Method for 2, 5-dimethoxyacyl-1, 4-cyclohexanedione amination by reaction kettle

Abstract

The invention discloses a method for 2, 5-dimethoxyacyl-1, 4-cyclohexanedione amination by a reaction kettle. According to the invention, alcohol is adopted as the solvent in a reaction kettle, methylamine, aniline, 2, 2, 2-trifluoroethylamine, 2-methoxyethylamine, ethylamine or isopropylamine is respectively employed for reaction with 2, 5-dimethoxyacyl-1, 4-cyclohexanedione to obtain 1, 4-dialkylamino-2, 5-dimethoxyacyl-1, 4cyclohexanedione derivatives, which have strong fluorescence under both solid and solution states, also a reflux condensation device used in the conventional organic synthesis is avoided, and the cost is saved.

Description

technical field

[0001] The invention belongs to the technical field of organic fluorescent materials, and in particular relates to a method for aminating 2,5-dimethoxyacyl-1,4-cyclohexanedione by using a reaction kettle. Background technique

[0002] With the development of society and the progress of science and technology, fluorescent organic molecules have very extensive and important applications in the fields of analysis and detection, biological imaging and disease diagnosis. However, most of the traditional organic fluorescent molecules show strong fluorescence in the state of dilute solution, but because most of the fluorescent chromophores are rigid planar molecules with large π-conjugated systems, in high concentration or aggregated state,

[0003] The intermolecular π-π stacking interaction leads to energy non-radiative transition or the formation of substances that are not conducive to fluorescence emission, which eventually leads to fluorescence quenching and a ...

Examples

Embodiment 1

[0023] a. Add 658mg of 2,5-dimethoxyacyl-1,4-cyclohexanedione and 2.46mL of 30% methylamine methanol solution in 10mL of methanol as solvent in the reaction kettle;

[0024] b. Put it in an oven at 150°C and react for 8 hours;

[0025] c. Suction filtration with Buchner funnel, rinse and dry with methanol to obtain 455 mg of product, yield 60%.

[0026] The obtained compound 1, 1 H NMR (400MHz, CDCl 3 ): δ8.84(s, 2H), 3.74(s, 6H), 3.24(s, 4H), 2.96(d, J=5.2Hz, 6H). 13 C NMR (400MHz, CDCl 3 ): δ169.8, 159.0, 83.3, 50.4, 29.2, 26.6.

Embodiment 2

[0028] a. Add 658mg of 2,5-dimethoxyacyl-1,4-cyclohexanedione and 2.74mL of aniline to the reaction kettle with 10mL of methanol as the solvent;

[0029] b. Put it in an oven at 150°C and react for 8 hours;

[0030] c. Suction filtration with Buchner funnel, rinse and dry with methanol to obtain 633 mg of product, yield 56%.

[0031] The obtained compound 2, 1 H NMR (400MHz, CDCl 3 ): δ10.7(s,2H),7.1-7.4(m,10H),3.68(s,6H),3.42(s,4H). 13 C NMR (400MHz, CDCl 3 ): δ169.6, 157.0, 139.4, 129.3, 124.9, 89.0, 51.0, 28.0.

Embodiment 3

[0033] a. Add 658mg of 2,5-dimethoxyacyl-1,4-cyclohexanedione and 2.61mL of 2-methoxyethylamine to the reaction kettle with 10mL of methanol as solvent;

[0034] b. Put it in an oven at 150°C and react for 8 hours;

[0035] c. Suction filtration with Buchner funnel, rinse and dry with methanol to obtain 590mg of the product with a yield of 57%.

[0036]The obtained compound 3, 1H NMR, 400MHz, CDCl3: δ9.03(s, 2H), 3.71(s, 6H), 3.55(t, 4H), 3.47(q, 4H), 3.42(s, 6H), 3.24( s, 4H); 13C NMR, 400MHz, CDCl3: δ169.7, 157.6, 84.1, 71.8, 59.1, 50.5, 42.3, 26.9.

technical field

[0001] The invention belongs to the technical field of organic fluorescent materials, and in particular relates to a method for aminating 2,5-dimethoxyacyl-1,4-cyclohexanedione by using a reaction kettle. Background technique

[0002] With the development of society and the progress of science and technology, fluorescent organic molecules have very extensive and important applications in the fields of analysis and detection, biological imaging and disease diagnosis. However, most of the traditional organic fluorescent molecules show strong fluorescence in the state of dilute solution, but because most of the fluorescent chromophores are rigid planar molecules with large π-conjugated systems, in high concentration or aggregated state,

[0003] The intermolecular π-π stacking interaction leads to energy non-radiative transition or the formation of substances that are not conducive to fluorescence emission, which eventually leads to fluorescence quenching and a ...

Examples

Embodiment 1

[0023] a. Add 658mg of 2,5-dimethoxyacyl-1,4-cyclohexanedione and 2.46mL of 30% methylamine methanol solution in 10mL of methanol as solvent in the reaction kettle;

[0024] b. Put it in an oven at 150°C and react for 8 hours;

[0025] c. Suction filtration with Buchner funnel, rinse and dry with methanol to obtain 455 mg of product, yield 60%.

[0026] The obtained compound 1, 1 H NMR (400MHz, CDCl 3 ): δ8.84(s, 2H), 3.74(s, 6H), 3.24(s, 4H), 2.96(d, J=5.2Hz, 6H). 13 C NMR (400MHz, CDCl 3 ): δ169.8, 159.0, 83.3, 50.4, 29.2, 26.6.

Embodiment 2

[0028] a. Add 658mg of 2,5-dimethoxyacyl-1,4-cyclohexanedione and 2.74mL of aniline to the reaction kettle with 10mL of methanol as the solvent;

[0029] b. Put it in an oven at 150°C and react for 8 hours;

[0030] c. Suction filtration with Buchner funnel, rinse and dry with methanol to obtain 633 mg of product, yield 56%.

[0031] The obtained compound 2, 1 H NMR (400MHz, CDCl 3 ): δ10.7(s,2H),7.1-7.4(m,10H),3.68(s,6H),3.42(s,4H). 13 C NMR (400MHz, CDCl 3 ): δ169.6, 157.0, 139.4, 129.3, 124.9, 89.0, 51.0, 28.0.

Embodiment 3

[0033] a. Add 658mg of 2,5-dimethoxyacyl-1,4-cyclohexanedione and 2.61mL of 2-methoxyethylamine to the reaction kettle with 10mL of methanol as solvent;

[0034] b. Put it in an oven at 150°C and react for 8 hours;

[0035] c. Suction filtration with Buchner funnel, rinse and dry with methanol to obtain 590mg of the product with a yield of 57%.

[0036]The obtained compound 3, 1H NMR, 400MHz, CDCl3: δ9.03(s, 2H), 3.71(s, 6H), 3.55(t, 4H), 3.47(q, 4H), 3.42(s, 6H), 3.24( s, 4H); 13C NMR, 400MHz, CDCl3: δ169.7, 157.6, 84.1, 71.8, 59.1, 50.5, 42.3, 26.9.

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