877-35-0

Usage

Chemical Properties

Pale Yellow Oil

InChI:InChI=1/C10H11BrO/c1-2-9(11)10(12)8-6-4-3-5-7-8/h3-7,9H,2H2,1H3

Upstream product

• 495-40-9 propiophenone 
• 26074-52-2 2-bromo-butyryl bromide 
• 71-43-2 benzene 
• 22118-12-3 2-bromobutanoyl chloride 
• 100-47-0 benzonitrile 
• 104-51-8 1-butylbenzene 
• 622-76-4 1-phenyl-1-butyne 
• 66498-51-9 α,α-dibromobutyrophenone 

Downstream Products

• 20662-91-3 5-Ethyl-4-phenyl-oxazol 
• 101282-59-1 2-(4-chloro-phenoxy)-1-phenyl-butan-1-one 
• 103206-51-5 2-phenoxy-1-phenylbutan-1-one 
• 101746-82-1 2-hydroxy-1-phenyl-butan-1-one-(methyl-phenyl-acetal) 
• 100964-32-7 2-hydroxy-1-phenyl-butan-1-one-diethylacetal 
• 54034-47-8 1-oxo-1-phenylbutan-2-yl acetate 
• 669-32-9 4-ethyl-5-phenyl-1⁽³⁾H-imidazole 
• 109938-37-6 2-[1]naphthyloxy-1-phenyl-butan-1-one 
• 33119-67-4 5-ethyl-4-phenyl-oxazol-2-ylamine 
• 104217-20-1 4-ethyl-5-phenyl-1,3-dihydro-imidazol-2-one 
• 408332-79-6 2-(N-methylamino)-1-phenyl-1-butanone 
• 495-40-9 propiophenone 
• 62576-10-7 2,5-diethyl-4-phenyl-oxazole 
• 16183-46-3 2-hydroxy-1-phenylbutan-1-one 

Relevant academic research and scientific papers

Designer Cathinones N-Ethylhexedrone and Buphedrone Show Different In Vitro Neurotoxicity and Mice Behaviour Impairment

N-Ethylhexedrone (NEH) and buphedrone (Buph) are emerging synthetic cathinones (SC) with limited information about their detrimental effects within central nervous system. Objectives: To distinguish mice behavioural changes by NEH and Buph and validate th

Aldol-Tishchenko Reaction of α-Oxy Ketones: Diastereoselective Synthesis of 1,2,3-Triol Derivatives

α-Oxy ketones, easily accessible by conventional routes, can be selectively deprotonated generating an enolate intermediate, which upon treatment with paraformaldehyde undergoes an aldol-Tishchenko reaction, leading to relevant 1,2,3-triol fragments in a totally diastereoselective manner. The excellent stereocontrol in the generation of a quaternary stereocenter is attributed to stereoelectronic effects in the Evans intermediate. This methodology allows overcoming some limitations of our previously reported strategy, based on the reaction of α-lithiobenzyl ethers with esters and paraformaldehyde, broadening the scope of the obtained polyols. Synthetic applications of this process include the preparation of a new dilignol model and some functionalized oxetanes.

Enantioselective Synthesis of Nitrogen-Nitrogen Biaryl Atropisomers via Copper-Catalyzed Friedel-Crafts Alkylation Reaction

Nitrogen-nitrogen bonds containing motifs are ubiquitous in natural products and bioactive compounds. However, the atropisomerism arising from a restricted rotation around an N-N bond is largely overlooked. Here, we describe a method to access the first enantioselective synthesis of N-N biaryl atropisomers via a Cu-bisoxazoline-catalyzed Friedel-Crafts alkylation reaction. A wide range of axially chiral N-N bisazaheterocycle compounds were efficiently prepared in high yields with excellent enantioselectivities via desymmetrization and kinetic resolution. Heating experiments showed that the axially chiral bisazaheterocycle products have high rotational barriers.

Dehydration-fragmentation mechanism of cathinones and their metabolites in ESI-CID

Various cathinone-derived designer drugs (CATs) have recently appeared on the drug market. This study examined the mechanism for the generation of dehydrated ions for CATs during electrospray ionization collision-induced dissociation (ESI-CID). The genera

Design, synthesis and broad-spectrum Bcr-Abl inhibitory activity of novel thiazolamide-benzamide derivatives

Bcr-Abl plays an important role in the pathogenesis and development of chronic myeloid leukemia (CML). But Bcr-Abl is prone to mutation, so it increases the difficulty of clinical treatment. Therefore, it is crucial to design a new class of broad-spectrum Bcr-Abl inhibitors. Herein, forty novel thiazolamide-benzamide derivatives were synthesized and evaluated their broad-spectrum Bcr-Abl inhibitory activities. The newly synthesized compounds were characterized by using spectrum data (1H NMR, APCI-MS and IR) and elemental analysis. The protein kinase results indicated that eight compounds (3a, 3e, 3m, 3n, 3p, 4c, 4f, 4g) showed high activities to wild-type and T315I mutation. The most potent compound 3m exhibited an Abl IC50 value as low as 1.273 μM and showed inhibition to the T315I mutant with IC50 value 39.89 μM. 3m could prove to be a new promising lead compound for the further development of broad-spectrum Bcr-Abl inhibitors to overcome clinical acquired resistance.

