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Ferrocene derivative and preparation method thereof

A technology of ferrocene derivatives and derivatives, applied in chemical instruments and methods, metallocene, organic chemistry, etc., to achieve the effects of high efficiency, short reaction time, and simple preparation method

Active Publication Date: 2018-11-09
ANHUI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Its addition in gasoline has a good anti-shock effect, but it is limited due to the deposition of iron oxide on the spark plug and affects ignition. For this reason, some people use iron-exhausting mixture to reduce iron deposition.

Method used

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  • Ferrocene derivative and preparation method thereof
  • Ferrocene derivative and preparation method thereof
  • Ferrocene derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] A ferrocene derivative, the structural formula of the ferrocene derivative is:

[0048]

[0049] The preparation method of above-mentioned ferrocene derivatives, comprises the following steps:

[0050] (1) Using 830mmol of sodium hydride as a catalyst, add 200mmol of dimethyl malonate and 440mmol of propargyl bromide into 210mL of anhydrous acetonitrile in an ice-water bath, stir and react for 8 hours at 0-5°C, and wash the product with water. Extracted with ethyl acetate, and spin-dried under reduced pressure to obtain a brown-yellow solid product, namely compound 1;

[0051]

[0052] (2) Mix 80mmol compound 1 with 200mmol phenylethynyl bromide in Pd(PPh 3 ) 2 Cl 2 / CuI anhydrous and oxygen-free catalytic system (2.56mmol / 0.85mmol), the molar ratio of Pd(PPh 3 ) 2 Cl 2 : CuI=3:1, with 336mmol triethylamine as base, 150mL anhydrous acetonitrile as solvent, stirring and reacting at room temperature for 12 hours, the product was washed with water, extracted wi...

Embodiment 2

[0061] A ferrocene derivative, the structural formula is:

[0062]

[0063] A kind of synthetic method of ferrocene derivative, described synthetic method comprises the following steps:

[0064] (1) With sodium hydride 830mmol as a catalyst, 200mmol dimethyl malonate and 440mmol propargyl bromide were added to 210mL of anhydrous acetonitrile in an ice-water bath, stirred and reacted for 8 hours, the product was washed with water, extracted with ethyl acetate, and Press and spin dry to obtain a brownish-yellow solid product, namely compound 1;

[0065]

[0066] (2) Mix 80mmol of compound 1 with 200mmol of p-methylphenylethynyl bromide in Pd(PPh 3 ) 2 Cl 2 / CuI anhydrous and oxygen-free catalytic system (2.56mmol / 0.85mmol), the molar ratio of Pd(PPh 3 ) 2 Cl 2 : CuI=3:1, with 336mmol triethylamine as base, 150ml anhydrous acetonitrile as solvent, stirred and reacted at room temperature for 12 hours, the product was washed with water, extracted with ethyl acetate, spi...

Embodiment 3

[0076] A ferrocene derivative, the structural formula of the ferrocene derivative is:

[0077]

[0078] A kind of synthetic method of ferrocene derivative, described synthetic method comprises the following steps:

[0079] (1) With sodium hydride 830mmol as a catalyst, 200mmol dimethyl malonate and 440mmol propargyl bromide were added to 210mL of anhydrous acetonitrile in an ice-water bath, stirred and reacted for 8 hours, the product was washed with water, extracted with ethyl acetate, and Press and spin dry to obtain a brownish-yellow solid product, namely compound 1;

[0080]

[0081] (2) Mix 80mmol compound 1 with 200mmol p-ethylphenylethynyl bromide in Pd(PPh 3 ) 2 Cl 2 / CuI anhydrous and oxygen-free catalytic system (2.56mmol / 0.85mmol), the molar ratio of Pd(PPh 3 ) 2 Cl 2 : CuI=3:1, with 336mmol triethylamine as base, 150ml anhydrous acetonitrile as solvent, stirred and reacted at room temperature for 12 hours, the product was washed with water, extracted wi...

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Abstract

The invention provides a ferrocene derivative and a preparation method thereof. Compared with the prior art, in the absence of catalyst and additive as well as protection and with toluene as a solvent, a tetra-alkyne substrate reacts with ferrocene at 104-114 DEG C, wherein the reaction process comprises the following steps: cyclization of the tetra-alkyne substrate, generation of a benzyne intermediate through a HDDA reaction, and 4+2 cycloaddition reaction between the highly active benzyne intermediate and the cyclopentadiene of ferrocene to obtain the ferrocene derivative. The method breaksthrough the former knowledge that the ferrocene cannot experience a cycloaddition reaction, and also shows a broader application prospect in chemical production and clinical medicine. Moreover, the preparation method provided by the invention has the advantages of simplicity and convenience, high efficiency and short reaction time.

Description

technical field [0001] The invention belongs to the field of organic compounds, and specifically relates to a ferrocene derivative and a preparation method thereof. Background technique [0002] Ferrocene is an organic transition metal compound with aromatic properties. It is orange-yellow powder at room temperature, with camphor odor. Melting point 172°C-174°C, boiling point 249°C, sublimation above 100°C; insoluble in water, easily soluble in organic solvents such as benzene, ether, gasoline, diesel oil, etc. It does not react with acid, alkali and ultraviolet rays, has stable chemical properties, and does not decompose within 400 degrees. Its molecules are polar, with high thermal stability, chemical stability and radiation resistance. It has a wide range of applications in industry, agriculture, medicine, aerospace, energy saving, environmental protection and other industries. Ferrocene can be used as a rocket fuel additive, an antiknock agent for gasoline, a curing a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/02
CPCC07F17/02
Inventor 胡益民郑晓杰
Owner ANHUI NORMAL UNIV
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