1,3,8-Trihydroxy-11H-benzofuro[2,3-b][1]benzopyran-11-one synthesis
- Product Name:1,3,8-Trihydroxy-11H-benzofuro[2,3-b][1]benzopyran-11-one
- CAS Number:98094-87-2
- Molecular formula:C15H8O6
- Molecular Weight:284.22
1156-78-1
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Yield:98094-87-2 66%
Reaction Conditions:
with 2,3-dicyano-5,6-dichloro-p-benzoquinone in tetrahydrofuran at 60; for 0.75 h;Inert atmosphere;
Steps:
4.2.6. Lupinalbin A (3)23
DDQ (79.0 mg, 0.349 mmol) was added under N2 to a solution of 4 (100 mg, 0.35 mmol) in THF (20 mL). The reaction mixture was heated to 60 °C with stirring for 15 min. Additional DDQ (79.0 mg, 0.349 mmol) was added to the mixture and stirring was continued at the same temperature for 30 min. The solvent was evaporated and the crude mixture purified by column chromatography using Hex/EtOAc as eluent to give coumaronochromone 3 (66 mg, 66%) as a white solid: 3 was recrystallized from Hex/EtOAc (1:4) to afford white needle-like crystals, which decomposed at 278.4-280.0 °C (lit.refPreviewPlaceHolder14 mp >300 °C); IR (neat) νmax 3327, 3101, 2922, 1622, 1436, 1029, 822 cm-1; 1H NMR (CD3OD, 400 MHz) δ 7.75 (1H, d, J=8.4 Hz, H-6'), 6.99 (1H, d, J=1.9 Hz, H-3'), 6.89 (1H, dd, J=1.9 and 8.4 Hz, H-5'), 6.46 (1H, d, J=2.0 Hz, H-8), 6.27 (1H, d, J=2.0 Hz, H-6); 13C NMR (CD3OD, 100 MHz) δ 180.0 (C, C-4), 166.2 (C, C-2), 165.2 (C, C-7), 164.0 (C, C-5), 157.8 (C, C-4'), 156.6 (C, C-8a), 151.9 (C, C-2'), 122.5 (CH, C-6'), 115.2 (CH, C-5'), 114.7 (C, C-1'), 104.5 (C, C-4a), 100.9 (CH, C-6), 99.5 (C, C-3), 98.7 (CH, C-3'), 95.8 (CH, C-8); HRMS-ESI m/z [M-H]- calcd for C15H7O6 283.0243, found 283.0239.
References:
Selepe, Mamoalosi A.;Drewes, Siegfried E.;Van Heerden, Fanie R. [Tetrahedron,2011,vol. 67,# 45,p. 8654 - 8658] Location in patent:experimental part
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