159000-54-1

Basic information

• Product Name: 2,4-Pyrrolidinedicarboxylicacid,(2R,4S)-rel-(9CI)
• Synonyms: 2,4-Pyrrolidinedicarboxylicacid,(2R,4S)-rel-(9CI)
• CAS NO: 159000-54-1
• Molecular Formula: C6H9NO4
• Molecular Weight: 159.13996
• Product Categories: PYRROLE;CARBOXYLICACID
• Mol File: 159000-54-1.mol

Chemical Properties

• Boiling Point: 355.3±42.0 °C(Predicted)
• Appearance: /
• Density: 1.456±0.06 g/cm3(Predicted)
• PKA: 2.09±0.40(Predicted)
• CAS DataBase Reference: 2,4-Pyrrolidinedicarboxylicacid,(2R,4S)-rel-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Pyrrolidinedicarboxylicacid,(2R,4S)-rel-(9CI)(159000-54-1)
• EPA Substance Registry System: 2,4-Pyrrolidinedicarboxylicacid,(2R,4S)-rel-(9CI)(159000-54-1)

Safety Data

• Hazardous Substances Data: 159000-54-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,4-Pyrrolidinedicarboxylic acid, (2R,4S)-rel-(9CI) is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique stereochemistry allows for the development of enantiomerically pure drugs, which can exhibit different biological activities and reduce potential side effects.
Used in Agrochemical Industry:
In the agrochemical industry, 2,4-Pyrrolidinedicarboxylic acid, (2R,4S)-rel-(9CI) is utilized in the synthesis of agrochemicals, such as pesticides and herbicides. Its specific stereochemistry enables the development of more effective and targeted agrochemicals with reduced environmental impact.
Used as a Chelating Agent:
2,4-Pyrrolidinedicarboxylic acid, (2R,4S)-rel-(9CI) has been investigated for its potential as a chelating agent. Its ability to form stable complexes with metal ions can be applied in various fields, such as wastewater treatment, where it can help remove heavy metals from industrial effluents.
Used as a Building Block in Organic Synthesis:
2,4-Pyrrolidinedicarboxylicacid,(2R,4S)-rel-(9CI) serves as a versatile building block in the synthesis of various organic compounds. Its unique structure and reactivity make it a valuable component in the development of new molecules with potential applications in materials science, pharmaceuticals, and other industries.

Upstream product

• 130830-73-8 N-(benzyloxycarbonyl)-cis-4-carboxy-L-proline 
• 51-35-4 4R-4-hydroxyproline 
• 130830-60-3 1-benzyl 2-ethyl(2S,4R)-4-[[(4-methylbenzene)sulfonyl]oxy]pyrrolidine-1,2-dicarboxylate 
• 130830-69-2 N-(benzyloxycarbonyl)-cis-4-carboxy-L-proline dimethyl ester 
• 130830-65-8 N-(benzyloxycarbonyl)-cis-4-cyano-L-proline ethyl ester 
• 130830-62-5 N-(benzyloxycarbonyl)-trans-4-(tosyloxy)-D-proline ethyl ester 
• 130830-72-7 N-(benzyloxycarbonyl)-cis-4-carboxy-D-proline dimethyl ester 
• 130830-68-1 N-(benzyloxycarbonyl)-cis-4-cyano-D-proline ethyl ester 
• 130930-28-8 N-(benzyloxycarbonyl)-trans-4-hydroxy-D-proline ethyl ester 
• 130830-76-1 N-(benzyloxycarbonyl)-cis-4-carboxy-D-proline 
• 2584-71-6 cis-hydroxy-D-proline 
• 130830-63-6 N-(benzyloxycarbonyl)-cis-4-(tosyloxy)-D-proline ethyl ester 
• 130830-71-6 N-(benzyloxycarbonyl)-trans-4-carboxy-D-proline dimethyl ester 
• 130830-67-0 N-(benzyloxycarbonyl)-trans-4-cyano-D-proline ethyl ester 

Relevant articles and documents

Selenium-containing photosensitizer as well as preparation method and application thereof

The invention discloses a selenium-containing photosensitizer as well as a preparation method and application thereof. A novel selenium-containing photosensitizer with an anti-tumor angiogenesis effect is synthesized for a first time. The selenium-containing photosensitizer can be applied to treatment on skin scale cancer and is remarkable in effect, the dosage of the selenium-containing photosensitizer is far lower than that of 5-ALA in the market, in addition is free of antibiotics, free of drug resistance and small in side effect, and is safe and non-toxic and economic and practical; in addition, because of the limited light penetration function and other factors, a tumor treatment effect can be achieved even for tumor tissue without light dynamic response through tumor angiogenesis inhibition.

