27309-55-3

Usage

Type of compound

Ketone, Methyl ketone

Usage

Building block in the synthesis of various pharmaceuticals and organic compounds, used in research and development for the creation of new drugs and materials

Potential applications

Medicine, chemistry, and materials science

Versatility

Versatile chemical structure and reactivity

Upstream product

• 1068-55-9 isopropylmagnesium chloride 
• 1885-29-6 anthranilic acid nitrile 
• 574754-03-3 C₁₀H₁₅NO 
• 116707-09-6 1-(2-fluorophenyl)-2-methylpropan-1-one 
• 5408-59-3 1-(2-chlorophenyl)-2-methyl-propan-1-one 
• 209223-84-7 1-(2′-bromophenyl)-2-methylpropan-1-one 
• 1071084-07-5 1-(2-iodophenyl)-2-methylpropan-1-one 
• 507-19-7 t-butyl bromide 
• 108665-93-6 3-isopropyl-1,3-dihydroindol-2-one 
• 75-26-3 isopropyl bromide 
• 67-56-1 methanol 
• 551-93-9 2-aminoacetophenone 
• 552-89-6 2-nitro-benzaldehyde 
• 529-23-7 o-aminobenzaldehyde 

Downstream Products

• 500593-84-0 2,2,2-trichloro-N-[2-(isopropylcarbonyl)phenyl]acetamide 
• 106718-49-4 3-(1'-methylethyl)-2,1-benzisoxazole 
• 74333-54-3 o-azidophenyl isopropyl ketone 
• 169504-70-5 1,3-dihydro-5-(2-propyl)-3(R,S)-[(benzyloxycarbonyl)-amino]-2H-1,4-benzodiazepin-2-one 
• 129122-46-9 2-(4-fluorophenyl)-4-(1-methylethyl)-3-quinoline-carboxylic acid, ethyl ester 
• 61485-19-6 3-isopropyl-1H-indazole 
• 93330-81-5 4-isopropyl-2-phenyl-quinazoline 
• 1392323-06-6 N-(2-(3-methylbut-1-en-2-yl)phenyl)benzamide 
• 1392323-28-2 C₁₈H₁₈BrNO 
• 1333822-90-4 N-[2-(2-methylpropanoyl)phenyl]benzamide 
• 85847-59-2 N-(2-Isobutyryl-phenyl)-formamide 

Relevant academic research and scientific papers

Ir(iii)-Catalysed electrooxidative intramolecular dehydrogenative C-H/N-H coupling for the synthesis of N-H indoles

Herein, an iridium(iii)-catalysed electrooxidative intramolecular dehydrogenative C-H/N-H coupling of unprotected 2-alkenyl anilines is described. The developed method allows the synthesis of a variety of 3-substituted N-H indole scaffolds under undivided electrolytic conditions. Mechanistic studies suggest that the reaction proceeds through the electro-oxidation induced reductive elimination pathway.

Synthesis of 1-Amino-2,2,2-trifluoroalkylphosphonates from Alkene-Tethered Trifluoroacetimidoyl Chlorides

The reaction of alkene-tethered trifluoroacetimidoyl chlorides with trialkyl phosphites furnishes 1-amino-2,2,2-trifluoroalkylphosphonates. The products were generated in moderate to good yields, and the scalability of this process was showcased. Partial hydrolysis of the phosphonate moiety was achieved. The cyclization is proposed to occur via formation of an imidoyl phosphonate intermediate that becomes susceptible to nucleophilic attack at nitrogen through the strong electron-withdrawing groups at the imidoyl carbon.

Nickel/Photo-Cocatalyzed Asymmetric Acyl-Carbamoylation of Alkenes

An unprecedented asymmetric acyl-carbamoylation of pendant alkenes tethered on aryl carbamic chlorides with both aliphatic and aromatic aldehydes has been developed via the cooperative catalysis of a chiral nickel-PHOX complex and tetrabutylammonium decatungstate. This reaction represents the first example of merging hydrogen-atom-transfer photochemistry and asymmetric transition metal catalysis in difunctionalization of alkenes. Using this protocol, a variety of oxindoles bearing a challenging quaternary stereogenic center are furnished under mild conditions in highly enantioselective manner.

