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 5

Calculated using the Chemistry Development Kit 2.12

Property Name	Property Value
Molecular Formula	C₁₀H₁₃N
Molecular Weight	147.22 g/mol
Exact Mass	147.1048 Da
InChI	InChI=1S/C10H13N/c1-2-6-10(7-3-1)11-8-4-5-9-11/h1-3,6-7H,4-5,8-9H2
InChIKey	VDQQJMHXZCMNMU-UHFFFAOYSA-N
SMILES	C1=CC=C(C=C1)N2CCCC2
Number of Atoms	24
Number of H-Bond Acceptors	1
Number of H-Bond Donors	0
Atoms in the Largest π-System	7
XLogP	2.2

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)