5424-88-4

Upstream product

• 917-64-6 methyl magnesium iodide 
• 75-16-1 methylmagnesium bromide 
• 63785-35-3 2,3-bis-(4-methoxy-phenyl)-valeronitrile 
• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 
• 42762-48-1 (E)-2-(4-methoxyphenyl)pent-2-enal 
• 506-82-1 dimethylcadmium 

Downstream Products

• 101564-54-9 3,4-bis-(4-hydroxy-phenyl)-hexan-2-one 
• 53530-34-0 3,4-bis-(4-methoxy-phenyl)-hexan-2-ol 
• 84-16-2 hexestrol 
• 83303-82-6 (3R*,4S*)-3,4-bis(4-hydroxyphenyl)-2-hexanone 
• 28231-25-6 meso-hexestrol dimethyl ether 

Relevant academic research and scientific papers

Regioselective and Stereoselective Heck-Matsuda Arylations of Trisubstituted Allylic Alkenols and Their Silyl and Methyl Ether Derivatives to Access Two Contiguous Stereogenic Centers: Expanding the Redox-Relay Process and Application in the Total Synthesis of meso-Hexestrol

Novel palladium-catalyzed redox-relay Heck arylation reactions of trisubstituted allylic alkenols were developed employing silyl and methyl ethers. The reactions proceeded under mild conditions in moderate to high yields in an excellent anti diastereoselectivity to form α,β-disubstituted methyl ketones containing two contiguous stereocenters. The new redox-relay arylations using silyl and methyl ethers of the starting alkenols demonstrate that the presence of a free hydroxyl group is not a sine qua non condition for an effective redox-relay process as previously thought. Deuterium-labeled alkenols 2-d-10a, 2-d-10b, and 2-d-10c permitted tracking the palladium-hydride reinsertion steps in the conversion of the starting free alcohols, silyl, and methyl ethers into the corresponding methyl ketone 3-d-11a, with >98% deuterium retention. Moreover, the synthetic potential of the method was demonstrated with a straightforward synthesis of the meso-hexestrol in 4 steps, in 41% overall yield from alkenol 10a.

Nonsteroidal Estrogens: Synthesis and Estrogen Receptor Binding Affinity of Derivatives of (3R*,4S*)-3,4-Bis(4-hydroxyphenyl)hexane (Hexestrol) and (2R*,3S*)-2,3-Bis(4-hydroxyphenyl)pentane (Norhexestrol) Functionalized on the Side Chain

A series of nonsteroidal, side-chain functionalized estrogens based on (3R*,4S*)-3,4-bis(4-hydroxyphenyl)hexane (hexestrol) and (2R*,3S*)-2,3-bis(4-hydroxyphenyl)pentane (norhexestrol) has been prepared; these include amide, diazo ketone, ester, alcohol, ketone, fluoro,bromo, iodo, and saturated hydrocarbon derivatives.Analysis of the binding affinity of these compounds to the uterine estrogen receptor, measured by competitive binding assay, reveals trends that can be related to the steric size, the hydrophobicity, and the hydrogen bond accepting character of the side-chain substituents.Comparison of binding affinities between norhexestrol and hexestrol derivatives indicates that, in general, the norhexestrols show significantly higher receptor binding affinities, making this series of compounds ideally suited as functional probes for the estrogen receptor.