109801-25-4

Usage

Derivative of

Butanedione

Common use

Flavoring agent in food products

Structural modification

Addition of a fluorine atom and a phenyl group

Potential applications

Pharmaceutical and agrochemical industries

Safety precautions

Proper handling and storage procedures should be followed to ensure safety and minimize potential hazards.

Upstream product

• 38109-75-0 E-4-phenyl-4-trimethylsiloxy-3-buten-2-one 
• 93-91-4 1-phenylbutan-1,3-dione 
• 73922-81-3 4-phenyl-but-3-yn-2-ol 
• 1817-57-8 4-phenyl-3-butyne-2-one 
• 128753-04-8 2-phenyliodonio-1-phenylbutane-1,3-dione 
• 98-86-2 acetophenone 
• 62961-61-9 (Z)-4-hydroxy-4-phenyl-3-buten-2-one 
• 5908-41-8 benzoyltrimethylsilane 

Downstream Products

• 936499-05-7 C₁₃H₁₇FO₂Si 
• 1093227-91-8 C₁₆H₂₅FO₂Si₂ 

Relevant academic research and scientific papers

N-Fluoro Perfluoroalkylsulphonimides: Efficient Reagents for the Fluorination of 1,3-Dicarbonyl Derivatives

Fluorination of 1,3-dicarbonyl derivatives with N-fluoro sulphonimides afforded either 2-fluoro or 2,2-difluoro products in high yields.

N-Fluorobisimides. Efficient reagents for the fluorination of 1,3-dicarbonyl derivatives

Fluorination of 1,3-dicarbonyl derivatives with N-fluorobisimides, (CF3SO2)2NF (1), results in the formation of 2-fluoro- or 2,2-difluoro-1,3-dicarbonyl analogs, depending on the reaction conditions.High yields are obtained for a variety of structural types.In the case of 1,3-dicarbonyl derivatives with low enol content, only the sodium enolates react with 1.Thus 1 has been demonsrtated to be perhaps the best fluorinating reagent for the fluorination of 1,3-dicarbonyl derivatives.All of the 2-fluoro-1,3-dicarbonyl products exist predominantly as keto tautomers.

Highly enantioselective Michael addition of 2-fluoro-1,3-diketones to nitroalkenes

Highly enantioselective Michael addition of 2-fluoro-1,3 diketones to nitroalkenes was developed, and the desired adducts were obtained in good chemical yields with moderate to good diastereoselectivties and excellent enantioselectivities. Subsequent stereoselective reduction of the carbonyl groups led to the preparation of a functionalized fluoroisostere of glycerol that contains four continuous stereogenic centers.

Organocatalytic Asymmetric Cascade Michael-acyl Transfer Reaction between 2-Fluoro-1,3-diketones and Unsaturated Thiazolones: Access to Fluorinated 4-Acyloxy Thiazoles

Quinine derived bifunctional urea catalyzed cascade Michael-acyl transfer reaction of 5-alkenyl thiazolones and monofluorinated β-diketones has been developed. The fluorine containing 4-acyloxy thiazoles were synthesized in high yields and good diastereo-and excellent enantioselectivities. Synthetic transformations, including synthesis of 4-hydroxy thiazoles, have been demonstrated.

Gold-catalyzed Fluorination of Alkynyl Esters and Ketones: Efficient Access to Fluorinated 1,3-Dicarbonyl Compounds

We developed an efficient synthesis of 2-fluoro-1,3-dicarbonyl compounds using readily available alkynyl ketones or esters as starting material. The key step is the insertion of hydrogen fluoride (HF) to the gold carbene intermediate generated from cationic gold catalyzed addition of N-oxides to alkynyl ketones or esters. This method gives excellent chemical yields and regioselectivity with good functional group tolerance. (Figure presented.).

Controlling reactivity through liquid assisted grinding: The curious case of mechanochemical fluorination

We have identified an example of a mechanochemically milled organic reaction where liquid-assisted grinding controls the selectivity, such a phenomenon has not been reported/observed before. It was found that upon milling dibenzoylmethane with Selectfluor in the absence of any solvent, a 3:1 ratio of monofluorinated:difluorinated product was observed. Whereas, addition of 0.125 mL of acetonitrile (～10% of the total volume of materials present) to the ground reaction mixture afforded 50:1 selectivity. Furthermore, this phenomenon is applicable to a small range of diketone substrates thus far explored. Additionally, we have demonstrated that difluorination can be achieved by simply switching from adding acetonitrile to addition of sodium carbonate. Most notable, in the latter case, is the reduced reaction time compared to a conventional solvent approach, 2 hours in the mill and 24 hours in the flask.

Mild and selective α-fluorination of carbonyl compounds (ketones, 1,3-diketones, β-ketoesters, α-nitroketones, and β-ketonitriles) with Selectfluor (F-TEDA-BF4) in imidazolium ILs [BMIM/PF6 or BMIM/NTf2] with Br?nsted-acidic IL [PMIM(SO3H)/OTf] as promoter

Structurally diverse ketones, 1,3-diketones, and β-ketoesters, were selectively monofluorinated with Selectfluor (F-TEDA-BF4) (1 equiv) in [BMIM][PF6] as solvent and [PMIM(SO3H)][OTf] as promoter under mild conditions. In selected cases, the monofluorinated products were transformed to the gem-difluoro derivatives by employing an additional equivalent of Selectfluor, and gem-difluoro-derivatives were synthesized directly from the substrates by employing 2 equiv of Selectfluor. The method was extended to monofluorination of representative α-nitroketones and β-ketonitriles using [BMIM][NTf2] without the need for promoters. The described method offers the added advantage of recycling and reuse of the IL solvent. (Chemical Equation Presented).

Facile synthesis of 2-fluoro-1,3-dicarbonyl compounds with aqueous hydrofluoric acid mediated by iodosylarenes

Direct fluorination of 1,3-dicarbonyl compounds including 1,3-diketones, 3-oxo esters, and 3-oxoamides was conducted using aqueous hydrofluoric acid with the aid of iodosylarenes, giving the corresponding 2-fluorinated products in good to high yields. Among the used iodosylarenes, o-iodosyltoluene was found to be the most effective, and the yield of 2-fluorinated products was improved. Georg Thieme Verlag Stuttgart New York.

Catalytic fluorination of 1,3-dicarbonyl compounds using iodoarene catalysts

Catalytic fluorination of 1,3-dicarbonyl compounds with aqueous hydrofluoric acid proceeded efficiently with the aid of iodoarene catalysts in the presence of m-CPBA as a terminal oxidant. o-Iodotoluene, o-iodoanisole, and o-ethyliodobenzene showed a high

Reaction of iodonium ylides of 1,3-dicarbonyl compounds with HF reagents

Reaction of dibenzoylmethane with (diacetoxyiodo)benzene in the presence of KOH in MeCN quantitatively gave the corresponding iodonium ylide, which was treated with a HF reagent to afford the corresponding 2-fluorinated dibenzoylmethane in 14-50% yields.