Synthesis and Spatial Structure of (E)-1-(2-(4-Bromobutoxy)-6-Hydroxy-4-Methoxyphenyl-3-Phenylprop-2-en-1-one

Turdybekov К.M. Zhanymkhanova P.Z. Mukusheva G.K. Gatilov Y.V.
2023 E.A. Buketov Karaganda University Publish house

Eurasian Journal of Chemistry
2023 #110 Issue 2 69 - 75 pp.

(E)-1-(2-(4-bromobutoxy)-6-hydroxy-4-methoxyphenyl-3-phenylprop-2-en-1-one was synthesized from the pinostrobin molecule. The tetrahydropyran cycle was opened in acetone under heating (50–60 °C) mixtures of components for 16 hours in the presence of 3 moles of K₂CO₃ and 1,4-dibromobutane. The resulting substance is a yellow powder of the composition C₂₀H₂₁BrO₄, mp 83.7–86.6 °C. The structure of the obtained compound was established on the basis of the data of elemental analysis, IR and NMR spectra. As a result of X-ray diffraction analysis, it was found that the hydrogen atoms in the C8=C9 bond take the trans-conformation. The rotation of the С1…С6 phenyl ring (flat with an accuracy of ±0.008 Å) relative to the С10…С15 cycle (flat with an accuracy of ±0.004 Å) is 14.3°. In the crystal, the molecules are linked by an intramolecular hydrogen bond O4-H….O1 (distances O-H 0.95(8) Ǻ, O····O 2.469(6) Ǻ, H····O 1.58 (8) Ǻ, angle O-H····O 153(7)°). The formation of (E)-1-(2-(4-bromobutoxy)-6-hydroxy-4-methoxy-1-phenylprop-2-en-1-one can be explained by the ease of the retro-Michael reaction of the pyran ring and the subsequent O-alkylation of the resulting chalcone. Carrying out the reaction in the presence of other bases (cesium car-bonate, triethylamine) did not lead to success. The starting substance (pinostrobin) was completely converted into oligomeric compounds.

(E)-1-(2-(4-bromobutoxy)-6-hydroxy-4-methoxyphenyl-3-phenylprop-2-en-1-one , chalcone , flavone , IR spectroscopy , NMR spectroscopy , phenolic compounds , X-ray analysis

Text of the article Перейти на текст статьи

Karagandy University of the name of academician E.A. Buketov, Universitetskaya str., 28, Karaganda, 100024, Kazakhstan
Karaganda Medical University, Erubaev str., 40, Karaganda, 100000, Kazakhstan
N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Lavrentiev Avenue, 9, Novosibirsk, 630090, Russian Federation

Karagandy University of the name of academician E.A. Buketov
Karaganda Medical University
N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry

10 лет помогаем публиковать статьи Международный издатель

Книга Публикация научной статьи Волощук 2026 Book Publication of a scientific article 2026