5621-43-2

Upstream product

• 140-88-5 ethyl acrylate 
• 50-00-0 formaldehyd 
• 2832-14-6 triethyl 1,1,3-propanetricarboxylate 

Downstream Products

• 18545-83-0 diethyl 2-methylglutarate 
• 32749-55-6 1-benzyl-6-oxopiperidine-3-carboxylic acid 
• 4606-65-9 (S)-(hydroxymethyl)piperidine 
• 63579-89-5 triethyl pentane-1,3,5-tricarboxylate 
• 98-78-2 3-Oxo-cyclopentanecarboxylic acid 

Relevant academic research and scientific papers

Poly(α-methyleneglutarimide)s from radical polymerization of α-methyleneglutarimides

α-Methyleneglutaric acid, a metabolite of niacin (nicotinic acid), can be easily converted to its cyclic anhydride. We report here the first conversion of α-methyleneglutaric anhydride to (a series of) α-methyleneglutarimides. These monomers can be radically polymerized to the title polymers. These have relatively high glass transition properties compared to the lower homologs derived from itaconimides (α-methylenesuccinimides).

A new and rapid access towards exo-methylene-δ-valerolactones from (cyclopropyl)methylstannanes

Lewis-acid catalysed ring-opening of functionalised (cyclopropyl) methylstannane 10, in the presence of aldehydes or ketones, was found to afford the corresponding aldol adducts in high yields. Subsequent lactonisation under acid catalysis led quantitativ

O-(α-Phenylethyl)hydroxylamine as a ‘chiral ammonia equivalent’: synthesis and resolution of 5-oxopyrrolidine- and 6-oxopiperidine-3-carboxylic acids

An approach to the synthesis and resolution of five- and six-membered lactams (i.e., 5-oxopyrrolidine- and 6-oxopiperidine-3-carboxylic acids) is described. The method relies on the one-pot Michael reaction—cyclization of itaconic acid or diethyl homoitaconate and enantiopure O-(α-phenylethyl)hydroxylamine as a ‘chiral ammonia equivalent’. It is shown that this chiral auxiliary can be used for the separation of diastereomeric lactam products and then easily removed by catalytic hydrogenolysis.

PRODRUGS OF PROSTATE SPECIFIC MEMBRANE ANTIGEN (PSMA) INHIBITOR

Methods and compounds are disclosed for treating a disease or condition by inhibiting PSMA (Prostate Specific Membrane Antigen) using prodrugs of 2-PMPA.

Stereo- and chemoselective cross-coupling between two electron-deficient acrylates: An efficient route to (Z, E)-muconate derivatives

A Ru-catalyzed direct oxidative cross-coupling reaction of acrylates was developed. It offers a straightforward and atom-economical protocol for the synthesis of functionalized (Z,E)-muconate derivatives in moderate to good yields with good stereo- and chemoselectivities. The conjugated muconates bearing differentiable terminal functionality can be selectively transformed into versatile synthetic intermediates widely used in organic synthesis.

A convenient general synthesis of 3-substituted 2H-chromene derivatives

Reactions of 2-hydroxybenzaldehydes and 2-hydroxy-1-naphthaldehydes with various activated alkenes under Baylis-Hillman conditions have been shown to proceed with regioselective cyclisation to afford the corresponding 3-substituted chromene derivatives. In some cases competitive dimerisation of the alkene component was observed, and direct dimerisation in the absence of the aldehyde has been explored.

Ruthenium-mediated selective head-to-tail dimerization of acrylic and α,β-unsaturated carbonyl compounds: Generation of an acrylate-hydride complex C5Me5Ru(PCy3)(CH2=CHCO 2Et)H

The ruthenium-hydride complex C5Me5Ru(PCy3)H3 (1a) was found to be a selective catalyst precursor for the head-to-tail dimerization of acrylic and α,β-unsaturated carbonyl compounds to produce bifunctional 1,5-dicarbonyl compounds. A new ruthenium species C5Me5Ru(PCy3)(CH2=CHCO 2Et)H (6a) was independently generated from the substitution reaction of 1a with ethyl acrylate. The exclusive formation of the head-to-tail dimers suggested that, the tertiary phosphine, generated from the substitution reaction of 6a with an olefin, was the active species for the dimerization reaction.

Nucleophile-Catalysed Additions of Aldehydes and Ketones to Acrylic Compounds: The Effectiveness of High Pressures

The preparation of a wide range of compounds of general type: CH2=C(Z)-CR1R2OH (Z = CN, COOR, CHO,; R1,R2 = H, alkyl, aryl) from the reaction of CH2=CHZ with aldehydes and ketones, is effectively catalysed by tertiary amines especially DABCO.Rates are found to be very strongly accelerated by high pressures (2-10 kbar) which alone permits the additions of ketones or of crotonic acid derivatives to take place.In the absence of carbonyl acceptors novel oligomers of acrylic compounds form.

Reactions of Cyanide Ions with α,β-Unsaturated Esters, IV. - Reactions to Carbocycles

Sodium cyanide reacts with diethyl 2-methylenealkanedioates 1a-c and 8a-h to give simple or alkylated ethyl 2-cyano-3-oxo-1-cycloalkanecarboxylates 5a-c and 9a-h, respectively.From these the 3-oxo-1-cycloalkanecarboxylic acids 6a-c and 10a-h, respectively