Dihydroquinine Base – Fine Chemical

Dihydroquinine Base – DHQ (CAS-No. 522-66-7) is a cinchona alkaloid closely related to quinine. Compared to Quinine Base the double bond is hydrogenated, but the stereochemistry is the same. DHQ is widely used as a chiral ligand / chiral catalyst in asymmetric synthesis. Well-known derivatives of Dihydroquinine like (DHQ)₂PHAL, (DHQ)₂AQN or (DHQ)₂PYR enable highly enantioselective reactions. Please take a look into our free of charge Chiral Catalyst Search Database, containing a wide variety of examples.

Physical properties

Dihydroquinine Base (CAS-No.: 522-66-7) is a white or almost white, crystalline powder which is soluble in methanol. The melting point is 172.5 °C. This compound is not hygroscopic and contains less than1.0 % water. DHQ could be stored at ambient conditions in well-closed, light-resistant containers.

Synonyms

DHQ, Hydroquinine, (8S,9R)-10,11-Dihydro-6`-methoxycinchonan-9-ol, (8α,9R)-10,11-Dihydro-6`-methoxycinchonan-9-ol and (R)-[(2S,4S,5R)-5-Ethyl-1-azabicyclo[2.2.2]oct-2-yl](6-methoxyquinolin-4-yl)methanol.

NMR-data

The following spectroscopic techniques were used to provide structural evidence for Dihydroquinine Base by NMR technology: 1H NMR, 13C NMR, 1H-1H COSY, 1H-13C HSQC, 13C-1H HMBC, 1H-1H NOESY, 15N-1H HMBC.

NMR spectra of the structural elucidation can be viewed here: