128811-42-7

Basic information

• Product Name: 1-Pyrrolidinecarboxylic acid, 2-oxo-5-(phenylmethyl)-, 1,1-dimethylethyl ester, (5R)-
• CAS NO: 128811-42-7
• Molecular Formula: C16H21NO3
• Molecular Weight: 275.348
• Mol File: 128811-42-7.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 1-Pyrrolidinecarboxylic acid, 2-oxo-5-(phenylmethyl)-, 1,1-dimethylethyl ester, (5R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Pyrrolidinecarboxylic acid, 2-oxo-5-(phenylmethyl)-, 1,1-dimethylethyl ester, (5R)-(128811-42-7)
• EPA Substance Registry System: 1-Pyrrolidinecarboxylic acid, 2-oxo-5-(phenylmethyl)-, 1,1-dimethylethyl ester, (5R)-(128811-42-7)

Safety Data

• Hazardous Substances Data: 128811-42-7(Hazardous Substances Data)

Usage

Chemical class

Pyrrolidine carboxylic acids

Derivative of

Gamma-aminobutyric acid (GABA)

Psychoactive effects

Yes

Uses

Nootropic, anxiolytic substance

Availability

Sold as a dietary supplement

Legal status

Banned in several countries

Potential risks

Abuse, addiction, and significant effects on the central nervous system

Upstream product

• 128811-39-2 tert-butyl (2R)-2-(iodomethyl)-5-oxopyrrolidine-1-carboxylate 
• 591-51-5 phenyllithium 
• 197006-05-6 (R)-[1-benzyl-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-ethyl]-carbamic acid tert-butyl ester 
• 63-91-2 L-phenylalanine 
• 2033-24-1 cycl-isopropylidene malonate 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 128811-37-0 tert-butyl (2R)-2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate 
• 128811-38-1 tert-butyl (2R)-2-(bromomethyl)-5-oxopyrrolidine-1-carboxylate 
• 132618-89-4 methyl (E,4S)-4-(((benzyloxy)carbonyl)amino)-5-phenylpent-2-enoate 
• 59830-60-3 benzyl (1S)-(1-formyl-2-phenylethyl)carbamate 
• 109579-08-0 (S)-[1-benzyl-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 63328-11-0 (5R)-5-benzylpyrrolidin-2-one 
• 128811-31-4 tert-butyl (2R)-2-<<(tert-butyl)dimethylsilyloxy>methyl>-5-oxopyrrolidine-1-carboxylate 

Downstream Products

• 809278-68-0 (S)-5-Benzyl-3-[1-pyridin-4-yl-meth-(E)-ylidene]-pyrrolidin-2-one 
• 194598-26-0 (S)-5-Benzyl-3-[1-pyridin-3-yl-meth-(E)-ylidene]-pyrrolidin-2-one 
• 228864-44-6 (R)-Benzyl 5-phenyl-4-<(tert-butoxycarbonyl)amino>pentanoate 
• 368870-63-7 (3R,5R)-tert-butyl 5-benzyl-3-methyl-2-oxopyrrolidine-1-carboxylate 
• 194655-89-5 (3S,5R)-3,5-Dibenzyl-pyrrolidin-2-one 
• 809278-83-9 (2R,4S)-2-Benzyl-5-[(3S,5R)-5-benzyl-3-(3-cyanomethoxy-benzyl)-2-oxo-pyrrolidin-1-yl]-4-hydroxy-pentanoic acid ((1S,2R)-2-hydroxy-indan-1-yl)-amide 
• 809278-82-8 3-{(3S,5R)-5-Benzyl-1-[(2S,4R)-2-hydroxy-4-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-2-oxo-pyrrolidin-3-ylmethyl}-benzoic acid methyl ester 

Relevant articles and documents

SYNTHESIS AND APPLICATION OF CHIRAL SUBSTITUTED POLYVINYLPYRROLIDINONES

Chiral polyvinylpyrrolidinone (CSPVP), complexes of CSPVP with a core species, such as a metallic nanocluster catalyst, and enantioselective oxidation reactions utilizing such complexes are disclosed. The CSPVP complexes can be used in asymmetric oxidation of diols, enantioselective oxidation of alkenes, and carbon-carbon bond forming reactions, for example. The CSPVP can also be complexed with biomolecules such as proteins, DNA, and RNA, and used as nanocarriers for siRNA or dsRNA delivery.

Synthesis, antimycobacterial activity and influence on mycobacterial InhA and PknB of 12-membered cyclodepsipeptides

In recent years, several small natural cyclopeptides and cyclodepsipeptides were reported to have antimycobacterial activity. Following this lead, a synthetic pathway was developed for a small series of 12-membered ring compounds with one amide and two ester bonds (cyclotridepsipeptides). Within the series, the ring system proved to be necessary for growth inhibition of Mycobacterium smegmatis and Mycobacterium tuberculosis in the low micromolar range. Open-chain precursors and analogues were inactive. The compounds modulated autophosphorylation of the mycobacterial protein kinase B (PknB). PknB inhibitors were active at μM concentration against mycobacteria while inducers were inactive. PknB regulates the activity of the mycobacterial reductase InhA, the target of isoniazid. The activity of the series against Mycobacterium bovis BCG InhA overexpressing strains was indistinguishable from that of the parental strain suggesting that they do not inhibit InhA. All substances were not cytotoxic (HeLa > 5 μg/ml) and did not show any significant antiproliferative effect (HUVEC > 5 μg/ml; K-562 > 5 μg/ml). Within the scope of this study, the molecular target of this new type of small cyclodepsipeptide was not identified, but the data suggest interaction with PknB or other kinases may partly cause the activity.

Catalytic enantioselective Steglich rearrangements using chiral N-heterocyclic carbenes

The evaluation of a range of enantiomerically pure NHCs, prepared in situ from imidazolinium or triazolium salt precatalysts, to promote the catalytic enantioselective Steglich rearrangement of oxazolyl carbonates to their C-carboxyazlactones, is reported. Modest levels of enantioselectivity (up to 66% ee) are observed using oxazolidinone derived NHCs.