28009-80-5

Usage

Uses

Used in Chemical Synthesis:
DI-TERT-BUTYL 1,3-ACETONEDICARBOXYLATE is used as a synthetic intermediate for the production of di-tert-butyl 2,3-pentadienedioate. This application is significant because it allows for the creation of new compounds with potential applications in various industries, such as pharmaceuticals, materials science, and more.

InChI:InChI=1/C13H22O5/c1-12(2,3)17-10(15)7-9(14)8-11(16)18-13(4,5)6/h7-8H2,1-6H3

Upstream product

• 558-17-8 tert-Butyl iodide 
• 542-05-2 acetonedicarboxylic acid 
• 115-11-7 isobutene 
• 463-51-4 Ketene 
• 1663-67-8 malonoyl dichloride 
• 75-65-0 tert-butyl alcohol 
• 40052-13-9 mono-tert-butyl malonate 
• 40204-26-0 malonic acid monobenzyl ester 

Downstream Products

• 1577256-57-5 C₂₂H₃₃NO₆ 

Relevant academic research and scientific papers

General Approach to the Synthesis of Poliquinenes. 8. Synthesis of Triquinacene, 1,10-Dimethyltriquinacene, and 1,10-Cyclohexanotriquinacene

The synthesis of tricyclo4,10>deca-2,5,8-triene (1), 1,10-dimethyltricyclo4,10>deca-2,5,8-triene (3), and tetracyclo1,8.04,8>tetradeca-2,5,13-triene (4) has been accomplished via the reaction of 1,2-dicarbonyl compounds with di-tert-butyl 3-oxoglutarate (Weiss reaction).Condensation of glyoxal 5a with di-tert-butyl 3-oxoglutarate (6b) gave the tetra-tert-butyl cis-dioxobicyclooctane-2,4,6,8-tetracarboxylate 7b in 93percent yield.This bisenol 7b was converted into the bisenol ether 9b regiospecifically (90percent yield).This transformation was followed by monoalkylation (KH, allyl iodide; -58 deg C) and hydrolysis to generate 2-allyl-cis-bicyclooctane-3,7-dione in 90percent overall yield from 9b.The mixture of epimiric 2-allyl-3,7-diones 11a,b was transformed (O3; DMS) into the mixture of epimiric aldehydes 12a,b.This process was followed by aldol cyclization (2 N HCl, THF) to provide the diastereomeric mixture of of endo-(13a) and exo-(13b) triquinane monols in 85percent yield.Reduction of 13a,b with borane-THF (0 deg C) generated the stereoisomeric mixture of triols 14a,b which were subjected to an HPMA-mediated dehydration sequence to provide triquinacene (1), accompanied by small amounts of isotriquinacene.The mixture of trienes were converted into pure 1 by exposure to p-TSA in methylene chloride-pentane.Substitution of biacetyl (5b) for glyoxal 5a in the Weiss reaction, followed by the analogous steps detailed in the synthesis of 1, provided 1,10-dimethyltriquinacene (3).In addition, the synthesis of 1,10-cyclohexanotriquinacene (4), another centro-substituted triquinacene, has been accomplished by substitution of cyclohexane-1,2-dione (23) for 5a in the condensation, followed by the same sequence of reactions presented above for 1 and 3.

An expedient synthesis of spirooxindoles incorporating 2-amino pyran-3-carbonitrile unit employing dialkyl acetone-1,3-dicarboxylates

Spirooxindoles are a class of molecules possessing significant biological effects such as antiviral, antifungal, antibacterial and anticancer properties. Herein we report a series of spirooxindole molecules having 2-amino pyran-3-carbonitrile and with two ester groups. These molecules were prepared by the reaction of dialkyl acetone-1,3-dicarboxylate and isatilidenes in the presence of triethyl amine.

A convenient method for the synthesis of 3,6-dihydroxybenzene-1,2,4,5-tetracarboxylic acid tetraalkyl esters and a study of their fluorescence properties

A mild, efficient and simple method for the synthesis of 3,6-dihydroxy-1,2,4,5-tetracarboxylic tetraalkyl esters using cerium(IV) ammonium nitrate mediated oxidation of 1,3-acetone dicarboxylates has been developed. The detailed absorption and emission studies of the synthesized compounds reveal that these molecules have appreciable quantum yields and possess large Stokes shift values.

Self-condensation of activated malonic acid half esters: A model for the decarboxylative Claisen condensation in polyketide biosynthesis

The reaction of a malonic acid half oxyester with a N-hydroxysuccinimidyl ester-forming reagent resulted in self-condensation to provide the corresponding 1,3-acetonedicarboxylic acid diester. This new method does not require a divalent metal chelator or a coordinating solvent for successful condensation.

Process for preparing (+)-2,3-dihydro-1H-pyrrolo[1,2-a]pyrrole-1,7-dicarboxylates

2,3-Dihydro-1H-pyrrolo[1,2-a]pyrrole-1,7-dicarboxylates of the formula, STR1 in which each R is independently H or lower alkyl, are prepared from di(lower alkyl) 1,3-acetone-dicarboxylates.