Cas no 186268-77-9 (Methyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl)-pyrrolidine-2-carboxylate)

Methyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl)-pyrrolidine-2-carboxylate is a chiral ester derivative featuring a pyrrolidine backbone and a 3,3-dimethyl-2-oxopentanoyl moiety. Its stereospecific (2S) configuration makes it valuable for asymmetric synthesis and pharmaceutical intermediates, particularly in the development of bioactive compounds. The compound's rigid structure, conferred by the pyrrolidine ring, enhances stability, while the ketone and ester functionalities offer versatile reactivity for further derivatization. Its application spans organocatalysis and peptidomimetic research, where precise stereocontrol is critical. The 3,3-dimethyl substitution on the pentanoyl group further contributes to steric hindrance, influencing selectivity in synthetic pathways. This compound is typically handled under inert conditions due to its sensitivity to hydrolysis.
Methyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl)-pyrrolidine-2-carboxylate structure
186268-77-9 structure
Product Name:Methyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl)-pyrrolidine-2-carboxylate
CAS No:186268-77-9
MF:C13H21NO4
MW:255.31014418602
MDL:MFCD02179273
CID:66289
PubChem ID:9837960
Update Time:2025-10-29

Methyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl)-pyrrolidine-2-carboxylate Chemical and Physical Properties

Names and Identifiers

    • Methyl (2S)-1-(1,2-dioxo-3,3-dimethypentyl)-2-pyrrolidinecarboxylate
    • Methyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl)-pyrrolidine-2-carboxylate
    • Methyl (2S)-1-
    • Methyl (2S)-1-(1,2-dioxo-3
    • Methyl(2S)-1- (1,2-dioxo-3,3-dimethylpentyl) -2- pyrrolidinecarboxylate
    • METHYL(2S)-1-(1,2-DIOXO-3,3-DIMETHYPENTYL)-2-PYRROLIDINECARBOXYLATE
    • (S)-Methyl1-(3,3-dimethyl-2-oxopentanoyl)pyrrolidine-2-carboxylate
    • methyl (2S)-1-(1,2-dioxo-3,3-dimethylpentyl)-2-pyrrolidinecarboxylate
    • SCHEMBL2004442
    • 1-(3,3-Dimethyl-1,2-dioxopentyl)-L-proline methyl ester
    • VLNHKSCDLQIJMI-VIFPVBQESA-N
    • AKOS025393352
    • methyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl)pyrrolidine-2-carboxylate
    • EG-0048
    • 186268-77-9
    • (S)-Methyl 1-(3,3-dimethyl-2-oxopentanoyl)pyrrolidine-2-carboxylate
    • methyl (2S)-1-(1,2-dioxo-3,3-dimethylpentyl) -2-pyrrolidinecarboxylate
    • AKOS015991367
    • methyl(2S)-1-(1,2-dioxo-3,3-dimethylpentyl)-2-pyrrolidinecarboxylate
    • A898407
    • DTXSID901206474
    • MFCD02179273
    • methyl (2S)-1-(1,2-dioxo-3,3-dimethylpentyl)-2-pyrrolidine-carboxylate
    • MDL: MFCD02179273
    • Inchi: 1S/C13H21NO4/c1-5-13(2,3)10(15)11(16)14-8-6-7-9(14)12(17)18-4/h9H,5-8H2,1-4H3/t9-/m0/s1
    • InChI Key: VLNHKSCDLQIJMI-VIFPVBQESA-N
    • SMILES: O(C)C([C@@H]1CCCN1C(C(C(C)(C)CC)=O)=O)=O

Computed Properties

  • Exact Mass: 255.14705815g/mol
  • Monoisotopic Mass: 255.14705815g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 18
  • Rotatable Bond Count: 6
  • Complexity: 362
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.8
  • Topological Polar Surface Area: 63.7?2

Experimental Properties

  • Density: 1.118
  • Boiling Point: 338.661°C at 760 mmHg
  • Flash Point: 158.617°C
  • Refractive Index: 1.484
  • PSA: 63.68000
  • LogP: 1.09360

Methyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl)-pyrrolidine-2-carboxylate Pricemore >>

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Additional information on Methyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl)-pyrrolidine-2-carboxylate

Methyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl)-pyrrolidine-2-carboxylate (CAS No. 186268-77-9): A Comprehensive Overview

Methyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl)-pyrrolidine-2-carboxylate, identified by its CAS number 186268-77-9, is a compound of significant interest in the field of pharmaceutical chemistry and biochemistry. This molecule, characterized by its complex structure, has garnered attention due to its potential applications in drug development and synthetic biology. The detailed examination of its chemical properties, synthesis methods, and emerging research applications provides a comprehensive understanding of its significance in modern scientific endeavors.

The molecular structure of Methyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl)-pyrrolidine-2-carboxylate consists of a pyrrolidine core modified with a methyl ester group and a (3,3-dimethyl-2-oxopentanoyl) side chain. This configuration imparts unique stereochemical and electronic properties to the molecule, making it a versatile building block in organic synthesis. The presence of the chiral center at the 2-position of the pyrrolidine ring (2S configuration) is particularly noteworthy, as it influences the molecule's biological activity and interactions with biological targets.

In recent years, there has been a growing interest in the development of chiral auxiliaries and ligands for asymmetric synthesis. Methyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl)-pyrrolidine-2-carboxylate has been explored as a potential candidate in this context. Its rigid pyrrolidine framework provides a stable scaffold for further functionalization, while the ester group offers opportunities for derivatization into more complex molecules. Such properties make it an attractive choice for researchers aiming to develop enantiomerically pure compounds with tailored biological activities.

The synthesis of Methyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl)-pyrrolidine-2-carboxylate involves multi-step organic transformations, including condensation reactions, esterification, and stereoselective modifications. Advanced synthetic techniques such as enzymatic resolution and chiral auxiliary-assisted methods have been employed to achieve high enantiomeric purity. These synthetic strategies not only highlight the compound's synthetic utility but also showcase the advancements in modern organic chemistry methodologies.

One of the most compelling aspects of Methyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl)-pyrrolidine-2-carboxylate is its potential application in medicinal chemistry. The pyrrolidine scaffold is a common motif in biologically active molecules, particularly in drugs targeting neurological disorders and metabolic diseases. Studies have demonstrated that derivatives of this compound exhibit promising pharmacological properties, including inhibitory effects on specific enzymes and receptors. These findings have spurred further research into developing novel therapeutic agents based on this structural motif.

Recent research has also explored the role of Methyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl)-pyrrolidine-2-carboxylate in drug discovery pipelines. Its ability to serve as a precursor for more complex molecules makes it a valuable tool in combinatorial chemistry and high-throughput screening assays. By leveraging its structural features, researchers can design libraries of derivatives with diverse biological activities, accelerating the identification of lead compounds for further development.

The compound's stability under various conditions is another critical factor contributing to its utility in pharmaceutical applications. Methyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl)-pyrrolidine-2-carboxylate exhibits good solubility in common organic solvents and remains stable under ambient conditions, making it suitable for both laboratory-scale synthesis and industrial production processes. These characteristics enhance its feasibility as an intermediate in large-scale drug manufacturing.

In conclusion, Methyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl)-pyrrolidine-2-carboxylate (CAS No. 186268-77-9) represents a significant advancement in pharmaceutical chemistry. Its unique structural features, synthetic versatility, and potential biological applications make it a valuable asset in drug development efforts. As research continues to uncover new uses for this compound, its importance in the field is likely to grow even further.

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