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 2

Calculated using the Chemistry Development Kit 2.12

Property Name	Property Value
Molecular Formula	C₁₉H₂₆O₆
Molecular Weight	350.41 g/mol
Exact Mass	350.1729 Da
InChI	InChI=1S/C19H26O6/c1-5-23-17(20)19(18(21)24-6-2,13-16(25-22)14(3)4)12-15-10-8-7-9-11-15/h7-11,16,22H,3,5-6,12-13H2,1-2,4H3
InChIKey	OOAHACCKSMRWGP-UHFFFAOYSA-N
SMILES	CCOC(=O)C(CC1=CC=CC=C1)(CC(C(=C)C)OO)C(=O)OCC
Number of Atoms	51
Number of H-Bond Acceptors	6
Number of H-Bond Donors	1
Atoms in the Largest π-System	6
XLogP	3.4

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)