7153-14-2

Usage

InChI:InChI=1/C10H16O/c1-2-3-6-9-7-4-5-8-10(9)11/h6H,2-5,7-8H2,1H3/b9-6-

Upstream product

• 108-94-1 cyclohexanone 
• 123-72-8 butyraldehyde 
• 23029-03-0 1-acetoxy-6-bromo-cyclohexene 
• 3390-13-4 2-propyl-1,3-dioxolane 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 4461-87-4 1,1-dimethoxybutane 
• 34737-52-5 2-Chlor-2-butylcyclohexanon 
• 52190-35-9 2-(methylthio)cyclohexanone 
• 154911-47-4 2-Butyl-2-methylthiocyclohexanone 
• 1126-18-7 2-butylcyclohexanone 

Downstream Products

• 75359-68-1 2-(3-Methyl-1-propyl-but-3-enyl)-cyclohexanone 
• 75359-69-2 2-(1-Propyl-but-3-enyl)-cyclohexanone 
• 75359-75-0 2-(3-Oxo-1-propyl-butyl)-cyclohexanone 
• 85392-03-6 5⁽⁶⁾-decenoic acid 
• 85392-04-7 6-decenoic acid 
• 5579-78-2 ε-decalactone 
• 94803-58-4 3-phenyl-4-propyl-1-oxa-2-aza-spiro[4.5]dec-2-en-6-one oxime 
• 89225-11-6 2-[1-(5-Methyl-furan-2-yl)-butyl]-cyclohexanone 
• 94753-80-7 3-phenyl-4-propyl-1-oxa-2-aza-spiro[4.5]dec-2-en-6-one 
• 1126-18-7 2-butylcyclohexanone 
• 16899-10-8 6-hydroxydecanoic acid 

Relevant academic research and scientific papers

One-pot synthesis of 2-alkyl cycloketones on bifunctional Pd/ZrO2 catalyst

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.

A milk lactone perfume continuous compound into method (by machine translation)

The invention belongs to the technical field of synthetic perfume, and in particular relates to a milk lactone perfume continuous compound into a method, including the role of the alkali under the condition of the aldol reaction, then by hydrogenation reaction, Baeyer - Villiger oxidation, acid continuous hydrolysis, dehydrating and gets milk lactone perfume; the aldol condensation reactions include: part of the as a footing of a cyclohexanone with a alkali mixing, heating processing, the rest [...] butyraldehyde mixture of cyclohexanone with, side drop edge added stirring, and after dropping to continue stirring, thermal insulation reaction-butyraldehyde content to 1% following the end of the reaction; static divider separating the oil, collected and recycled water; collecting oil layer after washing the processing and then transferred to the distillating still distillation recovery excessive cyclohexanone mechanically, the collection of the condensation product of the pan bottom; the invention by adding cyclohexanone in a different way, improving the yield of the aldol condensation reaction; and, of the present invention under the conditions of reaction temperature, can step from an aldol condensation product. (by machine translation)

A ε - decalactone with synthetic perfume production method (by machine translation)

The invention belongs to the technical field of spice production, and in particular relates to relates to a ε - decalactone with synthetic perfume production method, including: (1) preparing an aqueous alkali; (2) the preparation of cyclohexanone and butyraldehyde mixture A; (3) the alkali is added to the reactor, the footing cyclohexanone is added to the mix in the reactor; (4) is added to the mixture in the reactor A drop, side drop edge added stirring, after dropping to continue stirring, thermal insulation to react to the detected in-butyraldehyde content of 1% until the following; (5) the step (4) and the product and sequentially through the hydrogenation, separation and purification, oxidation, obtained after the separation and purification of the ε - decalactone synthetic perfume; the invention to butyraldehyde and cyclohexanone as the starting material to aldol condensation reaction, and then after hydrogenation of peracetic acid oxidation ring enlargement reaction synthesis ε - decalactone perfume, to excessive cyclohexanone as the reaction solvent, recovery after mechanically, reduce the reaction solvent separation and purification, and raw materials are easy, the reaction yield is high. (by machine translation)

