Chromone derivative and synthesis method thereof
A synthetic method and derivative technology, applied in organic chemistry and other fields, can solve the problems of limited substrates and cumbersome synthesis of raw materials, and achieve the effects of simple post-processing, good yield, and simple synthesis
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Embodiment 1
[0028] Example 1: Synthesis of 2-methyl-3-(cis-1-phenyl-2-formyl ethyl) enyl chromone
[0029]
[0030] 1-(2'-bromophenyl)-2-phenylethynyl ketone, ethyl acetoacetate, Cs 2 CO 3 , Fe(ClO 4 ) 3 9H 2 O, N, N-dimethylacetamide, the consumption of raw material is o-bromoacetylenone 1-(2'-bromophenyl)-2-phenylethynyl ketone 0.3mmol, ethyl acetoacetate 0.3mmol, inorganic base ( Cs 2 CO 3 )0.6mmol, solvent 3ml, iron salt (Fe(ClO 4 ) 3 9H 2 O) 0.06mmol, reacted at 100°C for 2 hours to obtain the target product formula (IA), a yellow liquid, and the separation yield was 81%.
[0031] NMR data: 1 H NMR (400MHz, CDCl 3 , Me 4 Si) δ1.02-1.09(m, 3H), 2.13(s, 3H), 3.97-4.03(m, 2H), 6.55(s, 1H), 7.18-7.30(m, 4H), 7.32-7.36(m , 1H), 7.39-7.41(m, 2H), 7.52-7.57(m, 1H), 8.13(d, J=7.2Hz, 1H); 13 C NMR (100.6MHz, CDCl 3 , Me 4 Si): δ13.64, 18.68, 59.95, 117.81, 120.73, 121.28, 123.06, 124.97, 126.35, 126.99, 128.93, 129.88, 133.58, 138.47, 148.55, 156.30, 162.69, 1675.23
[003...
Embodiment 2
[0033] Example 2: Synthesis of 2-methyl-3-(cis-1-4'-chloro-phenyl-2-formyl ethyl) enyl chromone
[0034]
[0035]1-(2'-bromophenyl)-2-(4'-chloro)phenylethynyl ketone, ethyl acetoacetate are selected for o-bromoacetylenone, 1,3-dicarbonyl compound, inorganic base, iron salt and solvent respectively 、Cs 2 CO 3 , Fe(ClO 4 ) 3 9H 2 O, N, N-dimethylacetamide, the amount of raw materials is o-bromoacetylenone 1-(2'-bromophenyl)-2-(4'-chloro)phenylethynyl ketone 0.3mmol, ethyl acetoacetate 0.3mmol, 0.6mmol of inorganic base, 3ml of solvent, and 0.06mmol of iron salt were reacted at 100°C for 3 hours to obtain the target product formula (IB), a yellow liquid, and the separation yield was 72%.
[0036] NMR data: 1 H NMR (400MHz, CDCl 3 , Me 4 Si): δ1.14-1.19(m, 3H), 2.23(s, 3H), 4.05-4.14(m, 2H), 6.61(s, 1H), 7.27-7.32(m, 2H), 7.34-7.39( m, 1H), 7.42-7.46(m, 3H), 7.63-7.67(m, 1H), 8.20(d, J=7.2Hz, 1H); 13 C NMR (100.6MHz, CDCl 3 , Me 4 Si) δ13.57, 18.60, 59.99, 117.78, 1...
Embodiment 3
[0038] Example 3: Synthesis of 2-methyl-3-(cis-1-4'-methyl-phenyl-2-formyl ethyl) enyl chromone
[0039]
[0040] 1-(2'-bromophenyl)-2-(4'-methyl)phenylethynyl ketone, ethyl acetoacetate Esters, Cs 2 CO 3 , Fe(ClO 4 ) 3 9H 2 O, N, N-dimethylacetamide, the amount of raw materials is o-bromoacetylenone 1-(2'-bromophenyl)-2-(4'-methyl)phenylethynyl ketone 0.3mmol, ethyl acetoacetate 0.3mmol of ester, 0.6mmol of inorganic base, 3ml of solvent, and 0.06mmol of iron salt were reacted at 100°C for 3 hours to obtain the target product formula (IC), a yellow liquid, and the separation yield was 75%.
[0041] NMR data: 1 H NMR (400MHz, CDCl 3 , Me 4 Si): δ1.13-1.18(m, 3H), 2.22(s, 3H), 2.32(s, 3H), 4.02-4.14(m, 2H), 6.62(s, 1H), 7.11-7.15(m, 2H), 7.27-7.44(m, 4H), 7.59-7.64(m, 1H), 8.21(d, J=7.6Hz, 1H); 13 C NMR (100.6MHz, CDCl 3 , Me 4 Si): δ13.57, 18.53, 20.76, 59.74, 117.70, 119.50, 121.23, 122.99, 124.81, 126.22, 126.82, 129.58, 133.44, 135.43, 140.11, 148.44, 156.21,...
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