Preparation method for pyrrolidine-2-carboxylic acid derivatives

The present invention relates to the field of medical synthesis, in particular to a preparation method for pyrrolidine-2-carboxylic acid derivatives. The present invention adopts the following technical solution: providing a compound having a structure of formula (E), wherein R is R1 or R2, R1 is C1-C6 an alkyl, benzyl, p-methoxybenzyl, or p-nitrobenzyl group, and R2 is hydrogen; R3 is a protecting group of the carboxyl group; and P1 is a protecting group on nitrogen.

An enantioselective route to pyrrolidines: Removal of the chiral template from homochiral pyrroloimidazoles

Two-step reductive removal of the chiral template from optically active pyrroloimidazoles, available from 1,3-dipolar cycloaddition of homochiral 4,5-dihydroimidazolium ylides, gives optically active substituted pyrrolidines. Selective manipulation of the substituents affords, e.g., naturally occurring and other optically active proline derivatives, and optically active pyrrolizidines and indolizidines.

Method of inhibiting the transport of L-glutamate to treat CNS disorders

A method of inhibiting the transport of a neurotransmitter away from the synapse comprising contacting a neurotransmitter transporter with a compound having the structure STR1 wherein STR2 or CONHR 3 in any combination and and wherein R 2 =OR 3, NR 3 2, alkyl, or substituted alkyl and R 3 =alkyl or substituted alkyl.

Asymmetric synthesis of 4-substituted prolines as conformationally constrained amino acid analogues

Treatment of readily available chiral building block 1 with (2R)-2,3-O- isopropylideneglyceraldehyde (5) provides a new route for asymmetric synthesis of 2,4-disubstituted pyrrolidines. Several proline-amino acid chimeras: proline-leucine, proline-lysine, proline-arginine and proline- glutamic acid, are synthesized in highly diastereomerically pure forms.

Asymmetric synthesis of 2,4-disubstituted pyrrolidines

A new strategy for asymmetric synthesis of 2,4-disubstituted pyrrolidines is described, starting from readily available chiral building blocks 1 and (2R)-2,3-O-isopropylideneglycealdehyde (6).

Stereospecific synthesis of cis-2,4-pyrrolidinedicarboxylic acid and cis-2,5-piperidinedicarboxylic acid

Lactams derived from hetero Diels-Alder adducts were stereospecifically converted into cis-2,4-pyrrolidinedicarboxylic acid and cis-2,5- piperidinedicarboxylic acid by ruthenium tetroxide oxidation. Optically active (2S,4S)-(-)-2,4-pyrrolidinedicarboxylic acid and (2R,4R)-(+)-2,4- pyrrolidinedicarboxylic acid were synthesized from (1S,4R)-(+)-2- azabicyclo[2.2.1]hept-5-en-3-one and (1R,4S)-(-)-2-azabicyclo[2.2.1]hept-5- en-3-one, respectively.

An enantioselective route to pyrrolidines: Removal of the chiral template from homochiral pyrroloimidazoles

Two-step reductive removal of the chiral template from optically active pyrroloimidazoles, available from 1,3-dipolar cycloaddition of homochiral imidazolinium ylides, gives optically active substituted pyrrolidines. Selective manipulation of the substituents affords, e.g. naturally occurring proline derivatives and homochiral pyrrolizidines.

Asymmetric Synthesis of α-Amino Acids via Cationic Aza-Cope Rearrengements

Ene-iminium intermediates resulting from reaction between glyoxal and β-amino alcohols rearrange by an aza-Cope process.Three different tandem reactions are thus carried out; their first component is this cationic rearrangement, the second step being either an iminium hydrolysis, a nucleophile-induced ene-iminium cyclization or a Mannich reaction.The last two sequences lead to homochiral proline derivatives.

Conformationally Defined Neurotransmitter Analogues. Selective Inhibition of Glutamate Uptake by One Pyrrolidine-2,4-dicarboxylate Diastereomer

In order to determine the conformational requirements for binding of L-glutamate to the proteins involved in the process of neurotransmission, rigid analogues containing an embedded glutamate moiety have been prepared.These "conformer mimics", the pyrrolidine-2,4-dicarboxylates 4, 7, 11, and 14, were synthesized from commercially available trans-4-hydroxy-L-proline and cis-4-hydroxy-D-proline, and then were tested for their ability to inhibit the high-affinity transport of -L-glutamate into synaptosomes and to block the binding of radioligands to the NMDA (N-methyl-D-aspartate), KA (kainate), and QA (quisqualate) glutamate neurotransmitter receptor sites.While none of the four analogues binds effectively to the excitatory receptors, the L-trans-isomer 7 is a potent and selective competitive inhibitor of L-glutamate transport.These results delineate a specific structural/conformational preference for binding to the uptake system that is distinct from that required for binding to the NMDA, KA, and QA receptors.