Pd-catalyzed regiodivergent synthesis of diverse oxindoles enabled by the versatile heck reaction of carbamoyl chlorides

We report herein a miscellaneous oxindole synthesis bearing an all-carbon quaternary center, enabled by Pd-catalyzed intramolecular cyclization followed by multiple intermolecular Heck reactions of both easily accessible alkene-tethered carbamoyl chlorides and olefins. This protocol obviates the use of prefunctionalized olefinic reagents, exhibits excellent functional group tolerance, and features fascinating reactive versatility.

The Reaction of o-Aminoacetophenone N-Tosylhydrazone and CO2 toward 1,4-Dihydro-2H-3,1-benzoxazin-2-ones

A transition-metal-free reaction of o-aminoacetophenone N-tosylhydrazone and CO2 has been developed, leading to a series of 1,4-dihydro-2H-3,1-benzoxazin-2-ones in moderate to good yields. This procedure proceeds with the sequential fixation of CO2 by amino leading to carbamic acid and the intra- molecular insertion of hydroxyl to carbene. (Figure presented.).

Manganese catalyzed α-methylation of ketones with methanol as a C1 source

The direct α-methylation of ketones with methanol under hydrogen borrowing conditions using a well-defined manganese PN3P complex as a pre-catalyst was, for the first time, achieved. The reactions typically proceed at 120 °C for 20 h with 3 mol% pre-catalyst loading and in the presence of NaOtBu (50 mol%) as base. The scope of the reaction was extended to the α-methylation of esters.

Gold-catalyzed cyclization of 1-(2′-Azidoaryl) propynols: Synthesis of polysubstituted 4-quinolones

An unprecedented gold-catalyzed procedure for the synthesis of polysubstituted 4-quinolones from 1-(2′-Azidoaryl) propynols is described. The reaction undergoes an intramolecular nucleophilic attack of the azide group to the Au-Activated triple bonds in a 6-endo-dig manner and subsequent gold-Assisted expulsion of N2 to furnish an α-imino gold carbene intermediate, which triggers a 1,2-carbon migration and finally is converted to 2,3-disubstituted 4-quinolone.

TBHP as Methyl Source under Metal-Free Aerobic Conditions To Synthesize Quinazolin-4(3H)-ones and Quinazolines by Oxidative Amination of C(sp3)–H Bond

tert-Butyl hydroperoxide (TBHP) served as the methyl source under metal-free aerobic conditions in the oxidative amination of the C(sp3)–H bond to synthesize quinazolin-4(3H)-ones and quinazolines from 2-aminobenzamides and 2-carbonyl-substituted anilines, respectively.

Direct Electrophilic C?H Alkynylation of Unprotected 2-Vinylanilines

Unprotected aromatic amines can be used as directing groups in metal-catalyzed C?H alkynylations of alkenes. By using low amounts of an IrIIIcatalyst in combination with alkynylbenziodoxolones as electrophilic alkyne-transfer reagents, highly desirable 1,3-enynes were isolated in excellent yields of up to 98 % with Z stereoselectivity. A broad substrate scope as well as the high synthetic utility of the 1,3-enynes render this new method an efficient approach for the synthesis of five- and six-membered heterocycles. Further derivatizations of the 1,3-enynes to highly substituted quinolines through AuI- and N-bromosuccinimide-mediated exo-dig cyclizations were demonstrated.

NH2-directed C-H alkenylation of 2-vinylanilines with vinylbenziodoxolones

The first directing-group-mediated C-H alkenylation with alkenyl-λ3-iodanes as electrophilic alkene-transfer reagents has been developed. The application of free aromatic amines as challenging but synthetically valuable directing groups in combination with an IrIII catalyst enabled the synthesis of highly desirable 1, 3- dienes in excellent yields of up to 98% with high to perfect (Z, E) stereoselectivity. A broad substrate scope and further synthetic modifications are demonstrated.