CAS 960050-59-3 (8α, 9S)-(+)-9-Amino-cinchonan-6'-ol, min. 90%

Synonyms

(8S,9S)-9-Aminocinchonan-6'-ol;MFCD27978392;960050-59-3;(8a,9S)-(+)-9-Amino-cinchonan-6'-ol;

IUPAC Name

4-[(S)-amino-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]methyl]quinolin-6-ol;

Molecular Weight

309.413g/mol

Molecular Formula

C19H23N3O;

Canonical SMILES

C=CC1CN2CCC1CC2C(C3=C4C=C(C=CC4=NC=C3)O)N;

InChI

InChI=1S/C19H23N3O/c1-2-12-11-22-8-6-13(12)9-18(22)19(20)15-5-7-21-17-4-3-14(23)10-16(15)17/h2-5,7,10,12-13,18-19,23H,1,6,8-9,11,20H2/t12-,13-,18-,19-/m0/s1;

InChI Key

BVEMLWTWKOYCIY-OYUDYFSCSA-N;

Complexity

442

Covalently-Bonded Unit Count

Defined Atom Stereocenter Count

Exact Mass

309.184g/mol

H-Bond Acceptor

H-Bond Donor

Heavy Atom Count

Monoisotopic Mass

309.184g/mol

Rotatable Bond Count

Topological Polar Surface Area

62.4A^2

Application

The purpose of (8α, 9S)-(+)-9-Amino-cinchonan-6'-ol, min. 90%, is to facilitate a variety of complex organic reactions and transformations, including [2+3]-dipolar cycloaddition of cyclic enones and the activation of α,β-unsaturated carbonyl compounds, which encompasses processes like vinylogous α-ketol rearrangement and vinylogous Michael addition involving β-substituted α,β-unsaturated cyclohexanones. Additionally, this product supports Michael addition reactions, such as the coupling of α-nitroacetate to α,β-unsaturated ketones, and diastereodivergent Michael additions to α-substituted, α,β-unsaturated ketones. It also plays a vital role in the α-benzoyloxylation of α-branched aldehydes, facilitates [4+2]-cycloadditions involving β-substituted α,β-unsaturated cyclohexanones with polyconjugated malonitriles, and enables vinylogous organocascade catalysis, which is crucial for controlling remote stereochemistry in the synthesis of spirocyclic oxindoles.

March 6, 2025

Effective Catalyst for Enone Reactions

After using (8α, 9S)-(+)-9-Amino-cinchonan-6'-ol from Alfa Chemistry in our research, the product significantly enhanced [2+3]-dipolar cycloadditions of cyclic enones, improving efficiency and outcomes. It's a reliable choice for enone experiments.