Dihydroquinine

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.

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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.578
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 checkY
    Key: LJOQGZACKSYWCH-WZBLMQSHSA-N checkY
  • 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
  • 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
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).
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Infobox references

See also

References
  1. "Dihydroquinine chemical information". ChemIndustry.com.
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