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Iso-longitolanone based hexahydroquinazoline-2-amine Schiff base Zn<2+> fluorescent probe as well as preparation method and application thereof

A kind of technology of felanone-based hexahydroquinazoline and amine Schiff base, which is applied in the field of fine organic synthesis and can solve the problem of not synthesizing hexahydroquinazoline-2-amine Schiff base compound and the like

Inactive Publication Date: 2017-05-10
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, no hexahydroquinazolin-2-amine Schiff base compound has been synthesized and used for Zn 2+ Related reports on ion detection

Method used

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  • Iso-longitolanone based hexahydroquinazoline-2-amine Schiff base Zn&lt;2+&gt; fluorescent probe as well as preparation method and application thereof
  • Iso-longitolanone based hexahydroquinazoline-2-amine Schiff base Zn&lt;2+&gt; fluorescent probe as well as preparation method and application thereof
  • Iso-longitolanone based hexahydroquinazoline-2-amine Schiff base Zn&lt;2+&gt; fluorescent probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The synthetic method of isolongifanonyl hexahydroquinazolin-2-amine Schiff base compound, the synthetic process is:

[0033]

[0034] Specific steps are as follows:

[0035]1) Preparation of 7-benzylidene isolongifanone:

[0036] Add 2.2g of isolongifolanone, 1.06g of benzaldehyde, 0.51g of sodium ethoxide and 30mL of ethanol into a three-necked flask equipped with a stirrer, a thermometer and a reflux condenser in sequence, and heat to reflux at 80-90°C for reaction. After about 4 hours of reaction, the conversion rate of isolonganone reaches over 95% (GC tracking detection). The reactant was extracted 3 times with 20 mL of ethyl acetate, the organic phases were combined, and washed several times with saturated brine until neutral; the organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated to recover the solvent to obtain 7-benzylidene iso The crude longifolanone was recrystallized from ethanol-ethyl acetate to obtain colorless and trans...

Embodiment 2

[0043] A certain amount of 1-((((6,6,10,10-tetramethyl-4-phenyl-5,7,8,9,10,10α-hexahydro-6H-6α,9-methanomethene Benzo[h]-2-quinolyl)imino)methyl)naphthalene-2-ol was dissolved in HEPES buffer solution (1×10 -5 M), the same Zn 2+ Ions are dissolved in HEPES buffer solution to make a concentration of 0~2.1×10 -5 M's solution. Different concentrations of Zn were measured 2+ Ion pair 1-(((6,6,10,10-tetramethyl-4-phenyl-5,7,8,9,10,10α-hexahydro-6H-6α,9-methanobenzene And [h]-2-quinolinyl)imino)methyl)naphthalene-2-ol's ultraviolet absorption spectrum, such as figure 1 shown. The results show that the ultraviolet absorption of the compound at around 320nm is significantly enhanced, indicating that the compound can interact with Zn 2+ The ions are complexed.

Embodiment 3

[0045] A certain amount of 1-((((6,6,10,10-tetramethyl-4-phenyl-5,7,8,9,10,10α-hexahydro-6H-6α,9-methanomethene Benzo[h]-2-quinolyl)imino)methyl)naphthalene-2-ol was dissolved in HEPES buffer solution (1×10 -5 M), its solution is colorless and transparent, along with Zn 2+ Ions (1×10 -5 M) adding, the solution becomes bright yellow rapidly, observes under 365nm ultraviolet light, as figure 2 Shown, a: compound added Zn under sunlight 2+ Photos of before and after ions; b: compound added Zn under 365nm UV light 2 + Ion before and after photos, adding Zn 2+ The solution of ions emits a strong green fluorescence, and by adding an equimolar amount of K + , Na + , Cu 2+ , Hg 2+ , Pb 2+ , Mg 2+ , Fe 3+ , Fe 2+ , Ni 2+ , Cd 2+ ,Co 2+ , Mn 2+ and other metal ions, it will not lead to the enhancement of the fluorescence of the compound, indicating that the compound can be used as an effective recognition Zn 2+ Ionic fluorescent probes.

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Abstract

The invention discloses an iso-longitolanone based hexahydroquinazoline-2-amine Schiff base Zn<2+> fluorescent probe as well as a preparation method and an application thereof. The preparation method comprises steps as follows: iso-longitolanone which is a derivative of longifolene as a natural renewable resource is taken as a raw material and is subjected to condensation with benzaldehyde, and 7-benzylidene-iso-longitolanone is produced; 7-benzylidene-iso-longitolanone is subjected to condensation and cyclization with guanidine hydrochloride, and 6,6,10,10-tetramethyl-4-phenyl-5,7,8,9,10 alpha-hexahydro-6H-6 alpha,9-methano-benzo[h] quinazoline-2-amine is obtained and subjected to condensation with 2-hydroxy-1-naphthaldehyde, 1-(((6,6,10,10- tetramethyl-4-phenyl-5,7,8,9,10alpha-hexahydro-6H-6alpha,9-methano-benzo[h]-2-quinolyl) imidogen)methyl)naphthalene-2-phenol is obtained, the compound can only react with Zn<2+> to form a complex, and the complex emits green fluorescence under the irradiation of 365 nm ultraviolet light and can be taken as the fluorescent probe for Zn<2+>concentration detection.

Description

technical field [0001] The invention belongs to the technical field of fine organic synthesis, and relates to an isolonganonyl hexahydroquinazolin-2-amine Schiff base zinc ion fluorescent probe and a preparation method and application thereof. Background technique [0002] Zn 2+ It is one of the essential trace elements for the human body. It is widely distributed in the blood and cells of the human body, and plays a vital role in the growth and development of the human body, genetic reproduction, and body immunity. Free zinc ions are distributed in almost all important tissues of the human body. However, due to the special and stable chemical structure of zinc ions, conventional detection methods such as ultraviolet-visible spectroscopy and cyclic voltammetry are not suitable for the detection of zinc ions. However, other traditional detection methods such as spectrophotometry and chemiluminescence also have many shortcomings. The fluorescent probe method has the advantag...

Claims

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Application Information

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IPC IPC(8): C07D239/70C09K11/06G01N21/64
CPCC07D239/70C09K11/06G01N21/6428
Inventor 王石发王忠龙徐徐谷文杨益琴匡洪波王芸芸杨丽娟姜倩张燕刘艳芳
Owner NANJING FORESTRY UNIV
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