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Chemical Structure| 20727-61-1 Chemical Structure| 20727-61-1

Structure of 20727-61-1

Chemical Structure| 20727-61-1

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Product Details of [ 20727-61-1 ]

CAS No. :20727-61-1
Formula : C16H12O4
M.W : 268.26
SMILES Code : O=C1/C(OC2=CC(O)=CC=C12)=C\C3=CC=C(OC)C=C3
MDL No. :MFCD23146074

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Application In Synthesis of [ 20727-61-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 20727-61-1 ]

[ 20727-61-1 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 50-00-0 ]
  • [ 20727-61-1 ]
  • [ 494-52-0 ]
  • (2Z)-6-hydroxy-2-(4-methoxybenzylidene)-7-[(2S)-2-(pyridin-3-yl)piperidin-1-yl]methyl}-1-benzofuran-3(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With dmap; In ethanol;Reflux; General procedure: A hot solution of 6-hydroxyaurone 2a-e (2 mmol) in absolute EtOH (15 ml) was treated by adding anabasine (1) (0.80 ml, 5 mmol), paraformaldehyde (150 mg, equivalent to 5 mmol of formaldehyde), and DMAP (5 mg). The reaction mixture was refluxed for 12-16 h, then cooled and the solvent was evaporated at reduced pressure. The obtained residue was purified by silica gel column chromatography using EtOAc as eluent. (2Z)-6-Hydroxy-2-(4-methoxybenzylidene)-7-[(2S)-2-(pyridin-3-yl)piperidin-1-yl]methyl}-1-benzofuran-3(2H)-one (3a). Yield 337 mg (76%), yellow crystals, mp 193-195. 1H NMR spectrum (400 MHz, CDCl3), delta, ppm (J, Hz): 1.46-1.62 (1H, m), 1.69-1.89 (3H, m), 1.89-2.01 (2H, m), 2.28-2.41 (1H, m), 3.26-3.37 (1H, m) and 3.41-3.50 (1H, m, CH and CH2 piperidine); 3.64 (1H, d, J = 14.9) and 3.93 (1H, d, J = 14.9, CH2); 3.86 (3H, s, 4'-OCH3); 6.60 (1H, d, J = 8.4, H-5); 6.72 (1H, s, =CHAr); 6.97 (2H, d, J = 8.4, H-3',5'); 7.31 (1H, dd, J = 8.0, J = 4.8, H-5''); 7.53 (1H, d, J = 8.4, H-4); 7.73 (2H, d, J = 8.4, H-2',6'); 7.76-7.82 (1H, m, H-4''); 8.53 (1H, dd, J = 4.8, J = 1.6, H-6''); 8.65 (1H, d, J = 2.3, H-2''). 13C NMR spectrum (125 MHz, CDCl3), delta, ppm: 24.6; 25.6; 36.0; 51.2; 54.2; 55.5; 67.0; 104.5; 111.8; 113.5; 113.8; 114.6; 124.3; 124.8; 125.3; 133.0; 135.0; 137.6; 146.8; 149.7; 160.8; 165.4; 166.5; 182.7. Mass spectrum, m/z (Irel, %): 443 [M+H]+ (100). Found, %: C 73.05; H 6.70; N 6.56. C27H26N2O4. Calculated, %: C 73.28; H 5.92; N 6.33.
 

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