127911-15-3Relevant articles and documents
Influence of a non-micelle-forming surfactant on the electrocatalytic hydrogenation of carvone and limonene in aqueous medium at Raney nickel electrodes
Beraud,Lessard,Thomalla
, p. 1529 - 1535 (1997)
The electrocatalytic hydrogenation (ECH) of carvone (1) and limonene (8) at a Raney nickel cathode was studied in aqueous solutions containing a non-micelle-forming surfactant (didodecyldimethylammonium bromide, DDAB). The efficiency of ECH of these substrates was markedly increased compared to that observed previously with micelle-forming surfactants, and this for very low DDAB concentrations, as a consequence of strong adsorption of DDAB on the electrode. For the ECH of 8 in basic medium (pH 10), the major part of organic compounds (60-95%) was shown to be adsorbed on the electrode surface as an organic layer stabilized by an interfacial film of DDAB.
High-Throughput Synthesis of (S)-α-Phellandrene through Three-Step Sequential Continuous-Flow Reactions
Miller, Samuel J.,Ishitani, Haruro,Furiya, Yuichi,Kobayashi, Shū
supporting information, p. 192 - 198 (2021/02/05)
The combination of continuous-flow processing with heterogeneous catalysts allows for efficient, sustainable, multistep synthesis. Here, we report the continuous-flow synthesis of a valuable terpene product, phellandrene, from a readily available natural feedstock. The protocol consists of selective hydrogenation using a highly active and stable supported platinum catalyst, dehydrative hydrazone formation, followed by the Shapiro reaction. Appropriate design of the reactor allowed for high productivity and space-time yield. Phellandrene was synthesized on a 30-g scale over 6 h, giving high yields, purity, and productivity.
Selective carvone hydrogenation to dihydrocarvone over titania supported gold catalyst
Demidova,Suslov,Simakova,Simakova,Volcho,Salakhutdinov,Murzin
, p. 189 - 194 (2015/03/14)
Selective hydrogenation of natural carvone to industrially valuable dihydrocarvone was carried out at 100°C under hydrogen pressure over a 1.9wt.% Au/TiO2 catalyst. The gold catalyst has demonstrated high activity as well as stereo- and chemoselectivity in conjugated C=C double bond hydrogenation with predominant formation of trans-dihydrocarvone. The catalytic activity and trans-to cis-isomers ratio were shown to strongly depend on the solvent. In a range of C1 - C3 alcohol solvents both catalytic activity and trans-to cis-dihydrocarvone ratio increased following the order: 2-propanol a nearly complete carvone conversion (90%) after 13h in the case of methanol, with the trans-to cis-dihydrocarvone ratio being about 1.8. Based on the transition state theory a quantitative description of trans-to cis-dihydrocarvone ratio variations in different solvents was made.
Regioselective mono-deprotection of di-ferf-butylsilylene acetal derived from 1,3-diol with ammonium fluoride
Ohtawa, Masaki,Tomoda, Hiroshi,Nagamitsu, Tohru
supporting information, p. 113 - 118 (2014/02/14)
Here we report a novel and efficient method for the regioselective mono-deprotection of di-terf-butylsilylene acetals derived from 1,3-diols consisting of primary and secondary alcohols. The ammonium fluoride-mediated reactions of pyripyropene A derivative, thymidine and uridine derivatives, methyl β-D-glucofuranoside, and pyranoside derivatives each gave the corresponding primary alcohol with high regioselectivity.
