C80407
Cinchonidine
96%
Synonym(s):
(−)-Cinchonidine
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About This Item
Empirical Formula (Hill Notation):
C19H22N2O
CAS Number:
Molecular Weight:
294.39
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
EC Number:
207-622-3
Beilstein/REAXYS Number:
89690
MDL number:
Quality Level
assay
96%
form
powder
optical activity
[α]23/D −109.2°, c = 1.5 in ethanol
mp
204-206 °C (lit.)
SMILES string
O[C@@H]([C@@H]1C[C@@H]2CCN1C[C@@H]2C=C)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-KODHJQJWSA-N
Gene Information
human ... CYP2D6(1565)
General description
Cinchonidine is a cinchona alkaloid, which belongs to the orthorhombic crystal system and P212121 space group.
Application
The enantioselective hydrogenation of ethyl pyruvate in the presence of cinchonidine modified platinum/alumina catalyst leads to the enantiomeric excess of ethyl (R)-lactate.
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signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Sens. 1A
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Faceshields, Gloves, type N95 (US)
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The alkaloid cinchonidine.
Oleksyn BJ
Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials, 1832-1834 (1982)
Blaser HU, et al.
Studies in Surface Science and Catalysis, 67, 147-155 (1991)
Arkajyoti Sengupta et al.
The Journal of organic chemistry, 77(23), 10525-10536 (2012-11-17)
Mechanism and the origin of enantioselectivity in the decarboxylative protonation of α-amino malonate hemiester promoted by epicinchona-thiourea hybrid organocatalyst is established by using the DFT(M06-2X/6-311+G**//ONIOM2) computational methods. The origin of stereoselectivity rendered by this hybrid bifunctional catalyst in asymmetric protonation