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

A cyanoacrylate, hydroxynaphthyl technology, applied in the preparation of carboxylic acid nitrile, the preparation of organic compounds, luminescent materials, etc., can solve the problem of undetected fluoride ions and the like

Inactive Publication Date: 2014-04-09
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] Preparation of 1.6'-hydroxynaphthyl-2-cyanoacrylate 2-(2-methoxyethoxy)ethoxyester

[0027] Into a 100ml flask were added 3.44g 6-hydroxy-2-naphthalenecarboxaldehyde, 4.62g 2-(2-(2-methoxyethoxy)ethoxy)2-cyanoacetate and 0.5g N,N-dimethylformaldehyde Alkyl-4-aminopyridine, then 30 ml of dry tetrahydrofuran was added. 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 with the eluent composition of ethyl acetate:n-hexane=1:1 (v / v) to obtain 7.24 g of a yellow solid. Yield 94%.

[0028] 2. Characterization of Compounds

[0029] Mp137.0~138.5℃.

[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=13.53Hz2H),10.45(s,1H).

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

Embodiment 2

[0049] Preparation of 1.6'-hydroxynaphthyl-2-cyanoacrylate methyl ester

[0050] 3.44g of 6-hydroxy-2-naphthalenecarboxaldehyde, 1.98g of methyl 2-cyanoacetate and 0.5g of N,N-dimethyl-4-aminopyridine were added to a 100ml flask, followed by 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 by silica gel column with the eluent composition of ethyl acetate:n-hexane=1:4 (v / v) to obtain 4.08 g of a yellow solid. Yield 81%.

[0051] 2. Characterization of Compounds

[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 methyl 6'-hydroxynaphthyl-2-cyanoacrylate. ...

Embodiment 3

[0061] Preparation of 1.6'-hydroxynaphthyl-2-cyanoethyl acrylate

[0062] Into a 100 ml flask were added 3.44 g of 6-hydroxy-2-naphthalenecarboxaldehyde, 2.26 g of ethyl 2-cyanoacetate and 0.5 g of N,N-dimethyl-4-aminopyridine, followed by 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 with the eluent composition of ethyl acetate:n-hexane=1:4 (v / v) to obtain 4.65 g of a yellow solid. Yield 87%.

[0063] 2. Characterization of Compounds

[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 ethyl 6'-hydroxynaphth...

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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, relates to acrylate compounds, in particular to 2-cyanoacrylate. Background technique [0002] Anions play important roles in life sciences and chemical processes, in fields such as biology, pathology, and environmental monitoring. Among them, fluoride ion is 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 to detect fluoride ions. For example, Wang Bingxiang et al. designed and synthesized a series of 1,5-diaryl-3-(2-hydroxy-4,6-dimethoxyphenyl)-2-pyrazoline compounds, and found that these compo...

Claims

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Application Information

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