81702-31-0

Basic information

• Product Name: 2,5-Pyrrolidinedicarboxylicacid,(2S,5S)-(9CI)
• Synonyms: 2,5-Pyrrolidinedicarboxylicacid,(2S,5S)-(9CI);(2S,5S)-2,5-Pyrrolidinedicarboxylic acid
• CAS NO: 81702-31-0
• Molecular Formula: C6H9NO4
• Molecular Weight: 159.14
• Product Categories: PYRROLE;Chiral Reagents
• Mol File: 81702-31-0.mol
• Article Data: 11

Chemical Properties

• Melting Point: 268 °C
• Boiling Point: 420.296°C at 760 mmHg
• Flash Point: 207.988°C
• Appearance: /
• Density: 1.457g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.535
• PKA: 1.79±0.40(Predicted)
• CAS DataBase Reference: 2,5-Pyrrolidinedicarboxylicacid,(2S,5S)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Pyrrolidinedicarboxylicacid,(2S,5S)-(9CI)(81702-31-0)
• EPA Substance Registry System: 2,5-Pyrrolidinedicarboxylicacid,(2S,5S)-(9CI)(81702-31-0)

Safety Data

• Hazardous Substances Data: 81702-31-0(Hazardous Substances Data)

Usage

General Description

2,5-Pyrrolidinedicarboxylic acid, also known as (2S,5S)-2,5-pyrrolidinedicarboxylic acid, is a chemical compound that consists of a pyrrolidine ring with two carboxylic acid functional groups. It is a rare enantiomer of 2,5-pyrrolidinedicarboxylic acid, with the (2S,5S) configuration, and has been identified as a component in certain natural products and pharmaceutical compounds. 2,5-Pyrrolidinedicarboxylicacid,(2S,5S)-(9CI) is known for its potential applications in drug development and medicinal chemistry, particularly for its ability to act as an intermediate for the synthesis of various pharmaceuticals and biologically active compounds. Additionally, 2,5-Pyrrolidinedicarboxylic acid (2S,5S) may also have potential uses in the field of materials science and organic synthesis.

InChI:InChI=1/C6H9NO4/c8-5(9)3-1-2-4(7-3)6(10)11/h3-4,7H,1-2H2,(H,8,9)(H,10,11)/t3-,4-/m0/s1

Upstream product

• 51483-87-5 1-Benzyl-2,5-pyrrolidindicarbonsaeure-dimethylester 
• 90088-52-1 dimethyl pyrrolidine-2,5-dicarboxylate 
• 868-72-4 dimethyl (2R,5S)-2,5-dibromohexanedioate 
• 126550-73-0 N-Boc-2-(S)-benzoyloxymethyl-5-(S)-benzyloxy methylpyrrolidine 
• 126550-69-4 2-((R)-1-Benzyloxymethyl-pent-4-enyl)-isoindole-1,3-dione 
• 157968-73-5 (2S,5S)-Pyrrolidine-1,2,5-tricarboxylic acid 1-tert-butyl ester 
• 126550-72-9 (2S,5S)-2-benzyloxymethyl-5-benzoyloxymethylpyrrolidine 
• 138528-06-0 (2S,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-hydroxymethylpyrrolidine 
• 126550-71-8 (S)-1-benzyloxy-2-benzoylaminohex-5-ene 
• 155418-40-9 (2S)-1-(benzyloxy)hex-5-en-2-ol 
• 126550-70-7 (R)-1-Benzyloxymethyl-pent-4-enylamine 
• 140147-95-1 (5S)-1-methoxycarbonyl-5-(2-methyl-1-propenyl)-L-proline methyl ester 
• 139963-88-5 (5S)-1-methoxycarbonyl-5-formyl-L-proline methyl ester 
• 185385-13-1 1-carbomethoxy-5-methoxy-L-proline methyl ester 

Downstream Products

• 52832-52-7 acido 2-fenil-2,3,5,6,7,7a-esaidro-1-oxo-3-tioxo-1H-pirrolo<1,2-c>imidazolo-5-carbossilico 

Relevant articles and documents

N-Heterocyclic dicarboxylic acids: Broad-spectrum inhibitors of metallo-β-lactamases with co-antibacterial effect against antibiotic-resistant bacteria

In an effort to identify novel, broad-spectrum inhibitors against the metallo-β-lactamases (MβLs), several N-heterocyclic derivatives were tested as inhibitors of MβLs CcrA, ImiS, and L1, which are representative enzymes from the distinct MβL subclasses. Three N-heterocyclic dicarboxylic acid derivatives were competitive inhibitors of CcrA and L1, exhibiting K i values ≤2 μM, while only 2,4-thiazolidinedicarboxylic acid (1b) was a competitive inhibitor of ImiS. Two 2-mercapto-1,3,4-thiadiazole derivatives were noncompetitive inhibitors of CcrA and ImiS, exhibiting K i values 7 μM; however, these same compounds did not inhibit L1. Two 2-mercapto-1,3,4-triazole derivatives were shown not to inhibit any of the tested MβLs. The N-heterocyclic derivatives were tested for antibacterial activity by examining the MIC values for existing antibiotics in the presence/absence of these derivatives. Consistent with the steady-state inhibition data, the inclusion of three N-heterocyclic dicarboxylic acid derivatives resulted in lower MIC values when using Escherichia coli BL21(DE3) cells containing the CcrA or L1 plasmids or Klebsiella pneumoniae (ATCC 700603), while 1b was the only dicarboxylic acid derivative to lower the MIC value of E. coli cells containing the ImiS plasmid. Inclusion of the 2-mercapto-1,3,4- thiadiazole derivatives resulted in lower MIC values for E. coli cells containing ImiS or L1 plasmids; however, these derivatives did not alter the MIC values for K. pneumoniae or E. coli cells containing the L1 plasmid. None of the N-heterocyclic derivatives affected the MIC of two methicillin resistant Staphylococcus aureus (MRSA) strains. Taken together, these studies demonstrate that N-heterocyclic dicarboxylic acids 1a-c and pyridylmercaptothiadiazoles 2a,b are good scaffolds for future broad-spectrum inhibitors of the MβLs.

An efficient synthesis of substituted prolines by the selective reduction and reductive cyanation of 2-pyrrolidones

Substituted pyrrolidones undergo selective reduction using Cp2ZrHCl (Schwartz's reagent) to form Δ1-pyrrolines, which can be isolated or directly cyanated and hydrolyzed to the corresponding proline. Short syntheses of glutamic semialdehyde (ethyl ester), the marine metabolite (2S,5S)-pyrrolidine-2,5-dicarboxylic acid, and the conformationally constrained amino acid 5,5-dimethylproline, are reported.

A convenient synthesis of enantiomeric pairs of 2,5-disubstituted pyrrolidines of C2-symmetry

By the use of (-)-1-phenylethylamine as a chiral auxiliary, three diastereomeric isomers of 2,5-bis(methoxycarbonyl)pyrrolidine derivatives are prepared from dimethyl rac-2,5-dibromadipate and separted by crystallization and chromatographic fractionation