43142-59-2Relevant academic research and scientific papers
Cross metathesis of α-methylene lactones II: γ- and δ-lactones
Raju, Ravinder,Allen, Laura J.,Le, Tri,Taylor, Christopher D.,Howell, Amy R.
, p. 1699 - 1701 (2007)
The cross metathesis reactivities of α-methylene-γ- butyrolactone and an α-methylene-δ-lactone have been investigated. α-Methylene-γ-butyrolactone undergoes rapid and efficient olefin isomerization in the presence of second-generation metathesis catalysts. However, cross metathesis can be achieved with the additive 2,6- dichlorobenzoquinone. In contrast, the α-methylene-δ-lactone neither isomerizes nor couples under similar conditions.
The clerodane ring system: Investigating the viability of a direct Diels-Alder approach
Merritt, Andrew T.,Pouwer, Rebecca H.,Williams, David J.,Williams, Craig M.,Ley, Steven V.
supporting information; experimental part, p. 4745 - 4747 (2011/08/05)
A direct synthetic approach to the spiro-γ-lactone clerodane ring system has been investigated. This work builds on that of Jung and highlights the inherent difficulties associated with the otherwise obvious Diels-Alder approach. The Royal Society of Chem
Synthesis of α-amino γ-butyrolactone derivatives by aziridination of α-ylidene γ-butyrolactones
Gasperi, Tecla,Loreto, M. Antonietta,Tardella, Paolo A.,Veri, Elisabetta
, p. 4953 - 4956 (2007/10/03)
The reactions of exocyclic α,β-unsaturated γ-lactones with NsONHCO2Et and CaO produce N-(ethoxycarbonyl) spiroaziridino γ-lactones. By reaction with acetic acid these products give ring opening reaction and acetylated N-protected α-amino γ-butyrolactones are obtained. The ring opening reaction is quantitative and highly regioselective.
Synthesis of α-Alkylidene-β-ethoxycarbonyl cyclopentanones and -γ-butyrolactones
Beji,Besbes,Amri
, p. 3947 - 3954 (2007/10/03)
Synthesis of (E,Z)-α-Alkylidene-β-ethoxycarbonyl cyclopentanones 5 and (E,Z)-α-alkylidene-γ-butyrolactones 7 by condensing phosphonates 3 or 6 with a variety of aldehydes in the presence of aqueous potassium carbonate (6-10M) as base is reported.
α-Spirocyclopentyl- and α-Spirocyclopropyl-γ-butyrolactones: Conformationally Constrained Derivatives of Anticonvulsant and Convulsant α,α-Disubstituted γ-Butyrolactones
Peterson, Eileen M.,Xu, Kun,Holland, Katherine D.,McKeon, Ann C.,Rothman, Steven M.,et al.
, p. 275 - 286 (2007/10/02)
To further study the putative γ-butyrolactone site of the GABAA/chloride channel complex, constrained derivatives of convulsant and anticonvulsant α,α-disubstituted γ-butyrolactones (α-spirocyclopropyl- and α-spirocyclopentyl-γ-butyrolactones) were synthesized and evaluated biologically.Most of the spirocyclopropyl agents were anticonvulsants when tested against pentylenetetrazole-induced seizures in mice.These agents effectively displaced 35-tert-butylbicyclophosphorothionate (35-TBTS), a ligand for the picrotoxin binding site of the GABAA/chloride channel, from rat neuronal membranes and affected the GABA-mediated current in hippocampal neurons.The monomethyl-substituted spirocyclopropyl agent with a methyl group cis to the carbonyl (15) potentiates GABA-induced current whereas the trans derivative (16) blocks the current.The only anticonvulsant in the spirocyclopentyl series was the unsubstituted spirocyclopentyl compound 2.All the other substituted spirocyclopentyl targets were inactive in vivo at the highest dose tested except for convulsant 9, which has a trans 2,5-dimethyl-substituted cyclopentyl ring.All the spirocyclopentyl derivatives displaced 35-TBPS from rat neuronal membranes very effectively, and they also all potentiated GABA-induced chloride current except for convulsant 9 which blocked the current.From the data obtained in this investigation, it appears that when the volume occupied above and below the lactone ring is as large as that occupied by spirocyclopentyl agent 9, convulsant activity is observed.Groups with less volume in these areas either are inactive in the behavioral test or have anticonvulsant activity.When bound to the GABAA/chloride channel,the larger molecules may stabilize the closed state of the channel whereas the smaller molecules may stabilize the open state.
Stereochemical consequence in the elimination of β-hydroxyalkylsilanes: Stereoselective formation of (Z)- and (E)-alkylidene-γ-butyrolactones
Yamomoto, Keiji,Tomo, Yoichi,Suzuki, Shigeaki
, p. 2861 - 2864 (2007/10/02)
Titanium(IV) chloride-mediated reaction of 4,5-dihydro-2-(trimethylsiloxy)-3-(trimethylsilyl)furan (1a) with acetaldehyde gave diastereomerically pure (3S*, 1′R*)-4,5-dihydro-3-(1′hydroxyethyl)-3-(trimethylsilyl)-2(3H)furanone (2a),
