74844-25-0

Upstream product

• 74844-24-9 N-tert-Butyl-4-hydroxy-4-(4-methoxy-phenyl)-2-methylene-butyramide 
• 123-11-5 4-methoxy-benzaldehyde 
• 17435-72-2 ethyl 2-bromomethyl-2-propenoate 
• 1000170-54-6 4-hydroxy-4-(4-methoxy-phenyl)-2-methylene-butyric acid 2,2,3,3,4,4,5,5,6,6,6-undecafluoro-hexyl ester 
• 50-00-0 formaldehyd 
• 1037575-48-6 3-diethoxyphosphoryl-5-(4-methoxyphenyl)-dihydrofuran-2(3H)-one 
• 4224-69-5 methyl 2-(bromomethyl)propenoate 

Relevant academic research and scientific papers

Titanocene(III) chloride mediated radical-induced one-pot synthesis of α-methylene-γ-butyrolactones

A simple and efficient methodology has been developed for the one-pot preparation of α-methylene-γ-butyrolactones by free-radical induced Barbier-type reaction of methyl 2-(bromomethyl)acrylate and aldehydes followed by in situ lactonization. The radical

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.

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

Synthesis and cytotoxic activity of γ-aryl substituted α-alkylidene-γ-lactones and α-alkylidene-γ-lactams

A series of 5-aryl-3-alkylidenedihydrofuran-2(3H)-ones 6a-g″ and 11a,b as well as 5-aryl-3-methylidenepyrrolidin-2-ones 10a-c and 12 were synthesized starting from 4-aryl-2-diethoxyphosphoryl-4-oxobutanoates 3a-g. Reaction sequence includes reduction or reductive amination of the carbonyl group, lactonization or lactamization step and finally the Horner-Wadsworth-Emmons olefination of aldehydes using thus obtained 5-aryl-3-diethoxyphosphoryl-3,4-dihydrofuran-2(5H)-ones 5a-g″ or 5-aryl-3-diethoxyphosphorylpyrrolidin-2-ones 9a-c. Furanones 6 and 11, as well as pyrrolidinones 10 and 12, were evaluated in vitro against mouse leukemia cell line L-1210 and two human leukemia cell lines HL-60 and NALM-6. Several of the obtained furanones proved to be very potent against all three cell lines with IC50 values lower than 6 μM. Structure-activity relationships of these compounds, as well as 5-alkyl or 5-arylmethyl-3-methylidenedihydrofuran-2(3H)-ones 13a-e, previously obtained in our laboratory, are discussed.

Fluorous tagging: An enabling isolation technique for indium-mediated allylation reactions in water

An efficient method was developed to allylate aldehydes using an aqueous indium-mediated allylation reaction with fluorous-tagged allyl halides, and to directly purify the products by fluorous solid phase extraction (F-SPE). The Royal Society of Chemistry

Enantioselective Dreiding-Schmidt reactions: Asymmetric synthesis and analysis of α-methylene-γ-butyrolactones

The zinc/silver-graphite mediated Dreiding-Schmidt reactions between aldehydes and the 2-bromomethyl-acrylate derived sultamamides (+)/(-)-28 or (+)/(-)-30 gave the corresponding substituted α-methylene-γ-butyrolactones with ee's up to 90%. Enantiomerically pure compounds were obtained by semipreparative HPLC using a chiral stationary phase.

Dimetalation of N-tert-Butylmethacrylamide: A New Synthetic Reagent

Dimetalation of N-tert-butylmethacrylamide with n-butyllithium gives a reagent equivalent to the dianion of methacrylic acid.Its reaction with various electrophiles and the transformation of certain primary products to α-methylene lactones is exemplified.