72277-18-0

Upstream product

• 64-17-5 ethanol 
• 4374-49-6 3-benzyl-3-phenylpropionic acid 
• 100-39-0 benzyl bromide 
• 7381-89-7 ethyl ester of (racemic) 2,3-diphenylcyclopropane-1-carboxylic acid 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 72277-01-1 diethyl 1-trimethylsilyloxy-3-phenyl-2-propenylphosphonate 
• 14371-10-9 (E)-3-phenylpropenal 
• 183678-79-7 3-(benzotriazol-1-yl)-3-ethoxy-1-phenyl-1-propene 
• 136290-37-4 1-((E)-1-Ethoxy-3-phenyl-allyl)-1H-[1,2,4]triazole 
• 1026409-03-9 1-((Z)-1-Ethoxy-3,4-diphenyl-but-1-enyl)-1H-[1,2,4]triazole 
• 451-40-1 phenyl benzyl ketone 
• 36032-75-4 triethyl phosphonoacetate 

Downstream Products

• 143747-70-0 3,4-diphenylbutan-1-ol 
• 939381-82-5 Methanesulfonic acid 3,4-diphenyl-butyl ester 

Relevant academic research and scientific papers

Rhodium Porphyrin Catalyzed Regioselective Transfer Hydrogenolysis of C-C σ-Bonds in Cyclopropanes with iPrOH

A new rhodium porphyrin catalyzed regioselective transfer hydrogenolysis of both activated and unactivated cyclopropanes employing iPrOH as the hydrogen source was discovered. The reaction mechanism for the C-C σ-bond activation of cyclopropanes was identified through an initial radical substitution with rhodium(II) metalloporphyrin radical to give a rhodium porphyrin alkyl, followed by hydrogenolysis with iPrOH to give the corresponding acyclic alkanes and regenerate rhodium(II) metalloporphyrin radical.

Pd-catalyzed cleavage of benzylic nitro bonds: New opportunities for asymmetric synthesis

Without a trace: Benzylic nitroalkanes are reduced to the corresponding parent alkanes in good yields by using a simple procedure involving heterolytic C-N bond cleavage (see scheme). Traceless removal of the nitro group leaves behind a stereogenic center that may otherwise be difficult to install. This reaction significantly expands the scope of building blocks that can be accessed. (Chemical Equation Presented)

Benzotriazole- and 1,2,4-triazole-stabilized allylic anions: Applications in syntheses of functionalized α,β-unsaturated ketones, γ-lactones, γ-lactams, and β-substituted esters

Deprotonated 1-(benzotriazol-1-yl)-1-ethoxy-2-hexene (7) reacted with alkyl halides, aldehydes, ketones, imines, and α,β-unsaturated esters to give exclusively the α-alkylated products 8a-c, 10a,b, 12, 14, 16, and 18a,b, respectively. Without isolation, these products were hydrolyzed under mild conditions to generate the corresponding simple or functionalized α,β-unsaturated ketenes 9a-c, 11a,b, 13, 15, 17, and 19a,b. Similar reactions with the phenyl-substituted analog 3-(benzotriazol-1-yl)-3-ethoxy-1-phenyl-1-propene (21) also gave the analogous α-products, but they were accompanied by small amounts of the γ-products in most cases. By contrast, deprotonation of the corresponding triazole derivative 29 with butyllithium followed by reactions with alkyl halides, aldehydes, ketones, or imines yielded exclusively γ-alkylated adducts 32, 34, 36, 38, 40, and 42. Intermediates 32, 34, 36, 38, 40, and 42 were readily converted into β-substituted esters 33a-c, γ-lactones 35a,b, 39, 41, and 43, and γ-lactams 37a-c on hydrolysis.

Structure-Activity Studies on Benzhydrol-Containing Nipecotic Acid and Guvacine Derivatives as Potent, Orally-Active Inhibitors of GABA Uptake

The introduction of lipophilic groups onto the ring nitrogen of nipecotic acid and guvacine, two known GABA uptake inhibitors, afforded potent, orally-active anticonvulsant drugs.A series of compounds is reported which explores the structure-activity relationships (SAR) in this series.Among the areas explored: side-chain SAR (aromatic-, heterocyclic-, and tricyclic-containing side chains) and modifications to the tetrahydropyridine ring.The benzhydrol ether-containing side chains afforded the most potent compounds with several exhibiting in vitro IC50 values for GABA uptake of 1 μM (including 5, Table I; 37, 43, Table IV; and 44, Table V).Compound 44 was selected for extensive evaluation and subsequently progressed to Phase 1 clinical trials with severe adverse effects seen after single dose administration to humans.

Silyl Phosphites. XVIII. Versatile Utility of α-(Trimethylsilyloxy)-alkylphosphonates as Key Intermediates for Transformation of Aldehydes into Several Carbonyl Derivatives

Carbonyl addition compounds of diethyl trimethylsilyl phosphite (DTMSP) with aldehydes were converted, by treatment with lithium diisopropylamide (LDA) followed by the successive alkylation and alkaline hydrolysis, to carbonyl derivatives involving aldehydes, unsymmetrical ketones, β,γ-unsaturated ketones, and carboxylic acids. β-Substituted carboxylic esters and γ-substituted lactones were prepared by use of the carbonyl addition compounds of DTMSP with α,β-unsaturated aldehydes.