- Mechanically Interlocked Profragrances for the Controlled Release of Scents
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The synthesis of a series of interlocked profragrances and the study of the controlled release of the corresponding scents are reported. The structures of the profragrances are based on a [2]pseudorotaxane scaffold with a fumaramate thread derived from perfumery alcohols and a tetrabenzylamido ring. The delivery of the scents was accomplished by sequential thermal dethreading and further enzymatic hydrolysis. Alternatively, the dethreading can be achieved by increasing the polarity of the solvent or photochemical isomerization. The temperature of dethreading can be modulated by the steric demand of the ends of the thread, which allows the selection of different precursor structures depending on the desired rates of delivery. The inputs and outputs for the controlled release of the interlocked profragrances correspond to those of YES or AND logic gates.
- Alajarin, Mateo,Berna, Jose,Lopez-Sanchez, Jorge,Pastor, Aurelia
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supporting information
p. 15045 - 15054
(2021/10/20)
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- SELECTIVE HYDROGENATION OF ALDEHYDE WITH RU/BIDENTATE LIGANDS COMPLEXES
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The present invention relates to processes for the reduction by hydrogenation, using molecular H2, of a C5-C20 substrate containing one or two aldehydes functional groups into the corresponding alcohol or diol, characterized in that said process is carried out in the presence of —at least one catalyst or pre-catalyst in the form of a ruthenium complex having a coordination sphere of the N2P2O2, wherein the coordinating atoms N2 are provided by a first bidentate ligand, the coordinating atoms P2 are provided by a second bidentate ligand and the coordinating atoms O2 are provided by two non-linear carboxylate ligands; and —optionally of an acidic additive.
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Paragraph 0211
(2014/09/03)
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- Transition-metal-catalyzed cyclopropanation of nonactivated alkenes in dibromomethane with triisobutylaluminum
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The cyclopropanation of nonactivated alkenes with inexpensive triisobutylaluminum (TIBA), in dibromomethane as solvent and reagent, is efficiently catalyzed by FeCl3 at ambient temperature. Catalytic amounts of CuI salts, CpTiCl3, and [CpFe(CO) 2]2 are similarly effective. 2-Methylpropane, generated after quench of excess TIBA can be trapped, and excess dibromomethane can be recycled, which makes the method industrially applicable. Solvent-free DIBAH or TIBA reduction of unsaturated carbonyl compounds, followed by in situ TIBA cyclopropanation of the unsaturated aluminum alcoholates in dibromomethane give cyclopropyl alkanols. Dienols such as geraniol, linalool or nor-radjanol are selectively cyclopropanated in their distal position, which allows the synthesis of flavor and fragrance compounds such as δ-citral, cis-javanol, and 7-methyl-georgywood. Uncontrollable exothermic events are avoided due to relatively low reaction temperatures made possible by the catalysts and by the addition mode of the reagents.[1]
- Brunner, Gerhard,Elmer, Susanne,Schroeder, Fridtjof
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supporting information; experimental part
p. 4623 - 4633
(2011/10/09)
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- PROCESS FOR PRODUCING α,β-UNSATURATED ALDEHYDE COMPOUNDS
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The present invention relates to processes for producing α,β-unsaturated aldehyde compounds and unsaturated alconhols with a good yield. There is provided a process for producing and α,β-unsaturated aldehyde compound including the step of subjecting a raw aldehyde compound to an intermolecular condensation reaction in the presence of an amine and a protonic acid having 4 to 20 carbon atoms or a salt thereof; and a process for producing an unsaturated alcohol including the step of subjecting the α,β-unsaturated aldehyde compound to a reduction reaction.
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Page/Page column 20-21
(2008/06/13)
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- METHOD FOR PRODUCING ALKYL-SUBSTITUTED BUTENOLS
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Alkyl-substituted butenols having the formula (I): R1-CH2-CH-CR2-CH2OH (I) wherein R1 is a saturated or olefinically unsaturated alkyl or cycloalkyl group having from 4 to 16 carbon atoms and wherein R1 is optionally substituted by an alkyl, cycloalkyl, aryl or alkaryl having up to 12 carbon atoms; R2 is hydrogen or an alkyl group having from 1 to about 6 carbon atoms are produced by a process which comprises: (1) reacting an aldehyde of the formula (II): R1-CH2-CHO (II) wherein R1 has the same meaning as in formula (I), with the corresponding lower aldehyde to form an unsaturated aldehyde in an inert organic solvent; (2) continuously contacting an optionally calcined copper/zinc catalyst with the unsaturated aldehyde under isothermal conditions at temperatures of from about 45 to about 60° C. and under a hydrogen pressure of from 1 to about 300 bar.
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- (E)-(R)-2-alkyl-4-(2,2,3,-Trimethylcyclopent-3-en-1-yl)-2-buten-1-ol, process for preparing the same, and use thereof
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An (E)-(R)-2-alkyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)-2-buten-1-ol represented by formula (I): wherein R represents an alkyl group having 1 to 3 carbon atoms, and a process for preparing the same comprising hydrogenating a corresponding (E)-(R)-2-alkyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)-2-buten-1-al in the presence of a ruthenium-phosphine complex as a catalyst, a base comprising an alkali metal or an alkaline earth metal, and an amine. The compound (I) has an excellent sandalwood oil odor.
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- Process for preparing unsaturated alcohol
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The object of the present invention resides in efficiently providing unsaturated alcohol from an α,β-unsaturated aldehyde. The present invention provides a process for preparing unsaturated alcohol by selectively reducing the aldehyde group of an α,β-unsaturated aldehyde in the presence of a primary or a secondary alcohol having 2 to 8 carbon atoms using an aluminum alcoholate to produce an unsaturated alcohol such as compounds represented by the formula (III). STR1 (wherein R represents an alkyl group having 1 to 3 carbon atoms) wherein the reaction is carried out with addition of a protonic acid.
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- Synthesis and Structure Elucidation of a New Potent Sandalwood-Oil Substitute
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New derivatives of campholenaldehyde ( = 2-(2,2,3-trimethylcyclopent-3-enyl)ethanal) bearing two cyclopropane moieties were synthesized, and the structure of the stereoisomer responsible for its exceptionally strong, diffusive, and natural sandalwood-oil scent, ((1S,2S)-1-methyl-2-{[(1S,3R,5R)-1,2,2-trimethylbicyclo[3.1.0]hex-3- yl]methyl}cyclopropyl)methanol (13a), was elucidated.
- Bajgrowicz, Jerzy A.,Frank, Iris,Fráter, Georg,Hennig, Michael
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p. 1349 - 1358
(2007/10/03)
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