26613-71-8

Upstream product

• 6005-95-4 acide tetrahydro-2-oxo-5-phenylfurane-3-carboxylique 
• 87763-90-4 3-bromo-1-phenyl-but-3-en-1-ol 
• 13007-90-4 bis(triphenylphosphine)nickel⁽⁰⁾ dicarbonyl 
• 75366-42-6 4-Methoxy-2-methylene-4-phenyl-butyric acid ethyl ester 
• 87044-52-8 1-Phenyl-3-(tetrahydro-pyran-2-yloxymethyl)-but-3-en-1-ol 
• 98351-71-4 4-hydroxy-N-(α-methylbenzyl)-2-methylene-4-phenyl-butanamide 
• 95905-50-3 3-Benzenesulfonylmethyl-5-phenyl-dihydro-furan-2-one 
• 10029-04-6 ethyl 2-(hydroxymethyl)acrylate 
• 100-52-7 benzaldehyde 
• 72707-66-5 2-(bromomethyl)acrylic acid 
• 133285-88-8 ethyl 2-(methoxycarbonyloxymethyl)acrylate 
• 1064188-21-1 ZnBrCH₂C(CH₂)COOC₂H₅ 
• 17435-72-2 ethyl 2-bromomethyl-2-propenoate 
• 75142-67-5 2-(trimethylsilylmethyl)-4-phenyl-γ-butyrolactone 

Downstream Products

• 109958-04-5 (4S)-2-methylene-4-phenyl-γ-butyrolactone 
• 1038783-21-9 (R)-4-hydroxy-N,N-dimethyl-2-methylidene-4-phenylbutanamide 
• 103186-04-5 4-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-4-phenyl-butyric acid 

Relevant academic research and scientific papers

Reactivity of functionalized allyltrihalostannanes: An easy entry to α-methylene-γ-lactones

Stable ester monoallyltin halides 2 are prepared in excellent yields and react easily with aldehydes and ketones under very mild conditions, to provide a usefull access to various α- methylene-γ-lactones.

GENERAL SYNTHESIS OF EXOMETHYLENE-γ-LACTONES VIA THE RETRO-DIELS-ALDER REACTION

New synthetic methods of tulipalin A were deviced via the retro-Diels-Alder reaction and the generality was demostrated by the synthesis of several α-methylene-γ-alkyl-γ-butyrolactones.

REFORMATSKY-TYPE REACTIONS IN AQUEOUS MEDIA. USE OF BROMOMETHYLACRYLIC ACID FOR THE SYNTHESIS OF α-METHYLENE-γ-BUTYROLACTONES.

A new method for the preparation of α-methylene-γ-butyrolactones is described.

Synthesis of α-Methylene-γ-butyrolactones: A Structure-Activity Relationship Study of Their Allergenic Power

Thirty-five α-methylene-γ-butyrolactones has been prepared and their allergenic properties tested on the skin of guinea pigs experimentally sensitized to (a) alantolactone (1), (b) isoalantolactone (2), and (c) α-methylene-γ-butyrolactone (3).The two firs

Diastereoselective Alkene Hydroesterification Enabling the Synthesis of Chiral Fused Bicyclic Lactones

Palladium-catalysed diastereoselective hydroesterification of alkenes assisted by the coordinative hydroxyl group in the substrate afforded a variety of chiral γ-butyrolactones bearing two stereocenters. Employing the carbonylation-lactonization products as the key intermediates, the route from the alkenes with single chiral center to chiral THF-fused bicyclic γ-lactones containing three stereocenters was developed.

Mechanistic Studies of the TRIP-Catalyzed Allylation with Organozinc Reagents

3,3-Bis(2,4,6-triisopropylphenyl)-1,1-binaphthyl-2,2-diyl hydrogenphosphate (TRIP) catalyzes the asymmetric allylation of aldehydes with organozinc compounds, leading to highly valuable structural motifs, like precursors to lignan natural products. Our previously reported mechanistic proposal relies on two reaction intermediates and requires further investigation to really understand the mode of action and the origins of stereoselectivity. Detailed ab initio calculations, supported by experimental data, render a substantially different mode of action to the allyl boronate congener. Instead of a Br?nsted acid-based catalytic activation, the chiral phosphate acts as a counterion for the Lewis acidic zinc ion, which provides the activation of the aldehyde.

Synthesis and QSAR study of novel α-methylene-γ-butyrolactone derivatives as antifungal agents

Thirty-six new α-benzylidene-γ-lactone compounds based α-methylene-γ-butyrolactone substructure were prepared and characterized by spectroscopic analysis. All compounds were evaluated for antifungal activities in vitro against six plant pathogenic fungi and the half maximal inhibitory concentration (IC50) against Botrytis cinerea and Colletotrichum lagenarium were investigated. Compounds 5c-3 and 5c-5 with the halogen atom exhibited excellent fungicidal activity against B. cinerea (IC50?=?22.91, 18.89?μM). The structure-activity relationships (SARs) analysis indicated that the derivatives with electron-withdrawing substituents at the meta- or para-positions improves the activity. Via the heuristic method, the generated quantitative structure-activity relationship (QSAR) model (R2?=?0.961) revealed a strong correlation of antifungal activity against B. cinerea with molecular structures of these compounds. Meanwhile, the cytotoxicity of 20 representative derivatives was tested in the human tumor cells line (HepG2) and the hepatic L02 cells line, the result indicated that the synthesized compounds showed significant inhibitory activity and limited selectivity. Compound 5c-5 has the highest fungicidal activity with IC50?=?18.89?μM (against B. cinerea.) but low cytotoxicity with IC50?=?35.4?μM (against HepG2 cell line) and IC50?=?68.8?μM (against Hepatic L02 cell line). These encouraging results can be providing an alternative, promising use of α-benzylidene-γ-lactone through the design and exploration of eco-friendly fungicides with low toxicity and high efficiency.

Isatin Derived Spirocyclic Analogues with α-Methylene-γ-butyrolactone as Anticancer Agents: A Structure-Activity Relationship Study

Design, synthesis, and evaluation of α-methylene-γ-butyrolactone analogues and their evaluation as anticancer agents is described. SAR identified a spirocyclic analogue 19 that inhibited TNFα-induced NF-?°B activity, cancer cell growth and tumor growth in an ovarian cancer model. A second iteration of synthesis and screening identified 29 which inhibited cancer cell growth with low-?M potency. Our data suggest that an isatin-derived spirocyclic α-methylene-γ-butyrolactone is a suitable core for optimization to identify novel anticancer agents.

Catalytic, nucleophilic allylation of aldehydes with 2-substituted allylic acetates: Carbon-carbon bond formation driven by the water-gas shift reaction

The ruthenium-catalyzed allylation of aldehydes with allylic acetates has been expanded to incorporate substituents at the 2-position of the allylic components. Allylic acetates bearing a variety of substituents (CO 2-t-Bu, COMe, Ph, CH(OEt)su

New antifungal scaffold derived from a natural pharmacophore: Synthesis of α-methylene-γ-butyrolactone derivatives and their antifungal activity against Colletotrichum lagenarium

Thirty new and thirty-four known analogues were designed and synthesized to improve the potential use of the α-methylene-γ-butyrolactone ring, a natural pharmacophore. All structures were confirmed by 1H and 13C NMR, MS, and single-c