4136-26-9

Usage

InChI:InChI=1/C13H16O3/c1-13(2)7-10(14)8-5-11(15-3)12(16-4)6-9(8)13/h5-6H,7H2,1-4H3

Upstream product

• 89980-69-8 3,4-dimethoxyphenylmagnesium bromide 
• 90-05-1 2-methoxy-phenol 
• 51458-29-8 5,6-dimethoxy-1,1-dimethyl-2,3-dihydro-1H-indane 
• 98910-57-7 2-methoxyphenyl mesylate 
• 541-47-9 3-Methylbutenoic acid 
• 2231-66-5 2,2-dimethyl-5-(propan-2-ylidene)-1,3-dioxane-4,6-dione 
• 91-16-7 1,2-dimethoxybenzene 
• 83923-91-5 5-hydroxy-6-methoxy-3,3-dimethylindan-1-one 
• 74-88-4 methyl iodide 
• 98910-54-4 2'-methoxyphenyl 3-methylbut-2-enoate 
• 37637-88-0 N-formamido-3-methyl-2-butenamide 
• 3350-78-5 3,3-Dimethylacryloyl chloride 

Downstream Products

• 97337-98-9 1,1-dimethyl-indan-5,6-diol 
• 81323-52-6 C₂₀H₂₄N₂O₄S 

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.

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.

Diamide compound and drugs containing the same

The present invention provides diamide derivatives represented by the following general formula (1): wherein A is a phenyl group or the like, which may be substituted, B is —CH═CH—, —C═C—, —(CH═CH)2—, —C≡C—CH═CH—, —CH═CH—C≡C—, phenylene or the

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.

Improved Preparation of 5,6-Dialkoxy-1,1-dimethylindenes, Precocene Analogues Lacking the Pyranyl Oxygen Atom

The use of methanesulfonic acid as solvent and catalyst in the cyclocondensation of 1,2-dialkoxybenzenes with 3-methylbut-2-enoyl chloride to afford indanones 3, thus allowing the preparation of indenes 4 with improved overall yields, is reported.Additionally, structure of dimeric compound 7a, formed in high yield by thermal treatment of 4a has been determined by combination of spectroscopic means and selective deuterations. - Keywords: Precocene Analogues, Methanesulfonic Acid, Indenes

Analogues of Antijuvenile Hormones

Several analogues of precocenes I and II have been synthsized, including derivatives of 6,7-dihydroxy-2,2-dimethylchromen, 7,8-dihydroxy-2,2-dimethylchromen, 7-hydroxy-2,2-dimethyl-6-nitrochromene, and 6-amino-7-hydroxy-2,2-dimethylchromen. 5,6-Dimethoxy-3,3-dimethylindene was also synthesized.Improved procedures for the dehydration of chroman-4-ols to chromens and for the reduction of chroman-4-ones to chroman-4-ols are reported.Analogues have been tested for activity in the brown planthopper Nilaparvatus lugens Stal.None had significant morphogenetic effects, but two possessed insecticidal activity and showed both antagonism and synergism when used in cojunction with permethrin.