Acenaphthene derivative compound and its application
A technology of compound and alkyl, applied in the field of novel acenaphthene derivative compounds, can solve the problem of high application cost, and achieve the effects of low cost, simple operation and low preparation cost
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Embodiment 1
[0031] Preparation of 5-(10-undecylenoyl)-ethylaminoacenaphthylene compound and its chiral products.
[0032]Preparation of 5-acetylacenaphthene. Add 120ml of dichloromethane in a 500ml round bottom flask and pre-cool in an ice-water bath, then add 16g of aluminum trichloride and 4.4g of acetyl chloride. Dissolve 10.4g of acenaphthylene (A) in 60ml of dichloromethane, add to the aforementioned flask, react at room temperature for 20 to 45 minutes, then pour into ice water, then wash the organic phase with saturated sodium carbonate solution and distilled water respectively. The organic phase was dried to remove water, and dichloromethane was removed, and recrystallized with ether-n-hexane to obtain 5-acetylacenaphthene (B), with a melting point of 66.5-68.5°C.
[0033] Preparation of 5-ethylaminoacenaphthene. Dissolve 2.5 g of substance B in 100 ml of isopropanol, then add 5.5 g of sodium cyanoborohydride and 27 g of ammonium acetate NH 4 Ac, seal and stir at 90-95°C for 16...
Embodiment 2
[0038] Example 2 Preparation of 5-(10-undecylenoyl)-isobutylaminoacenaphthylene compound and its chiral product. Preparation of 5-isobutyrylacenaphthene. Add 120ml of dichloromethane in a 500ml round bottom flask and pre-cool in an ice-water bath, then add 15g of aluminum trichloride and 5.9g of isobutyryl chloride. Dissolve 10.2g of acenaphthene in 60ml of dichloromethane, add it to the aforementioned flask, react at room temperature for 35-65 minutes, then pour into ice water, and then wash the organic phase with saturated sodium carbonate solution and distilled water respectively. The organic phase was dried to remove water, dichloromethane was distilled off under reduced pressure, and crystallized and purified with ether-n-hexane to obtain 6.5 g of light yellow 5-isobutyryl acenaphthene with a yield of 52% and a melting point of 101-102.5°C.
[0039] Preparation of 5-isobutylaminoacenaphthene. Dissolve 2.5g of 5-isobutyryl acenaphthene in 100ml of isopropanol, then add 6...
Embodiment 3
[0043] Preparation of 5-(vinyl)-ethylaminoacenaphthylene compound and its chiral products.
[0044] Preparation of 5-acetylacenaphthene and 5-ethylaminoacenaphthene. The first and second steps of this example are to synthesize 5-acetylacenaphthene and 5-ethylaminoacenaphthene respectively. Since the product and preparation method are exactly the same as those in Example 1, the specific description thereof is omitted.
[0045] Preparation of 5-(vinyl)-ethylaminoacenaphthene. Dissolve the 5-ethylaminoacenaphthene produced in the previous step reaction in 50ml of dichloromethane, then add 10ml of saturated sodium bicarbonate solution, then add 1.5g of vinyl acid chloride to the reaction solution, and stir for 20 to 60 minutes at room temperature . The organic phase was dried and concentrated to obtain the crude product. Then, using dichloromethane and methanol as eluents, it was purified by silica gel column chromatography to obtain 1 g of light yellow crystal 5-(vinyl)-ethyla...
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