96090-12-9

Upstream product

• 105515-33-1 (2E)-3-(4-bromophenyl)prop-2-en-1-ol 
• 3650-78-0 methyl (E)-4-bromocinnamate 
• 59114-88-4 ethyl (2E)-3-(3-bromophenyl)prop-2-enoate 
• 3132-99-8 m-bromobenzoic aldehyde 
• 589-87-7 1,4-bromoiodobenzene 
• 1122-91-4 4-bromo-benzaldehyde 
• 24393-53-1 ethyl 4-bromocinnamate 
• 105515-33-1 3-(4-bromophenyl)prop-2-en-1-ol 
• 1826-67-1 vinyl magnesium bromide 
• 1200-07-3 trans-4-bromocinnamic acid 
• 58824-56-9 1-(p-bromophenyl)prop-2-en-1-ol 
• 49678-04-8 trans-4-bromocinnamaldehyde 
• 24393-53-1 ethyl (E)-3-(4-bromophenyl)-2-propenoate 
• 49678-04-8 4-bromocinnamaldeyde 

Downstream Products

• 96090-13-0 3-[(E)-3-(4-Bromo-phenyl)-allyl]-pyridine 
• 96090-14-1 3-[1-(4-Bromo-phenyl)-allyl]-pyridine 
• 111678-41-2 4-[1-(4-Bromo-phenyl)-allyl]-isoquinoline 
• 111678-40-1 4-[(E)-3-(4-Bromo-phenyl)-allyl]-isoquinoline 
• 124855-00-1 6-<1-(4-bromophenyl)-1-propen-3-yl>-2,3-dihydro-5-benzofuranol 
• 111678-30-9 3-[(E)-3-(4-Bromo-phenyl)-allyl]-quinoline 
• 111678-31-0 3-[1-(4-Bromo-phenyl)-allyl]-quinoline 
• 86668-30-6 (E)-1-bromo-4-(3-phenylprop-1-enyl)benzene 
• 1214913-12-8 [1-(4-bromophenyl)allyl]dimethylphenylsilane 
• 1214913-16-2 C₁₇H₁₉BrSi 
• 1259080-25-5 (R)-N-((3R,4S)-3-(4-bromophenyl)-6-methylhept-1-en-4-yl)-2-methylpropane-2-sulfinamide 
• 1259080-07-3 (R)-N-((1R,2R)-2-(4-bromophenyl)-1-phenylbut-3-enyl)-2-methylpropane-2-sulfinamide 
• 1259080-71-1 C₂₀H₂₄BrNOS 
• 1277184-91-4 (3R,4aS,9S,9aR)-9-(4-bromophenyl)-7-nitro-3-propyl-1,2,3,4,4a,9,9a,10-octahydroacridine-2,2(1H)-dicarbonitrile 

Relevant academic research and scientific papers

Thermal proteome profiling efficiently identifies ribosome destabilizing oxazolidinones

Identifying the targets of bioactive small molecules is a challenging endeavor for which no general solution currently exists. Classical affinity purification experiments suffer from the need to functionalise a bioactive compound and link it to a solid support, which may interfere with target binding. A modern mass spectrometry-based proteomics technique that has partially circumvented this problem is thermal proteome profiling (TPP), which determines the effect of an unmodified small molecule on the thermal stability of the whole proteome simultaneously. Here, we use TPP to identify the mode-of-action of a newly-discovered autophagy inhibitor based on oxazolidinones often employed as chiral auxiliaries. Surprisingly, a significant portion of all ribosomal proteins were found to be destabilized by the inhibitor, highlighting the utility of this technology for determining a challenging mode-of-action.

Synthesis of Enantioenriched 3,4-Disubstituted Chromans through Lewis Base Catalyzed Carbosulfenylation

A method for the catalytic, enantioselective, carbosulfenylation of alkenes to construct 3,4-disubstituted chromans is described. Alkene activation proceeds through the intermediacy of enantioenriched, configurationally stable thiiranium ions generated from catalytic, Lewis base activation of an electrophilic sulfenylating agent. The transformation affords difficult-to-generate, enantioenriched, 3,4-disubstituted chromans in moderate to high yields and excellent enantioselectivities. A variety of substituents are compatible including electronically diverse functional groups as well as several functional handles such as aryl halides, esters, anilines, and phenols. The resulting thioether moiety is amenable to a number of functional group manipulations and transformations. Notably, the pendant sulfide was successfully cleaved to furnish a free thiol which readily provides access to most sulfur-containing functional groups which are present in natural products and pharmaceuticals.

