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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Calculated using the Chemistry Development Kit 2.12

Property Name	Property Value
Molecular Formula	C₁₆H₂₀O₅
Molecular Weight	292.33 g/mol
Exact Mass	292.1311 Da
InChI	InChI=1S/C16H20O5/c1-3-20-14(18)16(10-11-17,15(19)21-4-2)12-13-8-6-5-7-9-13/h5-9,11H,3-4,10,12H2,1-2H3
InChIKey	YWMRNXWIDCNHKJ-UHFFFAOYSA-N
SMILES	CCOC(=O)C(CC=O)(CC1=CC=CC=C1)C(=O)OCC
Number of Atoms	41
Number of H-Bond Acceptors	5
Number of H-Bond Donors	0
Atoms in the Largest π-System	6
XLogP	3.1

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)