Research Article: 3-Ethyl-8-meth­oxy-4-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranos­yloxy)quinolin-2(1H)-one

Date Published: June 01, 2010

Publisher: International Union of Crystallography

Author(s): Roman Kimmel, Marek Nečas, Stanislav Kafka, Janez Košmrlj, Robert Vícha.


The structure of the title compound, C26H31NO12, contains an essentially planar quinoline skeleton, with the maximum deviation from the best plane being 0.055 (2) Å, and an oxane ring in a classical chair conformation with the following Cremer and Pople puckering parameters: Q = 0.586 (2) Å, θ = 11.5 (2)° and ϕ = 309.4 (10)°. One acetyl group displays rotational disorder with occupancies of 0.634 (8):0.366 (8). The crystal packing is stabilized by N—H⋯O hydrogen bonds, which link mol­ecules into chains along the a axis. The packing is further stabilized by weak C—H⋯O interactions. The absolute configurations on the carbons in the oxane ring correspond to those of the commercial starting material and are unchanged in the well known mechanism of the Koenigs–Knorr synthesis.

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For the synthesis of related compounds and their biological activity, see Kimmel et al. (2010 ▶); Suzuki et al. (2007 ▶). For puckering parameters, see Cremer & Pople (1975 ▶).




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