- Synthesis process of natural delta-decalactone
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The invention relates to a synthesis process of natural delta-decalactone, and belongs to the technical field of food additives, and the natural delta-decalactone is obtained by taking furfural and n-amyl alcohol as raw materials through chlorination, Grignard coupling, Piancatelli rearrangement, hydrogenation and oxidation. The purity of the delta-decalactone prepared in the synthesis process of the natural delta-decalactone can reach 98% or above, the natural degree detected by isotope mass spectrometry C14 is 95% or above, and the problems that the synthesis route of the delta-decalactone is complex and the yield is low are solved; and the experimental method is simple, convenient and feasible, the reaction condition is mild, the experimental condition is easy to realize and control, and the method has the characteristics that the raw materials are easy to obtain and rich in source, the yield is relatively high, the used catalyst can be repeatedly used and the like.
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Paragraph 0018; 0024; 0044-0052
(2022/01/10)
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- One-pot synthesis of 2-alkyl cycloketones on bifunctional Pd/ZrO2 catalyst
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2-Alkyl cycloketones are essential chemicals and intermediates for synthetic perfumes and pesticides, which are conventionally produced by multistep process including aldol condensation, separation and hydrogenation. In present work, a batch one-pot cascade approach using aldehydes and cycloketones as the raw materials, and a bifunctional Pd/ZrO2 catalyst was developed for the synthesis of 2-alkyl cycloketones, e.g., cyclohexanone and cycloheptanone. Very high aldehydes (except for paraldehyde with large steric hindrance) conversion and high yields for 2-alkyl cycloketones (e.g., 99 % of conversion for n-butanal and 76 wt.% of yield for 2-butyl cyclohexanone) were obtained at mild temperature of 140 °C. After 10 cycles of reuse, Pd/ZrO2 catalyst showed slight deactivation (ca. 5 % conversion and 10 % yield losses), due to the coke on the catalyst. However, the performance of the catalyst was completely recovered after an oxidative regeneration.
- Xue, Weiyang,Gu, Bin,Wu, Huiling,Liu, Mengyang,He, Songbo,Li, Jingmei,Rong, Xin,Sun, Chenglin
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- Chemo-Enzymatic Oxidative Rearrangement of Tertiary Allylic Alcohols: Synthetic Application and Integration into a Cascade Process
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A chemo-enzymatic catalytic system, comprised of Bobbitt's salt and laccase from Trametes versicolor, allowed the [1,3]-oxidative rearrangement of endocyclic allylic tertiary alcohols into the corresponding enones under an Oxygen atmosphere in aqueous media. The yields were in most cases quantitative, especially for the cyclopent-2-en-1-ol or the cyclohex-2-en-1-ol substrates without an electron withdrawing group (EWG) on the side chain. Transpositions of macrocyclic alkenols or tertiary alcohols bearing an EWG on the side chain were instead carried out in acetonitrile by using an immobilized laccase preparation. Dehydro-Jasmone, dehydro-Hedione, dehydro-Muscone and other fragrance precursors were directly prepared with this procedure, while a synthetic route was developed to easily transform a cyclopentenone derivative into trans-Magnolione and dehydro-Magnolione. The rearrangement of exocyclic allylic alcohols was tested as well, and a dynamic kinetic resolution was observed: α,β-unsaturated ketones with (E)-configuration and a high diastereomeric excess were synthesized. Finally, the 2,2,6,6-tetramethyl-1-piperidinium tetrafluoroborate (TEMPO+BF4?)/laccase catalysed oxidative rearrangement was combined with the ene-reductase/alcohol dehydrogenase cascade process in a one-pot three-step synthesis of cis or trans 3-methylcyclohexan-1-ol, in both cases with a high optical purity. (Figure presented.).
- Brenna, Elisabetta,Crotti, Michele,De Pieri, Matteo,Gatti, Francesco G.,Manenti, Gabriele,Monti, Daniela
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supporting information
p. 3677 - 3686
(2018/06/04)
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- Kinetic Patterns of Condensation of Alkyl- and Cycloalkylcyclopentanones with Dihydric Alcohols in the Presence of Polyoxomolybdate Modified with Oxides of Rare-Earth Elements
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The results of condensation of C5–C7 alkyl- and cycloalkyl-substituted cyclopentanones with diatomic vicinal alcohols in the presence of polyoxomolybdate modified with gadolinium oxide are considered. Kinetic patterns are investigated and a kinetic model of the process is proposed. It was established that alkyl- and cycloalkyl derivatives of dioxaspironone are formed directly by two parallel-consecutive routes and through the stages of the preparation of the corresponding hemiacetal. The ratio of the rate constants of these routes depends on the composition and structure of the starting ketones and diols.
