Jump to content

Cinchonine

From Wikipedia, the free encyclopedia

This is an old revision of this page, as edited by 69.173.127.110 (talk) at 18:42, 17 January 2020 (Changed SMILES to match IUPAC name -- one stereocenter was inverted). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Cinchonine
Cinchonine
Names
IUPAC name
(S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.850 Edit this at Wikidata
KEGG
UNII
  • 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 checkY
    Key: KMPWYEUPVWOPIM-LSOMNZGLSA-N checkY
  • InChI=1/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
    Key: KMPWYEUPVWOPIM-LSOMNZGLBY
  • O[C@H]([C@H]1C[C@@H]2CC[N@]1C[C@@H]2C=C)c1ccnc2ccccc12
Properties
C19H22N2O
Molar mass 294.39 g/mol
Melting point 260-263
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Cinchonine is an alkaloid found in Cinchona officinalis. It is used in asymmetric synthesis in organic chemistry. It is a stereoisomer and pseudo-enantiomer of cinchonidine.