Skytanthine is a monoterpene alkaloid with the following properties. Analysis: C 11 H 21 N. 1 H

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Skytanthine is a monoterpene alkaloid with the following properties. Analysis: C11H21N. 1H NMR: two CH3 doublets (J = 7 Hz) at δ = 1.20 and 1.33 ppm; one CH3 singlet at δ = 2.32 ppm; other hydrogens give rise to broad signals at δ = 1.3 – 2.7 ppm. IR: no bands ≥ 3100 cm-1. Deduce the structures of skytanthine and degradation products A, B, and C from this information.

CI 1. -CO,.H, CH.CI, 1. CHẠI 2. Ag.O, H,O 3. Д 1. 0,, CH,CI, 2. Zn, H.O 2. КОН, Н.О Skytanthine C1H23N → CH,=0 + CH2NO A в IR: i = 1646 cm- IR: = 1715 cm- Careful oxidation CH;COOH + C,H19NO CH3 C IR: i = 3620 cm-! ČH,N(CH3)2


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Organic Chemistry structure and function

ISBN: 978-1429204941

6th edition

Authors: K. Peter C. Vollhardt, Neil E. Schore

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