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857270

Sigma-Aldrich

(+)-Cinchonine

85%

Sinónimos:

Cinchonine monohydrochloride dihydrate, NSC 6176

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About This Item

Fórmula empírica (notación de Hill):
C19H22N2O
Número de CAS:
118-10-5
Peso molecular:
294.39
Beilstein/REAXYS Number:
89689
EC Number:
204-234-6
MDL number:
MFCD00064372
UNSPSC Code:
12352104
PubChem Substance ID:
24888435
NACRES:
NA.22

assay

85%

form

solid

optical activity

[α]23/D +228°, c = 0.5 in ethanol

mp

258-260 °C (lit.)

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

Pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302,H317

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1A

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análisis (COA)

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Sigma-Aldrich

22620

Quinine

Cinchonine catalyzed diastereo-and enantioselective Michael addition of a-lithiated phosphonates to nitroalkenes.
Rai V, et al.
Tetrahedron Asymmetry, 18(22), 2719-2726 (2007)
The molecular and crystal structure of the alkaloid cinchonine.
Oleksyn B, et al.
Acta Crystallographica Section B, Structural Science, 35(2), 440-444 (1979)
Song CE.
Cinchona Alkaloids in Synthesis and Catalysis: Ligands, Immobilization and Organocatalysis, 2-3 (2009)
Chensong Pan et al.
Journal of the American Society for Mass Spectrometry, 16(2), 263-270 (2005-02-08)
A method with carbon nanotubes functioning both as the adsorbent of solid-phase extraction (SPE) and the matrix for matrix assisted laser desorption/ionization mass spectrometry (MALDI-MS) to analyze small molecules in solution has been developed. In this method, 10 microL suspensions
Yu-Hua Liao et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(21), 6679-6687 (2012-04-14)
An asymmetric conjugate addition of 3-monosubstituted oxindoles to a range of (E)-1,4-diaryl-2-buten-1,4-diones, catalyzed by commercially available cinchonine, is described. This organocatalytic asymmetric reaction affords a broad range of 3,3'-disubstituted oxindoles that contain a 1,4-dicarbonyl moiety and vicinal quaternary and tertiary
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