5739-83-3

Usage

InChI:InChI=1/C7H12O3/c1-7(2,9)5-4-6(8)10-3/h4-5,9H,1-3H3/b5-4+

Upstream product

• 922-67-8 propynoic acid methyl ester 
• 67-63-0 isopropyl alcohol 
• 2258-65-3 4-methyl-pent-3-enoic acid methyl ester 
• 504-85-8 4-methyl-pent-3-enoic acid 
• 1775-44-6 (2E)-4-methylpent-2-enoic acid 
• 73281-90-0 methyl 4-chlorophenylsulfinylacetate 
• 78-84-2 isobutyraldehyde 
• 124818-71-9 (3,3-dimethyl-oxiranyl)-acetic acid methyl ester 
• 67-56-1 methanol 

Downstream Products

• 79749-96-5 5,5-dimethyl-4-(phenylthio)-4,5-dihydrofuran-2(3H)-one 
• 344305-99-3 4-Benzenesulfonyl-5,5-dimethyl-dihydro-furan-2-one 
• 77199-32-7 4,4-dimethyl-3-(phenylthio)-2-buten-4-olide 

Relevant academic research and scientific papers

The reaction of photochemically generated α-hydroxyalkyl radicals with alkynes: a synthetic route to γ-butenolides

The photomediated generation of α-hydroxyalkyl radicals from simple acyclic and cyclic alcohols, and acyclic diols, and their subsequent carbon-carbon bond forming reaction with propiolate esters and acetylenedicarboxylates, gives a mixture of a β-(hydroxyalkyl)enoate, the result of a formal cis addition, and the unsaturated lactone (γ-butenolide) resulting from the spontaneous cyclization of the corresponding trans addition product. Treatment of the cis adduct with NBS converts it to the same lactone, and so the method overall constitutes a particularly direct route to this important structural unit. Cyclic alcohols give rise to spiro-γ-butenolides. The use of supported photomediators simplifies product isolation and allows for the recovery and reuse of the photomediator.

Addition of sec-alcohols to alkynes through a radical process using NHPI/CoII/O2 system

α-Hydroxy carbon radicals generated from alcohols by the action of NHPI smoothly added to electron-deficient alkynes like acetylenedicarboxylates. For instance, the reaction of 2-propanol with dimethyl acetylenedicarboxylate afforded maleate derivative 3, 3-methoxycarbonyl-4,4-dimethyl-2-buten-4-olide (4), and a fused bis-γ-butyrolactone 5 formed by further addition of 2-hydroxy-2-propyl radical to 4. Copyright

Regioselectivity in the ene reaction of singlet oxygen with alkenes bearing an electron withdrawing group at β-position

Electronic repulsions between a perepoxide intermediate and the allylic functionality in the product forming transition state, direct the regioselectivity in the photooxygenation of trisubstituted alkenes bearing an electron withdrawing group at β-position.

A versatile synthesis of butenolides: Total synthesis of (+/-)-mintlactone

The butenolide monoterpenes, mintlactone and isomintlactone, have been synthesized by a new method for the preparation of butenolides from α,β-unsaturated esters by deconjugation, epoxidation and rearrangement.

SELECTIVE REACTIONS OF THIOLATE ANIONS WITH 4-HYDROXY-E-2-ALKENOIC ESTERS OR 4-METHANESULFONYLOXY-E-2-ALKENOIC ESTERS. SYNTHESIS OF 2-ALKEN-4-OLIDES (Δα,β-BUTENOLIDES) AND E,E-2,4-ALKADIENOIC ESTERS

Methyl 4-hydroxy-E-2-alkenoates prepared from aldehydes in one step, undergo the Michael reactions with thiolate anions to give 4-alkanolide derivatives, which are converted into 2-alken-4-olides.Methyl 4-methanesulfonyloxy-E-2-alkenoates undergo the substitution reactions, and subsequent treatments give methyl E,E-2,4-alkadienoates.