61892-54-4

Upstream product

• 35504-82-6 2-methyl-4-oxo-pent-2c-enoic acid 
• 75-36-5 acetyl chloride 
• 7541-65-3 Essigsaeure-(3,5-dimethyl-2-oxo-5H-furan-5-yl)ester 
• 658063-52-6 (+/-)-4,5-dihydro-2,4-dimethylfuran 
• 91199-00-7 4-Hydroxy-5-hydroxymethyl-3-methyl-dihydro-furan-2-one 
• 91075-37-5 C₂₀H₂₂O₈S₂ 
• 91075-27-3 3-Hydroxy-2-methyl-3-oxiranyl-propionic acid methyl ester 
• 79909-59-4 ethyl (Z)-2-methyl-6-methylthio-4,6-dioxohex-2-enoate 
• 3740-58-7 2,4-dimethyl-Δ3-γ-butyrolactone 
• 6641-83-4 2-methyl-4-oxopentanoic acid 
• 78804-65-6 (2-Methoxycarbonyl-pent-4-enyl)-trimethyl-ammonium; iodide 
• 69637-61-2 2-Dimethylaminomethyl-pent-4-enoic acid methyl ester 
• 51122-89-5 methyl 2-(2'-propenyl)propenoate 
• 4743-96-8 2-methylidenepent-4-enoic acid 

Downstream Products

• 71339-41-8 lepiochlorin 
• 664336-41-8 5-benzylaminomethyl-3-methyl-2(5H)-furanone 

Relevant academic research and scientific papers

Identifying the important structural elements of brominated furanones for inhibiting biofilm formation by Escherichia coli

A collection of structurally closely related furanones was synthesized to identify the most important structural elements in brominated furanones for inhibiting the formation of bacterial biofilms. The results suggest that a conjugated exocyclic vinyl bro

Synthesis of lepiochlorin, a chlorinated antibiotic, by use of electrochemical haloalkoxylation

Lepiochlorin is an antibiotic butenolide, a chlorinated metabolite of a fungus cultivated by a leaf-cutting ant. It was synthesized from 2-methyl-4-oxopentanoic acid by the electrochemical chloromethoxylation of 2-methyl-2,4-pentadien-4-olide in the MeOH-NH//4Cl-(Pt-Pt) system followed by hydrolysis in a mixed solution of dioxane-H//2O-concd HCl (25/10/1 V/V/V) in 38% overall yield. 14 reefs.

Synthesis of natural fimbrolides

Starting from citraconic anhydride, a three-step approach to fimbrolide congener is reported by taking the advantage of a regioselective Grignard reaction with an anhydride, followed by a dehydrative cyclization and double bromination-dehydrobromination s

FURANONE DERIVATIVES AND METHODS OF MAKING SAME

Novel synthesis methods, to the products of such novel methods, and to uses of these products. In particular, the present invention provides methods for the reactions of furanones, in particular fimbrolides, with amines. The invention has particular application in the synthesis of halogenated 1,5-dihydro-pyrrol-2-one, 5-halomethylene substituted 1,5-dihydropyrrol-2-ones (lactam analogues of fimbrolides), 5-amino substituted furanones and 5-aminomethylene-2(5H)-furanones and their synthetic analogues. The invention also relates to novel compounds and uses thereof.

A SHORT EFFICIENT SYNTHESIS OF 4-HYDROXY-5-(1-HYDROXYALKYL)-γ-BUTYROLACTONES

The cycloaddition of α,β-epoxyaldehydes or ketones (2) with the ketene acetal MeHC=C(OMe)2 (1) gives epoxyoxetanes (3) in high yields.Without isolation they can be transformed into 4-hydroxy-5-(1-hydroxyalkyl)-γ-butyrolactones (6) via the epoxy esters 4 and trihydroxy esters (5).The lactones 6 appear to be valuable precursors for the synthesis of 5-(1-hydroxyalkyl)-3-methyl-2-5H-furanones (7) and 3-methyl-5-ylidene-2-5H-furanones (8)

β-Amino Ester Enolate as an Acrylate Anion Equivalent for the Synthesis of α-Methylene Esters, Acids, and Lactones

The lithium enolate (18) of methyl 3-(dimethylamino)propionate (17) has been developed as a synthetic equivalent of the α-anion (15) of acrylic acid.The enolate, obtained by treatment of the free ester (17) with lithium diisopropylamide, may be alkylated with a variety of alkyl halides to give products which may be considered to be protected acrylate esters.Unmasking is accomplished by quaternization with methyl iodide followed by DBN-induced elimination to give the free acrylates.The products derived from allylic halides may conveniently be converted into α-methylene lactones.

USE OF METHYL 3-(N,N-DIMETHYLAMINO)PROPIONATE AS A SYNTHON FOR THE CONSTRUCTION OF α-METHYLENE γ-BUTYROLACTONES

The lithium enolate of methyl 3-(N,N-dimethylamino)propionate reacts with allylic halides to give alkylation products which may be converted into α-methylene γ-butyrolactones by a reaction sequence which includes iodolactonization among other simple steps.

The Synthesis of 5-Alkylidenefuran-2(5H)-ones

5-Alkylidenefuran-2(5H)-ones can be synthesized efficiently from S-methyl 5-oxo-2,5-dihydro-furanylidenealkanethioates by treatment with Raney nickel.The ylidenealkanethioates are prepared from the Wittig reactions between cyclic anhydrides and (methylthi

1,6-Additionen an 3-Methyl-5-methyliden-2(5H)-furanon-Derivate

The anions of thiophenol, methyl malonate and malononitrile react with 3-methyl-5,6-dihydro-2(4H)-benzofuranone (1c) by the formation of the corresponding 1,6-addition products cis-5c (63percent), trans-6 (42percent) and trans-7 (76percent), respectively.