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Setoclavine

From Wikipedia, the free encyclopedia
Setoclavine
Names
IUPAC name
6,8β-Dimethyl-9,10-didehydroergolin-8α-ol
Systematic IUPAC name
(6aR,9S)-7,9-Dimethyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinolin-9-ol
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C16H18N2O/c1-16(19)7-12-11-4-3-5-13-15(11)10(8-17-13)6-14(12)18(2)9-16/h3-5,7-8,14,17,19H,6,9H2,1-2H3/t14-,16+/m1/s1
    Key: BGVUWLLRNRBDAY-ZBFHGGJFSA-N
  • O[C@]3(/C=C2/c4cccc1c4c(c[nH]1)C[C@H]2N(C3)C)C
Properties
C16H18N2O
Molar mass254.333 g·mol−1
Appearanceprisms
Melting point229 to 234[1] °C (444 to 453 °F; 502 to 507 K)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Setoclavine is anergot alkaloid.[2]

References

[edit]
  1. ^J. E. Saxton (1960). "The Indole Alkaloids". InThe Alkaloids,Vol. VII, (R. H. F. Manske, Ed.), pp. 4-183, New York: Academic Press.
  2. ^Liras, S; Lynch, CL; Fryer, AM; Vu, BT; Martin, SF (2001). "Applications of vinylogous Mannich reactions. Total syntheses of the Ergot alkaloids rugulovasines a and B and setoclavine".Journal of the American Chemical Society.123 (25):5918–24.doi:10.1021/ja010577w.PMID 11414824.


Ergolines
(incl.lysergines)
Clavines
(6,8-dimethylergolines)
Lysergamides
(lysergic acid amides)
Ergopeptines
(peptide ergolines)
Partial ergolines
Related compounds
Natural sources


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