109640-27-9

Upstream product

• 4286-15-1 (S)-2-phenylbutyric acid 
• 100-66-3 methoxybenzene 
• 4160-51-4 1-(4-methoxyphenyl)-1-butanone 
• 144930-50-7 mesityl(phenyl)iodonium triflouromethanesulfonate 
• 90-27-7 2-Phenylbutyric acid 

Downstream Products

• 109640-29-1 (1R,2S)-(-)-1-(4-methoxyphenyl)-1,2-diphenyl-1-butanol 
• 109640-36-0 1-[4-((1R,2R)-1,2-Diphenyl-butyl)-phenoxy]-2,3,5,6-tetrafluoro-4-trifluoromethyl-benzene 
• 109640-37-1 1-[4-((1S,2R)-1,2-Diphenyl-butyl)-phenoxy]-2,3,5,6-tetrafluoro-4-trifluoromethyl-benzene 
• 109717-24-0 (1S,2R)-1-<4-<2-(dimethylamino)ethoxy>phenyl>-1,2-diphenylbutane 
• 6462-61-9 1-(4-methoxyphenyl)-1,2-diphenylbutane 
• 6462-60-8 4-((1S,2R)-1,2-Diphenyl-butyl)-phenol 
• 6462-60-8 4-((R)-1,2-Diphenyl-butyl)-phenol 

Relevant academic research and scientific papers

Enantioselective α-Arylation of Ketones via a Novel Cu(I)-Bis(phosphine) Dioxide Catalytic System

A novel catalytic system based on copper(I) and chiral bis(phosphine) dioxides is described. This allows the arylation of silyl enol ethers to access enolizable α-arylated ketones in good yields and enantiomeric excess up to 95%. Noncyclic ketones are amenable substrates with this method, which complements other approaches based on palladium catalysis. Optimization of the ligand structure is accomplished via rational design driven by correlation analysis. Preliminary mechanistic hypotheses are also evaluated in order to identify the role of chiral bis(phosphine) dioxides.

Synthesis, Conformational Considerations, and Estrogen Receptor Binding of Diastereoisomers and Enantiomers of 1-phenyl>-1,2-diphenylbutane (Dihydrotamoxifen)

As part of a study into nonisomerizable antiestrogens, the diastereoisomeric dihydrotamoxifens 7 and 8 were prepared by catalytic transfer hydrogenation of (Z)- and (E)-tamoxifen and were shown by NMR spectrometry to exist in preferred conformations with hydrogen atoms in an antiperiplanar relationship.The corresponding 4-hydroxy derivatives 9 and 10 were prepared from hydrogenated precursors of (Z)- and (E)-4-hydroxytamoxifen.The relative binding affinities (RBA) of the compounds to estrogen receptors are consistent with the assigned conformations and parallel reported data on derivatives of the nonsteroidal estrogen hexestrol.The growth-inhibitory activity against the MCF-7 human breast cancer cell line in vitro was for 10 comparable to that of 4-hydroxytamoxifen, although increasing the concentration from 10-8 to 10-6 M did not significantly improve the growth inhibition.The derivative 9 analogous to (E)-4-hydroxytamoxifen antagonized the growth-stimulating effect of added estradiol and is therefore also an antiestrogen but at low concentration (10-8 M) in the absence of estradiol, MCF-7 cell growth was stimulated, indicating an estrogenic influence.The enantiomers of the dihydrotamoxifen 8 were individually prepared from the resolved enantiomers of 2-phenylbutanoic acid, the key reaction step being a lithium-ammonia reduction of the 1-(4-methoxyphenyl)-1,2-diphenyl-1-butanol to generate the triphenylbutane.The enantiomers of 8 gave identical RBA values in cytosol.