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;

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

MSDS

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COA

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Spec Sheet

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Application

1. [2+3]-dipolar cycloaddition of cyclic enones.

2. Activation of α,β-unsaturated carbonyl compounds:

a) vinylogous α-ketol rearrangement.

b) vinylogous Michael addition of β-substituted α,β-unsaturated cyclohexanones.

3. Michael addition

a) α-nitroacetate to α,β-unsaturated ketones.

b) Diastereodivergent Michael addition to α-substituted, α,β-unsaturated ketones.

4. α-benzoyloxylation of α-branched aldehydes.

5. [4+2]-cycloadditions of β-substituted α,β-unsaturated cyclohexanones with polyconjugated malonitriles.

6. Vinylogous organocascade catalysis with control of remote stereochemistry in the synthesis of spirocyclic oxindoles.