Scopine

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Scopine
Scopine.svg
Scopine 3D.png
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
PubChem CID
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 tropane alkaloid found in a variety of plants including Mandragora root, [2] Senecio mikanioides (Delairea odorata), [3] Scopolia carniolica , [4] and Scopolia lurida . [5]

Scopine can be prepared by the hydrolysis of scopolamine. [1] [6] [7] It can also be prepared in three steps from N-methoxycarbonylpyrrole and 1,1,3,3-tetrabromoacetone; the reagents are combined in a [4+3] cycloaddition, followed by a diastereoselective reduction with diisobutylaluminum hydride, and finally a Prilezhaev epoxidation with trifluoroperacetic acid affords scopine. [8]

HKRedSynth.png

Alkaloids

References

  1. 1 2 Werner, Gottfried; Schmidt, K.-H. (1967). "Die darstellung von scopin aus scopolamin". Tetrahedron Letters. 8 (14): 1283–1284. doi:10.1016/S0040-4039(00)90685-3. PMID   6044210.
  2. ↑ Staub, H. (1962). "The chemical constituents of the Mandragora root. II. The alkaloids". Helvetica Chimica Acta. 45 (7): 2297–2305. doi:10.1002/hlca.19620450703.
  3. ↑ Adams, Roger; Gianturco, Maurizio (1957). "Senecio alkaloids: mikanoidine, the alkaloid from Senecio mikanoides". Journal of the American Chemical Society. 79: 166–169. 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. ↑ Meinwald, J.; Chapman, O. L. (1957). "Alkaline hydrolysis of scopolamine methoxymethochloride: a new route to scopine". Journal of the American Chemical Society. 79 (3): 665–666. doi:10.1021/ja01560a042.
  7. ↑ Willstatter, Richard; Berner, Endre (1923). "Hydrolysis of scopolamine". Berichte der Deutschen Chemischen Gesellschaft B. 56 (5): 1079–1082. doi:10.1002/cber.19230560515.
  8. ↑ Hayakawa, Y.; Baba, Y.; Makino, S.; Noyori, R. (1978). "Carbon-carbon bond formation promoted by transition metal carbonyls. 19. General synthesis of tropane alkaloids via the polybromo ketone-iron carbonyl reaction". J. Am. Chem. Soc. 100 (6): 1786–1791. doi:10.1021/ja00474a021.
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