5331-13-5

Usage

Appearance

White crystalline solid.

Odor

Distinctive sweet odor.

Usage

Synthesis of various pharmaceuticals, flavoring agent in the food industry.

Potential applications

Anti-inflammatory and analgesic agent.

Versatility

Potential building block for the synthesis of various organic compounds.

Upstream product

• 110-89-4 piperidine 
• 14252-32-5 1-phenyl-hex-1-yn-3-one 
• 107-87-9 2-Pentanone 
• 105-54-4 butanoic acid ethyl ester 
• 98-86-2 acetophenone 
• 106-31-0 butanoic acid anhydride 
• 137919-74-5 Benzoyl-n-butyryl-methan (Enolform); 1-Phenyl-1-hydroxy-3-oxo-hexen-⁽¹⁾ 
• 98-88-4 benzoyl chloride 
• 93-99-2 benzoic acid phenyl ester 
• 932-90-1 syn-benzaldehyde oxime 
• 6919-61-5 N-methoxy-N-methylbenzamide 
• 141-75-3 butyryl chloride 
• 70-11-1 α-bromoacetophenone 
• 3282-32-4 2-diazo-acetophenone 

Downstream Products

• 20716-16-9 3-p-Anisoyloxy-1-phenylhexen-⁽²⁾-on 
• 20716-10-3 2-p-Anisoyl-1-phenylhexan-1,3-dion 
• 20716-15-8 3--1-phenyl-hexen-(2)-on 
• 90015-79-5 6-phenyl-4-propyl-2(1H)-pyrimidinone 
• 627501-19-3 ethyl 4-benzoyl-5-n-propylisoxazolo-3-carboxylate 
• 63297-52-9 1-phenylheptane-1,4-dione 
• 627501-26-2 4-phenyl-3-n-propylisoxazolo-[3,4-d]pyridazin-7⁽⁶⁾-one 
• 89967-05-5 4-phenyl-6-propyl-pyrimidine 
• 89967-23-7 2-Chloro-4-phenyl-6-propyl-pyrimidine 
• 89967-12-4 1-(6-Phenyl-pyrimidin-4-yl)-propan-1-one oxime 
• 67073-98-7 6-phenyl-4-propionylpyrimidine 

Relevant academic research and scientific papers

Variations in the blaise reaction: Conceptually new synthesis of 3-amino enones and 1,3-diketones

Organic compounds with 3-amino enone or 1,3-diketone functional groups are extremely important, as they can be converted into a plethora of heterocyclic or carbocyclic compounds, or can be used as ligands in metal complexes. We have achieved a new, easy, straightforward and convenient synthesis of 3-amino enones and 1,3-diketones starting from aryl/heteroaryl/alkyl nitriles and 1-aryl/alkyl 2-bromoethanones. The reaction is a variation of the classical Blaise reaction, and it works with zinc and trimethylsilyl chloride as an activator. By running the hydrolysis of the reaction intermediate with HCl (3 N aq.) at 0-30 °C or at 100 °C, it is possible to form either 3-amino enones or 1,3-diketones, respectively. The newly developed method was used for the synthesis of avobenzone, an ingredient of sun-screen lotions. Furthermore, an easy synthesis of (Z)-3-amino-1-[4-(tertbutyl) phenyl]-3-(4-methoxyphenyl)prop-2-en-1-one, with UV/Vis absorption characteristics similar to those of avobenzone, was also achieved.

Direct oxidative coupling of enamines and electron-deficient amines: TBAI/TBHP-mediated synthesis of substituted diaminoalkenes under metal-free conditions

A metal-free cross-coupling of enamines and electron-de fi cient amines through oxidative C(sp2)-N bond formation has been realized by using TBAI as catalyst and TBHP as oxidant. This novel strategy allows for an efficient organocatalytic synthesis of the synthetically useful diaminoalkene derivatives and is highlighted by appealing features such as readily available of the starting materials, wide substrate scope and transition-metal-free characteristics. (Chemical Equation Presented).

Formation of functionalized 2H-azirines through phio-mediated trifluoroethoxylation and azirination of enamines

A variety of enaminones and enamine carboxylic esters were converted to trifluoroethoxylated 2H-azirines through reactions with PhIO in trifluoroethanol (TFE). The cascade reaction is postulated to proceed via a PhIO-mediated oxidative trifluoroethoxylation and a subsequent azirination of the α-trifluoroethoxylated enamine intermediates.