- Alimardanov, Kh. M.,Velieva,Dadashova
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p. 1882 - 1889
(2019/02/24)
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- HYDROSILANE/LEWIS ACID ADDUCT, PARTICULARLY ALUMINUM, IRON, AND ZINC, METHOD FOR PREPARING SAME, AND USE OF SAID SAME IN REACTIONS FOR REDUCING CARBONYL DERIVATIVES
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Disclosed is an adduct between a Lewis acid, preferably aluminum trichloride, iron trichloride, or zinc dichloride, and a hydrosilane;—a method for preparing same; and a method for for reducing, particularly, an aldehyde, a ketone, an α,β-unsaturated ketone, an imine, or an α,β-unsaturated imine.
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Paragraph 0214; 0215; 0216; 0217; 0218
(2018/02/28)
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- Novel cyclopentanol compounds
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The present invention pertains to novel cyclopentanols and their unexpected advantageous use thereof in enhancing, improving or modifying the fragrance of perfumes, colognes, toilet waters, fabric care products, personal products, and the like. One fragrance formulation contains an olfactory acceptable amount of a compound:- wherein R1 represents a C1-C2 hydrocarbon group; and wherein R2 represents a C2-C9 hydrocarbon group.
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- PROCESS FOR PRODUCING 2-ALKYLCYCLOALKANONE
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The present invention relates to a process for producing 2-alkylcycloalkanones with a high yield and a high purity. In addition, the present invention also relates to a process for producing lactones as a useful perfume material for cosmetics, flavors, etc. More specifically, the present invention relates to a process for producing a 2-alkylcycloalkanone represented by the following general formula (2) which includes the step of subjecting a 2-(1-hydroxyalkyl)-cycloalkanone to dehydration and hydrogenation reaction in a flow of a hydrogen gas under a pressure of from 20 to 200 kPa (absolute pressure) in the presence of an acid and a platinum group metal catalyst; and a process for producing a lactone which includes the step of subjecting the 2-alkylcycloalkanone to oxidation reaction using a percarboxylic acid: wherein n is an integer of 1 or 2; and R1 and R2 are each independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms with the proviso that R1 and R2 may form a ring through a carbon atom adjacent thereto.
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Page/Page column 10
(2012/08/28)
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- METHOD FOR PRODUCING OF 2-ALKYL-2-CYCLOALKEN-1-ONE
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The present invention relates to [1] a process for producing a 2-alkyl-2-cycloalken-1-one represented by the following general formula (2), which includes the step of subjecting a 2-(1-hydroxyalkyl)cycloalkan-1-one to dehydration and isomerization in the co-existence of an acid and a platinum group metal catalyst, and [2] a process for producing an alkyl(3-oxo-alkylcycloalkyl)acetate which is useful as a perfume material, using the 2-alkyl-2-cycloalken-1-one: wherein n is an integer of 1 or 2; and R1 and R2 are each independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms with the proviso that R1 and R2 may form a ring through a carbon atom adjacent thereto.
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- PROCESS FOR PRODUCING A 2-ALKYL-2-CYCLOALKENE-1-ONE
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The present invention relates to a process for producing a 2-alkyl-2-cycloalken-1-one represented by the following general formula (2), including the step of reacting a 2-alkylidene cycloalkanone in the presence of a palladium and/or platinum catalyst which is treated in the following steps (a) and (b); and a method for activating the palladium and/or platinum catalyst including the following steps (a) and (b): Step (a): activating the palladium and/or platinum catalyst in an atmosphere containing a hydrogen gas; and Step (b): replacing the hydrogen gas being present as the atmosphere for the catalyst in the step (a), with an inert gas to remove the hydrogen gas out of the reaction system, wherein m is 0 to 3; n is 1 or 2; R1 and R2 are each independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms; and R3 is an alkyl group having 1 to 5 carbon atoms. In accordance with the present invention, the 2-alkyl-2-cycloalken-1-one can be produced with a high purity and a high productivity.
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Page/Page column 8
(2011/01/12)
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- METHOD FOR PRODUCING OF 2-ALKYL-2-CYCLOALKEN-1-ONE
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The present invention relates to [1] a process for producing a 2-alkyl-2-cycloalken-1-one represented by the following general formula (2), which includes the step of subjecting a 2-(1-hydroxyalkyl)cycloalkan-1-one to dehydration and isomerization in the co-existence of an acid and a platinum group metal catalyst, and [2] a process for producing an alkyl(3-oxo-alkylcycloalkyl)acetate which is useful as a perfume material, using the 2-alkyl-2-cycloalken-1-one: wherein n is an integer of 1 or 2; and R1 and R2 are each independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms with the proviso that R1 and R2 may form a ring through a carbon atom adjacent thereto.
