81369-77-9Relevant academic research and scientific papers
Oxidative dimerization of (E)- and (Z)-2-propenylsesamol with O2 in the presence and absence of laccases and other catalysts: Selective formation of carpanones and benzopyrans under different reaction conditions
Constantin, Mihaela-Anca,Conrad, Juergen,Merisor, Elena,Koschorreck, Katja,Urlacher, Vlada B.,Beifuss, Uwe
, p. 4528 - 4543 (2012)
The oxidative dimerization of 2-propenylsesamol to carpanone with O 2 as the oxidant, which probably proceeds as a domino phenol oxidation/anti-β,β-radical coupling/intramolecular hetero Diels-Alder reaction, can be efficiently catalyzed by laccases. Experiments with laccases and other catalysts like a Co(salen) type catalyst and PdCl2 clearly demonstrate that the diastereoselectivity of the carpanone formation does not depend on the catalyst but on the double-bond geometry of the substrate. With (E)-2-propenylsesamol as the substrate, carpanone and a so far unknown carpanone diastereoisomer are formed in a 9:1 ratio. When (Z)-2-propenylsesamol is used as starting material, carpanone is accompanied by two carpanone diastereoisomers unknown so far in a 5:1:4 ratio. All three carpanone diastereoisomers have been separated by HPLC, and their structures have been elucidated unambiguously by NMR spectroscopy, DFT calculations, and spin work analysis. When the oxidation of 2-propenylsesamol with O2 is performed in the absence of any catalyst two diastereoisomeric benzopyrans are formed, probably as the result of a domino oxidation/intermolecular hetero Diels-Alder reaction. Under these conditions, carpanone is formed in trace amounts only.
ANODIC OXIDATION OF 2-PROPENYLPHENOLS
Iguchi, Masanobu,Nishiyama, Atsuko,Eto, Hideo,Yamamura,Shosuke
, p. 939 - 942 (2007/10/02)
Anodic oxidation of 2-propenylphenols in MeOH was carried out under various conditions, using an undivided cell, to afford several oxidation products including the corresponding asatone-, carpanone-, arylpropanoid-, and austrobailignan-type compounds.Among them, the carpanone-type neolignans can be produced via the corresponding bis-o-quinonemethides.