Novel benzene-based carbamates for ache/bche inhibition: Synthesis and ligand/structure-oriented sar study

A series of new benzene-based derivatives was designed, synthesized and comprehensively characterized. All of the tested compounds were evaluated for their in vitro ability to potentially inhibit the acetyl-and butyrylcholinesterase enzymes. The selectivity index of individual molecules to cholinesterases was also determined. Generally, the inhibitory potency was stronger against butyryl-compared to acetylcholinesterase; however, some of the compounds showed a promising inhibition of both enzymes. In fact, two compounds (23, benzyl ethyl(1-oxo-1-phenylpropan-2-yl)carbamate and 28, benzyl (1-(3-chlorophenyl)-1-oxopropan-2-yl) (methyl)carbamate) had a very high selectivity index, while the second one (28) reached the lowest inhibitory concentration IC50 value, which corresponds quite well with galanthamine. Moreover, comparative receptor-independent and receptor-dependent structure–activity studies were conducted to explain the observed variations in inhibiting the potential of the investigated carbamate series. The principal objective of the ligand-based study was to comparatively analyze the molecular surface to gain insight into the electronic and/or steric factors that govern the ability to inhibit enzyme activities. The spatial distribution of potentially important steric and electrostatic factors was determined using the probability-guided pharmacophore mapping procedure, which is based on the iterative variable elimination method. Additionally, planar and spatial maps of the host–target interactions were created for all of the active compounds and compared with the drug molecules using the docking methodology.

Synthesis of α,β-dibromo ketones by photolysis of α-bromo ketones with N-bromosuccinimide: Photoinduced β-bromination of α-bromo ketones

Irradiation of α-bromopropiophenones in the presence of NBS results in the formation of α,β-dibromopropiophenones, which can be viewed as β-bromination of α-bromopropiophenones. The reaction is believed to go through a series of reactions; photoinduced C–Br bond cleavage, elimination of HBr to give α,β-unsaturated ketone intermediates, and addition of Br2, which are formed by the reaction between HBr and NBS. From mechanistic studies of the reaction, we have also found a very convenient method for α-debromination of the α,β-dibromopropiophenones which is by simple irradiation of the dibromo ketones in acetone or 2-propanol without the use of any additives. Our results demonstrate that bromine can be added into or eliminated from the alpha, beta, or both positions to the carbonyl group by photochemical methods, which make synthetic options of bromine containing carbonyl compounds versatile.

2-Amino-4-arylthiazoles through One-Pot Transformation of Alkylarenes with NBS and Thioureas

Treatment of alkylarenes with N-bromosuccinimide in a mixture of ethyl acetate and water at 60 °C, a mixture of acetonitrile and water at 80 °C, or a mixture of diethyl carbonate and water under irradiation with a tungsten lamp, followed by a reaction with thioureas or arenethioamides provided the corresponding 2-amino- 4-arylthiazoles or 2,4-diarylthiazoles in good to moderate yields, respectively, in one pot. The present reaction is an efficient one-pot transformation method of alkylarenes into 2-amino-4-arylthiazoles and 2,4-diarylthiazoles directly under mild and transition-metal-free conditions.

Synthesis of α-heterosubstituted ketones through sulfur mediated difunctionalization of internal alkynes

Synthesis of α-heterosubstituted ketones was achieved through sulfur mediated difunctionalization of internal alkynes in one pot. The reaction design involves: phenyl substituted internal alkyne attacking triflic anhydride activated diphenyl sulfoxide to

Preparation method of alpha-bromoketone

The invention relates to a method for preparing alpha-bromoketone by ketone shown as a structural formula below. The method comprises the following steps: firstly dropwise adding a dichloromethane solution of dimethylsulfoxide (1.5 equiv) into a dichloromethane solution of oxaloyl bromide (1.5 equiv) at a temperature of minus 10 DEG C, dropwise adding the raw material ketone, then returning to a room temperature or heating to 30 DEG C for reaction to obtain a corresponding alpha-bromoketone compound; the yield is 80-95 percent.