Cas no 527751-18-4 ((1S,3R)-3-Amino-2,2-dimethylcyclobutanecarboxylic acid)

(1S,3R)-3-Amino-2,2-dimethylcyclobutanecarboxylic acid is a chiral cyclobutane derivative featuring a rigid, constrained ring structure with stereochemically defined amino and carboxylic acid functional groups. Its unique geometry enhances conformational stability, making it valuable in medicinal chemistry for designing peptidomimetics and bioactive compounds. The steric hindrance from the dimethyl groups influences its reactivity and binding properties, while the amino and carboxyl groups provide versatile sites for further functionalization. This compound is particularly useful in asymmetric synthesis and as a building block for pharmaceuticals, where its structural rigidity can improve target selectivity and metabolic stability. High purity and well-defined stereochemistry ensure reproducibility in research and development applications.
(1S,3R)-3-Amino-2,2-dimethylcyclobutanecarboxylic acid structure
527751-18-4 structure
Product Name:(1S,3R)-3-Amino-2,2-dimethylcyclobutanecarboxylic acid
CAS No:527751-18-4
MF:C7H13NO2
MW:143.183622121811
CID:937451
PubChem ID:11344081
Update Time:2025-08-05

(1S,3R)-3-Amino-2,2-dimethylcyclobutanecarboxylic acid Chemical and Physical Properties

Names and Identifiers

    • (1S,3R)-3-Amino-2,2-dimethylcyclobutanecarboxylic acid
    • Cyclobutanecarboxylic acid, 3-amino-2,2-dimethyl-, (1S,3R)- (9CI)
    • (1S,3R)-3-AMINO-2,2-DIMETHYLCYCLOBUTANE-1-CARBOXYLIC ACID
    • 527751-18-4
    • SCHEMBL15362631
    • EN300-99503
    • 92772-95-7
    • (1S,3R)-3-Amino-2,2-dimethyl-cyclobutanecarboxylic acid
    • HEVNTZPOSTVEDU-RFZPGFLSSA-N
    • AKOS022186446
    • (1S,3R)-3-amino-2,2-dimethylcyclobutanecarboxylicacid
    • (1R,3S)-3-Amino-2,2-dimethylcyclobutanecarboxylic acid
    • Inchi: 1S/C7H13NO2/c1-7(2)4(6(9)10)3-5(7)8/h4-5H,3,8H2,1-2H3,(H,9,10)/t4-,5-/m1/s1
    • InChI Key: HEVNTZPOSTVEDU-RFZPGFLSSA-N
    • SMILES: OC([C@H]1C[C@H](C1(C)C)N)=O

Computed Properties

  • Exact Mass: 143.094628657g/mol
  • Monoisotopic Mass: 143.094628657g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 1
  • Complexity: 165
  • 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: -2.1
  • Topological Polar Surface Area: 63.3?2

(1S,3R)-3-Amino-2,2-dimethylcyclobutanecarboxylic acid Pricemore >>

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Additional information on (1S,3R)-3-Amino-2,2-dimethylcyclobutanecarboxylic acid

Exploring the Unique Properties and Applications of (1S,3R)-3-Amino-2,2-dimethylcyclobutanecarboxylic acid (CAS No. 527751-18-4)

(1S,3R)-3-Amino-2,2-dimethylcyclobutanecarboxylic acid (CAS No. 527751-18-4) is a specialized cyclobutane derivative that has garnered significant attention in pharmaceutical and biochemical research. This compound, characterized by its unique cyclobutane ring structure and amino-carboxylic acid functionality, serves as a valuable building block in drug discovery and peptide synthesis. Its stereochemistry, defined by the (1S,3R) configuration, plays a critical role in its biological activity and interactions with target molecules.

Researchers are increasingly interested in cyclobutane-based compounds due to their potential in designing novel therapeutics. The 2,2-dimethyl substitution on the cyclobutane ring enhances the compound's stability, making it a promising candidate for developing enzyme inhibitors and receptor modulators. Recent studies have explored its utility in addressing neurodegenerative diseases and metabolic disorders, aligning with current trends in precision medicine.

One of the most searched questions about (1S,3R)-3-Amino-2,2-dimethylcyclobutanecarboxylic acid revolves around its synthesis and purification methods. The compound is typically synthesized via asymmetric catalysis or chiral resolution techniques, ensuring high enantiomeric purity. Its carboxylic acid group allows for further derivatization, enabling the creation of peptide mimetics and small-molecule probes for biological studies.

In the context of green chemistry, this compound has also been evaluated for its potential in sustainable synthesis routes. The demand for eco-friendly pharmaceutical intermediates has driven innovations in its production, minimizing waste and energy consumption. This aligns with the growing focus on Environmental, Social, and Governance (ESG) principles in the chemical industry.

Another hot topic is the compound's role in structure-activity relationship (SAR) studies. Its rigid cyclobutane scaffold provides insights into how conformational constraints affect ligand-receptor binding, a key consideration in drug design. Researchers frequently search for bioisosteres and scaffold hopping strategies involving this molecule to optimize pharmacokinetic properties.

From an analytical perspective, 527751-18-4 is often characterized using NMR spectroscopy, mass spectrometry, and HPLC chiral separation. These techniques ensure the compound meets the stringent purity standards required for preclinical research and API development. The availability of high-quality reference standards for this compound has facilitated its adoption in high-throughput screening platforms.

As the pharmaceutical industry shifts toward targeted therapies, the demand for structurally diverse intermediates like (1S,3R)-3-Amino-2,2-dimethylcyclobutanecarboxylic acid continues to rise. Its compatibility with solid-phase peptide synthesis (SPPS) and click chemistry further expands its applications in bioconjugation and drug delivery systems.

In summary, CAS No. 527751-18-4 represents a versatile tool for medicinal chemists, combining structural novelty with functional adaptability. Its relevance in fragment-based drug discovery, peptidomimetics, and chemical biology ensures its continued prominence in cutting-edge research. Future directions may explore its utility in PROTACs (Proteolysis Targeting Chimeras) and other emerging therapeutic modalities.

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