6683-94-9

Usage

Compound type

Ketone

Organic compound class

Phenyl alkyl ketones

Usage

Production of fragrances and flavors, pharmaceutical industry

Odor

Strong, sweet, and floral

Applications

Perfumes, colognes, flavoring agent in food products, reagent in organic synthesis

Upstream product

• 131973-46-1 benzyltetrabutyl stiborane 
• 142-61-0 Hexanoyl chloride 
• 109-67-1 1-penten 
• 64-04-0 phenethylamine 
• 66-25-1 hexanal 
• 108-88-3 toluene 
• 1078-71-3 heptylbenzene 
• 110-43-0 n-pentyl methyl ketone 
• 16156-59-5 phenyl methanesulfonate 
• 64214-56-8 N-methoxy-N-methylhexanoamide 
• 6921-34-2 benzylmagnesium chloride 
• 14374-45-9 1-heptynylbenzene 
• 103-79-7 1-phenyl-acetone 
• 57918-71-5 1-Phenyl-2-propanone Potassium Enolate 

Downstream Products

• 65899-16-3 5-phenyl-6-undecanone 
• 143676-05-5 2-phenyl-oct-1-en-3-one 

Relevant academic research and scientific papers

Photoredox-Catalyzed Dehydrogenative Csp3-Csp2Cross-Coupling of Alkylarenes to Aldehydes in Flow

Executing photoredox reactions in flow offers solutions to frequently encountered issues regarding reproducibility, reaction time, and scale-up. Here, we report the transfer of a photoredox-catalyzed benzylic coupling of alkylarenes to aldehydes to a flow chemistry setting leading to improvements in terms of higher concentration, shorter residence times, better yields, ease of catalyst preparation, and enhanced substrate scope. Its applicability has been demonstrated by a multi-gram-scale reaction using high-power light-emitting diodes (LEDs), late-stage functionalization of selected active pharmaceutical ingredients (APIs), and also a photocatalyst recycling method.

Homobenzylic Oxygenation Enabled by Dual Organic Photoredox and Cobalt Catalysis

Activation of aliphatic C(sp3)-H bonds in the presence of more activated benzylic C(sp3)-H bonds is often a nontrivial, if not impossible task. Herein we show that leveraging the reactivity of benzylic C(sp3)-H bonds to achieve reactivity at the homobenzylic position can be accomplished using dual organic photoredox/cobalt catalysis. Through a two-part catalytic system, alkyl arenes undergo dehydrogenation followed by an anti-Markovnikov Wacker-type oxidation to grant benzyl ketone products. This formal homobenzylic oxidation is accomplished with high atom economy without the use of directing groups, achieving valuable reactivity that traditionally would require multiple chemical transformations.

Ni-Catalyzed β-Alkylation of Cyclopropanol-Derived Homoenolates

Metal homoenolates are valuable synthetic intermediates which provide access to β-functionalized ketones. In this report, we disclose a Ni-catalyzed β-alkylation reaction of cyclopropanol-derived homoenolates using redox-active N-hydroxyphthalimide (NHPI) esters as the alkylating reagents. The reaction is compatible with 1°, 2°, and 3° NHPI esters. Mechanistic studies imply radical activation of the NHPI ester and 2e β-carbon elimination occurring on the cyclopropanol.

Anti-Markovnikov Oxidation of β-Alkyl Styrenes with H2O as the Terminal Oxidant

Oxygenation of alkenes is one of the most straightforward routes for the construction of carbonyl compounds. Wacker oxidation provides a broadly useful strategy to convert the mineral oil into higher value-added carbonyl chemicals. However, the conventional Wacker chemistry remains problematic, such as the poor activity for internal alkenes, the lack of anti-Markovnikov regioselectivity, and the high cost and chemical waste resulted from noble metal catalysts and stoichiometric oxidant. Here, we describe an unprecedented dehydrogenative oxygenation of β-alkyl styrenes and their derivatives with water under external-oxidant-free conditions by utilizing the synergistic effect of photocatalysis and proton-reduction catalysis that can address these challenges. This dual catalytic system possesses the single anti-Markovnikov selectivity due to the property of the visible-light-induced alkene radical cation intermediate.

Addressing challenges in palladium-catalyzed cross-couplings of aryl mesylates: Monoarylation of ketones and primary alkyl amines

Mor(DalPhos) for Me(sylates): Described are the first examples of ketone mono-α-arylation and primary aliphatic amine monoarylation employing aryl methanesulfonate coupling partners. A range of functionalized aryl mesylates were employed with dialkyl ketones, and also with primary and secondary amines as well as the otherwise challenging coupling partners acetone and methylamine. Ad=adamantyl. Copyright

Two distinct classes of novel pyrazolinecarboxamides as potent cannabinoid CB1 receptor agonists

The synthesis and SAR of 3-alkyl-4-aryl-4,5-dihydropyrazole-1-carboxamides 1-23 and 1-alkyl-5-aryl-4,5-dihydropyrazole-3-carboxamides 24-27 as two novel cannabinoid CB1 receptor agonist classes were described. The target compounds elicited high

Formation of α-hydroxyketones via irregular Wittig reaction

Αddition reactions of (1-methoxyalkyl)triphenylphosphonium ylides, derived from the corresponding Wittig salts and n-BuLi, to aldehydes were investigated. It was revealed that the betaine LiX complexes, the primary adducts, were converted to α-hydroxyketones, prior to the formation of oxaphosphetanes, by addition of aqueous NH4Cl at low temperature.

4,5-Dihydro-(1H)-pyrazole derivatives as cannabinoid CB1 receptor modulators

This invention is directed to 4,5-dihydro-(1H)-pyrazole(pyrazoline) derivatives as cannabinoid CB1 receptor modulators, to pharmaceutical compositions containing these compounds, to methods for the preparation of these compounds, methods for pr

Facile synthesis of ketones from 1,1-disilylethenes via oxidation of gem-disilylalkanes

The oxidation of gem-disilylalkanes, which can be derived from 1,1-disilylethene, alkyllithiums and alkyl halides, affords the corresponding ketones.

C-H and C-C bond activation of primary amines through dehydrogenation and transimination

Matrix presented Dehydrogenation and subsequent transimination of primary amines offer a new pathway for C-H bond activation, ortho-alkylation, and C-C bond activation to afford a variety of ketones in the reaction of 1-alkene by a cocatalyt system of Rh(I) and 2-amino-3-picoline.