1575-46-8

Usage

Uses

Used in Pharmaceutical Industry:
3,4-Dimethyl-2,5-dihydrofuran-2-one is used as an intermediate in the synthesis of 3,4-Dimethyl-5-pentyl-2-furannonanoic Acid (D477715), an F3 furan fatty acid. 3,4-Dimethyl-2,5-dihydrofuran-2-one exhibits radical-scavenging ability and anti-inflammatory properties, making it a promising candidate for the development of new drugs and therapies in the pharmaceutical industry.
Used in Chemical Synthesis:
3,4-Dimethyl-2,5-dihydrofuran-2-one is also used as a key intermediate in the synthesis of various other compounds with potential applications in different industries. Its unique chemical structure allows for further modification and functionalization, leading to the development of new products with diverse properties and uses.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 31, p. 893, 1988 DOI: 10.1021/jm00400a001

InChI:InChI=1/C6H8O2/c1-4-3-8-6(7)5(4)2/h3H2,1-2H3

Upstream product

• 14387-99-6 ethyl 2,3-dimethyl-3-butenoate 
• 99174-61-5 ethyl 4-acetyloxy-3-hydroxy-2,3-dimethylbutyrate 
• 1575-54-8 5-hydroxy-3,4-dimethylfuran-2(5H)-one 
• 80248-68-6 4-hydroxy-3,4-dimethyl-dihydro-furan-2-one 
• 497-03-0 2-methylbut-2-enal 
• 201230-82-2 carbon monoxide 
• 41282-40-0 but-2-ynylamine 
• 4626-58-8 benzyl(but-2-yn-1-yl)amine 
• 155108-40-0 2,2-Diethoxy-2,5-dihydro-3,4-dimethyl-furan 
• 92835-21-7 Diethylphosphonopropionsaeure Kalium-Salz 
• 598-31-2 1-bromoacetone 
• 22742-89-8 2-methyl-2,3-butadiene-1-ol 
• 766-39-2 2,3-Dimethylmaleic anhydride 
• 124-38-9 carbon dioxide 

Downstream Products

• 20843-07-6 3,4-dimethylfuran 

Relevant academic research and scientific papers

Palladium-catalyzed [3+2] cycloaddition of carbon dioxide and trimethylenemethane under mild conditions

Carbon dioxide undergoes a Pd-catalyzed [3+2] cycloaddition with trimethylenemethane (TMM) under mild conditions (1 atm, 75 °C, 30 min) to produce a γ-butyroiactone product in 63% yield, when the Pd-TMM complex is generated from 2-(acetoxymethyl)-3-(trimethylsilyl)propene. The reaction reported here is more rapid than the all-carbon [3+2] cycloaddition, and only the γ-butyrolactone is produced in a competition experiment. With substituted substrates, the reaction is completely regioselective, producing the product derived from the kinetic Pd-TMM complex.

Expeditious microwave-assisted synthesis of 5-alkoxyoxazoles from α-triflyloxy esters and nitriles

A rapid and general access to diversely substituted 5-alkoxyoxazoles 2 (i.e., R1, R2 = alkyl, phenyl) from easily accessible α-triflyloxy/hydroxy esters 1 and nitriles with good yields (41-76%) is reported. The versatility of the cyc

Synthesis of a dimethylfuran-containing macrolide insect pheromone

The synthetic pathway to the furan-containing macrolide pheromone (1) of Galerucella beetles was shortened from 13 steps in the original synthesis to 10 steps, and the overall yield was increased greater than six-fold. A concise Reformatsky-based sequence of reactions was utilized to construct the key precursor, 2,3-dimethyl-2-butenolide. Reduction of the butenolide with diisobutylaluminum hydride afforded 3,4-dimethylfuran. A one-pot sequence of lithiation, alkylation by a tetrahydropyranyl (THP)-containing iodide, a second lithiation, and, finally, formylation gave the required tetrasubstituted furan intermediate, 3,4-dimethyl-5-[5-(tetrahydrofuran-2-yloxy)pentyl]-2-furaldehyde. To continue construction of the three-carbon acyl side chain, the aldehyde was converted to an unsaturated ester by a Horner-Wadsworth-Emmons (HWE) condensation with triethyl phosphonoacetate. After reduction of the double bond in the ester side chain and removal of protective groups, the lactone ring was closed using the Mitsunobu method, which is milder, is simpler, and could be accomplished with less solvent than the previous (Yamaguchi) method.

Synthesis of hetero atom modified pyrromethenones

A series of six heteroaromatic compounds, ethyl-/methyl-and dimethylfuranones, thiophenones, and cyclopentenones, was synthesized and condensed with a methyl methylpropionate substituted pyrrole, yielding the "right" half of open-chain tetrapyrroles. These compounds serve as light-inducible chromophores in the plant photoreceptor phytochrome. Three-dimensional structure analysis of the 10-oxapyrromethen-1-one 25 revealed a planar conformation, similar to the dipyrromethenone parent compound, stabilized by a hydrogen bond formed between the pyrrole proton and the furanone oxygen atom. All six pyrrole-substituted heteroaromatic derivatives 25-30 show absorbances in the visible spectrum with high molar extinction coefficients. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

TRISUBSTITUTED FURAN DERIVATIVES AS FRAGRANCES AND AROMA SUBSTANCES

The invention concerns a use of a compound having formula (I) wherein: a first of the radicals R1, R2, R3 , R4 denotes hydrogen, a second of the radicals R1, R2, R3 , R4 denotes an alkyl or alkenyl radical having 3 to 6 C atoms, and a third and a fourth of the radicals R1, R2, R3, R4mutually independently denote an alkyl or alkenyl radical having 1 to 6 C atoms, as a fragrance and/or aroma substance and/or as a means of rounding out and/or of imparting vibrancy, naturalness (authenticity), fullness, complexity and/or staying power to a basic fragrance and/or aroma substance blend.