Crystallization-Based Synthetic Route to Antimalarial Agent BRD5018: Diazocene Ring Formation via a Staudinger-aza-Wittig Reaction on an Azetidine-Ribose Template

The development of an entirely crystallization-based synthetic route to the antimalarial BRD5018 is described, which assembles a structurally complex bicyclic azetidine scaffold adorned with five stereogenic centers without the need for any chromatographic separations. A diastereoselective glycine ester Claisen rearrangement, diastereomeric salt resolution, and diastereoselective iodo-lactonization are utilized to provide an efficient access to three contiguous stereogenic centers on an acyclic template with the desired relative and absolute configurations. A tandem aziridine ring-opening/azetidine ring-closure on the derived 2-amino-1,4-diol template was developed to efficiently establish the all-cis trisubstituted azetidine scaffold with the proper ancillary functionality for end-game maneuvers. d-Ribose-2,3-acetonide provided a conveniently differentiated vicinal syn-diol suitable for the planned reductive amination/periodate cleavage/Staudinger-aza-Wittig sequence to form the eight-membered diazocene ring. An early quantitative installation of the diaryl acetylene moiety via a Sonogashira coupling on an electronically matched methyl 4-bromocinnamate circumvented a low-yielding, late-stage reaction in the first-generation synthesis. Multiple crystalline intermediates enabled the complete removal of chromatography from the synthesis resulting in a substantially reduced cost and waste generation with enhanced throughput and quality control.

Gold-Catalyzed Formal Hexadehydro-Diels-Alder/Carboalkoxylation Reaction Cascades

A dual gold-catalyzed hexadehydro-Diels-Alder/carboalkoxylation cascade reaction is reported. In this transformation, the gold catalyst participated in the hexadehydro-Diels-Alder step, switching the mechanism from a radical type to a cationic one, and then the catalyst activated the resulting aryne to form an ortho-Au phenyl cation species, which underwent a carboalkoxylation rearrangement rather than the expected aryne-ene reaction.

METHOD FOR SYNTHESIS OF DIAZABICYCLO[6.2.0]DECANE RELATED COMPOUNDS

A method for the synthesis of diazabicyclo[6.2.0]decane compounds is provided. The synthesis proceeds by stereoselective synthesis of a chiral lactone followed by azetidine formation via a series of chemoselective reactions. Bicyclization results with the

Radical-Cation Cascade to Aryltetralin Cyclic Ether Lignans Under Visible-Light Photoredox Catalysis

The development of concise, sustainable, and cost-effective synthesis of aryltetralin lignans, bearing either a fused lactone or cyclic ether, is of significant medicinal importance. Reported is that in the presence of Fukuzumi's acridinium salt under blue LED irradiation, functionalized dicinnamyl ether derivatives are converted into aryltetralin cyclic ether lignans with concurrent generation of three stereocenters in good to high yields with up to 20:1 diastereoselectivity. Oxidation of an alkene to the radical cation is key to the success of this formal Diels–Alder reaction of electronically mismatched diene and dienophile. Applying this methodology, six natural products, aglacin B, aglacin C, sulabiroin A, sulabiroin B, gaultherin C, and isoshonanin, are synthesized in only two to three steps from readily available biomass-derived monolignols. A revised structure is proposed for gaultherin C.

Biocatalytic dynamic kinetic reductive resolution with ketoreductase from: Klebsiella pneumoniae: The asymmetric synthesis of functionalized tetrahydropyrans

Ketoreductase from growing cells of Klebsiella pneumoniae (NBRC 3319) acts as an efficient reagent for converting racemic α-benzyl/cinnamyl substituted-β-ketoesters to the corresponding β-hydroxy esters with excellent yields and stereoselectivities (ee and de >99 %). The reactions described herein followed a biocatalytic dynamic kinetic reductive resolution (DKRR) pathway, which is reported for the first time with such substrates. It was found that the enzyme system can accept substituted mono-aryl rings with different electronic natures. In addition, it also accepts a substituted naphthyl ring and heteroaryl ring in the α-position of the parent β-ketoester. The synthesized enantiopure β-hydroxy esters were then synthetically manipulated to valuable tetrahydropyran building blocks.

P-Chiral Monophosphorus Ligands for Asymmetric Copper-Catalyzed Allylic Alkylation

Asymmetric copper-catalyzed allylic alkylation between allyl bromides and alkyl Grignard reagents using a P-chiral monophosphorus ligand is described. A range of terminal olefins bearing tertiary or quaternary carbon centers were formed in good branched/linear selectivities and excellent enantioselectivities at copper loadings as low as 0.5 mol %.

Olefin Oxyamination with Unfunctionalized N-Alkylanilines

N-Alkylanilines have rarely been used in oxyamination reactions, due to the normally necessary pre-functionalization of the N-atom. Also, the formation of aminium radical cations (ARCs) of anilines bearing alkyl substituents is plagued by the ARC's tendency to instantaneously convert to α-amino radicals or iminium ions. We present a readily available reagent combination that addresses both challenges, and thus allows for an oxyamination with N-alkylanilines via ARCs as the crucial reactive intermediates and excellent diastereoselectivity. (Figure presented.).

Synthesis and biological evaluation of phloroglucinol derivatives possessing α-glycosidase, acetylcholinesterase, butyrylcholinesterase, carbonic anhydrase inhibitory activity

A series of novel phloroglucinol derivatives were designed, synthesized, characterized spectroscopically and tested for their inhibitory activity against selected metabolic enzymes, including α-glycosidase, acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and human carbonic anhydrase I and II (hCA I and II). These compounds displayed nanomolar inhibition levels and showed Ki values of 1.14–3.92 nM against AChE, 0.24–1.64 nM against BChE, 6.73–51.10 nM against α-glycosidase, 1.80–5.10 nM against hCA I, and 1.14–5.45 nM against hCA II.