Chemistry:Dihydroquinine

Dihydroquinine

Names
IUPAC name (R)-[(2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
Other names (8α,9R)-10,11-Dihydro-6'-methoxycinchonan-9-ol
Identifiers
CAS Number	522-66-7 Y
3D model (JSmol)	Interactive image Interactive image
ChemSpider	108426 Y
PubChem CID	121515
UNII	31J3Q51T6L Y
InChI 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 Y Key: LJOQGZACKSYWCH-WZBLMQSHSA-N Y InChI=1/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-WZBLMQSHBC
SMILES O[C@@H](C1N2CCC(C(CC)C2)C1)C3=CC=NC4=CC=C(OC)C=C43 O(c4cc1c(nccc1[C@@H](O)[C@H]2N3CC[C@@H](C2)[C@@H](CC)C3)cc4)C
Properties
Chemical formula	C20H26N2O2
Molar mass	326.440 g·mol−1
Melting point	173–175 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Tracking categories (test):

• SizeSet

Dihydroquinine, also known as hydroquinine or DHQ, is an organic compound and as a cinchona alkaloid closely related to quinine. The specific rotation is −148° in ethanol. A derivative of this molecule is used as chiral ligand in the AD-mix for Sharpless dihydroxylation.

DHQ also inhibits growth of the parasite Toxoplasma gondii by inducing mitochondrial membrane damage, but does not disrupt host mitochondrial membrane potential, as well as reactive oxygen species (ROS) generation.

See also

• Dihydroquinidine