15288-87-6

Upstream product

• 10226-29-6 6-Bromo-2-hexanone 
• 98-88-4 benzoyl chloride 
• 35639-05-5 2-methyl-1-phenylcyclohex-2-enol 
• 579-07-7 1-Phenylpropane-1,2-dione 
• 5912-44-7 2-benzoyl-5-acetylthiophene 
• 15177-05-6 1-phenylhept-6-en-1-one 
• 4829-02-1 2-hydroxy-2-phenylcyclohexanone 
• 268750-57-8 4-methyl-5-phenylocta-1,7-diene-4,5-diol 
• 24400-75-7 ethylene-cetal de la bromo-5 pentanone-2 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 147032-71-1 1-phenyl-hept-2-ene-1,6-dione 
• 790220-75-6 (trans)-1-methyl-2-phenylcyclohexane-1,2-diol 
• 109139-15-3 2-tert-Butylperoxy-2-methyl-1-phenyl-cyclohexanol 
• 15288-74-1 1-phenyl-6-heptyn-1-one 

Downstream Products

• 15289-16-4 1-phenyl-5-acetylcyclopentne 
• 15289-15-3 1-acetyl-2-phenylcyclopent-2-ene 
• 15288-90-1 (2-methylcyclopent-1-en-1-yl)(phenyl)methanone 
• 121029-76-3 (2S,7S)-2-phenyl-7-methyloxepane 
• 121029-76-3 (2S,7S)-2-Methyl-7-phenyl-oxepane 
• 790220-75-6 cis-1-methyl-2-phenylcyclohexane-1,2-diol 
• 790220-75-6 (trans)-1-methyl-2-phenylcyclohexane-1,2-diol 
• 790220-75-6 (1R,2R)-1-Methyl-2-phenyl-cyclohexane-1,2-diol 

Relevant academic research and scientific papers

AlCl3-mediated aldol cyclocondensation of 1,6- and 1,7-diones to cyclopentene and cyclohexene derivatives

Exactly 1/3 mol of AlCl3 is sufficient to cyclize 1 mol of 1,?-dibenzoylbutane (or pentane) to a cyclopentenone (or hexenone) derivative in high yield at room temperature in 40 min to several hours. This condensation is driven by removing elements of water as HCl and Al(OH)3, and the product enones are exclusively unconjugated, unlike the base-catalyzed condensations providing thermodynamically more stable conjugated enones.

Unexpected TiIII/Mn-promoted pinacol coupling of ketones

Titanocene(III) chemistry has emerged in the last decades as an indispensable tool in C-C bond-forming reactions. In this context, pinacol and related reactions allow the stereoselective synthesis of vicinal diols. In this work, we present new applications of these reactions using as starting materials aromatic ketones. Simple and smooth reaction conditions have been developed and have been applied for inter- and intramolecular processes. We also describe that although Cp2TiCl is usually used as a monoelectronic reducing agent, it can be also used as an efficient Lewis acid.

Reactivities of mixed organozinc and mixed organocopper reagents, 2. Selective n-alkyl transfer in tri-n-butylphosphine-catalyzed acylation of n-alkyl phenylzincs; an atom economic synthesis of n-alkyl aryl ketones

Tri-n-butylphosphine-catalyzed acylation of mixed n-alkyl phenylzincs with aromatic acyl halides in THF is efficient in selective transfer of n-alkyl groups to produce n-alkyl aryl ketones in good yields. This route provides an atom economic organocatalyzed alternative to transition metal-catalyzed acylation of di-n-alkylzincs.

Electroreductive crossed pinacol coupling of aromatic ketones with aliphatic ketones and aldehydes

The intermolecular crossed pinacol coupling of aromatic ketones with aliphatic aldehydes and ketones was effected by electroreduction in the presence of chlorotrimethylsilane. The best result was obtained using a Pb cathode in Bu4NPF6/sub

Enolate generation under hydrogenation conditions: catalytic aldol cycloreduction of keto-enones.

