93085-31-5

Upstream product

• 1202160-43-7 2-hydroxy-2-(2-methoxyphenyl)adamantane 
• 94773-25-8 6,12-di(adamantane-22-spiro)-6H,12H-dibenzo[b,f][1,5]dioxocine 
• 700-58-3 2-Adamantanone 
• 578-57-4 2-bromoanisole 

Downstream Products

• 1202160-45-9 2-methoxy-2-(2-hydroxyphenyl)adamantane 
• 1352743-76-0 ethyl 4-{spiro[1,3-benzoxazine-4,2'-adamantane]-2-yl}benzoate 
• 1352743-74-8 2-(4-bromophenyl)spiro[1,3-benzoxazine-4,2'-adamantane] 
• 1352743-73-7 2′-phenylspiro[adamantane-2,4′-benzo[e][1,3]oxazine] 
• 1352743-75-9 2-(4-nitrophenyl)spiro[1,3-benzoxazine-4,2'-adamantane] 
• 1202160-55-1 N-(2-hydroxyethyl)-2-(2-hydroxyphenyl)-2-aminoadamantane 

Relevant academic research and scientific papers

In vitro investigation of the antimicrobial activity of a series of lipophilic phenols and naphthols

Five groups of phenols/naphthols (42 compounds in total) were synthesized and screened against Gram-positive Staphylococcus aureus and Bacillus subtilis, Gram-negative Escherichia coli and Klebsiella pneumoniae, and the fungus Candida albicans. Whereas co

Photochemical formation and chemistry of long-lived adamantylidene-quinone methides and 2-adamantyl cations

(Chemical Equation Presented) Hydroxymethylphenols strategically substituted with the 2-hydroxy-2-adamantyl moiety, AdPh 8-10, were synthesized, and their photochemical reactivity was investigated. On excitation to the singlet excited state, AdPh 8 undergoes intramolecular proton transfer coupled with a loss of H2O giving quinone methide 8QM. The presence of 8QM has been detected by laser flash photolysis (CH3CN-H2O 1:1, τ = 0.55 s) and UV-vis spectroscopy. Singlet excited states of AdPh 9 and 10 in the presence of H2O dehydrate giving 9QM and 10QM. Photochemically formed QMs are trapped by nucleophiles giving the addition products (e.g., Φ for methanolysis of 8 is 0.55). In addition, the zwitterionic 9QM undergoes an unexpected rearrangement involving transformation of the 2-phenyl-2-adamantyl cation into the 4-phenyl-2-adamantyl cation (Φ ～ 0.03). An analogous rearrangement was observed with methoxy derivatives 9a and 10a. Zwitterionic 9QM was characterized by LFP in 2,2,2-trifluoroethanol (τ = 1 μs). In TFE, in the ground state, AdPh 10 is in equilibrium with 10QM, which allowed for recording the 1H and 13C NMR spectra of the QM. Introduction of the adamantyl substituent into the o-hydroxymethylphenol moiety increased the quantum yield of the associated QM formation by up to 3-fold and significantly prolonged their lifetimes. Furthermore, adamantyl substituent made the study of the alkyl-substituted quinone methides easier by LFP by prolonging their lifetimes and increasing the quantum yields of formation. 2009 American Chemical Society.