synthesis of indanylideneacetylguadines 7a-i and their corresponding reduced compounds 8a-e has been achieved and their Na+/H+ exchange inhibitory activity evaluated. All the compounds studied exhibit significant inhibition of Na+/H+ exchanger activity. Promising activity is shown by compounds 7g, 8b and 8d. From the structure activity analysis, it appears that reduction of exocyclic double bond is associated with a marked increase in inhibitory activity.

An N.M.R. Investigation of the Mills-Nixon Effect

The 4J coupling constant, previously established as a probe of bond order, was used to examine the bond orders in a series of ortho-bridged compounds: benzocyclopropene, 1,2-dihydrobenzocyclobutene, indan and tetralin.No evidence for sterically induced bond fixation (i.e. the Mills-Nixon effect) was found, but some evidence for electronic distortion in the corresponding benzylic ketones was observed.The experimental results are in accord with SCF/MO calculations.