7509-25-3

Usage

Appearance

Yellow solid

Structure

Butadienone core substituted with two bromophenyl groups

Usage

a. Reagent in organic synthesis
b. Introduces 4-bromophenyl group into various molecules

Biological activity

Potential anti-tumor agent

Applications

a. Chemical synthesis
b. Medicinal uses

Additional use

Development of fluorescent sensors for detecting metal ions (e.g., mercury)

Upstream product

• 99-90-1 para-bromoacetophenone 
• 557-20-0 diethylzinc 

Downstream Products

• 1220957-76-5 C₁₆H₁₁Br₃O 
• 883847-63-0 4,6-bis(4-bromophenyl)-2H-pyran-2-one 
• 1416226-26-0 C₁₆H₁₄Br₂O₃ 
• 1403563-13-2 C₁₆H₁₄Br₂O 

Relevant academic research and scientific papers

Access to Cyclic β-Amino Acids by Amine-Catalyzed Enantioselective Addition of the γ-Carbon Atoms of α,β-Unsaturated Imines to Enals

Disclosed herein is a new catalytic approach for an efficient access to cyclic β-amino acids widely found in bioactive small molecules and peptidic foldamers. Our method involves addition of the remote γ-carbon atoms of α,β-unsaturated imines to enals by iminium organic catalysis. This highly chemo- and stereo-selective reaction affords cyclic β-amino aldehydes that can be converted to amino acids bearing quaternary stereocenters with exceptional optical purities. Our study demonstrates the unique power of organic catalytic remote carbon reactions in rapid synthesis of functional molecules.

Dynamic Kinetic Resolution of Allylic Azides via Asymmetric Dihydroxylation

The catalytic enantioselective preparation of densely functionalized amines is a fundamental synthetic challenge. To address this challenge, we report for the first time that the Winstein rearrangement can be enlisted as the racemization pathway in a dynamic kinetic resolution of allylic azides. Alkene functionalization by Sharpless dihydroxylation affords tertiary azides in excellent enantioselectivity (up to 99:1 er). This approach establishes the chirality of the tertiary azide, obviates the need to directly forge either a congested C-N or C-C bond at the new nitrogenous stereocenter, and establishes additional functionality. Several examples demonstrate further elaboration of this functionality.

Molecular and Merrifield supported chiral diamines for enantioselective addition of ZnR2 (R = Me, Et) to ketones

Chiral 1,2-ethylenediamines have been previously reported as active catalysts in the enantioselective addition reactions of ZnR2 to either methyl- or trifluoromethyl-ketones. Subtle changes in the molecular structure of different catalysts are described herein and lead to a dramatic effect in their catalytic activity. From these findings, we demonstrate the selective reactivity of the ligands used in the addition of ZnR2 (R = Me, Et) to methyl- and trifluoromethyl-ketones offering an enantioselective access either to chiral non-fluorinated alcohols or to chiral fluorinated tertiary alcohols. Considering the importance of the chiral trifluoromethyl carbinol fragment in several biologically active compounds, we have extended the scope of the addition reaction of ZnEt2 to several trifluoromethylketones catalyzed by (R,R)-1,2-diphenylethylenediamine derivatives. This work explores a homogeneous approach that provides excellent yields and very high ee and the use of a heterogenized tail-tied ligand affording moderate ee, high yields and allowing an easier handling and recycling.

Synthesis and antimalarial activity of 3,3-spiroanellated 5,6-disubstituted 1,2,4-trioxanes

Novel 3,3-spiroanellated 5-aryl, 6-arylvinyl-substituted 1,2,4-trioxanes 19-34 have been synthesized and appraised for their antimalarial activity against multidrug-resistant Plasmodium yoelii nigeriensis in Swiss mice by oral route at doses ranging from 96 mg/kg × 4 days to 24 mg/kg × 4 days. The most active compound of the series (compound 25) provided 100% protection at 24 mg/kg × 4 days, and other 1,2,4-trioxanes 22, 26, 27, and 30 also showed promising activity. In this model, β-arteether provided 100 and 20% protection at 48 mg/kg × 4 days and 24 mg/kg × 4 days, respectively, by oral route. Compound 25 displayed a similar in vitro pharmacokinetic profile to that of reference drug β-arteether. The activity results demonstrated the importance of an aryl moiety at the C-5 position on the 1,2,4-trioxane pharmacophore.

Zirconocene bis(perfluorooctanesulfonate) s-catalyzed highly efficient synthesis of 1,3,5-triaryl benzene via cyclotrimerization of ketones

Air-stable zirconocene bis(perfluoroctanesulfonate) s [Cp 2Zr]OSO2C8F17) 2] (1) with high Lewis acidity and high thermal stability was prepared by the reaction between Cp2ZrCl2 a

A New Approach to the Stereoselective Synthesis of β-methylchalcones

Many β-methylchalcone derivatives have been prepared from self condensation of aralkyl ketones mediated by tetrachlorosilane-ethanol in mild conditions. - Key words: aralkyl ketones; tetrachlorosilane; β-methylchalcones; triarylbenzene derivatives