69637-66-7

Upstream product

• 3853-06-3 methyl 3-(dimethylamino)propionate 
• 1521-51-3 rac-3-bromocyclohexene 
• 86428-48-0 (Z,E)-1-fluoro-1-methoxy-2-(phenylsulfinyl)-1-propene 
• 822-67-3 Cyclohex-2-enol 
• 69637-62-3 2-Cyclohex-2-enyl-3-dimethylamino-propionic acid methyl ester 
• 292638-85-8 acrylic acid methyl ester 
• 69637-65-6 (2-Cyclohex-2-enyl-2-methoxycarbonyl-ethyl)-trimethyl-ammonium; iodide 

Downstream Products

• 54109-55-6 2-Cyclohex-2-enyl-acrylic acid 
• 16822-06-3 cis-3-methylenehexahydrobenzofuran-2-one 
• 60916-75-8 (3aR,7aR)-3-Methylene-3a,4,5,7a-tetrahydro-3H-benzofuran-2-one 

Relevant academic research and scientific papers

NOUVELLE VOIE D'ACCES STEREOSELECTIVE AUX ESTERS ACRYLIQUES SON APPLICATION EN CHIMIE DES SUCRES

Regio- and stereo-selective synthesis of an acryl residue by treatment of an allyl alcohol with (Z,E)-1-fluoro-1-methoxy-2-phenylsulfinylpropene was performed in three consecutive reactions in the same flask; displacement of F- by the alcohol, Claisen rearrengement, and dehydrosulfinylation.Thus, 1,5-anhydro-2-deoxy-4,6-O-isopropylidene-D-arabino-hex-1-enitol gave methyl 3,7-anhydro-6,8-benzylidene-2,4,5-trideoxy-2-C-methylene-D-ribo-oct-4-enonate and methyl 2-O-allyl-4,6-dideoxy-α-D-erythro-hex-4-enopyranoside gave methyl (methyl 2-O-allyl-3,4,6-trideoxy-5-C-methyl-6-C-methylene-α-L-threo-hept-3-enopyranosyd)uronate, which has a chiral quaternary C-5 atom.

AN EASY AND EFFICIENT SYNTHESIS OF α-METHYLENE-γ,δ-UNSATURATED ESTERS FROM ALLYLIC ALCOHOLS

A new method for the regio- and stereo-specific introduction of an acrylic ester unit, via a one pot reaction is described.

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.

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.