59875-94-4

Upstream product

• 601-75-2 ethylmalonic acid 
• 557-20-0 diethylzinc 
• 120-46-7 1,3-diphenylpropanedione 
• 98-88-4 benzoyl chloride 
• 495-40-9 propiophenone 
• 100-52-7 benzaldehyde 
• 3282-32-4 2-diazo-acetophenone 
• 60669-63-8 2-ethyl-1,3-diphenyl-3-hydroxypropan-1-one 
• 98-86-2 acetophenone 
• 93-89-0 benzoic acid ethyl ester 
• 62961-62-0 (Z)-3-hydroxy-1,3-diphenyl-2-propen-1-one 
• 75-03-6 ethyl iodide 
• 66498-51-9 α,α-dibromobutyrophenone 
• 55552-69-7 2-ethylmalonyl dichloride 

Downstream Products

• 495-40-9 propiophenone 
• 65-85-0 benzoic acid 
• 100-52-7 benzaldehyde 
• 625096-50-6 (2S,3R)-1,3-diphenyl-2-ethyl-3-hydroxy-1-propanone 
• 4971-80-6 ethyl N-benzoylcarbamate 
• 1204746-39-3 C₂₁H₁₇N₃O₂S 
• 75621-09-9 α-diazobutyrophenone 
• 1229927-41-6 (1,10-phenanthroline)bis(2-ethyl-1,3-diphenyl-1,3-propanedionato)nickel(II) 
• 1229927-39-2 (2,2'-bipyridine)bis(2-ethyl-1,3-diphenyl-1,3-propanedionato)nickel(II) 
• 59875-98-8 4-ethyl-1-methyl-3,5-diphenyl-1H-pyrazole 
• 137743-32-9 9-(4-Ethyl-3,5-diphenyl-pyrazol-1-yl)-nonanoic acid 
• 62625-79-0 3,5-diphenyl-4-ethyl-1H-pyrazole 

Relevant academic research and scientific papers

Oxidative umpolung ?±-alkylation of ketones

We disclose a hypervalent iodine mediated ?±-alkylative umpolung reaction of carbonyl compounds with dialkylzinc as the alkyl source. The reaction is applicable to all common classes of ketones including 1,3-dicarbonyl compounds and regular ketones via their lithium enolates. The ?±-alkylated carbonyl products are formed in up to 93% yield. An ionic mechanism is inferred based on meticulous analysis, NMR studies, trapping and crossover experiments, and computational studies.

SAR-based optimization of 2-(1H-pyrazol-1-yl)-thiazole derivatives as highly potent EP1 receptor antagonists

We describe a medicinal chemistry approach for generating a series of 2-(1H-pyrazol-1-yl)thiazoles as EP1 receptor antagonists. To improve the physicochemical properties of compound 1, we investigated its structure-activity relationships (SAR).

Base-free two-step synthesis of 1,3-diketones and β-ketoesters from α-diazocarbonyl compounds, trialkylboranes, and aromatic aldehydes

We describe a convergent, base-free two-step synthesis of 1,3-diketones and β-ketoesters from α-diazocarbonyl compounds, trialkylboranes, and aromatic aldehydes in a three-component process. The synthetic potential of this protocol was underscored by the

Enantioselective borohydride reduction catalyzed by optically active cobalt complexes

The highly enantioselective borohydride reduction of aromatic ketones or imines to the corresponding alcohols was developed in the presence of a catalytic amount of an optically active cobalt(II) complex catalyst. This enantioselective reduction is carried out using a precisely premodified borohydride with alcohols such as tetrahydrofurfuryl alcohol, ethanol and methanol. High optical yields are obtained by choosing the appropriate alcohol as modifiers and a suitable β-ketoiminato ligand of the catalyst. The enantioselective borohydride reduction has been successfully applied to the preparation of optically active 1,3-diols, the stereoselective reduction of diacylferrocenes, and dynamic and/or kinetic resolution of 1,3-dicarbonyl compounds.

Pyrazole ligands: Structure - Affinity/activity relationships and estrogen receptor-α-selective agonists

We have found that certain tetrasubstituted pyrazoles are high-affinity ligands for the estrogen receptor (ER) (Fink et al. Chem. Biol. 1999, 6, 205-219) and that one pyrazole is considerably more potent as an agonist on the ERα than on the ERβ subtype (Sun et al. Endocrinology 1999, 140, 800-804). To investigate what substituent pattern provides optimal ER binding affinity and the greatest enhancement of potency as an ERα-selective agonist, we prepared a number of tetrasubstituted pyrazole analogues with defined variations at certain substituent positions. Analysis of their binding affinity pattern shows that a C(4)-propyl substituent is optimal and that a p-hydroxyl group on the N(1)-phenyl group also enhances affinity and selectivity for ERα. The best compound in this series, a propylpyrazole triol (PPT, compound 4g), binds to ERα with high affinity (ca. 50% that of estradiol), and it has a 410-fold binding affinity preference for ERα. It also activates gene transcription only through ERα. Thus, this compound represents the first ERα-specific agonist. We investigated the molecular basis for the exceptional ERα binding affinity and potency selectivity of pyrazole 4g by a further study of structure-affinity relationships in this series and by molecular modeling. These investigations suggest that the pyrazole triols prefer to bind to ERα with their C(3)-phenol in the estradiol A-ring binding pocket and that binding selectivity results from differences in the interaction of the pyrazole core and C(4)-propyl group with portions of the receptor where ERα has a smaller residue than ERβ. These ER subtype-specific interactions and the ER subtype-selective ligands that can be derived from them should prove useful in defining those biological activities in estrogen target cells that can be selectively activated through ERα.

REACTIONS OF POLYHALO FUNCTIONAL COMPOUNDS WITH METALS AND ELECTROPHILIC REAGENTS. XVI. CHEMICAL BEHAVIOR OF α,α-DIBROMO KETONES IN THE REFORMATSKII REACTION

Geminal α,α-dibromo ketones react with zinc and carbonyl compounds.Depending on the structures of the reactants, the nature of the solvent, and the reaction conditions, α,β-unsaturated ketones, α,β-epoxy ketones, or α-alkyl-β-diketones or their mixtures are formed.

Structure-Activity Relationships Associated with 3,4,5-Triphenyl-1H-pyrazole-1-nonanoic Acid, a Nonprostanoid Prostacyclin Mimetic

A series of phenylated pyrazoloalkanoic acid derivatives were synthesized and evaluated as inhibitors of ADP-induced human platelet aggregation. 3,4,5-Triphenyl-1H-pyrazole-1-nonanoic acid (8d), with an IC50 of 0.4 μM, was the most potent inhibitor identi