TY - JOUR
T1 - Heterogeneous catalysis for transformation of biomass derived compounds beyond fuels: synthesis of monoterpenoid dioxinols with analgesic activity
AU - Torozova, Alexandra
AU - Mäki-Arvela, Päivi
AU - Aho, Atte
AU - Kumar, Narendra
AU - Smeds, Annika
AU - Peurla, Markus
AU - Sjöholm, Rainer
AU - Heinmaa, Ivo
AU - Korchagina, Dina V.
AU - Volcho, Konstantin P.
AU - Salakhutdinov, Nariman F.
AU - Murzin, Dmitry
N1 - tk.
3pk
iok
PY - 2015
Y1 - 2015
N2 - Catalytic synthesis of a dioxinol compound, (2S,4aR,8R,8aR)-4,4,7-trimethyl-2-phenyl-4a,5,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-8-ol, exhibiting analgesic activity was demonstrated over Femodified beta zeolite. During interactions between cis-verbenol oxide and benzaldehyde, two main reactions occurred. In the first reaction, namely isomerization of verbenol oxide both cyclopentenic hydroxyketone, oxetane as well as a cyclohexyl compound, (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol were formed. In the second parallel reaction the target compound was generated. The highest yield of the target compound was achieved in the reaction between verbenol oxide and benzaldehyde at their molar ratio of 1:133 with the bifunctional iron modified Fe-H-Beta-150 catalyst at 70 degrees C giving a much higher yield than reported earlier in the literature, being 46 mol-% at complete conversion of verbenol oxide.
AB - Catalytic synthesis of a dioxinol compound, (2S,4aR,8R,8aR)-4,4,7-trimethyl-2-phenyl-4a,5,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-8-ol, exhibiting analgesic activity was demonstrated over Femodified beta zeolite. During interactions between cis-verbenol oxide and benzaldehyde, two main reactions occurred. In the first reaction, namely isomerization of verbenol oxide both cyclopentenic hydroxyketone, oxetane as well as a cyclohexyl compound, (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol were formed. In the second parallel reaction the target compound was generated. The highest yield of the target compound was achieved in the reaction between verbenol oxide and benzaldehyde at their molar ratio of 1:133 with the bifunctional iron modified Fe-H-Beta-150 catalyst at 70 degrees C giving a much higher yield than reported earlier in the literature, being 46 mol-% at complete conversion of verbenol oxide.
KW - Addition
KW - Dioxinol
KW - Terpenoid
KW - Zeolite
KW - Addition
KW - Dioxinol
KW - Terpenoid
KW - Zeolite
KW - Addition
KW - Dioxinol
KW - Terpenoid
KW - Zeolite
U2 - 10.1016/j.molcata.2014.10.023
DO - 10.1016/j.molcata.2014.10.023
M3 - Artikel
SN - 1381-1169
VL - 397
SP - 48
EP - 55
JO - Journal of Molecular Catalysis A: Chemical
JF - Journal of Molecular Catalysis A: Chemical
ER -