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Method for synthesizing amino-modified NIT nitroxide free radicals

A technology of nitroxide free radical and amino modification, which is applied in the direction of organic chemistry, can solve the problems of low yield and difficulty of nitroxide free radical, etc., and achieve the effect of multiple reaction types, low density and high reactivity

Inactive Publication Date: 2015-04-29
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Usually, free radicals need to be connected to a specific molecular structure through a functional group, so if the free radical is connected to a highly reactive functional group, its application range will be expanded. Amino is an active functional group that can undergo multiple reactions in high yields. However, in the prior art, It is very difficult to synthesize NIT-like nitroxide free radicals from fatty aldehydes, and the yield is extremely low

Method used

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  • Method for synthesizing amino-modified NIT nitroxide free radicals
  • Method for synthesizing amino-modified NIT nitroxide free radicals
  • Method for synthesizing amino-modified NIT nitroxide free radicals

Examples

Experimental program
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Effect test

Embodiment 1

[0031] 1. Dissolve 4 grams of N-(2-acetaldehyde)phthalimide and 3 grams of N,N'-dihydroxy-2,3-dimethyl-2,3-butanediamine in 70mL 0.1 mL of formic acid was added dropwise into 60% ethanol aqueous solution, stirred and reacted at 25°C for 24 hours, suction filtered and washed to obtain 4.2 g of white solid product A with a yield of 65%.

[0032] 2. Dissolve 1 gram of compound A in 50 mL of ethanol, add 0.1 gram of hydrazine hydrate, react at 60°C for 2 hours, cool to room temperature, filter with suction, remove the solvent to obtain a yellow oily liquid, dissolve in dichloromethane, and crystallize to obtain white Solid B 0.5 g, yield 83%.

[0033] ESI-MS (m / z) = 190.1551. 1 H-NMR (300MHz, ppm, CDCl 3 )δ: 3,91(t,1H), 2.99(d,2H), 1.12(s,6H), 1.08(s,6H).

[0034] 3. Dissolve 0.5 g of compound B in 15 mL of methanol, add 5 g of lead dioxide, stir at room temperature for 2 hours, filter, and remove the solvent to obtain 0.3 g of red solid C with a yield of 61%.

[0035] ESI-MS ...

Embodiment 21

[0036] Example 21. Dissolving 4 grams of N-(2-acetaldehyde)phthalimide and 3 grams of N,N'-dihydroxy-2,3-dimethyl-2,3-butanediamine 0.1 mL of formic acid was added dropwise into 70 mL of 40% ethanol aqueous solution, stirred and reacted at 20°C for 24 hours, suction filtered and washed to obtain 4.0 g of white solid product A with a yield of 62%.

[0037] 2. Dissolve 1 gram of compound A in 50 mL of ethanol, add 0.1 gram of hydrazine hydrate, react at 60°C for 2 hours, cool to room temperature, filter with suction, remove the solvent to obtain a yellow oily liquid, dissolve in dichloromethane, and crystallize to obtain white Solid B 0.5 g, yield 83%.

[0038] 3. Dissolve 0.5 g of compound B in 15 mL of methanol, add 5 g of lead dioxide, stir at room temperature for 2 hours, filter, and remove the solvent to obtain 0.3 g of red solid C with a yield of 61%.

Embodiment 3

[0040] 1. Dissolve 4 grams of N-(2-acetaldehyde)phthalimide and 3 grams of N,N'-dihydroxy-2,3-dimethyl-2,3-butanediamine in 70mL 0.1 mL of formic acid was added dropwise into 80% ethanol aqueous solution, stirred and reacted at 25°C for 30 hours, suction filtered and washed to obtain 4.1 g of white solid product A with a yield of 63%.

[0041] 2. Dissolve 1 gram of compound A in 50 mL of ethanol, add 0.1 gram of hydrazine hydrate, react at 60°C for 2 hours, cool to room temperature, filter with suction, remove the solvent to obtain a yellow oily liquid, dissolve in dichloromethane, and crystallize to obtain white Solid B 0.5 g, yield 83%.

[0042]3. Dissolve 0.5 g of compound B in 15 mL of methanol, add 5 g of lead dioxide, stir at room temperature for 2 hours, filter, and remove the solvent to obtain 0.3 g of red solid C with a yield of 61%.

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Abstract

The invention discloses a method for synthesizing amino-modified NIT nitroxide free radicals. The method comprises the following steps: by taking N-(2-glyoxyl) phthalimide and N,N'-dyhydroxyl-2,3-dimethyl-2,3-butanediamine as raw materials, performing three steps such as condensation, hydrazinolysis and oxidization to obtain the amino-modified NIT nitroxide free radicals. The amino-modified NIT nitroxide free radicals have wide reaction and application values, and the yield is 60 percent or higher.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a method for synthesizing amino-modified NIT-like nitroxide free radicals. Background technique [0002] Nitroxide radical (NIT) was first synthesized by Ullman et al. in the 1970s. Since then, NIT radical has been widely used in paramagnetic probes. The nitroxide radical is a Л radical, and the unpaired electrons are in the Л* orbital. At the same time, the nitroxide radical itself is a spin carrier, which can directly coordinate with the metal ion to produce a strong magnetic exchange coupling. Based on this, nitrogen can be used Oxygen radicals interact with metal ions to selectively recognize specific metal ions. Usually, free radicals need to be connected to a specific molecular structure through a functional group, so if the free radical is connected to a highly reactive functional group, its application range will be expanded. Amino is an active functional group...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/24
CPCC07D233/24
Inventor 石志强李教富王永霞
Owner SHANDONG NORMAL UNIV
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