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 3

Calculated using the Chemistry Development Kit 2.12

Property Name	Property Value
Molecular Formula	C₂₅H₃₀O₇
Molecular Weight	442.50 g/mol
Exact Mass	442.1992 Da
InChI	InChI=1S/C25H30O7/c1-6-31-23(26)25(24(27)32-7-2)14-16-10-8-9-11-18(16)19(15-25)22-20(29-4)12-17(28-3)13-21(22)30-5/h8-13,19H,6-7,14-15H2,1-5H3
InChIKey	OUMRTVOPWLRSTF-UHFFFAOYSA-N
SMILES	CCOC(=O)C1(CC2=C(C=CC=C2)C(C1)C3=C(C=C(C=C3OC)OC)OC)C(=O)OCC
Number of Atoms	62
Number of H-Bond Acceptors	7
Number of H-Bond Donors	0
Atoms in the Largest π-System	9
XLogP	3.7

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)