93259-40-6

Usage

InChI:InChI=1/C17H13BrO/c18-16-12-10-15(11-13-16)17(19)9-5-4-8-14-6-2-1-3-7-14/h1-13H/b8-4+,9-5+

Upstream product

• 99-90-1 para-bromoacetophenone 
• 104-55-2 3-phenyl-propenal 
• 14371-10-9 (E)-3-phenylpropenal 

Downstream Products

• 1415681-05-8 methyl 4'-bromo-3-phenethyl-[1,1'-biphenyl]-4-carboxylate 

Relevant academic research and scientific papers

Highly regioselective introduction of aryl substituents via asymmetric 1,4-addition of boronic acids to linear α,β,γ,δ-unsaturated ketones

An efficient palladium(II)-catalyzed regioselective asymmetric 1,4-conjugate addition of arylboronic acids to linear α,β,γ,δ-unsaturated ketones is developed using phosphapalladacycle catalysts. The relevant 1,4-products were obtained exclusively with per

Asymmetric 1,4-Conjugate Addition of Diarylphosphines to α,β,γ,δ-Unsaturated Ketones Catalyzed by Transition-Metal Pincer Complexes

An enantioselective asymmetric 1,4-addition of diarylphosphines to linear α,β,γ,δ-unsaturated dienones was developed. A series of chiral PCP- and PCN-transition-metal (Pd, Pt and Ni) pincers, themselves prepared catalytically via asymmetric hydrophosphination, were sequentially screened to reveal the roles of backbone architecture and metal ion in catalyst design. The selected ester-functionalized PCP-palladium pincer afforded the chiral 1,4-phosphine adducts in excellent yields with up to >99% ee. The same catalyst when utilized for the hydrophosphination of an α,β,γ,δ-unsaturated malonate ester also revealed the critical role played by the ester functionality on the ligand backbone in dictating the enantioselectivity of the 1,6-adduct.

NHC-catalyzed annulation of enals to 2,4-dien-1-ones: Efficient diastereoselective synthesis of 1,3-diaryl-4-styrenyl cyclopentenes

Nucleophilic heterocyclic carbene (NHC)-catalyzed annulation strategy has been utilized for the efficient synthesis of styrenyl-substituted cyclopentenes from 2,4-dienones. Georg Thieme Verlag Stuttgart New York.

Synthesis, structure, growth and characterization of an organic crystal: 1,5-diphenylpenta-2,4-dien-1-one

1,5-Diphenylpenta-2,4-dien-1-one (DDO) chalcone single crystals, synthesized by a base-catalysed aldol condensation reaction between cinnamaldehyde and acetophenone, have been grown by the slow evaporation of an ethanol solution. The crystals belong to the orthorhombic system with centrosymmetric space group Pbca. The DDO crystals are transparent in the visible region and have a lower optical cut-off at ～445 nm with a band-gap energy of 2.87 eV. Thermogravimetry/differential scanning calorimetry thermal analysis shows that the crystal is stable up to 375 K and it has a good chemical stability. The vibrational patterns of the chalcone have been investigated by Fourier transform IR and Fourier transform Raman spectroscopy. Microhardness studies were also carried out to elucidate the mechanical behaviour. Theoretical calculations were performed using the Hartree-Fock method with 6-31G(d,p) as the basis set, and the first-order hyperpolarizability is 7.077 × 10 -30 electrostatic units, which is >25 times that of urea. The crystalline perfection evaluated by high-resolution X-ray diffraction analysis reveals multiple peaks. The molecular packing leads to a centrosymmetric arrangement, resulting in zero second harmonic generation [χ(2) = 0] efficiency. Interestingly, the bromo- and chloro-substituted chalcones are good nonlinear optical materials.

Design, synthesis, and bioactivities screening of a diaryl ketone-inspired pesticide molecular library as derived from natural products

Three natural products, 1,5-diphenylpentan-1-one, 1,5-diphenylpent-2-en-1-one, and 3-hydroxy-1,5-diphenylpentan-1-one, with good insecticidal activities were extracted from Stellera chamaejasme L. Based on their shared diaryl ketone moiety as 'pharmacophores', a series of diaryl ketones were synthesized and tested for insecticidal activity, acetylcholinesterase inhibitory activity, and antifungal activity. All synthesized compounds showed poor insecticidal and acetylcholinesterase inhibitory activities. Compound III with a furyl ring showed strong activities against plant pathogenic fungi. The IC50 of compound (E)-1-(2,4-dichlorophenyl)-3-(furan-2-yl)- -prop-2-en-1-one (III2) was 1.20mg/L against Rhizoctonia solani, suggesting its strong potential as a novel antifungal drug.

Domino multicomponent michael - Michael - Aldol reactions under phase-transfer catalysis: Diastereoselective synthesis of pentasubstituted cyclohexanes

A simple, efficient, and environmental friendly domino multicomponent reaction to construct new cyclohexane derivatives with five new stereocenters, one of them quaternary, under phasetransfer catalysis is reported. This novel one-pot reaction allows the

Ultrasound-promoted synthesis of 1,5-diarylpenta-2,4-dien-1-ones catalyzed by activated barium hydroxide

1,5-Diarylpenta-2,4-dien-1-ones were synthesized with ultrasound irradiation in the presence of activated barium hydroxide as catalyst. Compared to conventional methods, the present methodology offers several advantages such as excellent yields, simple procedure, short reaction times, and milder conditions.

KF-Al2O3 induced the condensation of 2-nitrofluorene and para-substituted acetophenones with aromatic aldehydes

In the presence of KF-Al2O3 as a solid base, 2-nitrofluorene 1 condensed with aromatic aldehydes 2a-f in methanol to give 2-nitrodibenzofulvenes 3a-f in high yield. The para-substituted acetophenones 4a-f reacted with cinnamic aldehyde to give 1, 5-diaryl-2, 4-pentadien-1-ones 6a-f in moderate yield.