Cas no 811836-44-9 ((2S)-bicyclo[2.2.2]octane-2-carboxylic acid)

(2S)-Bicyclo[2.2.2]octane-2-carboxylic acid is a chiral bicyclic carboxylic acid characterized by its rigid, three-dimensional structure. The bicyclo[2.2.2]octane scaffold imparts high steric hindrance and conformational stability, making it valuable in asymmetric synthesis and medicinal chemistry. The (2S)-enantiomer offers precise stereochemical control for applications in chiral auxiliaries, ligands, and peptidomimetics. Its constrained geometry enhances binding selectivity in molecular recognition processes. The carboxylic acid functionality allows for further derivatization, enabling integration into complex architectures. This compound is particularly useful in the design of bioactive molecules, where its structural rigidity can improve pharmacokinetic properties. High purity and well-defined stereochemistry ensure reproducibility in research and industrial applications.
(2S)-bicyclo[2.2.2]octane-2-carboxylic acid structure
811836-44-9 structure
Product Name:(2S)-bicyclo[2.2.2]octane-2-carboxylic acid
CAS No:811836-44-9
MF:C9H14O2
MW:154.206263065338
MDL:MFCD30322204
CID:3408957
PubChem ID:6928767
Update Time:2025-05-20

(2S)-bicyclo[2.2.2]octane-2-carboxylic acid Chemical and Physical Properties

Names and Identifiers

    • BICYCLO[2.2.2]OCTANE-2-CARBOXYLIC ACID, (2S)-
    • (1R,2S,4R)-bicyclo[2.2.2]octane-2-carboxylic acid
    • (2S)-bicyclo[2.2.2]octane-2-carboxylic acid
    • (S)-Bicyclo[2.2.2]octane-2-carboxylic acid
    • PNKGHXVHKCJNBW-RRQHEKLDSA-N
    • SCHEMBL5417560
    • MFCD30322204
    • E73589
    • 811836-44-9
    • PS-17544
    • Bicyclo[2.2.2]octane-2-carboxylicacid,(2S)-
    • CS-0434598
    • MDL: MFCD30322204
    • Inchi: 1S/C9H14O2/c10-9(11)8-5-6-1-3-7(8)4-2-6/h6-8H,1-5H2,(H,10,11)/t6?,7?,8-/m0/s1
    • InChI Key: PNKGHXVHKCJNBW-RRQHEKLDSA-N
    • SMILES: OC([C@H]1CC2CCC1CC2)=O

Computed Properties

  • Exact Mass: 154.099379685g/mol
  • Monoisotopic Mass: 154.099379685g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 1
  • Complexity: 168
  • 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: 2.3
  • Topological Polar Surface Area: 37.3?2

(2S)-bicyclo[2.2.2]octane-2-carboxylic acid Pricemore >>

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(2S)-bicyclo[2.2.2]octane-2-carboxylic acid Suppliers

Amadis Chemical Company Limited
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(CAS:811836-44-9)(2S)-bicyclo[2.2.2]octane-2-carboxylic acid
Order Number:A1091207
Stock Status:in Stock
Quantity:1g
Purity:99%
Pricing Information Last Updated:Thursday, 29 August 2024 20:03
Price ($):1650.0

Additional information on (2S)-bicyclo[2.2.2]octane-2-carboxylic acid

Introduction to (2S)-bicyclo[2.2.2]octane-2-carboxylic Acid (CAS No. 811836-44-9)

(2S)-bicyclo[2.2.2]octane-2-carboxylic acid, identified by the Chemical Abstracts Service registry number CAS No. 811836-44-9, is a significant compound in the field of organic chemistry and pharmaceutical research. This bicyclic carboxylic acid derivative has garnered attention due to its unique structural properties and potential applications in drug development and synthetic chemistry.

The molecular structure of (2S)-bicyclo[2.2.2]octane-2-carboxylic acid consists of a bicyclic framework with a carboxylic acid functional group at the 2-position, making it a valuable intermediate in the synthesis of more complex molecules. The stereochemistry at the carbon atom adjacent to the carboxyl group, specifically the (S) configuration, contributes to its distinct chemical behavior and reactivity patterns.

In recent years, there has been growing interest in the applications of such strained cyclic compounds in medicinal chemistry. The rigid bicyclic scaffold of (2S)-bicyclo[2.2.2]octane-2-carboxylic acid provides a stable platform for further functionalization, enabling the design of novel pharmacophores with enhanced binding affinity and selectivity towards biological targets.

One of the most compelling aspects of this compound is its utility as a building block in the synthesis of peptidomimetics and protease inhibitors. The bicyclic core mimics natural amino acid sequences, allowing for the development of drugs that can interact with specific enzymes or receptors more effectively than linear analogs. This has led to several promising studies exploring its potential in treating various diseases, including cancer and inflammatory disorders.

Recent advancements in computational chemistry have further highlighted the importance of (2S)-bicyclo[2.2.2]octane-2-carboxylic acid in drug design. Molecular modeling studies have demonstrated that the compound's rigid structure can be tailored to fit into specific binding pockets of target proteins, improving drug efficacy and reducing off-target effects. These findings have opened new avenues for rational drug design and optimization.

The synthesis of (2S)-bicyclo[2.2.2]octane-2-carboxylic acid presents unique challenges due to its strained cyclic system, but recent methodologies have improved its accessibility. Catalytic hydrogenation and asymmetric synthesis techniques have enabled researchers to produce this compound with high enantioselectivity, which is crucial for pharmaceutical applications where stereochemistry plays a critical role.

In addition to its role in drug development, (2S)-bicyclo[2.2.2]octane-2-carboxylic acid has been investigated for its potential in materials science and polymer chemistry. Its rigid structure and functional groups make it a suitable candidate for designing novel polymers with specific mechanical properties or for use as a chiral catalyst in organic transformations.

The compound's stability under various conditions has also been studied extensively, providing insights into its long-term behavior in different environments. These studies are essential for understanding how it might perform in real-world applications, such as in pharmaceutical formulations or industrial processes.

As research continues to uncover new applications for (2S)-bicyclo[2.2.2]octane-2-carboxylic acid, its significance in both academic and industrial settings is likely to grow. The compound's unique structural features and versatility make it a valuable asset for chemists and pharmacologists working on innovative solutions to complex chemical and biological problems.

The future prospects for this compound are promising, with ongoing studies exploring its role in next-generation therapeutics and advanced materials. By leveraging cutting-edge synthetic methods and computational tools, researchers are poised to unlock even more potential from this remarkable molecule.

Recommended suppliers
Amadis Chemical Company Limited
(CAS:811836-44-9)(2S)-bicyclo[2.2.2]octane-2-carboxylic acid
A1091207
Purity:99%
Quantity:1g
Price ($):1650.0
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