29043-98-9

Upstream product

• 136021-08-4 (3E)-dihydro-3-iodomethylene-5-methyl-5-phenyl-2(3H)-furanone 
• 77407-45-5 4-Hydroxy-2-methylene-4-phenyl-pentanoic acid (2-methoxy-phenyl)-amide 
• 97191-29-2 dihydro-3-((N,N-dimethylamino)methyl)-5-methyl-5-phenyl-2(3H)-furanone 
• 98-86-2 acetophenone 
• 17435-72-2 ethyl 2-bromomethyl-2-propenoate 
• 85924-68-1 2-phenylhex-5-en-2-ol 
• 1586792-09-7 methyl 4-hydroxy-4-methyl-2-methylene-4-phenylbutanoate 
• 98-83-9 isopropenylbenzene 
• 80997-76-8 6-bromo-5-methyl-5-phenyl-4-oxa-1-hexyne 
• 727665-22-7 2-phenylhex-5-enyl acetate 
• 727665-28-3 4-acetoxy-2-methylene-4-phenylpentanoic acid methyl ester 
• 81011-49-6 2-Methyl-4-methylene-2-phenyl-tetrahydro-furan 

Downstream Products

• 129661-94-5 3-hydroxy-5-methyl-5-phenyl-5H-furan-2-one 

Relevant academic research and scientific papers

α-Methylene-γ-butyrolactones with molluscicidal activity

The α-methylene-γ-butyrolactones 1-28 were tested in vitro for molluscicidal activity against Biomphalaria glabrata. The racemic compound 25 shows the best activity. The synthesis was carried out by modified Reformatzky reaction of the corresponding carbo

4-(Dimethylamino)pyridine as a catalyst for the lactonization of 4-hydroxy-2-methylenebutanoate esters

The catalytic action of 4-(dimethylamino)pyridine (DMAP) in lactonizing 4-hydroxy-2-methylenebutanoate esters to 2-methylene-γ-butyrolactones is described. The use of DMAP, which functions as an excellent complement to the more traditional acid-catalyzed lactonization protocol, allows for the synthesis of 2-methylene-γ-butyrolactones containing acid-sensitive groups under essentially neutral conditions.

Dibromomethane as one-carbon source in organic synthesis: A versatile methodology to prepare the cyclic and acyclic α-methylene or α-keto acid derivatives from the corresponding terminal alkenes

Ozonolysis of mono-substituted alkenes A-1 followed by reacting with a preheated mixture of CH2Br2-Et2NH affords α-substituted acroleins A-2 in good yields. Under very mild reaction conditions, these α-substituted acroleins A-2 can be easily converted to α-methylene esters A-4, which could be further converted to the corresponding α-keto esters A-5. This methodology can be also applied to the preparation of α-methylene lactones B-4, α-methylene lactams, and α-keto lactones B-5 with various ring sizes.

Electrogenerated Zinc as the Catalyst in the Allylation of Carbonyl Compounds. Direct Synthesis of α-Methylene-γ-Lactones

The electroreduction of a catalytic amount of ZnBr2 in acetonitrile provided a active Zn*, able to catalyze the reductive coupling of allyl bromides and chlorides with carbonyl compounds with high regioselectivity.Substituted α-methylene γ-lactones were o

ALKYLIDENE LACTONE SYNTHESIS

The iodoalkylidene lactones formed by reaction of alkenes with acetylenic acids in the presence of N-iodosuccinimide and subsequent free radical cyclisation, can be de-iodinated photochemically or alkylated with lithium diorganocuprate reagents to yield a variety of α-alkylidene lactones.

Manganese(III) γ-Lactone Annulation with Substituted Acids

Manganese(III) acetate oxidation of several HOOCCH2X, X = electron withdrawing group, in the presence of alkenes led to the formation of α-substituted γ-lactones.Chloroacetic acid gave α-chloro-γ-lactones, which were converted in two steps to the corresponding α,β-unsaturated γ-lactones. 3-Chloropropanoic acid led to the α-methylene γ-lactone after base induced elimination of HCl.Cyanoacetic acid produced α-cyano γ-lactones which could be hydrolytically decyanated or converted to the α-methylene γ-lactones in two steps.Potassium methyl malonate was oxidized and annulated onto alkenes to give α-carbomethoxy γ-lactones in reasonable yields.The method demonstrates a general route into several useful types substituted γ-lactones.

DIANION OF N-(o-METHOXYPHENYL)-2-METHYLPROPENAMIDE: A NEW REAGENT FOR THE CONVENIENT SYNTHESIS OF α-METHYLENE-γ-BUTYROLACTONES FROM CARBONYL COMPOUNDS

Dianion of N-(o-methoxyphenyl)-2-methylpropenamide was successfully generated on treatment of the amide with t-BuOK-BuLi at -78 degC in THF and utilized as the key reagent for the synthesis of γ-substituted α-methylene-γ-butyrolactones.

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