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    522-66-7

    Catalog No. EBD278571

    CAS 522-66-7

    Name (1R)-((2S,4S,5R)-5-Ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methanol

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    Basic Information

    Synonyms: hydroquinine (1R)-((2S,4S,5R)-5-Ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methanol

    Molecular Formula: C20H26N2O2

    Molecular Weight: 326.43

    MDL Number: MFCD00151107

    Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Drug Synthesis Building Blocks

    Product Description:
    Hydroquinine is a cinchona alkaloid, specifically a dihydro derivative of quinine. It is a stereoisomer of hydroquinidine and shares the core structure of other cinchona alkaloids, featuring a quinoline moiety linked to a quinuclidine ring via a secondary alcohol bridge. Its primary and most significant application is in the field of antimalarial chemotherapy. Hydroquinine itself possesses antimalarial activity and has been used as an active pharmaceutical ingredient (API) for the treatment of malaria, particularly in regions where quinine resistance is a concern. It serves as a key chiral intermediate or precursor in the semi-synthesis of other potent antimalarial drugs and bioactive compounds. Furthermore, due to its inherent chirality and basic nitrogen atoms, it is widely employed as a chiral catalyst or chiral base in asymmetric synthesis, facilitating the creation of enantiomerically enriched molecules. Beyond its medicinal use, hydroquinine finds application as a flavoring agent in beverages and as a reference standard in analytical chemistry. It is a versatile chiral building block in organic synthesis, especially for constructing complex nitrogen-containing heterocycles.
    Physical Properties

    Melting Point: 168-176 °C(lit.)

    Boiling Point: 498.4 °C at 760 mmHg

    Flash Point: 255.2 °C

    Density: 1.2 g/cm3

    mg g kg ml l t