31919-47-8

Usage

Molecular weight

396.57 g/mol

Physical state

White, crystalline solid

Uses

a. Photoinitiator in polymer and plastic production
b. Building block in organic synthesis
c. UV-absorbing component in sunscreen formulations

Stability

Relatively stable under normal conditions

Safety precautions

Handle and store with care due to potential phototoxicity and irritation to skin and eyes

InChI:InChI=1/C17H20O/c18-16(15-4-2-1-3-5-15)17-9-12-6-13(10-17)8-14(7-12)11-17/h1-5,12-14H,6-11H2

Upstream product

• 828-51-3 1-Adamantanecarboxylic acid 
• 23074-42-2 1-adamantanecarbonitrile 
• 2094-72-6 1-Adamantanecarbonyl chloride 
• 603-33-8 triphenylbismuthane 
• 768-90-1 1-Adamantyl bromide 
• 98-88-4 benzoyl chloride 
• 71-43-2 benzene 
• 50741-86-1 1-Methyladamantane-3-carboxylic acid chloride 
• 4406-72-8 2-phenyl[1,3,2]dioxaborolane 
• 108-86-1 bromobenzene 
• 60-29-7 diethyl ether 
• 768-93-4 1-iodoadamantane 
• 1033260-22-8 O-(triphenylsilyl)benzaldoxime 
• 201230-82-2 carbon monoxide 

Downstream Products

• 134753-54-1 1-(tricyclo<3.3.1.1^3,7>dec-1-yl)-1-phenylbut-2-yne-1,4-diol 
• 209789-96-8 1-adamantyl-1-phenyl-propargylic alcohol 
• 7131-11-5 1-benzyl(adamantane) 
• 7131-12-6 α-(1-adamantyl)-p-nitrotoluene 
• 7131-13-7 α-(1-adamantyl)-o-nitrotoluene 
• 125145-76-8 triethylgermyladamantylphenylcarbinol 
• 1359877-34-1 1-adamantyl-(4-aminophenyl)methanone 
• 1359877-36-3 1-adamantyl-(3-aminophenyl)methanone 
• 1207682-35-6 C₁₇H₁₉NO₃ 
• 1207682-36-7 C₁₇H₁₉NO₃ 
• 1245928-26-0 1-adamantyl-(4-nitrophenyl)methanol 
• 1359877-41-0 1-adamantyl-(3-nitrophenyl)methanol 
• 1359877-44-3 4-[1-adamantyl(methoxy)methyl]anilinium chloride 
• 1360051-02-0 4-[1-adamantyl(methoxy)methyl]aniline 

Relevant academic research and scientific papers

Direct formation of organomanganese bromides using Rieke manganese

The direct formation of organomanganese bromides can be accomplished under mild conditions from the direct oxidative addition to Rieke manganese to alkyl and thienyl bromides.

A Fast and General Route to Ketones from Amides and Organolithium Compounds under Aerobic Conditions: Synthetic and Mechanistic Aspects

We report that the nucleophilic acyl substitution reaction of aliphatic and (hetero)aromatic amides by organolithium reagents proceeds quickly (20 s reaction time), efficiently, and chemoselectively with a broad substrate scope in the environmentally responsible cyclopentyl methyl ether, at ambient temperature and under air, to provide ketones in up to 93 % yield with an effective suppression of the notorious over-addition reaction. Detailed DFT calculations and NMR investigations support the experimental results. The described methodology was proven to be amenable to scale-up and recyclability protocols. Contrasting classical procedures carried out under inert atmospheres, this work lays the foundation for a profound paradigm shift of the reactivity of carboxylic acid amides with organolithiums, with ketones being straightforwardly obtained by simply combining the reagents under aerobic conditions and with no need of using previously modified or pre-activated amides, as recommended.

Photoelimination of Nitrogen from Diazoalkanes: Involvement of Higher Excited Singlet States in the Carbene Formation

Although diazoalkanes are important carbene precursors in organic synthesis, a comprehensive mechanism of photochemical formation of carbenes from diazoalkanes has not been proposed. Synergies of experiments and computations demonstrate the involvement of higher excited singlet states in the photochemistry of diazoalkanes. In all investigated diazoalkanes, excitation to S1 results in nonreactive internal conversion to S0. On the contrary, excitation to higher-lying singlet states (Sn, n > 1) drives the reaction toward a different segment of the S1/S0 conical intersection seam and results in nitrogen elimination and formation of carbenes.