Hit-to-lead optimization of a series of carboxamides of ethyl 2-amino-4-phenylthiazole-5-carboxylates as novel adenosine A2A receptor antagonists

Herein we describe the discovery of a series of novel adenosine A 2A receptor antagonists. A successful hit-to-lead optimization of an HTS hit led to replacement of a metabolically labile ester moiety with a heteroaromatic group. A compound from the series, (cyclopropanecarboxylic acid [5-(5-methyl-[1,2,4]oxadiazol-3-yl)-4-phenyl-thiazol-2-yl]-amide, compound 13), was shown to be effective in reversing haloperidol-induced hypolocomotion, a model of motor dysfunction in Parkinson's Disease.

Iodomethane oxidative addition and CO migratory insertion in monocarbonylphosphine complexes of the type [Rh((C6H5)COCHCO((CH2)n CH3))(CO)(PPh3)]: Steric and electronic effects

The chemical kinetics, studied by UV/Vis, IR and NMR, of the oxidative addition of iodomethane to [Rh((C6H5)COCHCOR)(CO)(PPh3)], with R = (CH2)nCH3, n = 1-3, consists of three consecutive reaction steps that involves isomers of two distinctly different classes of RhIII-alkyl and two distinctly different classes of RhIII-acyl species. Kinetic studies on the first oxidative addition step of [Rh((C6H5)COCHCOR)(CO)(PPh3)] + CH3I to form [Rh((C6H5)COCHCOR)(CH3)(CO)(PPh 3)(I)] revealed a second order oxidative addition rate constant approximately 500-600 times faster than that observed for the Monsanto catalyst [Rh(CO)2I2]-. The reaction rate of the first oxidative addition step in chloroform was not influenced by the increasing alkyl chain length of the R group on the β-diketonato ligand: k1 = 0.0333 ([Rh((C6H5)COCHCO(CH2CH3))(C O)(PPh3)]), 0.0437 ([Rh((C6H5)COCHCO(CH2CH2CH 3))(CO)(PPh3)]) and 0.0354 dm3 mol-1 s-1 ([Rh((C6H5)COCHCO(CH2CH2 CH2CH3))(CO)(PPh3)]). The pKa′ and keto-enol equilibrium constant, Kc, of the β-diketones (C6H5)COCH2COR, along with apparent group electronegativities, χR of the R group of the β-diketones (C6H5)COCH2COR, give a measurement of the electron donating character of the coordinating β-diketonato ligand: (R, pKa′, Kc, χR) = (CH3, 8.70, 12.1, 2.34), (CH2CH3, 9.33, 8.2, 2.31), (CH2CH2CH3, 9.23, 11.5, 2.41) and (CH2CH2CH2CH3, 9.33, 11.6, 2.22).

Method for preparing chiral diphosphines

The invention concerns a method for preparing a compound of formula (1) wherein: A represents naphthyl or phenyl optionally substituted; and Ar1, Ar2independently represent a saturated or aromatic carbocyclic group, optionally substituted.

Asymmetric hydrogenation method of a ketonic compound and derivative

The present invention relates to a process for the asymmetric hydrogenation of a ketonic compound and derivative. The invention relates to the use of optically active metal complexes as catalysts for the asymmetric hydrogenation of a ketonic compound and derivative. The process for the asymmetric hydrogenation of a ketonic compound and derivative is characterized in that the asymmetric hydrogenation of said compound is carried out in the presence of an effective amount of a metal complex comprising as ligand an optically active diphosphine corresponding to one of the following formulae: STR1

InCl3: A new Lewis acid catalyst for reactions with α-diazocarbonyl compounds

The use of InCl3 as a Lewis acid catalyst in diazocarbonyl S-H insertion reactions, nitrile cyclizations and addition reactions to aldehydes and ketones is described.

A novel synthesis of 1,3-diketones by reaction of an α-bromoketone with acyl chlorides promoted by gallium triiodide

Promoted by gallium triiodide, an α-bromoketone, bromomethyl phenyl ketone, is treated with acyl chlorides to synthesize 1,3-diketones in good yields under mild and neutral conditions.

β-Diketone synthesis by reaction of α-haloketones with acid chlorides or acid anhydrides promoted by samarium triiodide

Promoted by SmI3, α-haloketones were reacted with acid chlorides or acid anhydrides and β-diketones were synthesized via intermediate samarium enolates.