Structure via PubChem · Public domain (PubChem)
hydroquinidine
Sign in to saveDihydroquinidine (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.
Chemical data
- Formula
- C20H26N2O2
- Molecular weight
- 326.4 g/mol
- IUPAC name
- (S)-[(2R,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
- SMILES
- CC[C@H]1CN2CCC1C[C@@H]2[C@H](C3=C4C=C(C=CC4=NC=C3)OC)O
- InChIKey
- LJOQGZACKSYWCH-NBGVHYBESA-N
- XLogP
- 3.1
- Polar surface area
- 45.6 Ų
- H-bond donors
- 1
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 326.199428
Show 4 more facts
- canonical SMILES
- CCC1CN2CCC1CC2C(C3=C4C=C(C=CC4=NC=C3)OC)O
- chemical formula
- C₂₀H₂₆N₂O₂
- isomeric SMILES
- CC[C@H]1CN2CCC1C[C@@H]2[C@H](C3=C4C=C(C=CC4=NC=C3)OC)O
- Commons category
- Dihydroquinidine
Sources (1)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
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.
The substance is also a class Ia antiarrhythmic medication.
Excerpted from Wikipedia’s “hydroquinidine” article, available under the CC BY-SA 4.0 licence.