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6'-hydroxyl naphthyl-2-cyanoacrylate and application thereof

A technology of cyanoacrylate and hydroxynaphthyl, which is applied in the field of acrylate compounds and 2-cyanoacrylate, and can solve the problems of undetected fluoride ion

Inactive Publication Date: 2015-03-18
SOUTHERN MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But there is no report that it is used to detect fluoride ions in aqueous solution and intracellular fluoride ions

Method used

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  • 6'-hydroxyl naphthyl-2-cyanoacrylate and application thereof
  • 6'-hydroxyl naphthyl-2-cyanoacrylate and application thereof
  • 6'-hydroxyl naphthyl-2-cyanoacrylate and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] 1. Preparation of 2-(2-(2-methoxyethoxy)ethoxy)ethyl 6'-hydroxynaphthyl-2-cyanoacrylate

[0027] In a 100ml flask, add 3.44g 6-hydroxy-2-naphthaldehyde, 4.62g 2-(2-(2-methoxyethoxy)ethoxy) 2-cyanoacetate and 0.5g N,N-di methyl-4-aminopyridine, and then add 30 ml of anhydrous tetrahydrofuran. After reacting at room temperature for 24 hours, the solvent was distilled off under reduced pressure, and the residual solid was purified with a silica gel column under the condition that the eluent composition was ethyl acetate:n-hexane=1:1 (v / v) to obtain 7.24 g of a yellow solid. Yield 94%.

[0028] 2. Compound Characterization

[0029] Mp 137.0~138.5℃.

[0030] 1 H NMR (400MHz, DMSO-d 6 ): δ3.22(s,3H),3.37~3.44(m,4H),3.52~3.56(m,10H),3.60~3.63(m,2H),3.74~3.76(m,2H),4.40~4.43 (m,1H),7.23(s,2H),7.85~7.90(dd,J=9.16Hz,J=21.16Hz,2H),8.13~8.16(dd,J=1.39,J=8.32Hz,1H), 8.42~8.46(d,J=13.53Hz 2H),10.45(s,1H).

[0031] 13 C NMR (100MHz, DMSO-d 6 ):δ57.98,65.32,68.06,69.59,69.73,...

Embodiment 2

[0049] 1. Preparation of methyl 6'-hydroxynaphthyl-2-cyanoacrylate

[0050] Add 3.44g of 6-hydroxy-2-naphthaldehyde, 1.98g of methyl 2-cyanoacetate and 0.5g of N,N-dimethyl-4-aminopyridine into a 100ml flask, and then add 30ml of anhydrous tetrahydrofuran. After reacting at room temperature for 24 hours, the solvent was distilled off under reduced pressure, and the residual solid was purified with a silica gel column under the condition that the eluent composition was ethyl acetate:n-hexane=1:4 (v / v) to obtain 4.08 g of a yellow solid. Yield 81%.

[0051] 2. Compound Characterization

[0052] 1 H NMR (400MHz, DMSO-d 6 ): δ3.71(s,3H),4.08~4.13(m,1H),7.23(s,2H),7.81~7.88(dd,2H),8.01~8.05(dd,1H),8.40~8.43(d ,2H),10.56(s,1H).

[0053] 13 C NMR (100MHz, DMSO-d 6 ): δ52.11, 100.34, 109.11, 117.22, 121.13, 123.41, 132.50, 136.32, 137.62, 155.17, 157.55, 161.31.

[0054] The above detection results confirm that the prepared compound is 6'-hydroxynaphthyl-2-methyl cyanoacrylate...

Embodiment 3

[0061] 1. Preparation of ethyl 6'-hydroxynaphthyl-2-cyanoacrylate

[0062] Add 3.44g of 6-hydroxy-2-naphthaldehyde, 2.26g of ethyl 2-cyanoacetate and 0.5g of N,N-dimethyl-4-aminopyridine into a 100ml flask, and then add 30ml of anhydrous tetrahydrofuran. After reacting at room temperature for 24 hours, the solvent was distilled off under reduced pressure, and the residual solid was purified with a silica gel column under the condition that the eluent composition was ethyl acetate:n-hexane=1:4 (v / v) to obtain 4.65 g of a yellow solid. Yield 87%.

[0063] 2. Compound Characterization

[0064] 1 H NMR (400MHz, DMSO-d 6 ):δ1.03(s,3H),4.11~4.13(m,2H),4.55~4.58(m,1H),7.11(s,2H),7.74~7.78(dd,2H),7.89~7.92(dd ,1H), 8.10~8.14(d,2H), 10.77(s,1H).

[0065] 13 C NMR (100MHz, DMSO-d 6 ): δ11.44, 56.11, 103.11, 109.53, 116.92, 121.73, 123.81, 131.97, 136.71, 137.23, 155.51, 158.44, 162.89.

[0066] The above test results confirm that the prepared compound is 6'-hydroxynaphthyl-2-cya...

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Abstract

The invention belongs to the field of organic chemistry, and in particular relates to 6'-hydroxyl naphthyl-2-cyanoacrylate. The chemical structure of the 6'-hydroxyl naphthyl-2-cyanoacrylate is shown in formula (I) which is as shown in the description, wherein R is methyl, ethyl, propyl and butyl, 2-(2-methoxy ethyoxyl) ethyoxyl or 2-(N,N-dimethyl) aminoethyl. The 6'-hydroxyl naphthyl-2-cyanoacrylate is obtained by performing reaction on 6'-hydroxyl-2-naphthaldehyde and 2-cyan-acetic ester. The 6'-hydroxyl naphthyl-2-cyanoacrylate has fluorine ion fluorescence recognition performance and can be used for detecting fluorine ions in cells.

Description

technical field [0001] The invention belongs to the field of organic chemistry and relates to acrylate compounds, in particular to 2-cyanoacrylate. Background technique [0002] Anions play important roles in life sciences and chemical processes, and play important roles in fields such as biology, pathology, and environmental monitoring. Among them, fluoride ions are beneficial to dental health and the treatment of osteoporosis. At the same time, it can also cause diseases such as urinary stones. Therefore, the design and synthesis of fluoride ion probes with good selectivity and high sensitivity have received great attention in recent years. [0003] Fluorescence imaging technology developed in recent years has the characteristics of fast, non-destructive, intuitive and high sensitivity, and has been widely used in the detection of fluoride ions. For example, Wang Bingxiang et al. designed and synthesized a series of 1,5-diaryl-3-(2-hydroxy-4,6-dimethoxyphenyl)-2-pyrazoli...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/41C07C253/30C09K11/06G01N21/64
Inventor 刘瑞源
Owner SOUTHERN MEDICAL UNIVERSITY
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