A kind of 1,5-dicarbonyl derivative and preparation method thereof

A derivative and dicarbonyl technology, applied in the field of 1,5-dicarbonyl derivatives and their preparation, can solve problems such as poor diastereoselectivity, and achieve the effects of complex and diverse structures and broad application prospects.

Inactive Publication Date: 2017-06-16
ANHUI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When using michael addition reaction to synthesize 1,5-dicarbonyl compounds, the diastereoselectivity of the reaction is not good

Method used

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  • A kind of 1,5-dicarbonyl derivative and preparation method thereof
  • A kind of 1,5-dicarbonyl derivative and preparation method thereof
  • A kind of 1,5-dicarbonyl derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] A kind of 1,5-dicarbonyl derivatives, its structural formula is:

[0041]

[0042] A kind of preparation method of 1,5-dicarbonyl compound, comprises the following steps:

[0043] (1) At 0°C, add 50g of acetophenone and 50mL of anhydrous ether into a dry three-necked flask; install a stirrer, dropping funnel and reflux condenser on the three-necked flask; Aluminum trichloride water, add 0.42mol bromine from the dropping funnel;

[0044] After adding bromine, immediately spin dry under reduced pressure to remove diethyl ether and generated hydrogen bromide, and a brownish-yellow solid is precipitated; then add a mixture of 10 mL of water and 10 mL of petroleum ether to the reaction flask, shake to remove the color, and filter to obtain a crude product. The crude product was recrystallized from methanol to give white 2-bromoacetophenone. That is, compound 1; such as image 3 Shown in the first step reaction.

[0045] (2) Add 1mol of compound 1, 2.2mol of isobutyral...

Embodiment 2

[0052] A kind of 1,5-dicarbonyl derivatives, its structural formula is:

[0053]

[0054] A kind of preparation method of 1,5-dicarbonyl compound, comprises the following steps:

[0055] (1) At 0°C, add 64.1g of p-chloroacetophenone and 50mL of anhydrous ether into a dry three-necked bottle; install a stirrer, dropping funnel and reflux condenser on the three-necked bottle; after starting stirring, add 0.5g anhydrous aluminum trichloride, add 0.42mol bromine from the dropping funnel;

[0056] After adding bromine, immediately spin dry under reduced pressure to remove diethyl ether and generated hydrogen bromide, and a brownish-yellow solid is precipitated; then add a mixture of 10 mL of water and 10 mL of petroleum ether to the reaction flask, shake to remove the color, and filter to obtain a crude product. The crude product was recrystallized from methanol to give white 2-bromo-p-chloroacetophenone. That is, compound 1; such as Figure 5 Shown in the first step reaction. ...

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Abstract

The invention provides a synthesis method of a 1,5-dicarbonyl compound. According to the method, under the conditions of employing triethylamine as alkali, an ionic liquid [BMIM] PF6 as a solvent and lithium tetrafluoroborate as an adjuvant, a series of novel 1,5-dicarbonyl compounds are generated through autoreaction of the prepared precursor compound; and the generated 1,5-dicarbonyl compounds have good non-corresponding stereoselectivity. Compared with an ordinary 1,5-dicarbonyl compound, the prepared 1,5-dicarbonyl compounds are complicated and diverse in structure, and also show a relatively wide application prospect in chemical production and clinical medicine.

Description

technical field [0001] The invention relates to the field of organic compounds, in particular to a 1,5-dicarbonyl derivative and a preparation method thereof. Background technique [0002] 1,5-dicarbonyl compounds are widely used in industrial production and scientific research. They are important intermediates in organic synthesis and fine chemicals, and are widely used in chemical industry, medicine, spices, chelating agents, coatings and other fields. [0003] In view of the importance of 1,5-dicarbonyl compounds, how to expand the synthetic route of 1,5-dicarbonyl compounds has aroused the active thinking of countless organic synthesizers and chemists, and came up with some very effective methods. [0004] One of the commonly used is the use of michael addition reaction to synthesize 1,5-dicarbonyl compounds. However, when using michael addition reaction to synthesize 1,5-dicarbonyl compounds, the diastereoselectivity of the reaction is not good. Contents of the inven...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/72C07C49/796C07C49/813
CPCC07C45/63C07C45/72C07C49/80C07C49/794C07C49/796C07C49/813Y02P20/54
Inventor 孟祥珍程东胡益民
Owner ANHUI NORMAL UNIV
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