109640-28-0

Basic information

• Product Name: (1S,2R)-(+)-1-(4-methoxyphenyl)-1,2-diphenyl-1-butanol
• Synonyms: (1S,2R)-(+)-1-(4-methoxyphenyl)-1,2-diphenyl-1-butanol
• CAS NO: 109640-28-0
• Molecular Weight: 332.442
• Mol File: 109640-28-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (1S,2R)-(+)-1-(4-methoxyphenyl)-1,2-diphenyl-1-butanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R)-(+)-1-(4-methoxyphenyl)-1,2-diphenyl-1-butanol(109640-28-0)
• EPA Substance Registry System: (1S,2R)-(+)-1-(4-methoxyphenyl)-1,2-diphenyl-1-butanol(109640-28-0)

Safety Data

• Hazardous Substances Data: 109640-28-0(Hazardous Substances Data)

Upstream product

• 78423-10-6 1-(4-methoxyphenyl)-2-phenylbutan-1-one 
• 100-58-3 phenylmagnesium bromide 
• 121-98-2 methyl 4-methoxybenzoate 
• 696-62-8 para-iodoanisole 
• 16282-16-9 1,2-diphenyl-butan-1-one 
• 938-79-4 (2R)-2-phenylbutanoic acid 
• 90-27-7 2-Phenylbutyric acid 
• 100-66-3 methoxybenzene 
• 109640-26-8 (R)-(-)-1-(4-methoxyphenyl)-2-phenyl-1-butanone 
• 13139-86-1 4-methoxyphenyl magnesium bromide 

Downstream Products

• 6462-19-7 (E)-[1-(4-methoxyphenyl)but-1-ene-1,2-diyl]dibenzene 
• 6462-18-6 (Z)-(1-(4-methoxyphenyl)but-1-ene-1,2-diyl)dibenzene 
• 69967-78-8 (1-(4-methoxyphenyl)but-1-ene-1,2-diyl)dibenzene 
• 6462-60-8 4-((S)-1,2-Diphenyl-butyl)-phenol 
• 109640-30-4 ((1R,2S)-1-(4-methoxyphenyl)butane-1,2-diyl)dibenzene 
• 109640-31-5 ((1S,2S)-1-(4-methoxyphenyl)butane-1,2-diyl)dibenzene 
• 109640-36-0 1-[4-((1R,2S)-1,2-Diphenyl-butyl)-phenoxy]-2,3,5,6-tetrafluoro-4-trifluoromethyl-benzene 
• 109640-36-0 1-[4-((1S,2S)-1,2-Diphenyl-butyl)-phenoxy]-2,3,5,6-tetrafluoro-4-trifluoromethyl-benzene 
• 109717-23-9 (1R,2S)-1-<4-<2-(dimethylamino)ethoxy>phenyl>-1,2-diphenylbutane 
• 109640-34-8 4-((1R,2S)-1,2-Diphenyl-butyl)-phenol 
• 109640-38-2 1-[4-((1R,2S)-1,2-Diphenyl-butyl)-phenoxy]-2,6-difluoro-3,5-bis-((R)-1-phenyl-ethoxy)-4-trifluoromethyl-benzene 

Relevant articles and documents

Synthesis of Highly Stereodefined Tetrasubstituted Acyclic All-Carbon Olefins via a Syn-Elimination Approach

An efficient synthesis of stereodefined tetrasubstituted acyclic all-carbon olefins has been developed via a bis(2,6-xylyl)phosphate formation of stereoenriched tertiary alcohols, followed by in situ syn-elimination of the corresponding phosphates under mild conditions. This chemistry tolerates a wide variety of electronically and sterically diverse substrates and generates the desired tetrasubstituted olefins in high yields and stereoselectivities (>95:5) in most cases. This stereocontrolled olefin synthesis has been applied to the synthesis of anticancer drug tamoxifen in three steps from commercially available 1,2-diphenylbutan-1-one in 97:3 stereoselectivity and 78% overall yield.

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.