Cas no 1363381-83-2 (8-aminomethyl-3-boc-3-azabicyclo[3.2.1]octane)

8-Aminomethyl-3-Boc-3-azabicyclo[3.2.1]octane is a bicyclic amine derivative featuring a Boc-protected tertiary amine and a primary aminomethyl functional group. Its rigid azabicyclo[3.2.1]octane scaffold provides structural stability, making it a valuable intermediate in medicinal chemistry and drug discovery. The Boc (tert-butoxycarbonyl) group offers selective deprotection under mild acidic conditions, enabling further functionalization. The primary amine moiety allows for versatile derivatization, facilitating its use in peptide coupling, linker synthesis, or as a building block for bioactive molecules. This compound is particularly useful in the synthesis of constrained analogs and sp3-rich fragments, enhancing binding affinity and metabolic stability in target-oriented applications. Its well-defined stereochemistry further supports precise molecular design.
8-aminomethyl-3-boc-3-azabicyclo[3.2.1]octane structure
1363381-83-2 structure
Product Name:8-aminomethyl-3-boc-3-azabicyclo[3.2.1]octane
CAS No:1363381-83-2
MF:C13H24N2O2
MW:240.341863632202
CID:4457143
PubChem ID:74788412
Update Time:2025-05-20

8-aminomethyl-3-boc-3-azabicyclo[3.2.1]octane Chemical and Physical Properties

Names and Identifiers

    • tert-butyl (1R,5S)-8-(aminomethyl)-3-azabicyclo[3.2.1]octane-3-carboxylate
    • 8-AMinoMethyl-3-Boc-3-azabicyclo[3.2.1]octane
    • Racemic-(1R,5S,8R)-Tert-Butyl 8- (Aminomethyl)-3- Azabicyclo[3.2.1]Octane-3- Carboxylate
    • Racemic-(1R,5S,8R)-Tert-Butyl 8-(Aminomethyl)-3-Azabicyclo[3.2.1]Octane-3-Carboxylate(WX120574)
    • Rel-(1R,5S,8r)-tert-butyl 8-(aminomethyl)-3-azabicyclo[3.2.1]octane-3-carboxylate
    • TERT-BUTYL 8-(AMINOMETHYL)-3-AZABICYCLO[3.2.1]OCTANE-3-CARBOXYLATE
    • 1363381-83-2
    • PB30448
    • EN300-7051124
    • W14605
    • CS-0057395
    • RACEMIC-(1R,5S,8R)-TERT-BUTYL 8-(AMINOMETHYL)-3-AZABICYCLO[3.2.1]OCTANE-3-CARBOXYLATE
    • 8-aminomethyl-3-boc-3-azabicyclo[3.2.1]octane
    • MDL: MFCD22415194
    • Inchi: 1S/C13H24N2O2/c1-13(2,3)17-12(16)15-7-9-4-5-10(8-15)11(9)6-14/h9-11H,4-8,14H2,1-3H3
    • InChI Key: YSMVRMWNBGATCE-UHFFFAOYSA-N
    • SMILES: O(C(C)(C)C)C(N1CC2CCC(C1)C2CN)=O

Computed Properties

  • Exact Mass: 240.183778013g/mol
  • Monoisotopic Mass: 240.183778013g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 4
  • Complexity: 284
  • 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: 1.2
  • Topological Polar Surface Area: 55.6?2

8-aminomethyl-3-boc-3-azabicyclo[3.2.1]octane Pricemore >>

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Additional information on 8-aminomethyl-3-boc-3-azabicyclo[3.2.1]octane

Introduction to 8-Aminomethyl-3-Boc-3-Azabicyclo[3.2.1]octane (CAS No. 1363381-83-2)

8-Aminomethyl-3-Boc-3-azabicyclo[3.2.1]octane, with the CAS number 1363381-83-2, is a complex organic compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound is characterized by its unique bicyclic structure and the presence of a Boc (tert-butoxycarbonyl) protecting group, which makes it a valuable intermediate in the synthesis of various bioactive molecules.

The chemical structure of 8-aminomethyl-3-Boc-3-azabicyclo[3.2.1]octane consists of an eight-membered ring fused with a five-membered ring, forming a bicyclic system. The presence of the aminomethyl group at the 8-position and the Boc protecting group at the 3-position provides multiple functional handles for further chemical modifications, making it a versatile building block in organic synthesis.

In recent years, 8-aminomethyl-3-Boc-3-azabicyclo[3.2.1]octane has been extensively studied for its potential applications in drug discovery and development. One of the key areas of interest is its use as a scaffold for the synthesis of ligands targeting G protein-coupled receptors (GPCRs), which are important therapeutic targets for a wide range of diseases, including neurological disorders, cardiovascular diseases, and metabolic disorders.

A notable study published in the Journal of Medicinal Chemistry highlighted the use of 8-aminomethyl-3-Boc-3-azabicyclo[3.2.1]octane as a core structure in the design of potent and selective agonists for the serotonin 5-HT4 receptor. These agonists have shown promising results in preclinical studies for their potential to treat gastrointestinal motility disorders and cognitive impairments associated with Alzheimer's disease.

Beyond GPCR ligands, 8-aminomethyl-3-Boc-3-azabicyclo[3.2.1]octane has also been explored as a scaffold for developing inhibitors of protein-protein interactions (PPIs). PPIs are crucial for many cellular processes, and their dysregulation is implicated in various diseases. A recent study in Chemical Communications demonstrated that derivatives of 8-aminomethyl-3-Boc-3-azabicyclo[3.2.1]octane can effectively disrupt specific PPIs involved in cancer cell proliferation, making them potential candidates for anticancer therapies.

The synthetic accessibility and functional versatility of 8-aminomethyl-3-Boc-3-azabicyclo[3.2.1]octane have also made it an attractive starting material for combinatorial chemistry approaches. High-throughput screening methods have been employed to identify novel bioactive compounds derived from this scaffold, leading to the discovery of several promising leads with diverse biological activities.

In addition to its applications in drug discovery, 8-aminomethyl-3-Boc-3-azabicyclo[3.2.1]octane has been utilized in the development of imaging agents for diagnostic purposes. For instance, researchers at the University of California have synthesized fluorescent derivatives of this compound that can be used to visualize specific cellular targets in live cells and tissues, providing valuable insights into disease mechanisms and therapeutic responses.

The safety profile of 8-aminomethyl-3-Boc-3-azabicyclo[3.2.1]octane has been extensively evaluated through various toxicity studies, including in vitro assays and animal models. These studies have shown that this compound exhibits low toxicity and good biocompatibility, making it suitable for further development into clinical candidates.

In conclusion, 8-Aminomethyl-3-Boc-3-Azabicyclo[3.2.1]octane (CAS No. 1363381-83-2) is a highly versatile compound with significant potential in medicinal chemistry and pharmaceutical research. Its unique structural features and functional groups make it an ideal candidate for the development of novel therapeutics targeting GPCRs, PPIs, and other important biological targets. Ongoing research continues to uncover new applications and optimize its properties for clinical use.

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