10218-59-4

Upstream product

• 2043-61-0 cyclohexanecarbaldehyde 
• 108-95-2 phenol 
• 108-94-1 cyclohexanone 
• 90-96-0 bis(p-methoxyphenyl)methanone 
• 10218-57-2 1,1'-(cyclohexylidenemethylene)bis(4-methoxy)benzene 
• 88837-75-6 1,1'-(cyclohexylmethylene)bis(4-methoxy)benzene 

Downstream Products

• 1227162-20-0 C₂₁H₂₄O₃ 
• 10218-58-3 C₂₃H₂₆O₄ 

Relevant academic research and scientific papers

Estrogenic activity of bis(4-hydroxyphenyl)methanes with cyclic hydrophobic structure

Monoalkylated bis(4-hydroxyphenyl)methanes (e.g., 1) are reported to show weak binding affinity for estrogen receptor (ER). We hypothesized that introduction of appropriately located hydrophobic substituents in these compounds would increase the binding affinity. Indeed, we found that bis(4-hydroxyphenyl)methane bearing a 3,3-dimethylcyclohexyl group (7) shows potent ERα binding affinity, comparable to that of estradiol. Bulkier substituents could be introduced at the 3,3-position without decreasing the affinity. However, the position of the substituents was critical: the 4,4-dimethylcyclohexyl derivative (2) showed very weak binding affinity. The compounds with high ER-binding affinity showed predominantly agonistic activity, together with weak antagonistic activity at high concentration, in cell proliferation assay with human breast cancer cell line MCF-7. Further structure-function studies of these compounds and their derivatives might lead to the development of more selective and potent estrogen receptor modulators.

Linear free-energy relationship analysis of a catalytic desymmetrization reaction of a diarylmethane-bis(phenol)

(Figure presented) Linear free-energy relationships have been found for enantioselectivity and various steric parameters in an enantioselective desymmetrization of symmetrical bis(phenol) substrates. The potential origin of this observation and the role of different steric parameters are discussed.

Metal cation-exchanged montmorillonite (Mn+-mont)-catalysed aromatic alkylation with aldehydes and ketones

The alkylation of aromatic compounds with aldehydes and ketones in the presence of a variety of metal cation-exchanged montmorillonites (Mn+-mont; Mn+ = Zr4+, Al3+, Fe3+, Zn2+, H+, Na+) has been investigated. Al3+- and Zr4+-Monts are revealed to be effective as catalysts, while no reaction takes place with Na+-mont. Al3+-Mont-catalysed alkylation of phenol with several aldehydes produces mainly or almost solely the corresponding gem-bis(hydroxyphenyl)alkanes (bisphenols) in good yields, while that with several ketones affords selectively the corresponding alkylphenols in moderate to good yields. The alkylation always occurs at the carbonyl carbon without any skeletal rearrangement and the kind of products depends much on the steric hindrance of an electrophilic intermediary carbocation. The alkylation of anisole, veratrole and p-cresol proceeds well, while that of toluene, benzene, chlorobenzene and nitrobenzene scarcely occurs.