Tandem Hock and Friedel–Crafts reactions allowing an expedient synthesis of a cyclolignan-type scaffold

Viktoria A. Ikonnikova, Cristina Cheibas, Oscar Gayraud, Alexandra E. Bosnidou, Nicolas Casaretto, Gilles Frison and Bastien Nay

Beilstein J. Org. Chem. 2024, 20, 162–169. https://doi.org/10.3762/bjoc.20.15

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Scheme 5

Calculated using the Chemistry Development Kit 2.12

Property Name	Property Value
Molecular Formula	C₂₄H₂₈O₇
Molecular Weight	428.48 g/mol
Exact Mass	428.1835 Da
InChI	InChI=1S/C24H28O7/c1-6-30-22(25)24(23(26)31-7-2)14-17(16-10-8-9-11-18(16)24)21-19(28-4)12-15(27-3)13-20(21)29-5/h8-13,17H,6-7,14H2,1-5H3
InChIKey	BKVZIRQGAWTNAI-UHFFFAOYSA-N
SMILES	CCOC(=O)C1(CC(C2=C1C=CC=C2)C3=C(C=C(C=C3OC)OC)OC)C(=O)OCC
Number of Atoms	59
Number of H-Bond Acceptors	7
Number of H-Bond Donors	0
Atoms in the Largest π-System	9
XLogP	3.5

Operator	Resulting query
aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)