Heteroatom-guided torquoselective olefination of α-oxy and α-amino ketones via ynolates

Ynolates were found to react with α-alkoxy-, α-siloxy-, and α -aryloxyketones at room temperature to afford tetrasubstituted olefins with high Z selectivity. Since the geometrical selectivity was determined in the ring opening of the β-lactone enolate intermediates, the torquoselectivity was controlled by the ethereal oxygen atoms. From experimental and theoretical studies, the high Z selectivity is in duced by orbital and steric interactions rather than by chelation. In a similar manner, α-dialkylamino ketones provided olefins with excellent Z selectivity. These products can be easily converted into multisubstituted butenolides and γ-butyrolactams in good yield.

Relay ring-closing metathesis (RRCM): A strategy for directing metal movement throughout olefin metathesis sequences

The title concept involves the use of structurally modified RCM substrates that contain extender arms, terminating in a remote reactive alkene. Initiation of an RCM sequence at that reactive alkene is followed by rapid intramolecular relay of the metal center to an initially less reactive alkene in the parent substrate. This permits one to control the relative timing (or direction) of a metathesis sequence. For example, one can reverse the inherent tendency of an unsymmetrical α,ω-diene substrate to close, say, left-to-right, to that of right-to-left. Four distinct types of application of the RRCM concept are demonstrated. Among other things, they show the preparation of tetrasubstituted electron-deficient alkenes using G1 [(Cy3P)2(Cl2)Ru=CHPh], complementary control of directionality (endedness), auxiliary benefits (enzyme specificity) from the incorporation of additional steric bulk, the activation of otherwise ineffective substrates for RCM closure, the use of unorthodox alkenes as initiation sites for ring closure, and control of product olefin geometry. Copyright

Ruthenium-Catalyzed Cyclocarbonylation of Allenyl Alcohols and Amines: Selective Synthesis of Lactones and Lactams

Allenyl alcohols such as 4-hydroxybuta-1,2-dienes and 5-hydroxypenta-1,2-dienes having a variety of substituents undergo cyclocarbonylation in the presence of a ruthenium catalyst under mild conditions selectively to give five- and six-membered lactones in a high yield with 100% atom economy. 5-Aminopenta-1,2-dines are also cyclocarbonylated to give γ-lactams. A possible carbonylation mechanism involving a ruthenium cluster intermediate is proposed on the basis of experimental results.

3-Phenylselanylfuran-2(5H)-one: A versatile building block in the synthesis of lignans. A new approach towards 3,4-dibenzyl γ-butyrolactones

Ready available 3-phenylselanylfuran-2(5H)-one undergoes tandem conjugate addition-alkylation by organocopper reagents to afford, with good yields and diastereoselectivities, 3,4-disubstituted-3-phenylselanyl-γ- butyrolactones, which can be transformed into naturally occurring compounds, such as lignans.

Convenient Synthesis of 2,2-Diethoxy-2,5-dihydrofurans, 2(5H)Furanones and 2-Ethoxyfurans. Crystal and Molecular Structure of a Barrelenone Diels-Alder Product

Reaction of 1,2-hydroxyketones 5 with (2,2-diethoxyvinylidene)triphenylphosphorane (2) or (2,2-diethoxyvinyl)triphenylphosphonium tetrafluoroborates 6 yields the 2,2-diethoxy-2,5-dihydrofurans 9.Depending on the reaction conditions used, the orthoesters 9 can be hydrolized to give 2(5H)furanones 10 and 2-ethoxyfurans 11, respectively. 4,5-Dimethyl-5,6-dihydro-2-pyranone (20) and 8-methoxycoumarin (23) are prepared, starting from (2,2-diethoxyvinyl)triphenylphosphonium tetrafluoroborate (6a) and 1-hydroxy-2-methyl-3-butanone (16) or 2-hydroxy-3-methoxy-benzaldehyde (21).The 2-ethoxyfuranes 11 readily undergo Diels-Alder reactions with 2-chloracrylonitrile (24), maleic anhydride (26), N-phenyl-1,2,4-triazoline-3,5-dione (28) and dimethyl acetylenedicarboxylate (30) to give the corresponding Diels-Alder products 25, 27, 29 and 31, respectively.Contrary to 2-ethoxyfuran 11b, 11a reacts with two equivalents of acetylene 30, to yield barrelenone 34.The structure of 34 unequivocally is established by X-ray structure analysis. - Keywords: 2,2-Diethoxy-2,5-dihydrofurans, 2(5H)Furanones, 2-Ethoxyfurans, Barrelenone, Diels-Alder Products, X-Ray