950-16-3

Upstream product

• 530-48-3 1,1-Diphenylethylene 
• 79-15-2 N-bromoacetamide 
• 34837-55-3 Phenylselenyl bromide 
• 599-67-7 1,1-diphenylethanol 
• 119-61-9 benzophenone 
• 373-53-5 fluoroiodomethane 

Downstream Products

• 882-59-7 1,1-diphenyloxirane 
• 4428-13-1 1,1,2-Triphenylethanol 
• 451-40-1 phenyl benzyl ketone 
• 13249-58-6 1-bromo-2,2-diphenylethylene 
• 109614-68-8 1,1-diphenyl-2-(piperazin-1-yl)ethan-1-ol 

Relevant academic research and scientific papers

Reversed isoniazids: Design, synthesis and evaluation against Mycobacterium tuberculosis

Novel reversed isoniazid (RINH) agents were synthesized by covalently linking isoniazid with various efflux pump inhibitor (EPI) cores and their structural motifs. These RINH agents were then evaluated for anti-mycobacterial activity against sensitive, isoniazid mono-resistant and MDR clinical isolates of M. tuberculosis and a selected number of compounds were also tested ex vivo for intracellular activity as well as in the ethidium bromide (EB) assay for efflux pump inhibition efficacy. The potency of some compounds against various strains of M. tuberculosis (4a–c, 7 and 8; H37Rv-MIC99 ≤1.25 μM, R5401-MIC99 ≤2.5 μM, X_61-MIC99 ≤5 μM) demonstrated the potential of the reversed anti-TB agent strategy towards the development of novel anti-mycobacterial agents to address the rapidly growing issue of resistance. Further, macrophage activity with >90% inhibition by 1a–c and 3b (MIC90 ≤13.42 μM) and inhibition of EB efflux demonstrated by these compounds are encouraging.

Exploiting a beast in carbenoid chemistry: Development of a straightforward direct nucleophilic fluoromethylation strategy

The first direct and straightforward nucleophilic fluoromethylation of organic compounds is reported. The tactic employs a fleeting lithium fluorocarbenoid (LiCH2F) generated from commercially available fluoroiodomethane. Precise reaction conditions were developed for the generation and synthetic exploitation of such a labile species. The versatility of the strategy is showcased in ca. 50 examples involving a plethora of electrophiles. Highly valuable chemicals such as fluoroalcohols, fluoroamines, and fluoromethylated oxygenated heterocycles could be prepared in very good yields through a single synthetic operation. The scalability of the reaction and its application to complex molecular architectures (e.g., steroids) are documented.

Transformation of tertiary benzyl alcohols into the vicinal halo-substituted derivatives using N-Halosuccinimides

The efficiency of direct conversion of tertiary alcohols bearing a-hydrogen atom to vicinal halohydrins-chlorohydrins and bromohydrins-under green reaction conditions was tested preliminarily on modeltertiary benzyl alcohols. Tertiary alcohols were successfully directly halogenated to vicinal halohydrins with N-halosuccinimide in aqueous media. The efficiency of the reaction in water was significantly improved in the presence of sodium dodecyl sulphate as the surfactant.

Palladium-catalyzed reaction of olefins with PhI(OAc)TBAB system: An efficient and highly selective bisfunctionalization strategy

The palladium-catalyzed reaction of olefins with PhI(OAc)TBAB system provides a novel, efficient, and highly selective bisfunctionalization strategy to introduce bromo and oxygen groups simultaneously. The substituents on the C=C bond control the regiosel

Et2Zn-mediated rearrangement of bromohydrins

(Chemical Equation Presented) A simple and highly efficient method for the rearrangement of bromohydrins mediated by Et2Zn to synthesize carbonyl compounds was described. Various β-bromo alcohols were treated with 0.6 equiv of Et2Zn to form a zinc complex in CH 2Cl2 at room temperature for 2 h, followed by 1,2-migration to give the corresponding carbonyl compounds. This remarkable and clean rearrangement is general for acyclic and cyclic bromohydrins, and a variety of ring-expansive and -contractive carbonyl compounds were obtained in good to excellent yields according to the feature of the starting bromohydrins. The functional group tolerance of organozinc reagents in this reaction will be useful in organic synthesis. The scope and limitations of this rearrangement process were also investigated.

Solid-state organic reactions proceeding by pulverization: Oxidation and halogenation with iodosobenzene and inorganic solid-supports

Pulverization-activation method was employed to accelerate solid-state organic reactions. Crushing and grinding of solid mixtures of hydrogen halide-treated silica gels, iodosobenzene and organic substrates in the absence of a solvent brought about smooth and rapid reactions to give halogenated and/or oxidized products in good yields. Various sulfides were smoothly converted to sulfonyl chlorides in one step in excellent yields. The surface of silica gel activated by pulverization serves as a reaction field on which reagent molecules can effectively encounter with each other.

PHOTOINDUCED REACTIONS OF 3β-ACETOXYCHOLESTA-5,7-DIENE, 3β-ACETOXYCHOLEST-5-ENE, TETRAPHENYLCYCLOPENTADIENE AND 1,1-DIPHENYLETHYLENE WITH OXYGEN IN THE PRESENCE OF PHENYLSELENYL BROMIDE

Whereas PhSeBr under irradiation with O2 in CH2Cl2 at -78 deg C acts as a photoxygenation catalyst to convert 3β-acetoxycholesta-5,7-diene and tetraphenylcyclopentadiene into the corresponding endoperoxides, and 3β-acetoxycholest-5-ene into 3β-acetoxycholest-5-en-7-one and the corresponding alcohols, it reacts with 1,1-diphenylethylene to give mainly a bromohydrin; bromine radicals arising by photodissociation of the PhSeBr are implicated as the active intermediates.