1128-85-4

Usage

Uses

Used in Pharmaceutical Synthesis:
3-Amino-1-phenyl-2-buten-1-one is used as a precursor in the pharmaceutical industry for its ability to facilitate the synthesis of various drugs. Its chemical reactivity allows for the creation of a wide range of medicinal compounds, contributing to the development of new treatments and therapies.
Used in Organic Chemistry Research and Development:
In the realm of organic chemistry, 3-APB is employed as an important intermediate in research and development. Its capacity to form different chemical bonds makes it instrumental in the exploration of novel chemical reactions and the synthesis of new organic compounds.
Used in Perfume Production:
3-Amino-1-phenyl-2-buten-1-one is also utilized in the fragrance industry, where it serves as a valuable chemical in the production of perfumes. Its unique properties enable the creation of distinct scents and contribute to the formulation of various perfume compositions.

InChI:InChI=1/C10H11NO/c1-8(11)7-10(12)9-5-3-2-4-6-9/h2-7H,11H2,1H3

Upstream product

• 1008-75-9 3-methyl-5-phenylisoxazole 
• 57-13-6 urea 
• 93-91-4 1-phenylbutan-1,3-dione 
• 100-52-7 benzaldehyde 
• 7664-41-7 ammonia 
• 98-86-2 acetophenone 
• 1336-21-6 ammonium hydroxide 
• 120-46-7 1,3-diphenylpropanedione 

Downstream Products

• 1226-92-2 1-phenyl-3-benzoylamino-2-buten-1-one 
• 23652-96-2 N-(1-methyl-3-oxo-3-phenyl-propenyl)-acetamide 
• 5220-61-1 (2-methylpyridin-3-yl)(phenyl)methanone 
• 16232-41-0 2-hydroxy-6-methyl-4-phenyl-nicotinonitrile 
• 35929-88-5 3-benzoyl-2-methyl-4-phenyl-1,4-dihydro-indeno[1,2-b]pyridin-5-one 
• 4240-97-5 2-hydroxy-4-methyl-6-phenyl-nicotinonitrile 
• 27337-94-6 1,4-dimethyl-2-oxo-6-phenyl-1,2-dihydro-pyridine-3-carbonitrile 
• 260247-89-0 (2-methyl-5,6,7,8-tetrahydroquinolin-3-yl)(phenyl)methanone 
• 28994-53-8 2-ethoxy-2,4-dimethyl-6-phenyl-2H-[1,3]oxazine 
• 63205-26-5 3-(Trichloracetamido)-1-phenyl-2-buten-1-on 
• 140706-32-7 3,7-diphenyl-2-hydroxy-5-methylpyrazolo<1,5-a>pyrimidine 
• 22192-06-9 3-benzoyl-2,6-dimethyl-4(1H)-pyridone 
• 113123-52-7 3-benzoyl-4-methyl-6-phenyl-2(1H)-pyridone 
• 102252-88-0 5-benzoyl-6-methyl-2(1H)-pyridinone 

Relevant academic research and scientific papers

Metal-Free Synthesis of Fully Substituted Pyridines via Ring Construction Based on the Domino Reactions of Enaminones and Aldehydes

An unprecedented domino reaction involving primary enaminones/enaminoesters and aldehydes has been developed for the synthesis of fully substituted pyridines. The construction of the products has been accomplished via the cascade generation of two C-C and

Syntheses of mixed chelate copper(II) complexes containing β-ketoaminato and diamine ligands: Solvatochromism study

Three new mixed-chelate Cu(II) complexes incorporating N,N,N′, N′-tetramethylenediamine (tmen) or N,N-dimethyl,N′-benzyl- ethylenediamine (dmben) as diamine chelate and a β-ketoaminato such as 4-amino-3-penten-2-onato (APO) or 3-amino-3-phenyl-2-buten-1-onato (APBO) with the general formula [Cu(β-ketoamine)(diamine)]ClO4 were prepared and characterized. Their solvatochromic properties were studied by visible spectroscopy. X-ray crystal analysis confirmed that copper (II) ion in [Cu(APO)(tmen)]ClO4 and[Cu(APBO)(tmen)]ClO4 is almost in a square planar environment. Structure of [Cu(APO)(dmben)]ClO4 was investigated by DFT calculation. The solvent-dependent visible spectroscopic absorption maxima, νmax, were analyzed using stepwise multiple linear regression (SMLR) method to find the best model explaining the observed positive solvatochromism. The analysis demonstrated that among different solvent parameters, donor number (DN) is a dominant factor responsible for the shift in the d-d absorption band of the complexes to the lower wavenumber with increasing its values. The importance of steric effect in the diamine ligand and more delocalization of pi-bands in the β-ketoamine on the spectral and SMLR measurements are discussed.