Iron-Catalyzed Cleavage Reaction of Keto Acids with Aliphatic Aldehydes for the Synthesis of Ketones and Ketone Esters

The radical–radical coupling reaction is an important synthetic strategy. In this study, the iron-catalyzed radical–radical cross-coupling reaction based on the decarboxylation of keto acids and decarbonylation of aliphatic aldehydes to obtain valuable aryl ketones is reported for the first time. Remarkably, when tertiary aldehydes were used as carbonyl sources, ketone esters were selectively obtained instead of ketones. The gram-scale preparation of aryl ketone through this strategy was easily achieved by using only 3 mol % of the iron catalyst. As a proof-of-concept, the bioactive molecule flurprimidol was synthesized in two steps by using this strategy.

Method for preparing aryl ketone based on iron-catalyzed free radical-free radical coupling reaction such as ketonic acid decarboxylation and fatty aldehyde de-carbonylation

The invention discloses a method for preparing an aryl ketone derivative based on a free radical-free radical cross-coupling reaction such as ketonic acid decarboxylation and fatty aldehyde de-carbonylation. The method comprises the following steps: reacting aryl-substituted ketonic acid with fatty aldehyde under the catalytic action of ferric triacetylacetonate to generate an aryl ketone derivative; the gram-grade reaction can be realized by the method only by using 3mol% of an iron catalyst; and the method has the advantages of no need of consumption of a large amount of a Lewis acid catalyst or a stoichiometric organic metal reagent, mild reaction conditions, one-step reaction, few by-products, wide substrate application range and scalable reaction, and overcomes the defects of large catalyst consumption, insufficient functional group tolerance, many by-products and the like in the prior art.

N-Heterocyclic Carbene-Catalyzed Radical Relay Enabling Vicinal Alkylacylation of Alkenes

The N-heterocyclic carbene-catalyzed radical relay enables the vicinal alkylacylation of styrenes, acrylates and acrylonitrile using aldehydes and tertiary alkyl carboxylic acid-derived redox-active esters. This protocol introduces tertiary alkyl groups and acyl groups to C-C double bonds with complete regioselectivity to produce functionalized ketone derivatives. The radical relay mechanism involves single electron transfer from the enolate form of a Breslow intermediate and radical addition of the resultant alkyl radical to the alkene followed by radical-radical coupling.

Ketone Synthesis by a Nickel-Catalyzed Dehydrogenative Cross-Coupling of Primary Alcohols

An intermolecular coupling of primary alcohols and organotriflates has been developed to provide ketones by the action of a Ni(0) catalyst. This oxidative transformation is proposed to occur by the union of three distinct catalytic cycles. Two competitive oxidation processes generate aldehyde in situ via hydrogen transfer oxidation or (pseudo)dehalogenation pathways. As aldehyde forms, a Ni-catalyzed carbonyl-Heck process enables formation of the key carbon-carbon bond. The utility of this rare alcohol to ketone transformation is demonstrated through the synthesis of diverse complex and bioactive molecules.

Ketone Synthesis by a Nickel-Catalyzed Dehydrogenative Cross-Coupling of Primary Alcohols

An intermolecular coupling of primary alcohols and organotriflates has been developed to provide ketones by the action of a Ni(0) catalyst. This oxidative transformation is proposed to occur by the union of three distinct catalytic cycles. Two competitive oxidation processes generate aldehyde in situ via hydrogen transfer oxidation or (pseudo)dehalogenation pathways. As aldehyde forms, a Ni-catalyzed carbonyl-Heck process enables formation of the key carbon-carbon bond. The utility of this rare alcohol to ketone transformation is demonstrated through the synthesis of diverse complex and bioactive molecules.

N-Heterocyclic Carbene-Catalyzed Decarboxylative Alkylation of Aldehydes

We found that N-heterocyclic carbene catalysis promoted the unprecedented decarboxylative coupling of aryl aldehydes and tertiary or secondary alkyl carboxylic acid-derived redox-active esters to produce aryl alkyl ketones. The mild and transition-metal-free reaction conditions are attractive features of this method. The power of this protocol was demonstrated by the functionalization of pharmaceutical drugs and natural product. A reaction pathway involving single electron transfer from an enolate form of Breslow intermediate to a redox ester followed by recombination of the resultant radical pair to form a carbon-carbon bond is proposed.

Nickel-Catalyzed Coupling of Arylzinc Halides with Thioesters

The Pd-catalyzed Fukuyama reaction of thioesters with organozinc reagents is a mild, functional-group-tolerant method for acylation chemistry. Its Ni-catalyzed variant might be a sustainable alternative to expensive catalytic Pd sources. We investigated the reaction of S-ethyl thioesters with aryl zinc halides with hetero- and homotopic Ni precatalysts and several ligands. The results show that both homo- and heterotopic species may contribute to catalysis. The substrate scope using an operationally homogeneous defined Ni complex was established. Acyl radicals are postulated as short-lived intermediates.