H-5'); 6.94 (2H, d, J = 8.6, H-3,5 Ar); 7.38 (2H, d, J = 8.6, H-2,6 Ar); 7.41-7.49 (3H, m, H Ph); 7.81 (1H, d,
J = 15.5, α-CH); 7.85-7.92 (2H, m, H Ph); 8.00 (1H, d, J = 15.5, β-CH); 8.27 (1H, d, J = 9.0, H-6'). Mass
spectrum, m/z: 361.4 [M+H]+, 383.5 [M+Na]+, 400.8 [M+K]+. Found, %: C 76.34; H 5.61. C23H20O4.
Calculated, %: C 76.65; H 5.59.
1
3-[4-(4-Methoxybenzyloxy)phenyl]-3-phenyl-2-propеn-1-one (1k). H NMR spectrum, δ, ppm (J, Hz):
3.74 (3H, s, OCH3); 5.09 (2H, s, CH2); 6.90-7.01 (4H, m, H Ar); 7.08 (2H, d, J = 8.8, H-2,6 Ar); 7.38 (2H, d,
J = 8.8, H-2,6 Ar); 7.54 (1H, td, J = 7.6, J = 1.7, H-5'); 7.81 (1H, d, J = 15.5, α-CH); 7.84-7.92 (3H, m, Н-3',4',
β-CH); 8.24 (1H, dd, J = 8.6, J = 1.6, H-6'). Mass spectrum, m/z: 361.4 [M+H]+, 400.8 [M+K]+. Found, %:
C 76.69; H 5.65. C23H20O4. Calculated, %: C 76.65; H 5.59.
Synthesis of the 3-Hydroxy-2-phenyl-4H-chromen-4-one Derivatives 4a-l (General Method). A
50% H2O2 solution (0.28 ml, 5 mmol) was added dropwise with stirring to a solution of the chalcone 1a-l
(1 mmol) and NaOH (0.20 g, 5 mmol) in 80% aqueous МеОН (20 ml). The solution was stirred for 2-15 h.
After the reaction completion, the mixture was neutralized with 5% НСl to рН 4-6 and evaporated at reduced
pressure and at temperature not exceeding 40°С. The residue was filtered off and recrystallized from aqueous
MeOH. Additional purification by repeated crystallization from THF–hexane or 2-PrOH–hexane mixtures was
needed for obtaining pure samples of compounds 4d,e. The yield of these compounds was determined by
1H NMR spectroscopy as the combined content of the title compound in all fractions.
1
7-(Benzyloxy)-3-hydroxy-2-phenyl-4H-chromen-4-one (4f). H NMR spectrum, δ, ppm (J, Hz): 5.20
(2H, s, CH2); 7.13 (1H, d, J = 8.7, H-6); 7.34-7.38 (2H, m, H Ph); 7.46-7.55 (7H, m, H Ph); 7.74 (1H, d, J = 8.7,
H-5); 8.22 (2H, d, J = 7.6, H-2',6'); 9.50 (1H, br. s, OH). Mass spectrum, m/z: 345.2 [M+H]+, 367.2 [M+Na]+.
Found, %: C 76.90; H 4.72. C22H16O4. Calculated, %: C 76.73; H 4.68.
1
3-Hydroxy-7-(4-methoxybenzyloxy)-2-phenyl-4H-chromen-4-one (4g). H NMR spectrum, δ, ppm
(J, Hz): 3.75 (3H, s, OCH3); 5.17 (2H, s, CH2); 6.95 (2H, d, J = 8.6, H-3,5 Ar); 7.07 (1H, dd, J = 9.0, J = 2.4,
H-6); 7.36 (1H, d, J = 2.3, H-8); 7.42 (2H, d, J = 8.6, H-2,6 Ar); 7.48 (1H, t, J = 7.3, H-4'); 7.52-7.57 (2H, m,
H-3',5'); 7.99 (1H, d, J = 8.9, H-5); 8.19 (2H, d, J = 8.4, H-2',6'); 9.42 (1H, br. s, OH). Mass spectrum, m/z:
375.5 [M+H]+, 397.5 [M+Na]+, 413.5 [M+K]+. Found, %: C 73.56; H 4.87. C23H18O5. Calculated, %: C 73.79;
H 4.85.
3-Hydroxy-2-[4-(4-methoxybenzyloxy)phenyl]-4H-chromen-4-one (4k). 1H NMR spectrum, δ,
ppm (J, Hz): 3.77 (3H, s, OCH3); 5.13 (2H, s, CH2); 6.97 (2H, d, J = 8.1, H-3,5 Ar); 7.21 (2H, d, J = 8.6,
H-3',5'); 7.43 (2H, d, J = 8.1, H-2,6 Ar); 7.47 (1H, t, J = 7.2, H-6); 7.74-7.83 (2H, m, H-7,8); 8.12 (1H, d,
J = 7.8, H-5); 8.21 (2H, d, J = 8.5, H-2',6'); 9.46 (1H, br. s, OH). Mass spectrum, m/z: 375.02 [M+H]+, 396.98
[M+Na]+, 412.99 [M+K]+. Found, %: C 73.69; H 4.86. C23H18O5. Calculated, %: C 73.79; H 4.85.
Quantum-chemical calculations were performed with the МОРАС 2009 software package [34].
Preliminary calculations of molecular geometry at equilibrium and estimation of electron density distribution
were performed with the semiempirical RM1 method [35]. Further geometry optimization and calculation of
thermodynamic characteristics (the entalphy and enthropy of the studied compounds and intermediates) was
performed with the РМ6 method [26]. Both methods were used in the software package. The nonspecific
interactions of the reaction system with aqueous medium were accounted for by using the COSMO method [36].
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