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

Downloads

Scheme 3

Calculated using the Chemistry Development Kit 2.12

Property Name	Property Value
Molecular Formula	[C₂₅H₃₁O₇]⁺
Molecular Weight	443.51 g/mol
Exact Mass	443.2070 Da
InChI	InChI=1S/C25H31O7/c1-6-31-23(26)25(24(27)32-7-2,17-18-11-9-8-10-12-18)14-13-20-21(29-4)15-19(28-3)16-22(20)30-5/h8-13,15-16H,6-7,14,17H2,1-5H3/q+1
InChIKey	BAZXKYDTHFAXMA-UHFFFAOYSA-N
SMILES	CCOC(=O)C(C/C=C/1\C(=CC(=[O+]C)C=C1OC)OC)(CC2=CC=CC=C2)C(=O)OCC
Number of Atoms	63
Number of H-Bond Acceptors	6
Number of H-Bond Donors	0
Atoms in the Largest π-System	10
XLogP	4.6

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)