Fullerene monomacrocyclic polyamine derivative and preparation method thereof
A technology of macrocyclic polyamine and fullerene single, applied in the field of fullerene single macrocyclic polyamine derivatives and its preparation, can solve the problem of changing the toxic effect
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Embodiment 1
[0062] 1) Preparation of N,N′,N″-Trip-toluenesulfonyldiethylenetriamine compound (1):
[0063] In an ice bath, add a solution of 126 g of p-toluenesulfonyl chloride dissolved in 300 mL of acetone and a solution of 91.2 g of anhydrous potassium carbonate dissolved in 200 mL of water into 20.6 g (0.20 mol) of diethylene triamine. The dripping time is about 1.5 h. Stir at room temperature for 4 h. Then the reactant was poured into ice water, then poured into water under stirring, filtered, the filter cake was washed with methanol and then suction filtered, and dried under vacuum to obtain N,N′,N″-tri-p-tosyldiethylenetri The white solid of the amine compound (1) was 103.2 g, and the yield was 91%.
[0064] 2) Preparation of N,O,O'-tri-p-toluenesulfonyl bis(2-hydroxyethyl)amine compound (2)
[0065] In an ice bath, add 300 mL of methylene chloride solution containing 126 g (0.66 mol) of p-toluenesulfonyl chloride dropwise to the reaction flask containing 21.0 g (0.2 mol) diethanolamin...
Embodiment 2
[0085] Prepare compounds (1) to (4) according to the preparation methods 1) to 4) in Example 1.
[0086] 5) Preparation of N,N′,N″-tri-tert-butoxyformyl-1,4,7,10-tetraazacyclododecane compound (5)
[0087] 1,4,7,10-tetraazacyclododecane compound (4) 5.0 g (29.0 mmol) and triethylamine 12.4 mL (89.3 mmol) dissolved in 150 mL of dichloromethane, slowly added dropwise at room temperature (Boc ) 2 A solution of 17.72 g (81.2 mmol) of dichloromethane in 120 mL was added dropwise within 3 hours. Stir at room temperature for 24 to 25 h, remove the solvent under reduced pressure, and column chromatography (petroleum ether: ethyl acetate=1:1) to obtain N,N′,N″-tri-tert-butoxyformyl-1,4 7,10-tetraazacyclododecane compound (5) as a white solid 10.50 g, yield: 76.8%. 1 H NMR (400 MHz, CDCl 3 ): δ = 3.60 (s, 4H), 3.37 (s, 4H), 3.28 (s, 4H), 2.86 (s, 4H), 1.45 (s, 9H), 1.44 (s, 18H) ppm.
[0088] 6) Preparation of 10-cyano-N,N′,N″-tri-tert-butoxyformyl-1,4,7,10-tetraazacyclododecane compound (6)...
Embodiment 3
[0101] Prepare compounds (1) to (4) according to the preparation methods 1) to 4) in Example 1.
[0102] 5) Preparation of N,N′,N″-tri-tert-butoxyformyl-1,4,7,10-tetraazacyclododecane compound (5)
[0103] 1,4,7,10-Tetraazacyclododecane (4) 6.0 g (34.8 mmol) and 15 mL (108.0 mmol) of triethylamine dissolved in 160 mL of dichloromethane, add slowly (Boc) at room temperature 2 O 20.42 g (93.6mmol) of 130 mL dichloromethane solution, add dropwise within 3 h. Stir at room temperature for 24h~25h, remove the solvent under reduced pressure, column chromatography (petroleum ether: ethyl acetate=1:1) to obtain N,N′,N″-tri-tert-butoxyformyl-1,4 7,10-tetraazacyclododecane compound (5) as a white solid 11.72 g, yield: 74.3%. 1 H NMR (400 MHz, CDCl 3 ): δ = 3.61 (s, 4H), 3.36 (s, 4H), 3.27 (s, 4H), 2.85 (s, 4H), 1.46 (s, 9H), 1.44 (s, 18H) ppm.
[0104] 6) Preparation of 10-cyano-N,N′,N″-tri-tert-butoxyformyl-1,4,7,10-tetraazacyclododecane compound (6)
[0105] In a 500 mL reaction flask, add N,...
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