- Method for synthesizing geranyl acetone through Carroll reaction
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The invention discloses a method for synthesizing geranyl acetone by Carroll reaction, which comprises the following steps: by using linalool as a raw material and aluminum oxide as a catalyst, dropwisely adding methyl acetoacetate under heating conditions, filtering the material after the reaction, and carrying out reduced pressure distillation to obtain the geranyl acetone. According to the method, aluminum oxide is used as the catalyst, the reaction yield is high, the catalyst can be separated through filtration and can be repeatedly used for 5-10 times, waste containing metal ions is not generated, no waste water is generated, environmental pollution is avoided, production is energy-saving and environment-friendly, and the by-products, methanol and carbon dioxide, have recycling value.
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Paragraph 0005; 0012-0016
(2021/01/29)
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- Capturing the Monomeric (L)CuH in NHC-Capped Cyclodextrin: Cavity-Controlled Chemoselective Hydrosilylation of α,β-Unsaturated Ketones
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The encapsulation of copper inside a cyclodextrin capped with an N-heterocyclic carbene (ICyD) allowed both to catch the elusive monomeric (L)CuH and a cavity-controlled chemoselective copper-catalyzed hydrosilylation of α,β-unsaturated ketones. Remarkably, (α-ICyD)CuCl promoted the 1,2-addition exclusively, while (β-ICyD)CuCl produced the fully reduced product. The chemoselectivity is controlled by the size of the cavity and weak interactions between the substrate and internal C?H bonds of the cyclodextrin.
- Bistri-Aslanoff, Olivia,Derat, Etienne,Leloux, Sébastien,Leyssens, Tom,Ménand, Micka?l,Meijide Suárez, Jorge,Riant, Olivier,Roland, Sylvain,Sollogoub, Matthieu,Xu, Guangcan,Zhang, Pinglu,Zhang, Yongmin
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supporting information
p. 7591 - 7597
(2020/03/23)
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- Method of preparing gamma-ketene from alpha, gamma-unsaturated diketene
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The invention provides a method of preparing gamma-ketene from alpha, gamma-unsaturated diketene. According to the method, single hydrogen silane is used as a silicon hydrogen reducing agent, a palladium complex is used as a catalyst, a Lewis acid is used as an auxiliary agent, and alpha, gamma-unsaturated diketene are subjected to silicon hydrogen reduction reactions to obtain gamma-ketene through a one-step method. The method has the advantages of mild conditions, simple operation, high product selectivity and yield, cheap and easily available silicon hydrogen reducing agent, high catalystactivity, little using amount, and low cost, and has potential of industrial scale-up.
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Paragraph 0056-0058
(2020/04/06)
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- A ruthenium complex compound for the selective hydrogenation of the dienone method
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The invention provides a selective hydrogenation of ruthenium complex α, γ - unsaturated dienone method, and in particular relates to a method for using the hydrogen in the catalyst under the action of the α, γ - unsaturated dienone is reduced to the corresponding γ - unsaturated ketone of the method, the catalyst employed for ruthenium complex, a ruthenium precursor and the ligand in-situ prepared. Major advantage of this invention is characterized in that the catalyst is composed of metal precursor and the ligand in-situ prepared, simple operation, high catalyst activity; pyridine, quinoline nitrogen-containing aromatic heterocycle such as the adding of the poisoned medicinal preparation, effectively restraining the product γ - unsaturated ketone transition hydrogenation reaction, an excellent selectivity, the cost is low.
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Paragraph 0050-0052
(2019/07/04)
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- Method for selectively hydrogenating alpha, beta-unsaturated carbonyl compound by cobalt complex
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The invention provides a method for selectively hydrogenating an alpha, beta-unsaturated carbonyl compound. The method for selectively hydrogenating the alpha, beta-unsaturated carbonyl compound comprises the steps that first, a cobalt metal precursor and a carbene ligand are coordinated in a solution to obtain a cobalt complex, and the cobalt complex selectively enables the alpha, beta-unsaturated carbonyl compound to be reduced into a corresponding saturated carbonyl compound in a hydrogen atmosphere under the activation of an activator. The method for selectively hydrogenating the alpha, beta-unsaturated carbonyl compound has the main advantages that cobalt is used as a catalyst, and metal cobalt is cheap and easy to obtain relative to noble metal such as palladium, ruthenium, osmium, iridium and platinum, and the catalyst cost is greatly reduced; secondly, the carbene ligand used in the method has the advantages of simple structure, low price, strong coordination ability with cobalt atoms compared with a commonly used phosphine ligand; and finally, the addition of the activator can further significantly increase the activity of the cobalt catalyst. The hydrogenation reaction condition is mild, the reaction rate is high, substantially no carbonyl hydrogenation side reaction occurs, and the carbonyl compound can be obtained in a high yield.
