6327-84-0

Usage

InChI:InChI=1/C17H16BrNO3/c1-21-15-5-3-4-14(11-15)19-17(20)9-6-12-10-13(18)7-8-16(12)22-2/h3-11H,1-2H3,(H,19,20)/b9-6+

Upstream product

• 631-22-1 diethyl dibromomalonate 
• 94-41-7 benzalacetophenone 
• 6935-75-7 2-bromo-1,3-diphenyl-2-propen-1-one 
• 105-53-3 diethyl malonate 
• 5292-53-5 diethyl benzalmalonate 
• 5633-34-1 (benzoylmethylene)dimethylsulfurane 
• 77670-30-5 diethyl 2-(3-oxo-1,3-diphenylpropyl)malonate 
• 532-27-4 1-chloroacetophenone 

Downstream Products

• 51615-57-7 trans-2-Benzoyl-3-phenyl-cyclopropan-1.1-dicarbonsaeure 
• 115823-40-0 (1R,5S,6R)-4-(Cyano-dimethyl-methyl)-2-oxo-4,6-diphenyl-3-oxa-bicyclo[3.1.0]hexane-1-carboxylic acid ethyl ester 
• 94011-49-1 diethyl phenacylmalonate 

Relevant academic research and scientific papers

Iodobenzene-Catalyzed Oxidative Cyclization for the Synthesis of Highly Functionalized Cyclopropanes

An iodobenzene-catalyzed oxidative cyclization of Michael adducts of activated methylene compounds with nitroolefins or chalcones is developed. m CPBA is used as oxidant together with Bu 4 NI for the generation of a highly reactive iodine(III) species to mediate the cyclopropanation via a ligand exchange and reductive elimination process. A range of highly functionalized cyclopropanes are synthesized with high diastereoselectivities.

Synergistic NaBH4Reduction/Cyclization of 2-Aroylcyclopropane-1-carboxylates: Synthesis of 3-Oxabicyclo[3.1.0]hexane Derivatives

An NaBH4reduction/cyclization reaction of readily available 2-aroyl-1-cyano-3-arylcyclopropane-1-carboxylate compounds was investigated. The process results in the stereoselective synthesis of 3-oxabicyclo[3.1.0]hexane derivatives in high yield

Hypoiodite-catalysed oxidative cyclisation of Michael adducts of chalcones with 1,3-dicarbonyl compounds: A facile and versatile approach to substituted furans and cyclopropanes

Through hypoiodite catalysis, oxidative cyclisation of Michael adducts of chalcones with 1,3-dicarbonyl compounds for divergent synthesis of either furans or cyclopropanes is developed. The selective synthesis of major products is achieved depending on the use of different reaction conditions or substrates.

Lewis acid-mediated transformations of trans-2-Aroyl-3-aryl-cyclopropane-1, 1-dicarboxylates into 2-pyrones and 1-indanones

trans-2-Aroyl-3-arylcyclopropane-1,1-dicarboxylates upon treatment with aluminium(III) chloride (AlCl3) underwent ring-opening, fragmentation, recombination and lactonization to give highly substituted 2-pyrones. Alternatively, when treated with titanium(IV) chloride (TiCl 4), the cyclopropane diesters underwent a Nazarov cyclization to afford 1-indanones with high diastereoselectivity.

Stereoselective cyclopropanation of α-bromochalcone with diethyl malonate promoted by K2CO3

A new Michael-initiated cyclopropanation reaction using α-bromochalcones as Michael acceptor was developed. Compared to previous works using arylidenemalonates as Michael acceptor, this novel protocol could improve the synthesis of trans-isomers of diethyl 2-benzoyl-3-phenyl- cyclopropane-1,1-dicarboxylates. More importantly, this method also provided the first access to the cis-isomers of these densely substituted cyclopropanes with the Michael-initiated ring closure (MIRC) strategy, albeit with a poor diastereoselectivity.

Highly diastereoselective synthesis of 1-pyrrolines via SnCl 4-promoted [3 + 2] cycloaddition between activated donor-acceptor cyclopropanes and nitriles

Activated donor-acceptor cyclopropanes underwent formal [3 + 2] cycloaddition with nitriles in the presence of SnCl4. The product 1-pyrrolines were isolated as single cis-diastereomers in moderate to good yields.

Solvent-controlled oxidative cyclization for divergent synthesis of highly functionalized oxetanes and cyclopropanes

An efficient solvent-controlled oxidative cyclization of Michael adducts of malonates with chalcones with the combination of iodosobenzene and tetrabutylammonium iodide is reported. Highly functionalized oxetanes and cyclopropanes were divergently synthes

Vicarious nucleophilic substitution of hydrogen in electrophilic alkenes

Carbanions containing leaving groups react in the presence of base with electrophilic alkenes giving products in which vinylic hydrogen is replaced with the carbanion moiety. They are formed via addition - β-elimination pathway analogous to the vicarious