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	[C₁₉H₂₅O₅]⁺
Molecular Weight	333.40 g/mol
Exact Mass	333.1702 Da
InChI	InChI=1S/C19H25O5/c1-5-22-17(20)19(18(21)23-6-2,12-13-24-15(3)4)14-16-10-8-7-9-11-16/h7-11,13H,3,5-6,12,14H2,1-2,4H3/q+1
InChIKey	JCXXDJFBBWJGMT-UHFFFAOYSA-N
SMILES	CCOC(=O)C(C[CH+]OC(=C)C)(CC1=CC=CC=C1)C(=O)OCC
Number of Atoms	49
Number of H-Bond Acceptors	5
Number of H-Bond Donors	0
Atoms in the Largest π-System	6
XLogP	4.5

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)