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Paragraph 0058-0060
(2019/11/20)
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- NOVEL USE OF PHENYL PHOSPHINIC ACID
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The present invention is directed towards a process for the manufacture of gamma, delta-unsaturated ketones of the general formula (III) by reacting a tertiary vinyl carbinol of the general formula (I) with an isopropenyl alkyl ether of the general formula (II) in the presence of a catalyst of the general formula (IV), wherein R1 and R6 are independently from each other methyl or ethyl, R3 is methyl, and R2 is a saturated or unsaturated linear, branched or cyclic hydrocarbyl group with 1 to 46 C atoms. The present invention is also directed towards the reaction mixture as such, i.e. the mixture of the compound of formula (I), the compound of formula (II) and the catalyst of formula (IV).
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- Γ, δ-higher unsaturated ketone and method for purifying process for preparing
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The invention discloses a preparation process of an advanced gamma and delta-unsaturated ketone. The preparation process of the advanced gamma and delta-unsaturated ketone comprises the following steps: adding an unsaturated alcohol and organic aluminum which serves as a catalyst, adding alkyl acetylacetate, carrying out reaction, and distilling by reducing pressure, wherein the unsaturated alcohol and the organic aluminum are added under the pressure of -0.06Mpa to 0.0Mpa, and the organic aluminum is used as the catalyst. The reaction selectivity is more than 99.5%, the conversion rate is more than 98%, and the yield of the product is more than 95% correspondingly. The prepared product is purified by adopting a purification process, thus the purity of the final product is more than 99.5%, the recovery rate of the final product is more than 99%, and the generation rate of wastes is less than 0.5%.
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Paragraph 0047; 0048; 0049; 0050; 0051; 0052; 0053-0057
(2016/11/28)
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- MANUFACTURE OF GAMMA-DELTA-UNSATURATED KETONES
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A process for the manufacture of gamma-delta-unsaturated ketones of formula (R1)(R2)C = CH - CH2 - CH2 - CO - R3 (I), wherein R1 is methyl or ethyl; R2 is a saturated or unsaturated linear or cyclic hydrocarbon residue and R3 is methyl or ethyl, by reacting a tertiary vinyl carbinol of formula (R1)(R2)C(OH) - CH = CH2 (II) with an isopropenyl methyl or ethyl ether of formula H3C-C(OR3) = CH2 (III) in the presence of an ammonium salt as catalyst.
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Page/Page column 4-5
(2010/05/13)
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- Catalytic decarbonylation of epoxyaldehydes: Applications to the preparation of terminal epoxides
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A catalytic decarbonylation reaction for epoxyaldehydes is reported. This reaction may be sequentially used with known asymmetric methods to access optically active mono- and disubstituted terminal epoxides, as illustrated for a key example. Georg Thieme Verlag Stuttgart.
- Morandi, Bill,Carreira, Erick M.
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experimental part
p. 2076 - 2078
(2011/04/15)
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- Enantioselective transfer hydrogenation of aliphatic ketones catalyzed by ruthenium complexes linked to the secondary face of β-cyclodextrin
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Ruthenium-η-arene complexes attached to the secondary face of β-cyclodextrin catalyze the enantioselective reduction (ee up to 98%) of aliphatic and aromatic ketones in aqueous medium in the presence of sodium formate (HCOONa).
- Schlatter, Alain,Woggon, Wolf-D.
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scheme or table
p. 995 - 1000
(2009/05/30)
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- Compounds having protected hydroxy groups
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The present invention relates to compounds with protected hydroxy groups of formula (I) These compounds are precursors for organoleptic agents, such as fragrances, and masking agents and for antimicrobial agents. When activated, the compounds of formula (I) are cleaved and form one or more organoleptic and/or antimicrobial compounds.
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- Compounds having protected hydroxy groups
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The present invention relates to compounds with protected hydroxy groups of formula (I) These compounds are precursors for organoleptic agents, such as fragrances, and masking agents and for antimicrobial agents. When activated, the compounds of formula (I) are cleaved and form one or more organoleptic and/or antimicrobial compounds.
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- Precursors for fragrant ketones and fragrant aldehydes
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The present invention refers to fragrance precursors of formula I for a fragrant ketone of formula II and one or more fragrant aldehydes or ketones of formula III and IV, These fragrance precursors are useful in perfumery, especially in the fine and functional perfumery.
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- Beta-ketoester compounds
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The beta-ketoesters of formula I are useful as precursors for organoleptic compounds, especially for flavors, fragrances and masking agents and antimicrobial compounds.
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- Ketone precursors for organoleptic compounds
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The invention discloses ketones of formula I: wherein, Y is an optionally substituted alkyl, cycloalkyl, or cycloalkylalkyl, wherein each alkyl group is straight or branched and each alkyl and cycloalkyl group is saturated or unsaturated; R1is hydrogen or a C1-6alkyl group that is substituted, saturated or unsaturated, straight or branched; A is a chromophoric substituted aromatic ring or ring system; n is an integer; and with the proviso that formula I is not 2-ethoxy-1-phenyl-ethanone. These compositions are useful for the delivery of organoleptic compounds, especially of flavors, fragrances, masking agents and antimicrobial compounds.
