Scopine

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Scopine
Names
IUPAC name
6β,7β-Epoxytropan-3α-ol
Systematic IUPAC name
(1R,2R,4S,5S,7s)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-ol
Other names
6,7-Epoxytropine; Scopanol; Scopin; 6β,7β-Epoxy-1αH,5αH-tropan-3α-ol
Identifiers
3D model (
JSmol
)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C8H13NO2/c1-9-5-2-4(10)3-6(9)8-7(5)11-8/h4-8,10H,2-3H2,1H3/t4-,5-,6+,7-,8+
    Key: FIMXSEMBHGTNKT-RZVDLVGDSA-N
  • O[C@@H]1C[C@H]2N(C)[C@@H](C1)[C@@H]3O[C@H]23
Properties
C8H13NO2
Molar mass 155.197 g·mol−1
Melting point 75 to 76 °C (167 to 169 °F; 348 to 349 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Scopine is a

Senecio mikanioides (Delairea odorata),[3] Scopolia carniolica,[4] and Scopolia lurida.[5]

Scopine can be prepared by the

diisobutylaluminum hydride, and finally a Prilezhaev epoxidation with trifluoroperacetic acid affords scopine.[8]

See also

References

  1. ^
    PMID 6044210
    .
  2. doi:10.1002/hlca.19620450703
    .
  3. doi:10.1021/ja01558a045
    .
  4. ^ Bendik, I.; Bauerova, O.; Bauer, S.; Mokry, J.; Tomko, J. (1958). "Alkaloids from Scopolia carniolica". Chemicke Zvesti. 12: 181–184.
  5. ^ Szymanska, Miroslawa (1967). "Alkaloids in Scopolia lurida. Chromatographic analysis. Isolation of cuscohygrine". Acta Poloniae Pharmaceutica. 24 (1): 59–64.
  6. doi:10.1021/ja01560a042
    .
  7. doi:10.1002/cber.19230560515
    .
  8. doi:10.1021/ja00474a021
    .
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