96212-87-2

Upstream product

• 97-93-8 triethylaluminum 
• 501-65-5 diphenyl acetylene 
• 96-10-6 diethylaluminium chloride 
• 557-20-0 diethylzinc 

Downstream Products

• 1232679-76-3 (E)-N-(1,2-diphenylbut-1-enyl)-N-methylaniline 
• 1232679-71-8 (E)-N-(1,2-diphenylbut-1-enyl)-N-phenylaniline 
• 1232679-75-2 (E)-N-(1,2-diphenylbut-1-enyl)-N-ethylaniline 
• 1232679-80-9 (E)-4-chloro-N-(4-chlorophenyl)-N-(1,2-diphenylbut-1-enyl)aniline 
• 1232679-77-4 (E)-N-(1,2-diphenylbut-1-enyl)-N-phenylnaphthalen-1-amine 
• 69967-79-9 ICI 77949 
• 13002-65-8 (E)-tamoxifen 
• 10540-29-1 tamoxifen 
• 6462-19-7 (E)-[1-(4-methoxyphenyl)but-1-ene-1,2-diyl]dibenzene 
• 905973-01-5 2,3-diphenylpent-2-enoic acid methyl ester 

Relevant academic research and scientific papers

DEVELOPMENT OF NEW SELECTIVE ESTROGEN RECEPTOR MODULATORS

The present disclosure concerns a new class of selective estrogen receptor modulators (SERMs). The disclosure also includes the identification of a previously unknown membrane associated estrogen receptor. Methods for making and using the disclosed SERMs

A Nickel-catalyzed carbozincation of aryl-substituted alkynes

The addition of dialkylzincs or diphenylzinc to substituted phenylacetylenes in the presence of catalytic amounts of Ni(acac)2 in THF:NMP mixtures produces syn-carbozincation products with good to excellent regio- and stereoselectivity. After quenching with an electrophile (iodine, acyl chloride, allyl bromide) tetrasubstituted olefines are obtained in good to satisfactory yields. An intramolecular version of the reaction is possible using a terminal triple bond bearing an iodine at a remote position. More substituted iodo-alkynes furnish only reductive elimination products. An application to a stereoselective synthesis of (Z)-tamoxifen (Z:E > 99:1) has been developed.

Synthesis of cis- and trans-tamoxifen

The synthesis of cis-tamoxifen, non antiestrogenic tetrasubstituted olefin, was achieved via carboalumination of diphenylacetylene as a key step.Conversion to the antiestrogenic trans-tamoxifen was achieved by facile cis-trans isomerization of the corresponding phenol by acid or catalysts.

Stereospecific Synthesis of (Z)-Tamoxifen via Carbometalation of Alkynylsilanes

A sterospecific synthesis of (Z)-tamoxifen, a tetrasubstituted alkene with antiestrogenic activity, is described.The key reaction that establishes the olefin stereochemistry is a carbometalation of phenyl(trimethylsilyl)acetylene with diethylaluminum chloride-titanocene dichloride.A key intermediate that would lead to (E)-tamoxifen was also prepared in an analogous stereospecific manner.