Synthetic method of epsilon-decalactone perfume

The invention belongs to the technical field of perfume synthesis, and particularly relates to a synthetic method of epsilon-decalactone perfume. The synthetic method comprises the following steps: (1) mixing an alkaline solution with a part of cyclohexanone, then dropwise adding a mixture of n-butyraldehyde and the rest of cyclohexanone into the mixture, carrying out stirring, and carrying out heat preservation for a reaction; (2) standing the reactants in the step (1), collecting a water layer, collecting an oil layer, and washing the oil layer with water to obtain a condensed product 2-butenyl cyclohexanone crude product; (3) carrying out distilling to recover cyclohexanone to obtain 2-butenyl cyclohexanone; (4) carrying out a hydrogenation reaction; (5) collecting a liquid-phase intermediate product 2-butyl cyclohexanone crude product, and carrying out distilling to obtain 2-butyl cyclohexanone; (6) carrying out an oxidation reaction; and (7) carrying out distilling purification toobtain the epsilon-decalactone perfume product. According to the invention, the cyclohexanone is added into the reaction system in different ways, the excess cyclohexanone is used as a reaction solvent through a stirring dripping technology, and the cyclohexanone is reused after being recycled, so that separation and purification processes of the reaction solvent are reduced, and a high reactionyield is ensured.

Reversal of enantioselectivity in aldol reaction: New data on proline/λ-alumina organic-inorganic hybrid catalysts

We report new results on the aldol reactions between aldehydes of three different types (aromatic, aliphatic and cycloaliphatic) and acetone/cycloalkanones as reaction partners, driven by organic-inorganic hybrid catalyst Pro/λ-Al2O3. In contrast to the homogeneous liquidphase reaction, over Pro/λ-Al2O 3reversal of the enantioselection in up to 20-40 % ee depending on the structure of the aldehyde was observed in reactions of acetone. Reversal of the ee in the presence of c-Al2O3cannot be generalized, as it has only been observed for acetone among the ketones studied by us. It was proven using methods of a great variety such as ultrasonic irradiation, reuse measurements on used catalyst and the filtrate of the first reaction, measurements on the L-Pro-L-Pro(OH) dipeptide, studies using mixtures of L-Pro and D-Pro that the organic-inorganic hybrid catalyst Pro/λ-Al 2O3formed in situ is responsible for reversal of the ee. In the reactions of cycloalkanones there is presumably competition between the liquid-phase and the surface reaction over Pro/ c-Al2O 3with preference for the former. Based on these results a surface reaction pathway was proposed. Although, the ees obtained under heterogeneous catalytic conditions are low, further studies may lead to application of this unusual phenomenon for obtaining chiral heterogeneous catalysts suitable for the preparation of the desired enantiomer of a chiral compound using the same chiral source. Springer Science+Business Media New York 2013.

SYNTHESES DE CYCLOHEXENONES α-SUBSTITUEES VIA LA THERMOLYSE DE CETOSULFOXYDES TERTIAIRES

The sulfenylation-dehydrosulfenylation method, combined with carbon-carbon bond forming reactions, has been applied to the synthesis of some α-functionalized cyclohexenones 3.Hence, the sodium anion of the 2-methylthiocyclohexanone in THF reacts with primary, allyl and benzyl halides as well as with Michael acceptors to lead to the tertiary ketosulfides 1a-j.Further oxidation by NaIO4 and thermolysis in boiling toluene of the resulting sulfoxides 2 have been performed.The scope and limitations of this strategy are also discussed. Key Words: α-functionalized cyclohexenones; tertiary ketosulfides and ketosulfoxides; sulfenylation and deshydrosulfenylation; thermolysis.

SOME ASPECTS OF THE REACTIONS OF SILYL ENOL ETHERS WITH 1,3-DIOXACYCLOALKANES

1,3-Dioxacycloalkanes react with silyl enol ethers like linear acetals. The yield of the unsaturated ketone is influenced by the type and size of the substituent in the second position of the ring. Formals do not undergo the above-mentioned reaction.

CHEMISTRY OF ENOL ETHERS. LXVIII. SILYL ENOL ETHERS IN A MODIFIED ALDOL-CROTONIC CONDENSATION. PRODUCTION OF α,β-UNSATURATED KETONES

By the condensation of the acetals of acetaldehyde, butyraldehyde, isobutyraldehyde, and acetone with the trimethylsilyl ethers of the enolic forms of cyclohexanone, cyclopentanone, and acetone in the presence of zinc chloride as catalyst and subsequent treatment of the reaction products with dilute hydrochloric acid the following α,β-unsaturated ketones were obtained: Ethylidene-, butylidene-, and isobutylidenecyclohexanones, the corresponding cyclopentanones, and methyl propenyl ketone.

α-Alkylation and α-alkylidenation of carbonyl compounds: Lewis acid-promoted phenylthioalkylation of o-silylated enolates

The O-silylated enolates of ketones, aldehydes, esters, and lactones can be phenylthioalkylated in the presence of Lewis acids; reductive or oxidative sulphur-removal gives the regiospecifically α-alkylated or alkylidenated carbonyl compounds.