Water-soluble o-nitrophenol-containing copper porphyrin and Schiff base copper porphyrin complex thereof, and synthesis method and application thereof
A technology of porphyrin complexes and copper nitrophenolate, which is applied in copper organic compounds, pharmaceutical formulations, organic active ingredients, etc., and can solve problems such as limiting the application of porphyrin compounds
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Embodiment 1
[0053] The synthesis of embodiment 1 water-soluble copper porphyrin (CuP-1) containing o-nitrophenol
[0054] (1) Synthesis of 5,10,15-tris-(4-pyridine)-20-(3-methoxyl-4-hydroxyl-5-nitro)phenyl-porphyrin
[0055] Weigh 1.97g (0.01mol) of 3-methoxy-4-hydroxyl-5 nitrobenzaldehyde, dissolve it in a 250ml three-neck flask with a mixture of 150ml propionic acid and 15ml propionic anhydride, heat and stir until completely dissolved, and wait for the system After the temperature reaches 130°C, quickly add 2.7ml (0.03mol) of 4-pyridinecarbaldehyde, then slowly dropwise add 2.6ml (0.04mol) of freshly distilled pyrrole dissolved in 10ml of propionic acid, complete the addition within 10min, and react at 140°C 2h. After the reaction, distill under reduced pressure, add 20ml of the remaining solvent, add anhydrous methanol (70ml) 3.5 times the volume of the remaining solvent, and stir at room temperature for 15-25min to wash away the pyrrole polymer generated during the reaction; freeze ...
Embodiment 2
[0063] Embodiment two, the synthesis of water-soluble Schiff base copper porphyrin complex (CuP-2)
[0064] (1) Synthesis of 5,10,15-tris-(4-pyridine)-20-(3-methoxy-4-hydroxyl-5-nitro)phenyl-porphyrin: same as Example 1.
[0065] (2) Synthesis of 5,10,15-tri-(4-pyridine)-20-(3-methoxyl-4-hydroxyl-5-amino)phenyl-porphyrin
[0066] Dissolve 100mg (0.14mmol) of 5,10,15-tris-(4-pyridine)-20-(3-methoxy-4-hydroxyl-5-nitro)phenyl-porphyrin in 60ml (6mol / l ) hydrochloric acid, stirring to dissolve it. Under the protection of argon, 158mg (0.7mmol) of stannous chloride hydrochloric acid solution was added to the above solution, and reacted at 65°C for 18h. After the reaction, neutralize and filter with 5mol / l sodium hydroxide solution, collect the filter cake, dissolve in the mixed solution (V / V=1 / 5) of methanol and dichloromethane, extract with water several times, and collect the organic phase , spin-dried to obtain a purple crude product. The crude product was dissolved in a sma...
Embodiment 3
[0077] Embodiment three, the synthesis of water-soluble Schiff base copper porphyrin complex (CuP-3)
[0078] (1) Synthesis of 5,10,15-tris-(4-pyridine)-20-(3-methoxy-4-hydroxyl-5-nitro)phenyl-porphyrin: same as Example 1.
[0079] (2) Synthesis of 5,10,15-tris-(4-pyridine)-20-(3-methoxy-4-hydroxyl-5-amino)phenyl-porphyrin: same as Example 2.
[0080] (3) 5,10,15-three-(4-pyridine)-20-(3-methoxy-4-hydroxyl-5-o-hydroxy m-methoxybenzimino)phenyl-porphyrin synthesis
[0081] A solution of 91mg (0.6mmol) o-vanillin in 20ml of methanol was added to a solution containing 100mg (0.15mmol) of 5,10,15-tri-(4-pyridine)-20-(3-methoxy-4- Hydroxy-5-amino)phenyl-porphyrin in 20ml DMF solution, then add 3-5 drops of glacial acetic acid dropwise, and reflux at 72°C for 48h. Glacial acetic acid addition is 0.06~0.1 times of 5,10,15-three-(4-pyridine)-20-(3-methoxy-4-hydroxyl-5-amino)phenyl-porphyrin molar weight, ice Acetic acid acts as a catalyst. After the reaction was completed, vacuum...
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