359343
Hydroquinidine
95%
Synonym(s):
(9S)-10,11-Dihydro-6′-methoxycinchonan-9-ol, Dihydroquinidine
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About This Item
Empirical Formula (Hill Notation):
C20H26N2O2
CAS Number:
Molecular Weight:
326.43
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
EC Number:
215-862-5
Beilstein/REAXYS Number:
91441
MDL number:
Quality Level
assay
95%
optical activity
[α]25/D +226°, c = 2 in ethanol
mp
169-170 °C (lit.)
functional group
hydroxyl
SMILES string
CC[C@H]1CN2CCC1CC2[C@@H](O)c3ccnc4ccc(OC)cc34
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
InChI key
LJOQGZACKSYWCH-LHHVKLHASA-N
Gene Information
human ... CYP2D6(1565)
General description
Hydroquinidine, a cinchona alkaloid, is a structural analog of quinidine. It shows antiarrhythmic effect.
Application
Hydroquinidine can be used as a chiral catalyst to prepare:
- Enantioselective axially chiral phosphamides by N-allylic alkylation reaction between Morita-Baylis-Hillamn (MBH) carbonate and phosphamides.
- Enantioselective α-amino phosphonates by hydrophosphonylation of N-aryl ketimines.
- Enantioselective α-hydrazino esters by α-hydrazination of 3-oxoindolines using azodicarboxylate via aza-Michael reaction.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Asymmetric Synthesis of Axially Chiral Phosphamides via Atroposelective N-Allylic Alkylation
Yang GH et al.
ACS Catalysis, 10, 2324-2333 (2020)
Comparison of serum hydroquinidine determination by fluorescence polarization immunoassay and liquid chromatography.
Tod M, et al.
Journal of Pharmaceutical and Biomedical Analysis, 8(3), 279-282 (1990)
Organocatalytic enantioselective amination of 2-substituted indolin-3-ones: A strategy for the synthesis of chiral $\alpha$-hydrazino esters
Yarlagadda S, et al.
Organic Letters, 19, 170-173 (2017)