134053-86-4

Basic information

• Product Name: Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-methoxy-, (3R-cis)- (9CI)
• Synonyms: Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-methoxy-, (3R-cis)- (9CI);(3R,8AS)-3-METHOXYHEXAHYDROPYRROLO[1,2-A]PYRAZINE-1,4-DIONE
• CAS NO: 134053-86-4
• Molecular Formula: C8H12N2O3
• Molecular Weight: 184.19248
• Product Categories: PIPERIDINE
• Mol File: 134053-86-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 447.8±45.0 °C(Predicted)
• Appearance: /
• Density: 1.31±0.1 g/cm3(Predicted)
• PKA: 11.42±0.40(Predicted)
• CAS DataBase Reference: Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-methoxy-, (3R-cis)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-methoxy-, (3R-cis)- (9CI)(134053-86-4)
• EPA Substance Registry System: Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-methoxy-, (3R-cis)- (9CI)(134053-86-4)

Safety Data

• Hazardous Substances Data: 134053-86-4(Hazardous Substances Data)

Usage

General Description

Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-methoxy-, (3R-cis)- (9CI) is a chemical compound with the molecular formula C7H9NO3. It has a hexahydro-3-methoxy- structure with a cis- configuration at the 3R position. Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-methoxy-, (3R-cis)- (9CI) is a derivative of pyrazine and is classified as a heterocyclic compound. It is an organic compound with potential pharmaceutical applications and may exhibit various biological activities. Further research is needed to fully understand the properties and potential uses of this chemical compound.

Upstream product

• 61058-42-2 Z-Pro-Gly-OMe 
• 134023-30-6 Boc-L-Pro-Gly(OMe)-OMe 
• 34290-72-7 tert-butyloxycarbonyl-prolyl-glycine methyl ester 
• 1319113-23-9 Cbz-L-Pro-Gly(OMe)-OMe 
• 205875-03-2 2-[((S)-1-tert-Butoxycarbonyl-pyrrolidine-2-carbonyl)-amino]-malonic acid dimethyl ester 
• 205875-04-3 methyl 1,4-dioxoperhydropyrrolo[1,2-a]pyrazine-3-carboxylate 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 67-56-1 methanol 
• 205875-05-4 (3S,6RS)-6-carboxy-1,3-trimethylene-2,5-piperazinedione 

Relevant articles and documents

3-Triphenylphosphonio-2,5-piperazinediones as new chiral glycine cation equivalents

3-Triphenylphosphonio-2,5-piperazinediones were effectively synthesized from homochiral valine or proline via Boc-Val-Gly-OMe, Boc-Pro-Gly-OMe or Cbz-Pro-Gly-OMe. Retention of configuration of the primary stereogenic center of the valine and proline moieties was observed. Diastereoselective nucleophilic substitution of the triphenylphosphonium group in 2,5-piperazinediones with S-, N-, P- and C-nucleophiles was observed. The configuration of the substitution products was assigned either by their hydrolysis and decarboxylation or based on the analysis of the H-C(3)-N-H coupling constants of 3-substituted-2,5- piperazinediones derived from proline. The trans-stereoselectivity was predominant in reactions of 3-triphenylphosphonio-1,6-trimethylene-2,5- piperazinediones with the nucleophiles investigated. The stereodifferentiating ability of the proline moiety is much stronger than that of the valine unit and allowed nucleophilic α-functionalization of the glycine moiety with good to excellent diastereoselectivity.

ANODIC OXIDATION OF N-ACYL AND N-ALKOXYCARBONYL DIPEPTIDE ESTERS AS A KEY STEP FOR THE FORMATION OF CHIRAL HETEROCYCLIC SYNTHETIC BUILDING BLOCKS

The anodic oxidation of N-protected dipeptide esters using chloride as a redox catalyst can be performed regioselectively at the C-terminal amino acid.With methanol as solvent, glycine as the C-terminal, and L-valine or L-proline as N-terminal amino acid methoxylation at the glycine residue takes place.Deprotection of this product leads to the (3S,6RS)-6-methoxy-2,5-piperazinedione (3) which can be applied as a chiral cationic glycine equivalent.The exchange of the methoxy group by C-nucleophiles takes place with high trans-diastereoselectivity under steric control by the substituent in 3-position.With branched amino acids at the C-terminus of the dipeptide ester the anodic oxidation in acetonitrile/methanol (95:5) as solvent with tetraethylammonium chloride as supporting electrolyte and redox catalyst leads to methyl imidazolidin-4-one-2-carboxylates.The cyclization takes place via the intermediate formation of the N-acylimino ester of the C-terminal amino acid.