Dihydroquinine

Dihydroquinine

IUPAC name (8alpha,9R)-10,11-Dihydro-6'-methoxycinchonan-9-ol
Identifiers
CAS number	522-66-7
PubChem	121515
ChemSpider	108426^Y
Jmol-3D images	Image 1 Image 2
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
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
Properties
Molecular formula	C₂₀H₂₆N₂O₂
Molar mass	326.43 g mol⁻¹
Melting point	173-175 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Dihydroquinine, also known as hydroquinine,^[1] 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.

References