857270
(+)-Cinchonine
85%
Synonym(s):
Cinchonine monohydrochloride dihydrate, NSC 6176
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About This Item
Empirical Formula (Hill Notation):
C19H22N2O
CAS Number:
Molecular Weight:
294.39
Beilstein:
89689
EC Number:
MDL number:
UNSPSC Code:
12352104
PubChem Substance ID:
NACRES:
NA.22
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Assay
85%
form
solid
optical activity
[α]23/D +228°, c = 0.5 in ethanol
mp
258-260 °C (lit.)
functional group
hydroxyl
SMILES string
[H][C@@]12CCN(C[C@H]1C=C)[C@]([H])(C2)[C@@H](O)c3ccnc4ccccc34
InChI
1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2/t13-,14-,18+,19-/m0/s1
InChI key
KMPWYEUPVWOPIM-QAMTZSDWSA-N
General description
(+)-Cinchonine, one of the alkaloids found in the barks of cinchona tree, is mainly used in the treatment of malaria. It belongs to the monoclinic crystal system and P21 space group. The solubility of cinchonine can be improved by the formation of inclusion complexes with cyclodextrins.
Application
(+)-Cinchonine, in the presence of lithium diisopropylamide (LDA) forms a complex, which can catalyze the asymmetric conjugate addition of benzyl- and alkylphosphonates to aromatic and heteroaromatic nitroalkenes to form the corresponding adducts.
Other Notes
remainder dihydrocinchonine
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral - Skin Sens. 1A
Storage Class Code
11 - Combustible Solids
WGK
WGK 1
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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The molecular and crystal structure of the alkaloid cinchonine.
Oleksyn B, et al.
Acta Crystallographica Section B, Structural Science, 35(2), 440-444 (1979)
Cinchonine catalyzed diastereo-and enantioselective Michael addition of a-lithiated phosphonates to nitroalkenes.
Rai V, et al.
Tetrahedron Asymmetry, 18(22), 2719-2726 (2007)
Song CE.
Cinchona Alkaloids in Synthesis and Catalysis: Ligands, Immobilization and Organocatalysis, 2-3 (2009)
Jiabing Jiang et al.
Journal of chromatography. A, 1218(24), 3763-3770 (2011-05-11)
We designed and synthesized a cinchonine derivative to be used as a novel chiral monomer. It was employed in a dual role of functional monomer and cross-linking monomer, displaying multi-binding sites for the template (S)-ketoprofen. Monodisperse molecularly imprinted core-shell microspheres
Wei Chen et al.
Organic & biomolecular chemistry, 5(5), 816-821 (2007-02-23)
The C3-selective enantioselective Michael-type Friedel-Crafts alkylations of indoles with nonchelating alpha,beta-unsaturated alkyl ketones, catalysed by a chiral primary amine derived from natural cinchonine, were investigated. The reactions, in the presence of 30 mol% catalyst, were smoothly conducted at 0 to
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