60043-08-5Relevant academic research and scientific papers
Synthesis and study of antiviral and anti-radical properties of aminophenol derivatives
Shadyro,Ksendzova,Polozov,Sorokin,Boreko,Savinova,Dubovik,Bizunok
, p. 2420 - 2423 (2008/09/21)
A number of sterically-hindered o-aminophenol derivatives have been synthesized, and their antiviral activity in parallel with reactivity towards commonly encountered free-radical intermediates was investigated. Of the compounds tested, the highest activity in suppressing replication of Herpes simplex type l viruses was displayed by N-acyl and N-aryl derivatives of 4,6-di-tert-butyl-2-aminophenol, which were able to interact with organic free radicals and, at the same time, manifested low reactivity towards reactive oxygen species.
Hypervalent and binuclear silicon and germanium derivatives from bis-(3,5-di-tert-butyl-2-phenol)-oxamide
Jiménez-Pérez, Víctor M.,Camacho-Camacho, Carlos,Ramos-Organillo, ángel,Ramírez-Trejo, Raúl,Pe?a-Hueso, Adrián,Contreras, Rosalinda,Flores-Parra, Angelina
, p. 5549 - 5554 (2008/03/18)
The reactions of bis-(3,5-di-tert-butyl-2-phenol)oxamide (1) with Cl2SiR2 (Me or Ph) or Cl2GeR2 (Me, nBu or Ph) in THF provided binuclear pentacoordinated silicon and germanium compounds: bis-(3,5-di-tert-butyl-2-oxo-phenyl)-oxamido-bis-dimethylsilane (2), bis-(3,5-di-tert-butyl-2-oxo-phenyl)-oxamido-bis-diphenylsilane (3), bis-(3,5-di-tert-butyl-2-oxo-phenyl)-oxamido-bis-dimethylgermane (4), bis-(3,5-di-tert-butyl-2-oxo-phenyl)-oxamido-bis-di-n-butylgermane (5) and bis-(3,5-di-tert-butyl-2-oxo-phenyl)-oxamido-bis-diphenylgermane (6). The mono-nuclear tetracoordinated silicon compounds N-acetyl-bis-(3,5-di-tert-butyl-2-oxo-phenyl)-amide-bis-(dimethylsilane) (8) and N-acetyl-bis-(3,5-di-tert-butyl-2-oxo-phenyl)-amide-bis-(diphenylsilane) (9) were synthesized from N-(3,5-di-tert-butyl-2-phenol)acetamide (7) and Cl2SiR2 (R = Me and Ph). Comparison of the 29Si NMR chemical shifts of the penta- (2 and 3) and tetracoordinated (8 and 9) silicon compounds provided information about the intramolecular coordination of the carbonyl group to the silicon atom. Compounds 3 and 6 were characterized by single-crystal X-ray analyses. They have planar hexacyclic structures where the central atoms present distorted tbp geometries with one nitrogen and two carbon atoms in equatorial positions and two oxygen atoms in apical positions.
Cyclodienones. Part 6. Preparation of 4-Azido-2,4,6-tri-t-butylcyclohexa-2,5-dienone and its Thermal, Photo-, and Acid-catalyzed Decomposition
Fukata, Gouki,Sakamoto, Naoya,Tashiro, Massashi
, p. 2841 - 2848 (2007/10/02)
Preparation of 4-azido-2,4,6-tri-t-butylcyclohexa-2,5-dienone (3) from 4-bromo-2,4,6-tri-t-butylcyclohexa-2,5-dienone (1) and sodium azide is described.Treatment of (3) with concentrated sulphuric acid afforded 2,6-di-t-butyl-p-benzoquinone (7) in 75percent yield, while the reaction at -10 deg C in chloroform solution gave a tri-t-butylazepinone (5) and 3,5-di-t-butyl-o-benzoquinone (8).Photolysis of (3) in benzene afforded 2,4-di-t-butylcyclopenta-2,4-dienone (11), which was isolated as the dimer (12).Thermolysis of (3) in boiling toluene gave 6-amino-2,4-di-t-butylphenol (17), 2,4,6,8-tetra-t-butyl-1H-phenoxazin-1-one (21), and 2-cyano-9,9a-dihydro-3,5,7,9a-tetra-t-butylcyclopentabenzoxazin-1(3aH)-one (22) in 15, 15 and 48percent yields, respectively.When the thermolysis was carried out with very low reagent concentrations, 5-cyano-2,4-di-t-butylcyclopenta-2,4-dienone (23), in addition to the phenol (17), was obtained.The compound (23) was also obtained by thermolysis of (3) in boiling acetic anhydride and in boiling toluene containing acetic anhydride.The reaction pathway for the formation of compounds (17), (22), and (23) on thermolysis of the azide (3) is also discussed.
CYCLOHEXADIENONES. 3. PREPARATION AND THERMAL DECOMPOSITION OF 4-AZIDO-2,4,6-TRI-t-BUTYL-2,5-CYCLOHEXADIEN-1-ONE
Fukata, Gouki,Sakamoto, Naoya,Tashiro, Masashi
, p. 1259 - 1264 (2007/10/02)
Reaction of 4-bromo-2,4,6-tri-tert-butyl-2,5-cyclohexadien-1-one (1) with sodium azide was carried out in DMF to afford 4-azido-2,4,6,-tri-tert-butyl-2,5-cyclohexadien-1-one (4) in 85percent yield.Thermal decomposition of 4 in boiling toluene gives 6-amino-2,4-di-tert-butylphenol (5), 2,4,6,8-tetra-tert-butylphenoxazin-1-one (7) and 2,4,6,8a-tetra-tert-butyl-7-cyano-8-oxo-5a,8a-dihydrocyclopentenobenzoxazine (8).However, the termal decomposition of 4 was carried out under highly diluted conditions to afford 5 and 2,4-di-tert-butyl-5-cyano-2,4-cyclopentadien-1-one (9)in 48 and 50percent yields, respectively.It was also found that the thermal decomposition of 4 in boiling toluene in the presence of acetic anhydride afforded 6-acetoamido-2,4-di-tert-butylphenol (6) and 9 in 47 and 50percent yields, respectively.The reaction pathways of the formation of 5, 8 and 9 were proposed in the present paper.
