Dihydroquinidine (also called hydroquinidine) is an organic compound, a cinchona alkaloid closely related to quinine. The specific rotation is +226° in ethanol at 2 g/100 ml. A derivative of this molecule is used as chiral ligand in the AD-mix for Sharpless dihydroxylation.

Dihydroquinidine
Names
IUPAC name
(S)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
Other names
(9S)-10,11-Dihydro-6'-methoxycinchonan-9-ol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.578 Edit this at Wikidata
UNII
  • InChI=1S/C20H26N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h4-6,8,11,13-14,19-20,23H,3,7,9-10,12H2,1-2H3/t13-,14-,19+,20-/m0/s1
    Key: LJOQGZACKSYWCH-LHHVKLHASA-N
  • [C@H](O)(C=1C2=C(C=CC(OC)=C2)N=CC1)[C@@]3([N@@]4C[C@H](CC)[C@H](C3)CC4)[H]
Properties
C20H26N2O2
Molar mass 326.440 g·mol−1
Melting point 169 to 172 °C (336 to 342 °F; 442 to 445 K)
Pharmacology
C01BA13 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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The substance is also a class Ia antiarrhythmic medication.[1]

See also

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References

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  1. ^ Drugs.com: International Drug Names for hydroquinidine.