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- -SIGMATROPIC REARRANGEMENTS OF THE ACETOACETATES OF ALLYL ALCOHOLS (CARROLL REACTION) AND ALLYLPHENYL ETHERS (CLAISEN REACTION) ON THE SURFACE OF ADSORBENTS
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A method has been developed for effecting rearrangements of allylacetoacetates to γ,δ-unsaturated ketones (Carroll rearrangement) and allylaryl ethers to the corresponding allylphenols (Claisen rearrangement) under conditions of adsorption on aluminum oxide and silica gel.The method provides a sharp reduction of the temperature of these reactions and improvement of their efficiency.
- Pogrebnoi, S. I.,Kal'yan, Yu. B.,Krimer, M. Z.,Smit, V. A.
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p. 733 - 739
(2007/10/02)
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- Efficient synthesis of pseudoionone by oxidative decarboxylation of allyl β-ketoesters
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The palladium catalyzed oxidative decarboxylation of allyl β-ketoesters is used, in mild conditions, to synthesize efficiently pseudoionone from technical grade myrcene.
- Mercier,Mignani,Aufrand,Allmang
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p. 1433 - 1436
(2007/10/02)
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- A ONE-POT PREPARATION OF α-HALO-CARBONYL AND α-HALO-SULFONYL COMPOUNDS BY HALO-DEACYLATION
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The reaction of β-ketoesters, β-diketones and β-sulfonylketones with N-halosuccinimides in the presence of a base gives α-halo-carbonyl and α-halo-sulfonyl derivatives by a one-pot halo-deacylation reaction.A facile synthesis of pseudo-ionone is described.
- Mignani, G.,Morel, D.,Grass, F.
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p. 5505 - 5508
(2007/10/02)
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- Palladium-Catalyzed Decarboxylation-Allylation of Allylic Esters of α-Substituted β-Keto Carboxylic, Malonic, Cyanoacetic, and Nitroacetic Acids
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Decarboxylation-allylation of allylic β-keto carboxylates using Pd(OAc)2-PPh3 or Pd2(dba)3*CHCl3-dppe as a catalyst proceeds smoothly to give α-allylated ketones.The reaction is highly regioselective.In some cases, diallylated ketones are obtained with allylic esters bearing an active proton(s).Also rhodium, molybdenum, and nickel complexes sre active catalysts in this reaction.Similarly allylic esters of α-substituted malonates, cyanoacetates, and nitroacetate undergo the palladium-catalyzed decarboxylation-allylation to afford allylated acetate, acetonitrile, and nitromethane, respectively.The mechanisms of these palladium-cataly zed decarboxylation-allylations are discussed
- Tsuji, Jiro,,Yamada, Toshiro,Minami, Ichiro,Yuhara, Masami,Nisar, Mohammad,Shimizu, Isao
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p. 2988 - 2995
(2007/10/02)
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- FACILE PALLADIUM CATALYZED DECARBOXYLATIVE ALLYLATION OF ACTIVE METHYLENE COMPOUNDS UNDER NEUTRAL CONDITIONS USING ALLYLIC CARBONATES
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Palladium catalyzed decarboxylative allylation of active methylene compounds proceeded under mild neutral conditions using allylic carbonates, which are much more reactive than allylic acetates or phenoxides used commonly in the reaction.
- Tsuji, Jiro,Shimizu, Isao,Minami, Ichiro,Ohashi, Yukihiro
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p. 4809 - 4812
(2007/10/02)
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- Structure and Biosynthesis of Cleomeprenols from the Leaves of Cleome spinosa
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Cleomeprenols isolated from Cleome spinosa L. (Capparidaceae) have been identified as nonaprenol (1), decaprenol (2), and undecaprenol (3), which are composed of an ω-terminal isoprene, three internal E-isoprene, and the remaining Z-isoprene residues, respectively.Feeding experiments using stereospecifically double-labelled radioactive mevalonate showed that all the cleomeprenols are composed of four biogenetically E- and the remaining biogenetically Z-isoprene residues.Occurence of the succesive cis-condensation of isoprene residues with (2E,6E,10E)-geranylgeranyl pyrophosphate was demonstrated by comparing the incorporation of a homologue of all-E-prenyl pyrophosphates with that of the corresponding 2Z-isomer.
- Suga, Takayuki,Shishibori, Tsuyoshi
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p. 2098 - 2104
(2007/10/02)
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- A FACILE SYNTHESIS OF METHYL (+/-)-10,11-EPOXY-3,7,11-TRIMETHYLDODECA-2,6-DIENOATE, THE INSECT JUVENILE HORMONE III
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A rapid synthesis of the title compound has been described.
- Biernacki, Wladyslaw
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p. 777 - 780
(2007/10/02)
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