Cinchonine

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This is an old revision of this page, as edited by Mykhal (talk | contribs) at 16:28, 22 May 2020 (let's call the long name systematic, and IUPAC the "natural" one based on cinchonane parent compound from Blue book 2013 (and confirmed by CAS)). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Cinchonine
Cinchonine
Names
IUPAC name
(9S)-cinchonan-9-ol[1][2]
Systematic IUPAC name
(S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](quinolin-4-yl)methanol
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.

References

  1. ^ "Common Chemistry - Substance Details - 118-10-5 : Cinchonan-9-ol, (9S)-". commonchemistry.org. Retrieved 22 May 2020.
  2. ^ IUPAC Chemical Nomenclature and Structure Representation Division (2013). "P-(Appendix 3, p. 1517)". In Favre, Henri A.; Powell, Warren H. (eds.). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. IUPACRSC. ISBN 978-0-85404-182-4.