35304-86-0

Usage

Uses

Used in Pharmaceutical Industry:
(Z)-5-Benzylidenefuran-2(5H)-one is used as a starting material for the synthesis of various pharmaceuticals and bioactive molecules due to its unique reactivity and properties. Its structure allows for the creation of a wide range of compounds with potential therapeutic applications.
Used in Drug Development and Research:
(Z)-5-Benzylidenefuran-2(5H)-one is used as a subject of interest in drug development and research because of its potential anti-inflammatory and antioxidant properties. These characteristics make it a valuable compound for exploring new treatments and therapies for various diseases and conditions.
Used in Organic Chemistry:
(Z)-5-Benzylidenefuran-2(5H)-one is used as a key intermediate in organic chemistry for the synthesis of complex molecules and compounds. Its unique structure and reactivity make it a versatile building block for creating a diverse array of chemical products.

InChI:InChI=1/C11H8O2/c12-11-7-6-10(13-11)8-9-4-2-1-3-5-9/h1-8H/b10-8+

Upstream product

• 332-77-4 2,5-dihydro-2,5-dimethoxyfuran 
• 100-52-7 benzaldehyde 
• 57258-53-4 5-benzylidene-2-oxo-2,5-dihydrofuran-3-carboxylic acid 
• 16900-64-4 4-phenylbut-1-en-3-yne-1,1-dicarboxylic acid 
• 497-23-4 2-buten-4-olide 
• 1609-92-3 (Z)-3-bromoacrylic acid 
• 536-74-3 phenylacetylene 
• 27948-29-4 (Z)-5-phenyl-2-penten-4-ynoic acid 
• 6214-35-3 (Z)-3-iodoprop-2-enoic acid 
• 3757-88-8 tributylstannylethynylbenzene 
• 676556-25-5 (Z)-5-(1-bromo-1-phenylmethylene)-2(5H)-furanone 
• 676556-29-9 (Z)-4-bromo-5-(phenylmethylene)furan-2-(5H)-one 
• 591-50-4 iodobenzene 
• 32323-44-7 5-(dibromomethylene)-2(5H)-furanone 

Relevant academic research and scientific papers

A convenient synthesis of γ-(Z)-alkylidene butenolides

A convenient synthesis of γ-(Z)-alkylidene butenolides starting from (Z)-3-bromopropenoic acid was described.

Regio- and stereoselective preparation of γ-alkylidenebutenolides or α-pyrones using a Stille reaction and palladium-catalysed oxacyclisation sequence

Synthesis of butenolides or α-pyrones from substituted tributylstannyl acetylides is highly dependant on the nature of the acetylide.

Ring-Closing Metathesis Reactions of Acyloxysulfones: Synthesis of γ-Alkylidene Butenolides

An acyloxysulfone ring-closing metathesis/sulfone elimination sequence has been developed for the preparation of various γ-alkylidene butenolides. The elimination is proposed to proceed via an E1cb mechanism leading to (Z)-γ-alkylidene butenolides as the major products.

Pd/C-Cu mediated direct and one-pot synthesis of γ-ylidene butenolides

10% Pd/C in combination with CuI, PPh3, and Et3N has been identified as an effective catalyst system for the coupling of (Z)-3-iodoacrylic acid with terminal alkynes in 1,4-dioxane leading to the one-pot synthesis of γ-ylidene butenolides. The methodology showed remarkable regio- and stereoselectivity as only the five-membered lactone ring products were formed with an exocyclic double bond possessing Z-geometry.

Copper-catalyzed preparation of γ-alkylidenebutenolides and isocoumarins under mild palladium-free conditions

A general and efficient copper(I)-catalyzed cross-coupling and heterocyclization reaction of terminal alkynes and β-iodo-α,β- unsaturated acid derivatives has been developed under very mild conditions. This method provides easy access from good to excellent yields of a variety of 5-ylidenebutenolides and 3-substituted isocoumarins with excellent regio- and stereoselectivity. This procedure does not require the use of any expensive supplementary additives, and is palladium-free.

A new, highly stereoselective synthesis of β-unsubstituted (Z)-γ-alkylidene-butenolides using bromine as a removable stereocontrol element

Several β-unsubstituted (Z)-γ-alkylidenebutenolides have been prepared in highly stereocontrolled fashion by implementing a steric directing group stratagem in the vinylogous aldol condensation of butenolides with aldehydes. Applications to the synthesis of the antitumor heptene (S)-melodorinol and a thiophenelactone from Chamaemelum nobile L. are described. Georg Thieme Verlag Stuttgart.

Regioselective synthesis of (E)-5-(tributylstannylmethylidene)-5H-furan-2- ones and (E)-3-(tributylstannylmethylidene)-3H-isobenzofuran-1-ones: Easy access to γ-alkylidenebutenolide and phthalide skeletons

Regio- and stereoselective synthesis of γ-alkylidene-butenolides and γ-alkylidenephthalides has been achieved through the palladium-catalysed tandem cross-coupling/cyclisation reactions of tributylstannyl-3-iodopropenoate or the 2-iodo benzoate derivatives with tributyltinacetylene. Iododestannylation occurred with inversion of the configuration of the exocyclic double bond in the case of butenolides, but with retention of configuration for the phthalide. The selectivity observed in the Stille reaction was found to be dependent on the nature of the vinyl or the aryl halide. Georg Thieme Verlag Stuttgart.

Regiocontrolled intramolecular cyclizations of carboxylic acids to carbon-carbon triple bonds promoted by acid or base catalyst

We systematically investigated, for the first time, the relationship between regioselectivity and acid/base effects in the cyclization reactions between carboxylic acids and carbon-carbon triple bonds. We found novel acid- and base-promoted cyclizations to selectively give isocoumarin or pyran-2(2H)-one and phthalide or furan-2(5H)-one skeletons, respectively, and established a catalytic version of regioselective heterocyclic ring synthesis. Density functional theory calculations and application to a short route to thunberginol A were also described.

A Novel Access to γ-Alkylidenebutenolides: Sequential Stille Couplings of Dibromomethylenebutenolides

γ-(Dibromomethylene)butenolide (2) and β-bromo-γ- (bromomethylene)butenolide (Z-5), both of which obtained from dibromolevulinic acid (6) in a single step, underwent Pd-catalyzed couplings with phenyl- or styryltributylstannane giving mono-bromobutenolides with excellent stereo- and regiocontrol. A second Stille coupling or the reduction with Zn dust led to bromine-free γ-alkylidenebutenolides as single stereoisomers.

Catalytic and selective conversion of (Z)-2-en-4-ynoic acids to either 2H-pyran-2-ones in the presence of ZnBr2 or (Z)-5-alkylidenefuran-2(5H)-ones in the presence of Ag2CO3

Treatment of (Z)-5-alkyl-2-en-4-ynoic acids (1), prepared by the Pd-catalyzed alkynylzinc-β-haloacrylic acid coupling, with 5-10 mol% of ZnBr2 can produce 6-alkyl-2H-pyran-2-ones (2) along with minor amounts of (Z)-5-alkylidenefuran-2(5H)-ones (3) in >90% combined yields, with often very high (≈95/5) pyranone/furanone ratios. On the other hand, lactonization of 1 catalyzed by Ag2CO3 provides a selective synthesis of (Z)-5-alkylidenefuran-2(5H)-ones (3) in >90% yields along with minor amounts (≤5%) of 2.