49816-69-5Relevant academic research and scientific papers
Regioselective catalysed H-ene reaction of allylsilanes with 3-butyn-2-one application to a new synthesis of (±)-γ-ionone
Audran, Gerard,Monti, Honore,Leandri, Gilbert,Monti, Jean-Pierre
, p. 3417 - 3418 (1993)
An unexpected ZnI2 catalysed regioselective H-ene reaction between allysilanes and butynone in the presence of molecular sieves 4A is reported. The silyl group dramatically enhanced the rate of the reaction which is used as a key for a new synt
Cyclization of pseudoionone into α-Ionone over heteropolyacid supported on mesoporous silica SBA-15
Rachwalik,Michorczyk,Ogonowski
experimental part, p. 1384 - 1390 (2012/02/02)
Cyclization of pseudoionone into α-ionone was performed over the series heteropolyacid supported on SBA-15 in liquid-phase at 363 and 373 K using a batch reactor. It has been demonstrated that the liquid-phase synthesis of α-ionone by pseudoionone cyclization can be efficiently achieved on heteropolyacid/SBA-15 materials. The high catalytic performance of PW 12/SBA-15 materials is due to their strong Bronsted acidity, high dispersion of active phase and also to absence of steric constraints for pseudoionone cyclization. PW12/SBA-15 catalysts are specially active and selective for this reaction giving predominantly α-ionone, as the main product, with high yield (about 60% at 373 K after 2 h) close to that obtained via the homogeneous synthesis. This catalytic system is more active and efficient in comparison with heteropolyacid supported on commercial silica. In order to achieve comparable amount of α-ionone, as is got for PW 12/SBA-15, belongs to apply five times more of the catalyst based on classical SiO2.
Synthesis of ionones on solid Br?nsted acid catalysts: Effect of acid site strength on ionone isomer selectivity
Díez,Apesteguía,Di Cosimo
experimental part, p. 267 - 274 (2010/11/19)
The effect of Br?nsted acid site strength on the liquid-phase conversion of pseudoionone to ionone isomers (α-, β- and γ-ionone) was studied on resin Amberlyst 35W, silica-supported heteropolyacid (HPAS) and silica-supported triflic acid (TFAS). Catalyst acidity was probed by temperature-programmed desorption of NH3 coupled with infrared spectra of adsorbed pyridine. The initial pseudoionone conversion rate followed the order: TFAS > Amberlyst 35W ≈ HPAS. Synthesis of the three ionone isomers occurred via a common cyclic carbocation intermediate formed from the activation of the pseudoionone molecule on Br?nsted acid sites. Initial ionone mixtures containing a α:β:γ isomer distribution of about 40:20:40 were formed, irrespective of the acid site strength. But the ionone mixture composition changed with the progress of the reaction because γ-ionone was consecutively converted to α-ionone on HPAS and Amberlyst 35W, whereas the stronger acid sites of TFAS converted γ-ionone to β-ionone.
Synthesis and olfactory evaluation of (+)- and (-)-γ-ionone
Fuganti, Claudio,Serra, Stefano,Zenoni, Alessandro
, p. 2761 - 2768 (2007/10/03)
The synthesis of enantiomerically pure (+)- and (-)-γ-ionone 3 is reported. The first step in the synthesis is the diastereoisomeric enrichment of 4-nitrobenzoate derivatives of racemic γ-ionol 12. The enantioselective lipase-mediated kinetic acetylation
CHIMIE DES FRAGRANCES, PARTIE II: SYNTHESE DE LA γ-IONONE ET DES CIS- ET TRANS-γ-IRONES
Leyendecker, Francois,Comte, Marie-Therese
, p. 85 - 92 (2007/10/02)
A new convergent synthesis of γ-ionone and cis- and trans-γ-irones is described.A tandem 1,4-addition functionnalisation reaction and a chemo- and regioselective olefination reaction are the key steps.A two dimensional NMR study allows the determination of the favoured configuration of one intermediate.
Isolation of (2Z,4E)-&γ-Ionylideneethanol from Cercospora cruenta, a Fungus Producing (+)-Abscisic Acid
Oritani, Takayuki,Niitsu, Munetaka,Kato, Taku,Yamashita, Kyohei
, p. 2819 - 2822 (2007/10/02)
(2Z,4E)-γ-Ionylideneethanol was separated from the mycelium of Cercospora cruenta, and its structure was confirmed by comparing the spectral data with those of an authentic specimen synthesized from γ-ionone.Gas chromatographic analysis of the extract showed the presence of a trace amount of (2Z,4E)-γ-ionylideneacetic acid.
Composition of pseudoionone and ionone based on the isomers of citral from the chlorotelomer of isoprene
Siirde, K. E.,Erm, A. Yu.,Vyalimyae, T. K.,Lyiveke, I. A.,Leets, K.V.
, p. 2230 - 2235 (2007/10/02)
It was shown that the synthetic isomers of citral, obtained from the monoadducts of the chlorotelomer of isoprene, only form E-enones during alkaline condensation with acetone.Under the influence of mineral acids the (3E, 5Z)- and (3E, 5E)-6,10-dimethyl-3,5,9-undecatrien-2-ones formed from the Z and E isomers of citral gave a mixture of α-, β-, and γ-ionones, hydroxyionone, and 10-hydroxypseudoionones.The isomeric (3E, 5Z)-(3E, 5E)6,8,8-trimethyl-3,5,9-decatrien-2-ones and (3E, 5E)-5,10-dimethyl-3,5,9-undecatrien-2-one, obtained from the skeletal isomers of citral, do not undergo cyclization under the indicated conditions.The isolated compounds were characterized by (13)C NMR spectroscopy.