[reaction: see text] Formal heterolytic activation of elemental hydrogen under Rh catalysis enables the reductive generation of enolates from enones under hydrogenation conditions. Enolates generated in this fashion participate in catalytic C-C bond formation via carbonyl addition to aldehyde and, as demonstrated in this account, ketone partners. Notably, the use of appendant dione partners enables diastereoselective formation of cycloaldol products possessing 3-stereogenic centers, including 2-contiguous quaternary centers.

Intercalation of multiple carbon atoms between the carbonyls of α-diketones

The reaction of open-chain or cyclic α-diketones with specific ω-alkenyl organometallics leads readily under the proper conditions to 1,2-diols bonded to terminal olefinic chains. With 1-phenyl-1,2-propanedione, biacetyl, and cyclohexane-1,2-dione, allylindation in aqueous THF proceeds readily at both adjacent carbonyls. For cyclododecane-1,2-dione, recourse must be made to allylmagnesium bromide for completing the second-stage condensation. Grignard reagents have also served well as reactants for biacetyl monoadducts. In contrast, monoallylated camphorquinone is reluctant to couple to Grignard reagents and reacts only when Barbier-type alkyllithium reactions are applied. The ring closing metatheses of these products have been examined. Where six-membered ring formation operates, cyclization can be performed directly on diols. When larger rings are involved, the diols will react only if structural preorganization capable of facilitating mutual approach of the two double bonds is at play. For this purpose, the prior conversion to a cyclic carbonate holds considerable utility. In the latter setting, saponification must precede the diol cleavage step which has been performed with lead tetraacetate. The latter reagent also exhibits the very beneficial effect of facilitating removal of ruthenium and phosphorus byproducts generated during the metathesis step. This chemistry conveniently lends itself to the controlled intercalation of multiple methylene groups between the carbonyl carbons of readily available α-diketones to deliver linear or cyclic products.

Tandem deployment of indium-, ruthenium-, and lead-promoted reactions. Four-carbon intercalation between the carbonyl groups of open-chain and cyclic α-diketones

(equation presented) An efficient strategy for the conversion of 1,2-diketones into saturated 1,6-diketones and Δ2,3/Δ3,4-unsaturated congeners thereof is reported.

Oxidative Cleavage of vic-Diols Using Copper(II) Bromide-Lithium t-Butoxide: A New Route to Unsymmetrical 1,5- and 1,6-Diketones

Unsymmetrical 1,6-diketones were obtained by the copper(II) bromide-lithium t-butoxide oxidation of 1,2-disubstituted 1,2-cyclohexanediols. The diols were easily prepared by the addition of Grignard reagents to 2-trimethylsiloxy-2-cyelohexenone followed by the hydrolysis and treatment of the resulting 2-hydroxycyclohexanones with the second Grignard reagents. Similarly, 1,5-Diketones were obtained using 2-trimethylsiloxy-2-cyclopentenone as a starting material.

DIRECT FORMATION OF FUNCTIONALIZED KETONES VIA THE COUPLING OF FUNCTIONALIZED ORGANOCOPPER REAGENTS WITH ACID CHLORIDES

Highly reactive copper solutions have been prepared by the lithium naphtalide reduction of copper(I) iodide/triphenyl-phosphine complex.These copper solutions react rapidly with functionalized alkyl halides to give organocopper reagents wich have been effectively trapped with acid chlorides giving functionalized ketones in good yields.Ester, nitrile, chloride, remote epoxide, and, to some degree, ketone groups can be tolerated by this approach.

A Convenient Synthesis of Acyclic 1,n-Diketones (n=5-8) from 2-t-Butylperoxycycloalkanones

The reaction of organolithium with 2-alkyl-2-t-butylperoxycycloalkanones, readily available from t-butylperoxylation of 2-alkylcycloalkanones, gave 2-t-butylperoxy-1-cycloalkanol derivatives quantitatively, thermal decomposition of which with or without an acid afforded 1,n-diketones (n=5-8) in excellent yields.