Cas no 474430-93-8 (2-(aminomethyl)cyclohexane-1-carboxylic acid)

2-(Aminomethyl)cyclohexane-1-carboxylic acid is a cyclohexane derivative featuring both an aminomethyl group and a carboxylic acid functional group, making it a versatile intermediate in organic synthesis and pharmaceutical applications. Its rigid cyclohexane backbone provides structural stability, while the functional groups allow for further derivatization, such as peptide coupling or amide formation. This compound is particularly useful in the design of bioactive molecules, including chiral auxiliaries and constrained peptidomimetics. Its balanced polarity ensures moderate solubility in both aqueous and organic solvents, facilitating diverse reaction conditions. The stereochemistry of the cyclohexane ring can also influence the selectivity of downstream reactions, making it valuable for asymmetric synthesis.
2-(aminomethyl)cyclohexane-1-carboxylic acid structure
474430-93-8 structure
Product Name:2-(aminomethyl)cyclohexane-1-carboxylic acid
CAS No:474430-93-8
MF:C8H15NO2
MW:157.210202455521
MDL:MFCD21318943
CID:2183161
PubChem ID:13039542
Update Time:2025-10-30

2-(aminomethyl)cyclohexane-1-carboxylic acid Chemical and Physical Properties

Names and Identifiers

    • Cyclohexanecarboxylic acid, 2-(aminomethyl)-(9ci)
    • 2-(aminomethyl)cyclohexane-1-carboxylic acid
    • 474430-93-8
    • SCHEMBL2687872
    • DB-275382
    • AKOS015229538
    • EN300-94353
    • 2-(Aminomethyl)cyclohexanecarboxylic acid
    • CYCLOHEXANECARBOXYLIC ACID, 2-(AMINOMETHYL)-
    • MDL: MFCD21318943
    • Inchi: 1S/C8H15NO2/c9-5-6-3-1-2-4-7(6)8(10)11/h6-7H,1-5,9H2,(H,10,11)
    • InChI Key: XOISOAJGMXHXPL-UHFFFAOYSA-N
    • SMILES: OC(C1CCCCC1CN)=O

Computed Properties

  • Exact Mass: 157.110278721Da
  • Monoisotopic Mass: 157.110278721Da
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 2
  • Complexity: 147
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 2
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -1.6
  • Topological Polar Surface Area: 63.3?2

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Additional information on 2-(aminomethyl)cyclohexane-1-carboxylic acid

Professional Introduction to 2-(aminomethyl)cyclohexane-1-carboxylic acid (CAS No. 474430-93-8)

2-(aminomethyl)cyclohexane-1-carboxylic acid, identified by the Chemical Abstracts Service Number (CAS No.) 474430-93-8, is a significant compound in the field of pharmaceutical chemistry and bioorganic synthesis. This molecule, featuring a cyclohexane ring substituted with an amino-methyl group and a carboxylic acid functional group at the 1-position, has garnered attention due to its versatile structural framework and potential applications in drug development and material science.

The structural motif of 2-(aminomethyl)cyclohexane-1-carboxylic acid makes it a valuable intermediate in the synthesis of chiral auxiliaries, ligands for asymmetric catalysis, and pharmacophores for novel therapeutic agents. The presence of both an amine and a carboxylic acid group allows for diverse chemical modifications, including amide bond formation, esterification, and condensation reactions, which are pivotal in constructing complex molecular architectures.

In recent years, there has been growing interest in the development of biologically active molecules derived from cyclohexane derivatives due to their favorable pharmacokinetic properties and reduced toxicity compared to acyclic analogs. The compound’s ability to serve as a precursor for peptidomimetics and protease inhibitors has been explored in several cutting-edge research studies. For instance, modifications of the 2-(aminomethyl)cyclohexane-1-carboxylic acid scaffold have led to the discovery of novel compounds with enhanced binding affinity to target proteins, demonstrating its utility in rational drug design.

One notable application of this compound is in the field of enzyme inhibition. Researchers have leveraged its structural features to design molecules that selectively inhibit key enzymes involved in metabolic pathways relevant to diseases such as diabetes and cancer. The flexibility of the cyclohexane ring provides a scaffold that can be fine-tuned to optimize interactions with enzymatic active sites, while the amine and carboxylic acid groups facilitate hydrogen bonding and ionic interactions, enhancing binding specificity.

The synthesis of 2-(aminomethyl)cyclohexane-1-carboxylic acid has also been optimized through various green chemistry approaches to improve yield and reduce environmental impact. Catalytic methods employing transition metals such as palladium and copper have been particularly effective in constructing the desired carbon-nitrogen bonds with high selectivity. These advancements align with the broader trend toward sustainable chemical manufacturing practices.

Another area where this compound has shown promise is in materials science. The incorporation of 2-(aminomethyl)cyclohexane-1-carboxylic acid into polymer matrices has led to the development of novel biodegradable materials with enhanced mechanical properties. The amine group can participate in cross-linking reactions with other functionalized polymers, creating networks that exhibit tunable degradation rates and biocompatibility. Such materials are being explored for use in drug delivery systems and tissue engineering applications.

The pharmacological potential of derivatives of 2-(aminomethyl)cyclohexane-1-carboxylic acid has also been investigated in preclinical studies. Researchers have synthesized analogs that exhibit inhibitory activity against kinases and other enzymes implicated in signal transduction pathways. The cyclohexane ring’s conformational flexibility allows for optimal alignment with biological targets, while the presence of multiple functional groups provides opportunities for further derivatization to enhance potency and selectivity.

Recent computational studies have further elucidated the structural properties of 2-(aminomethyl)cyclohexane-1-carboxylic acid, employing molecular modeling techniques to predict its behavior in biological systems. These simulations have helped identify key interaction points with potential drug targets, guiding the design of more effective derivatives. The integration of computational chemistry with experimental methodologies has accelerated the discovery process, enabling rapid screening of large libraries of compounds.

The compound’s role as a building block in medicinal chemistry is underscored by its versatility in forming diverse chemical linkages. Whether used as a precursor for peptidomimetics or as a ligand in catalytic systems, 2-(aminomethyl)cyclohexane-1-carboxylic acid continues to be a valuable asset in synthetic chemistry. Its applications span multiple disciplines, from pharmaceuticals to advanced materials, highlighting its broad utility and importance.

As research progresses, new methodologies for synthesizing and functionalizing 2-(aminomethyl)cyclohexane-1-carboxylic acid are expected to emerge, further expanding its applications. Collaborative efforts between academia and industry will be crucial in translating these advancements into tangible benefits for society. The continued exploration of this compound’s potential promises to yield innovative solutions across various scientific domains.

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