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Fluorenone derivative, preparation method of fluorenone derivative and redox method of synthetic fluorenone

A derivative, fluorenone technology, applied in the field of redox of tetrayne and polyene alkyne, can solve the problems of many steps, difficult separation and purification, etc.

Active Publication Date: 2015-02-25
ANHUI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The synthesis and utilization of cyclic compounds is a hotspot in the research of organic chemistry. The synthesis of cyclic compounds has certain complexity, because the synthesis of cyclic compounds from simple raw materials, especially compounds containing benzene rings, requires many steps. It is more difficult to separate and purify

Method used

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  • Fluorenone derivative, preparation method of fluorenone derivative and redox method of synthetic fluorenone
  • Fluorenone derivative, preparation method of fluorenone derivative and redox method of synthetic fluorenone
  • Fluorenone derivative, preparation method of fluorenone derivative and redox method of synthetic fluorenone

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Embodiment 1

[0031] A redox method for synthesizing fluorenones from tetraynes and polyenynes.

[0032]

[0033] A kind of fluorenone derivative, the structural formula of described fluorenone derivative is:

[0034]

[0035] R 1 , R 2 is hydrogen, straight-chain alkyl, branched-chain alkyl, halogen, alkoxy and their corresponding derivatives.

[0036] A kind of condensed ring aromatic hydrocarbon derivative, its structural formula is:

[0037]

[0038] The E=CO 2 R; R is straight-chain alkyl, branched-chain alkyl, etc., saturated hydrocarbons, unsaturated hydrocarbons and aromatic hydrocarbon groups. R 3 , R 4 is hydrogen, alkyl, halogen, alkoxy and their corresponding derivatives.

[0039] The structural formula of fluorenone derivatives is:

[0040]

[0041] The R 1 is methyl, R 2 for hydrogen.

[0042] It is a fluorenone derivative obtained from tetrayne and polyenyne through redox method.

[0043] The preparation method of fluorenone derivative comprises the fo...

Embodiment 2

[0052] In the preparation method, step a, precursor synthesis, includes the following steps:

[0053] (1) With sodium hydride as a catalyst, diisopropyl malonate and propargyl bromide were added to anhydrous acetonitrile in an ice-water bath, stirred and reacted for 8 hours, the product was washed with water, extracted with ethyl acetate, and spin-dried under reduced pressure , column chromatography (volume ratio ethyl acetate:petroleum ether=1:100) to obtain a white solid product, namely compound 1, wherein the molar ratio of diisopropyl malonate to propargyl bromide is 1:2.2-3.2;

[0054] (2) Mix compound 1 with phenylethynyl bromide in Pd(PPh 3 ) 2 Cl 2 / CuI anhydrous and oxygen-free catalytic system, using triethylamine as the base, anhydrous acetonitrile as the solvent, stirred and reacted at room temperature for 12 hours, the product was washed with water, extracted with ethyl acetate, spin-dried under reduced pressure, and column chromatography (Volume ratio ethyl ac...

Embodiment 3

[0060] A fluorenone derivative, the structural formula of the fluorenone derivative is:

[0061]

[0062] A kind of preparation method of fluorenone derivative, described preparation method comprises the following steps:

[0063] a. Precursor synthesis;

[0064] b. Synthesis of the target product;

[0065] c. Purification.

[0066] Wherein, a, precursor synthesis, comprises the following steps:

[0067] (1) Using sodium hydride as a catalyst, add 200mmol diisopropyl malonate and 440mmol propargyl bromide to an ice-water bath in anhydrous acetonitrile, stir and react for 8 hours, wash the product with water, extract with ethyl acetate, and depressurize Spin to dry, column chromatography (volume ratio ethyl acetate:petroleum ether=1:100) to obtain a white solid product, namely compound 1;

[0068]

[0069] (2) Mix 80mmol compound 1 with phenylethynyl bromide in Pd(PPh 3 ) 2 Cl 2 / CuI anhydrous and oxygen-free catalytic system, the molar ratio Pd(PPh 3 ) 2 Cl 2 : ...

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Abstract

The invention relates to a fluorenone derivative, a preparation method of the fluorenone derivative and a redox method of synthetic fluorenone. The preparation method includes a, performing precursor synthesis; b, performing target product synthesis; c, performing purifying. The fluorenone derivative is obtained by the redox method of four alkyne and polyenynes and serves as non-silver sensitive material applied widely. The fluorenone serving as a medical intermediate is used for synthesis of various drugs.

Description

technical field [0001] The invention relates to the field of organic compounds, in particular to a redox method for tetrayne and polyenyne. Background technique [0002] Fluorenone and its derivatives are a very important class of cyclic compounds. One of the main uses of fluorenone is as a raw material for functional polymer monomers, and bisphenol fluorene is one of them. The fluorene resin made from fluorenone has very excellent characteristics, such as high transparency, high refractive index, good heat resistance, and excellent formability after being dissolved in solvents. It is used as an epoxy resin modifier to improve environmental protection. The glass transition temperature and mechanical strength of epoxy resin. Fluorenone derivatives as non-silver photosensitive materials are another important application field. The imaging principle of this type of photosensitive material is to charge the material first, then expose the charged material to an image, and obta...

Claims

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Application Information

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IPC IPC(8): C07C49/675C07C45/67C07C69/753C07C67/333C07C67/32C07C27/00
CPCC07C45/67C07C45/79C07C45/80C07C49/675C07C67/343C07C2603/18C07C69/606C07C69/618
Inventor 胡琼徐奎文磊胡益民
Owner ANHUI NORMAL UNIV
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