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Method for preparing coumarin fluorescent agent through copper acetate catalysis

A technology for catalyzing preparation of coumarins, applied in chemical instruments and methods, luminescent materials, organic chemistry, etc., can solve the problems of many reaction steps, low reaction efficiency, and limited scope of application of the method, and achieves mild synthesis conditions, High chemoselectivity and controllable chemoselectivity

Active Publication Date: 2019-10-18
JIYANG COLLEGE OF ZHEJIANG A & F UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The known method of preparing coumarin fluorescent agent compounds is mainly obtained through multi-step coupling and series connection through transition metal catalysis, which has the disadvantages of many reaction steps, low reaction efficiency and not wide application range of the method.

Method used

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  • Method for preparing coumarin fluorescent agent through copper acetate catalysis
  • Method for preparing coumarin fluorescent agent through copper acetate catalysis
  • Method for preparing coumarin fluorescent agent through copper acetate catalysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Embodiment 1: Preparation of 3a product

[0043] At room temperature, add 2440 mg (3 mmol) 3,4,5-hexadecyloxytoluene and 583 mg (3.6 mmol) coumarin compound 2a, 54 mg (0.1 equiv) copper acetate, 912 mg ( 2equiv) DBU, 100 in 1,4-dioxane 10mL o C under the condition of reaction for 20 hours, after the reaction is completed and cooled, add 10 mL of saturated NaCl aqueous solution to the system, extract 3 times with ethyl acetate, 10 mL each time, combine the organic phases, and wash with anhydrous NaCl 2 SO 4 After drying, the solvent was evaporated, and 200-300 mesh silica gel column chromatography obtained 2720 mg of the compound 3a, with a yield of 93%. The H NMR spectrum of compound 3a is shown in figure 1 , the carbon NMR spectrum of compound 3a is shown in figure 2 , the FTIR spectrum of compound 3a is shown in image 3 .

[0044] Yellow powdery solid; mp: 69 °C.

[0045] 1 H NMR (500 MHz, CDCl 3 ): δ 7.63 (d, J = 9.5 Hz, 1 H, a), 7.37 (d, J =8.6 Hz, 1 H...

Embodiment 2

[0048] Embodiment 2: Preparation of 3b product

[0049] At room temperature, add 2440 mg (3 mmol) 3,4,5-hexadecyloxytoluene and 583 mg (3.6 mmol) coumarin compound 2b, 54 mg (0.1 equiv) copper acetate, 912 mg ( 2equiv) DBU, 100 in 1,4-dioxane 10mL o C under the condition of reaction for 20 hours, after the reaction is completed and cooled, add 10 mL of saturated NaCl aqueous solution to the system, extract 3 times with ethyl acetate, 10 mL each time, combine the organic phases, and wash with anhydrous NaCl 2 SO 4 After drying, the solvent was evaporated, and 200-300 mesh silica gel column chromatography obtained 2603 mg of the compound 3b with a yield of 89%. The H NMR spectrum of compound 3b is shown in Figure 4 , the C NMR spectrum of compound 3b is shown in Figure 5 , the FTIR spectrum of compound 3b is shown in Figure 6 . 4-(3,4,5-Tris-hexadecyloxy-benzyloxy)-chromen-2-one (3b) Yellow powdery solid; mp: 77°C.

[0050] 1 H NMR (500 MHz, CDCl 3 ): δ 7.74 (d, J =...

Embodiment 3

[0053] Embodiment 3: the preparation of 3c product

[0054] In a 25 mL round bottom flask at room temperature, add 2440 mg (3 mmol) 3,4,5-hexadecyloxytoluene and 634 mg (3.6 mmol) coumarin 2c, 54 mg (0.1 equiv) copper acetate, 912 mg ( 2equiv) DBU, 100 in 1,4-dioxane 10mL o C under the condition of reaction for 20 hours, after the reaction is completed and cooled, add 10 mL of saturated NaCl aqueous solution to the system, extract 3 times with ethyl acetate, 10 mL each time, combine the organic phases, and wash with anhydrous NaCl 2 SO 4 After drying, the solvent was evaporated, and 200-300 mesh silica gel column chromatography obtained 2668 mg of the compound 3c, with a yield of 90%. The H NMR spectrum of compound 3c is shown in Figure 7 , the C NMR spectrum of compound 3c is shown in Figure 8 , the FTIR spectrum of compound 3c is shown in Figure 9 . 4-Methyl-7-(3,4,5-tris-hexadecyloxy-benzyloxy)-chromen-2-one (3c) Yellow powdery solid; mp: 84 ℃.

[0055] 1 H NMR (...

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Abstract

The invention discloses a method for preparing a coumarin fluorescent agent through copper acetate catalysis. A substrate, namely 3,4,5-trihexaalkoxy methylbenzene, shown in a formula (I) and a coumarin compound shown in a formula (II) react in a reaction medium taking a 1,4-dioxane as a solvent under the effect of copper acetate as a catalyst and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), a targetproduct is prepared, and the coumarin fluorescent agent is prepared through post-treatment of the target product; and X in the formula (II) and X in a formula (III) are selected from one of oxygen, nitrogen and hydrogen. Raw materials are simple, convenient and easy to obtain, and the synthetic condition is mild; chemical selectivity is high and controllable; the reaction is conducted at the normal pressure and the mild temperature; the copper acetate serves as the catalyst, and is cheap and low in toxicity, the cost is saved, and the requirements for equipment are low; the adopted solvent, namely 1,4-dioxane, is inter-miscible with water, and post-treatment is convenient; and a catalysis system is wide in adaptability, and the obtain product has wide application in the field of preparation of fluorescent agents.

Description

technical field [0001] The invention belongs to the technical field of fluorescent material preparation, and in particular relates to a method for preparing a coumarin fluorescent agent catalyzed by copper acetate. Background technique [0002] Coumarin derivatives are a class of compounds and important dyes with many biological activities such as anti-virus. In recent years, the application of coumarin compounds in optoelectronics has also received attention. A typical fluorescent agent is generally formed by connecting a fluorophore to a receptor through a linker. The fluorophores reported in the literature involve compounds such as fluoresceins, rhodamines, cyanine dyes, naphthalimides, and coumarins. Fluorescent agents based on coumarins have gradually become a new research hotspot. The coumarin-based fluorescent agent has a benzopyrone structure, which has the advantages of high fluorescence quantum yield, large Stocks shift, adjustable photophysical and photochemical...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/16C07D311/46C07D311/68C09K11/06
CPCC07D311/16C07D311/46C07D311/68C09K11/06C09K2211/1088
Inventor 徐润生周思贤熊飞翔朱月儿
Owner JIYANG COLLEGE OF ZHEJIANG A & F UNIV
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