Structure-Activity Relationship Studies of Tetrahydroquinolone Free Fatty Acid Receptor 3 Modulators

Free fatty acid receptor 3 (FFA3, previously GPR41) is activated by short-chain fatty acids, mediates health effects of the gut microbiota, and is a therapeutic target for metabolic and inflammatory diseases. The shortage of well-characterized tool compounds has however impeded progress. Herein, we report structure-activity relationship of an allosteric modulator series and characterization of physicochemical and pharmacokinetic properties of selected compounds, including previous and new tools. Two representatives, 57 (TUG-1907) and 63 (TUG-2015), showed improved solubility and preserved potency. Of these, 57, with EC50 = 145 nM and a solubility of 33 μM, showed high clearance in vivo but is a preferred tool in vitro. In contrast, 63, with EC50 = 162 nM and a solubility of 9 μM, showed lower clearance and seems better suited for in vivo studies. Using 57, we demonstrate for the first time that FFA3 activation leads to calcium mobilization in murine dorsal root ganglia.

Synthesis of Thiazoles and Isothiazoles via Three-Component Reaction of Enaminoesters, Sulfur, and Bromodifluoroacetamides/Esters

A three-component strategy for the synthesis of thiazoles and isothiazoles has been developed by employing enaminoesters, fluorodibromoiamides/ester, and sulfur. The thiazoles and isothiazoles were formed via two C-F bond cleavages along with the formation of new C-S, C-N, and N-S bonds. The strategy provides high selectivity for the synthesis of thiazoles/isothiazoles, which have vital applications in drug discovery and development.

Β-carbonyl enamines compound and as the application of the preparation of plant pathogenic bacteria antibacterial agent (by machine translation)

The invention relates to a β-carbonyl compound and enamines preparation of plant pathogenic bacteria as the application of an antimicrobial agent. Commercially available antibacterial agent Mijunzhi as a positive control, the linear growth of the mycelium determination process 23 kind of target compound anthrax pathogenicbacteria the apple, corn curved spore pathogenic bacterium, pathogenic bacteria rice blast fungus, reducing bakanae disease of wheat, such as watermelon blighting pathogenicbacteria 5 common inhibiting activity of plant pathogenic fungi, the result shows that: the target compound has tries the fungus inhibiting effect of different degree. Compound 8, 11, 12, 14, 16 of the activity is better, for the majority of their pathogenic bacteria testing EC 50 half of the effect of the concentration value is higher than the positive control drug kresoxim-methyl. Especially compound 8 inhibition of anthrax pathogenicbacteria the apple active (EC 50 = 2.15μg/mL) compound and 12 the inhibitory activity of pathogenic bacterium curved spore (EC 50 = 9.14μg/mL) are Mijunzhi active (EC 50 = 15.45 & 76.06μg/mL) of 8 times, has potential development and application values. (by machine translation)

Asymmetric Hydrogenation of Isoxazolium Triflates with a Chiral Iridium Catalyst

The iridium catalyst [IrCl(cod)]2–phosphine–I2(cod=1,5-cyclooctadiene) selectively reduced isoxazolium triflates to isoxazolines or isoxazolidines in the presence of H2. The iridium-catalyzed hydrogenation proceeded in high-to-good enantioselectivity when an optically active phosphine–oxazoline ligand was used. The 3-substituted 5-arylisoxazolium salts were transformed into 4-isoxazolines with up to 95:5 enantiomeric ratio (e.r.). Chiral cis-isoxazolidines were obtained in up to 89:11 e.r., with no formation of their trans isomers, when the substrates had a primary alkyl substituent at the 5-position. The mechanistic studies indicate that the hydridoiridium(III) species prefers to deliver its hydride to the C5 atom of the isoxazole ring. The hydride attack leads to the formation of the chiral isoxazolidine via a 3-isoxazoline intermediate. Meanwhile, in the selective formation of 4-isoxazolines, hydride attack at the C5 atom may be obstructed by steric hindrance from the 5-aryl substituent.

Synthesis of 3-aminopyridin-2(1H)-ones and 1H-pyrido[2,3-b][1,4]oxazin- 2(3H)-ones

The interaction of 1,3-diketones with chloroacetamide produced N-(3-oxoalkenyl)chloroacetamides. Heating of N-(3-oxoalkenyl)chloroacetamides with an excess of pyridine in ethanol or butanol led to the formation of pyridin-2(1H)-ones, substituted with a py

Synthesis of 3-aminopyridin-2(1H)-ones and 1H-pyrido[2,3-b][1,4]oxazin-2(3H)-ones

The interaction of 1,3-diketones with chloroacetamide produced N-(3-oxoalkenyl)chloroacetamides. Heating of N-(3-oxoalkenyl)chloroacetamides with an excess of pyridine in ethanol or butanol led to the formation of pyridin-2(1H)-ones, substituted with a py

Synthesis and 3D-QSAR study of 1,4-dihydropyridine derivatives as MDR cancer reverters

A series of symmetrical and unsymmetrical 1,4-dihydropyridines were synthesized by a rapid, single pot microwave irradiation (MWI) based protocol along with conventional approach and characterized by NMR, IR and mass spectroscopic techniques. The compound

Direct β-acyloxylation of enamines via PhIO-mediated intermolecular oxidative C-O bond formation and its application to the synthesis of oxazoles

A direct β-acyloxylation of enamine compounds has been achieved by using iodosobenzene (PhIO) as an oxidant to realize the intermolecular oxidative C(sp2)-O bond formation between enamines and various carboxylic acids, including N-protected amino acids. The transformation tolerates a wide range of functional groups and furnishes a variety of β-acyloxy enamines that can be conveniently converted to oxazole compounds via cyclodehydration.