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Page/Page column 11-12
(2011/01/12)
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- Asymmetric hydrosilylation of ketones using trans-chelating chiral peralkylbisphosphine ligands bearing primary alkyl substituents on phosphorus atoms
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Asymmetric hydrosilylation of simple ketones with diphenylsilane proceeded at -40 °C in the presence of a rhodium complex (0.001 - 0.01 molar amount) coordinated with a trans-chelating chiral bisphosphine ligand bearing linear alkyl substituents on the phosphorus atoms, (R,R)-(S,S)-Et-, Pr-, or BuTRAP, giving the corresponding optically active (S)- secondary alcohols with up to 97% ee. The asymmetric hydrosilylation using TRAP ligands with bulkier P-substituents resulted in much lower enantioselectivities. The EtTRAP-rhodium catalyst was also effective for asymmetric hydrosilylation of keto esters with a coordination site for a rhodium atom (up to 98% ee). Optically active symmetrical diols were obtained with up to 99% ee from the corresponding diketones via the asymmetric reduction using 2.5 molar amounts of diphenylsilane.
- Kuwano, Ryoichi,Sawamura, Masaya,Shirai, Junya,Takahashi, Masatoshi,Ito, Yoshihiko
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p. 485 - 496
(2007/10/03)
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- Catalytic oxidation of alkyl- and cycloalkylcyclanones into lactones
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Pilot-plant syntheses of alkyl and cycloalkylcyclanones and their subsequent liquid-phase oxidation into lactones are described. Characteristics of resulting intermediates and target products are reported.
- Abbasov,Alimardanov,Suleimanova
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p. 621 - 626
(2007/10/03)
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- Total synthesis of adalinine: confirmaton of its structure
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Adalinine (2), a minor alkaloid of the coccinellid Adalia bipunctata, has been synthesized in racemic form in five steps starting from cyclopentanone.Direct comparison of the synthetic sample with the natuna compound confirms unambiguously the structure we previously proposed solely on the basis of spectral data.
- Broeders, F.,Braekman, J. C.,Daloze, D.
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p. 377 - 382
(2007/10/03)
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- Process for preparing optically active ketones
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A process for preparing an optically active ketone represented by formula (I): STR1 wherein R1 represents a hydrogen atom or an alkyl group having from 1 to 5 carbon atoms; and n represents 1 or 2, which comprises asymmetrically hydrogenating an α, β-unsaturated ketone represented by formula (II): STR2 wherein R1 and n are as defined above, in the presence of a ruthenium-optically active phosphine complex as a catalyst. An optically active ketone having a high optical purity can be prepared.
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- Original syntheses of epoxides involving organoselenium intermediates
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β-oxidoalkylselenonium salts and β-oxidoalkylselenones are valuable precursors of a large variety of epoxides. These species were synthesized by reaction of α-selenonio or α-selenonylalkylpotassium with carbonyl compounds or by reaction of a suitable base on β-hydroxyalkylselenonium salts or β-hydroxyalkylselenones, themselves obtained from β-hydroxyselenides. The most powerful method, based on the cyclization of β-hydroxyalkylselenonium salts is fully documented.
- Krief,Dumont,Van Ende,Halazy,Labar,Laboureur,Le
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p. 1203 - 1228
(2007/10/02)
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- AN EFFICIENT SYNTHETIC METHOD OF METHYL (+/-)-JASMONATE
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An efficient synthetic method of methyl (+/-)-jasmonate is described. 2-Pentynyl-2-cyclopentenone, the key intermediate in this route, was synthesized by applying the palladium-catalyzed enone formation from allyl β-keto carboxylate as a key reaction.
- Kataoka, Hideaki,Yamada, Toshiro,Goto, Kuniaki,Tsuji, Jiro
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p. 4107 - 4112
(2007/10/02)
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- Process for making alkyl cyclopentenones
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A process for making mixed 2- and 3-C1 -C10 alkyl-2-cyclopenten-1-ones from a corresponding alkylcyclopentadiene by epoxidation to the oxiranes, hydrolysis to the diols, dehydration of the diols and rearrangement of the resulting mixed alkylcyclopentenones. The resulting product can be used to make methylcyclopentenolone, a synthetic maple flavor.
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- Syntheses of Jasmonic Acid Related Compounds and Their Structure-Activity Relationships on the Growth of Rice Seedings
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Jasmonic acid (JA)-related compounds were synthesized, and their inhibitory activities on rice seedling growth were investigated.Three functions (C-1 CH2COOH or CH2COOCH3, C-2 (Z)-2'-pentenyl or n-pentyl and C-3 ketone or hydroxyl) were essential for exhibiting inhibitory activity in this series of compounds.A dihydro-JA-related compound, 4-acetylnonanoic acid, also showed inhibitory activity similar to JA.
- Yamane, Hisakazu,Sugawara, Jun,Suzuki, Yasushi,Shimamura, Etsuko,Takahashi, Nobutaka
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p. 2857 - 2864
(2007/10/02)
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