2518-53-8

Usage

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 3453, 1984 DOI: 10.1016/S0040-4039(01)91044-5

InChI:InChI=1/C10H16O2/c1-2-3-4-5-6-9-7-8-10(11)12-9/h7-9H,2-6H2,1H3

Upstream product

• 111-71-7 heptanal 
• 623-47-2 propynoic acid ethyl ester 
• 124-13-0 Octanal 
• 15469-77-9 dec-3-enoic acid 
• 2430-93-5 (3E)-dec-3-enoic acid 
• 120132-20-9 5-Hexyl-4-(toluene-4-sulfonyl)-tetrahydro-furan-2-ol 
• 120132-07-2 3-(Toluene-4-sulfonyl)-dec-1-en-4-ol 
• 100591-55-7 Carbonic acid 1-(2-benzenesulfinyl-ethyl)-heptyl ester methyl ester 
• 84547-46-6 1-Phenylsulfanyl-nonan-3-ol 
• 3761-92-0 n-hexylmagnesium bromide 
• 85870-04-8 1-(phenylsulfonyl)octan-2-ol 
• 93423-51-9 3-Benzenesulfonyl-4-hydroxy-decanoic acid phenylamide 
• 84477-16-7 methyl (+/-)-(2E)-4-hydroxydec-2-enoate 
• 20497-95-4 methyl 3-nitropropionate 

Relevant academic research and scientific papers

A facile synthesis of γ-butenolides via cyclization of 3-alkenoic acids with dimethyl sulfoxide and oxalyl bromide

The combination of dimethyl sulfoxide and oxalyl bromide was used to accomplish the cyclization of 3-alkenoic acids with the aid of a base to afford γ-butenolides, in which bromodimethylsulfonium salt generated in situ was proposed to serve as a Br+ source.

Convenient synthesis of 5-alkylfuran-2(5H)-ones

A convenient synthesis of 5-alkylfuran-2(5H)-ones are described starting from 3-nitropropanoate and aldehydes, promoted by neutral alumina, in 35-60% overall yields, via a condensation-lactonization-elimination pathway. Copyright

Pd-catalyzed 5-endo-trig-type cyclization of β,γ-unsaturated carbonyl compounds: An efficient ring closing reaction to give γ-butenolides and 3-pyrrolin-2-ones

The 5-endo-trig-type cyclization has been performed using a Pd-bis(isoxazoline) catalyst. The present cyclization of β,γ- unsaturated carbonyl compounds gave γ-butenolides and 3-pyrrolin-2-ones in good to excellent yields.

One-pot synthesis of 5-Alkylfuran-2(5H)-ones

5-Alkylfuran-2(5H)-ones can be efficiently obtained using a one-pot approach, starting from methyl 3-nitropropanoate and aldehydes, in ethyl acetate, with Amberlyst A-21 as catalyst, in 60-90% overall yield. Copyright Taylor & Francis Group, LLC.

A NEW SYNTHETIC METHOD FOR γ-BUTYROLACTOLS BY THE PALLADIUM-CATALYZED REGIOSELECTIVE OXIDATION OF 1-ALKEN-4-OLS

3-substituted 1-alken-4-ols were oxidized with PdCl2-benzoquinone regioselectively at the terminal carbon to afford cyclic hemiacetals (γ-butyroacetols), which were converted to γ-butiroacetones by the Jones oxidation.This reactions was applied to the synthesis of optically active deoxyribose and γ-butenolides.

Cyclization of 4-Hydroxy-(E)-2-alkenoic Esters: Simple Synthesis of Butenolides

Simple treatment of 4-hydroxy-(E)-2-alkenoic esters with benzenethiol leads to cyclization to give 3-phenylthio-4-alkanolides, which are easily converted into 3-phenylthio-2-alken-4-olides and 2-alken-4-olides (Δα,β-butenolides).

A NEW SYNTHESIS OF α,β-UNSATURATED γ- AND δ-LACTONS VIA INTRAMOLECULAR ACYLATION OF α-SULFINYL CARBANION

A new synthesis of α,β-unsaturated γ- and δ-lactones involving the intramolecular acylation of α-sulfinyl carbanion followed by pyrolisis is described.

NOUVELLE METHODE DE SYNTHESE DES γ-LACTONES ET (5H)FURANNONES-2-MONOSUBSTITUEES

3-monosubstituted γ-lactones and 5-mono- or 3,5-disubstituted 2-(5-H)-furanones have been prepared by the reaction of Grignard reagents with lactols.

DIANIONS OF N-MONOSUBSTITUTED-3-(PHENYLSULFONYL)PROPANAMIDES. CONVENIENT REAGENTS FOR THE SYNTHESIS OF 5-ALKYL-2(5H)-FURANONES

Treatment of N-phenyl-3-(phenylsulfonyl)propanamide with 2 equiv. of butyllithium at -78 deg C afforded the dianion.Aldehydes and ketones upon treatment with the dianion provided stable γ-hydroxy amides, which were converted in good yields to 5-alkyl-2(5H)-furanones.Optically active (R)- and (S)-5-octyl-2(5H)-furanones, and (R)- and (S)-5-tridecyl-2(5H)-furanones were prepared from aldehydes and the dianions, derived from chiral N-monosubstituted-3-(phenylsulfonyl)propanamides.