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- W2017749824 abstract "0• The structure was solved by direct ietJiods. The cyclohexyl group is pseudo-equatorial nil trans to the axial hydroxyl; the dihydropyran ring ; 1 half-chair distorted towards the d,e-diplanar con )(lllation . Hydrogen bonding between the coumarin arbonyl and the hydroxyl groups at an 0 · · · 0 istance of 2·834 (4) A is found. In CDC13 solution, Jis compound exists predominantly in the open-chain ; t:tofonn. itroduction. Michael-type addition of 4-alkyl- or 4rylbut-3-en-2-ones to 4-hydroxycoumarin produces 3ubstituted 4-hydroxycoumarins that may exist as yclic hemiketals (Ikawa, Stahmann & Link, 1944). ~h isomers are diastereomeric, and the configuration 1 {the. molecule in the crystal will depend on the steric mactions between the substituents on the dihydro lffan (hemiketal) ring. Substituents at the 2 and 4 llSitions have the largest interactions. The 2-hydroxyl r alkoxyl group normally prefers the axial con Imation, related to the anomeric effect. The 4..:udo-axial substituent will therefore have a short ia.ual contact while a 4-pseudo-equatorial substituent 1 1close to the coumarin carbonyl oxygen. Previously, 1 .l) was found to induce distortions in the dihydro IJ!an ring relative to (2) in both 4 placements (Valente, !&atarsiero & Schomaker, 1979). The present contri ltion extends this series to R = cyclohexyl, (3), a sub liluent envisioned to be larger than methyl, and bcribes the conformation of the distorted dihydro riran ring obtained in the crystal, and the structure in tlution revealed by nuclear magnetic resonance." @default.
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- W2017749824 date "1979-12-15" @default.
- W2017749824 modified "2023-09-25" @default.
- W2017749824 title "Structure of 4-cyclohexyl-3,4-dihydro-2-hydroxy-2-methyl-2H,5H-pyrano[3,2-c][1]benzopyran-5-one" @default.
- W2017749824 doi "https://doi.org/10.1107/s0567740879011535" @default.
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