Cas no 56683-56-8 (4'-Methoxycarbonylbenzo-15-crown 5-Ether)

4'-Methoxycarbonylbenzo-15-crown-5-Ether is a functionalized crown ether derivative featuring a benzo-15-crown-5 scaffold with a methoxycarbonyl substituent at the 4' position. This compound exhibits selective binding affinity for alkali and alkaline earth metal ions, making it useful in ion transport, extraction, and sensing applications. The methoxycarbonyl group enhances solubility in organic solvents and provides a reactive handle for further chemical modifications. Its well-defined cavity size (15-crown-5) ensures preferential complexation with smaller cations like Na? or K?. The product is commonly employed in synthetic chemistry, separation science, and as a building block for advanced macrocyclic systems. High purity grades are available for research and industrial use.
4'-Methoxycarbonylbenzo-15-crown 5-Ether structure
56683-56-8 structure
Product Name:4'-Methoxycarbonylbenzo-15-crown 5-Ether
CAS No:56683-56-8
MF:C16H22O7
MW:326.341685771942
MDL:MFCD06797129
CID:945786
PubChem ID:12520240
Update Time:2025-10-30

4'-Methoxycarbonylbenzo-15-crown 5-Ether Chemical and Physical Properties

Names and Identifiers

    • &nbsp
    • 4'-METHOXYCARBONYLBENZO-15-CROWN 5-ETHER (EP)
    • methyl 2,5,8,11,14-pentaoxabicyclo[13.4.0]nonadeca-1(15),16,18-triene-17-carboxylate
    • 4'-Methoxycarbonylbenzo-15-crown 5-Ether
    • Methyl 2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecine-15-carboxylate
    • M1489
    • T72631
    • 2,3-(4-Methoxycarbonylbenzo)-1,4,7,10,13-pentaoxacyclopentadec-2-ene
    • 56683-56-8
    • DTXSID10501174
    • CS-0435423
    • Methyl 2,3,5,6,8,9,11,12-octahydrobenzo[b][1,4,7,10,13]pentaoxacyclopentadecine-15-carboxylate
    • MDL: MFCD06797129
    • Inchi: 1S/C16H22O7/c1-18-16(17)13-2-3-14-15(12-13)23-11-9-21-7-5-19-4-6-20-8-10-22-14/h2-3,12H,4-11H2,1H3
    • InChI Key: PMGUUVHWCHSZKY-UHFFFAOYSA-N
    • SMILES: O1CCOCCOCCOCCOC2C=CC(C(=O)OC)=CC1=2

Computed Properties

  • Exact Mass: 326.13700
  • Monoisotopic Mass: 326.13655304g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 7
  • Heavy Atom Count: 23
  • Rotatable Bond Count: 2
  • Complexity: 336
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: nothing
  • Topological Polar Surface Area: 72.4?2

Experimental Properties

  • Color/Form: Not determined
  • Melting Point: 82 °C
  • PSA: 72.45000
  • LogP: 1.29420
  • Solubility: Not determined

4'-Methoxycarbonylbenzo-15-crown 5-Ether Security Information

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Additional information on 4'-Methoxycarbonylbenzo-15-crown 5-Ether

Introduction to 4'-Methoxycarbonylbenzo-15-crown 5-Ether (CAS No. 56683-56-8)

4'-Methoxycarbonylbenzo-15-crown 5-Ether, identified by the Chemical Abstracts Service Number (CAS No.) 56683-56-8, is a specialized organic compound that has garnered significant attention in the field of coordination chemistry and pharmaceutical research. This compound belongs to the class of crown ethers, which are macrocyclic polyethers characterized by their ability to selectively bind metal ions. The presence of a methoxycarbonyl group at the 4' position of the benzo ring and the incorporation of a 15-crown-5 moiety endows this molecule with unique structural and functional properties, making it a valuable tool in both academic studies and industrial applications.

The structure of 4'-Methoxycarbonylbenzo-15-crown 5-Ether consists of a benzoic acid derivative functionalized with a crown ether segment. The methoxycarbonyl group not only enhances the solubility of the compound in polar solvents but also provides a site for further chemical modifications, enabling its use in synthesizing more complex derivatives. The 15-crown-5 moiety, consisting of a cyclic arrangement of five oxygen atoms, is particularly effective in coordinating with alkali metals such as sodium, potassium, and lithium, which is a critical feature for its applications in catalysis and material science.

Recent research has highlighted the potential of 4'-Methoxycarbonylbenzo-15-crown 5-Ether in the development of novel pharmaceutical agents. Its ability to form stable complexes with metal ions has been explored in the context of drug delivery systems, where metal ion coordination can influence the bioavailability and efficacy of therapeutic compounds. For instance, studies have demonstrated that incorporating this crown ether into drug molecules can enhance their stability and improve their interaction with biological targets, thereby increasing their therapeutic potential.

In addition to its pharmaceutical applications, 4'-Methoxycarbonylbenzo-15-crown 5-Ether has found utility in the field of organic synthesis as a ligand in transition metal-catalyzed reactions. The crown ether segment facilitates the formation of stable metal complexes, which can act as catalysts for various organic transformations. This property has been particularly useful in cross-coupling reactions, where it aids in achieving high yields and selectivity. The methoxycarbonyl group also serves as a handle for further functionalization, allowing chemists to tailor the compound for specific synthetic needs.

One of the most intriguing aspects of 4'-Methoxycarbonylbenzo-15-crown 5-Ether is its role in supramolecular chemistry. The ability of crown ethers to form selective complexes with metal ions has enabled the design of complex molecular architectures through non-covalent interactions. This has opened up new possibilities in materials science, particularly in the development of self-assembling systems and molecular recognition devices. Researchers have leveraged this property to create novel materials with unique properties, such as sensors and molecular machines.

The latest advancements in computational chemistry have further enhanced our understanding of 4'-Methoxycarbonylbenzo-15-crown 5-Ether's behavior. Molecular modeling studies have revealed insights into its binding mechanism with metal ions, providing a basis for rational design of more effective coordination complexes. These computational approaches have also been used to predict the compound's reactivity and stability under various conditions, which is crucial for optimizing its applications.

In summary, 4'-Methoxycarbonylbenzo-15-crown 5-Ether (CAS No. 56683-56-8) is a multifaceted compound with significant potential in pharmaceuticals, catalysis, and materials science. Its unique structural features, including the methoxycarbonyl group and the 15-crown-5 moiety, make it an invaluable tool for researchers seeking to develop innovative solutions in these fields. As our understanding of its properties continues to grow, it is likely that new applications for this compound will emerge, further solidifying its importance in modern chemistry.

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