31366-85-5Relevant articles and documents
SYNTHESIS OF 2-SUBSTITUTED CHROMONES, CHROMANONES, AND THIO ANALOGUES USING ORGANOCOPPER REAGENTS
Clarke, Paul D.,Fitton, Alan O.,Suschitzky, Hans,Wallace, Timothy W.,Dowlatshahi, Hossein A.,Suschitzki, John L.
, p. 91 - 94 (1986)
Improved use of organocopper reagents provides a general route to unsymmetrical 2,2-dialkylchromanones and thiochromanones from chromones and thiochromones via a simple addition - oxidation - addition sequence
Insect Antifeedant Potential of Xanthohumol, Isoxanthohumol, and Their Derivatives
Stompor, Monika,Dancewicz, Katarzyna,Gabrys?, Beata,Anio?, Miros?aw
, p. 6749 - 6756 (2015)
Xanthohumol (14) and isoxanthohumol (6) derived from hop (Humulus lupulus L., Cannabaceae) and selected chalcone and chromene derivatives, obtained by chemical synthesis, were studied for antifeedant activity against the peach-potato aphid (Myzus persicae [Sulz.]). The study used also commercially available 4-chromanone (1), flavanone (4), naringenin (5), chromone (7), flavone (8), 7-aminoflavone (9), trans-chalcone (10), and 4-methoxychalcone (12). For chromone derivatives it was observed that the presence of a phenyl substituent at C-2 in the chromone (7) skeleton increased the insect antifeedant activity, and this activity was observed for a longer time. Also, the introduction of an amino group at C-7 of flavone (8) considerably increased the insect antifeedant activity, which was observed for the whole test time. Among the compounds examined, the strongest deterrents were isoxanthohumol (6), 7-methoxy-2,2-dimethylchroman-4-one (3), 7-aminoflavone (9), and 4-ethyl-4′-methoxychalcone (13).
Regioselectivity of the Claisen rearrangement in meta-allyloxy aryl ketones: An experimental and computational study, and application in the synthesis of (R)-(-)-pestalotheola D
Lucas, Catherine L.,Lygo, Barry,Blake, Alexander J.,Lewis, William,Moody, Christopher J.
supporting information; experimental part, p. 1972 - 1978 (2011/03/21)
A study of the regioselectivity of the Claisen rearrangement of meta-allyloxy aryl ketones showed that the electron-withdrawing carbonyl group has a major influence and strongly directs rearrangement to the more hindered ortho position. However, when the ketone is part of a ring structure, its electronic effect can be negated by conversion into its triisopropylsilyl enol ether, which dramatically reverses the regiochemistry of the Claisen rearrangement. DFT calculations suggest that the effect is electronic although there is also a steric effect of the bulky silyl group. This strategy for influencing the regiochemical outcome of the Claisen rearrangement was then employed in a short synthesis of the furo[2,3-g]chromene, (-)-pestalotheola D, that confirms the absolute stereochemistry of the natural product. A new strategy for influencing the regiochemical outcome of the Claisen rearrangement was developed and employed in a short synthesis of furo[2,3-g]chromene, (-)-pestalotheola D (see scheme), which confirms the absolute stereochemistry of the natural product.