Cas no 102389-88-8 (Dimethyl trans-(+/-)-pyrrolidine-3,4-dicarboxylate)

Dimethyl trans-(±)-pyrrolidine-3,4-dicarboxylate is a versatile intermediate in organic synthesis, particularly valued for its role in the preparation of pyrrolidine-based compounds. The trans-configuration of the dicarboxylate groups enhances its utility in stereoselective reactions, while the ester functionalities provide reactivity for further derivatization. This compound is commonly employed in pharmaceutical and agrochemical research due to its structural flexibility, enabling the synthesis of chiral building blocks and bioactive molecules. Its stability under standard conditions and compatibility with a range of reagents make it a practical choice for complex synthetic pathways. The racemic form (±) allows broad applicability in exploratory chemistry.
Dimethyl trans-(+/-)-pyrrolidine-3,4-dicarboxylate structure
102389-88-8 structure
Product Name:Dimethyl trans-(+/-)-pyrrolidine-3,4-dicarboxylate
CAS No:102389-88-8
MF:C8H13NO4
MW:187.193122625351
CID:2865160
PubChem ID:13539144
Update Time:2025-05-25

Dimethyl trans-(+/-)-pyrrolidine-3,4-dicarboxylate Chemical and Physical Properties

Names and Identifiers

    • (3S,4S)-Dimethyl pyrrolidine-3,4-dicarboxylate
    • Dimethyl (3S,4S)-pyrrolidine-3,4-dicarboxylate
    • Dimethyl trans-(+/-)-pyrrolidine-3,4-dicarboxylate
    • TRANS-PYRROLIDINE-3,4-DICARBOXYLIC ACID DIMETHYL ESTER
    • F19806
    • Trans (+/-)-pyrrolidine-3,4-dicarboxylic acid dimethyl ester
    • 111138-53-5
    • 3,4-DIMETHYL (3S,4S)-PYRROLIDINE-3,4-DICARBOXYLATE
    • 102389-88-8
    • AKOS022173294
    • SCHEMBL9151117
    • (3S,4S)-Dimethylpyrrolidine-3,4-dicarboxylate
    • Dimethyl trans-Pyrrolidine-3,4-dicarboxylate
    • Inchi: 1S/C8H13NO4/c1-12-7(10)5-3-9-4-6(5)8(11)13-2/h5-6,9H,3-4H2,1-2H3/t5-,6-/m1/s1
    • InChI Key: DEONENFBMPLKOR-PHDIDXHHSA-N
    • SMILES: O(C)C([C@@H]1CNC[C@H]1C(=O)OC)=O

Computed Properties

  • Exact Mass: 187.08445790 g/mol
  • Monoisotopic Mass: 187.08445790 g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 4
  • Complexity: 194
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -0.7
  • Topological Polar Surface Area: 64.599
  • Molecular Weight: 187.19

Dimethyl trans-(+/-)-pyrrolidine-3,4-dicarboxylate Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
TRC
D462505-25mg
Dimethyl trans-(+/-)-pyrrolidine-3,4-dicarboxylate
102389-88-8
25mg
$133.00 2023-05-18
TRC
D462505-50mg
Dimethyl trans-(+/-)-pyrrolidine-3,4-dicarboxylate
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$322.00 2023-05-18
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D462505-250mg
Dimethyl trans-(+/-)-pyrrolidine-3,4-dicarboxylate
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$563.00 2023-05-18

Additional information on Dimethyl trans-(+/-)-pyrrolidine-3,4-dicarboxylate

Recent Advances in the Study of Dimethyl trans-(+/-)-pyrrolidine-3,4-dicarboxylate (CAS: 102389-88-8)

Dimethyl trans-(+/-)-pyrrolidine-3,4-dicarboxylate (CAS: 102389-88-8) is a chiral pyrrolidine derivative that has garnered significant attention in the field of chemical biology and medicinal chemistry due to its versatile applications in drug discovery and development. This compound serves as a key intermediate in the synthesis of various bioactive molecules, including potential therapeutics for neurological disorders, infectious diseases, and cancer. Recent studies have explored its synthetic utility, pharmacological properties, and mechanistic insights, making it a focal point in contemporary research.

One of the most notable advancements in the study of this compound is its role in the synthesis of novel γ-aminobutyric acid (GABA) analogs. Researchers have demonstrated that Dimethyl trans-(+/-)-pyrrolidine-3,4-dicarboxylate can be efficiently transformed into GABAergic ligands, which exhibit promising activity in modulating neurotransmitter receptors. These findings are particularly relevant for the development of treatments for epilepsy, anxiety, and other central nervous system disorders. The compound's chiral centers also allow for the exploration of stereoselective interactions with biological targets, enhancing its potential as a scaffold for drug design.

In addition to its neurological applications, recent studies have highlighted the compound's utility in antimicrobial research. A 2023 publication in the Journal of Medicinal Chemistry reported the synthesis of pyrrolidine-based antimicrobial agents derived from Dimethyl trans-(+/-)-pyrrolidine-3,4-dicarboxylate. These agents exhibited potent activity against multidrug-resistant bacterial strains, underscoring the compound's potential in addressing the global antibiotic resistance crisis. The study also provided mechanistic insights into the compound's interaction with bacterial cell walls, offering a foundation for further optimization.

Another area of active research involves the use of this compound in cancer therapeutics. A team of researchers recently utilized Dimethyl trans-(+/-)-pyrrolidine-3,4-dicarboxylate as a precursor for the synthesis of small-molecule inhibitors targeting specific oncogenic pathways. Preliminary in vitro and in vivo studies have shown that these inhibitors effectively suppress tumor growth with minimal off-target effects. The compound's ability to serve as a versatile building block for diverse pharmacophores has been a key factor in these advancements.

From a synthetic chemistry perspective, recent efforts have focused on optimizing the production and purification of Dimethyl trans-(+/-)-pyrrolidine-3,4-dicarboxylate. Innovations in catalytic asymmetric synthesis have enabled the production of enantiomerically pure forms of the compound, which are critical for its application in chiral drug development. These methodological improvements not only enhance yield and purity but also align with the growing emphasis on sustainable and green chemistry practices in the pharmaceutical industry.

In conclusion, Dimethyl trans-(+/-)-pyrrolidine-3,4-dicarboxylate (CAS: 102389-88-8) continues to be a molecule of significant interest in chemical biology and medicinal chemistry. Its multifaceted applications in drug discovery, coupled with recent advancements in synthetic methodologies and mechanistic understanding, position it as a valuable tool for researchers. Future studies are expected to further explore its potential in addressing unmet medical needs, particularly in the realms of neurology, infectious diseases, and oncology.

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