359343

Hydroquinidine

95%

• Synonym(s): (9S)-10,11-Dihydro-6′-methoxycinchonan-9-ol, Dihydroquinidine
• Empirical Formula (Hill Notation): C₂₀H₂₆N₂O₂
• CAS Number: 1435-55-8
• Molecular Weight: 326.43
• Beilstein: 91441
• EC Number: 215-862-5
• MDL number: MFCD00135599
• UNSPSC Code: 12352005
• PubChem Substance ID: 24862070
• NACRES: NA.22

Properties

• 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)

Description

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.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H302
• Precautionary Statements: P264 - P270 - P301 + P312 - P501
• Hazard Classifications: Acute Tox. 4 Oral
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves