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2,2-diphenylcyclopropyl compound and synthesis method thereof

A technology of diphenylcyclopropanecarboxylic acid and synthesis method, applied in the directions of organic chemistry method, chemical instrument and method, preparation of organic compounds, etc., can solve the problem of unfavorable industrial production of cyclopropane compounds, long reaction time, low yield, etc. It is easy to industrialize large-scale production, the method is simple, and the synthesis method is simple.

Active Publication Date: 2019-08-16
ZHENGZHOU INST OF CHIRAL DRUGS RES CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method for synthesizing cyclopropane compounds has the disadvantages of long reaction time, harsh conditions, low yield, etc., which is unfavorable for the industrial production of cyclopropane compounds

Method used

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  • 2,2-diphenylcyclopropyl compound and synthesis method thereof
  • 2,2-diphenylcyclopropyl compound and synthesis method thereof
  • 2,2-diphenylcyclopropyl compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The present embodiment provides a kind of methyl 2,2-diphenylcyclopropanecarboxylate, its structural formula is:

[0027]

[0028] The synthetic method of this compound comprises: get 3.64g benzophenone and 10ml 50% hydrazine hydrate in 100ml ethyl acetate at 40 ℃ reflux 2.5h, cool crystallization after reaction finishes and obtain benzophenone hydrazone; Add 1.82g of manganese dioxide to the anhydrous ethyl acetate solution of hydrazone, stir at 30°C for 1.2h, distill off the ethyl acetate solvent under reduced pressure at room temperature after the reaction, and then redissolve the residue In ethyl acetate, the ethyl acetate solvent was distilled off again under reduced pressure to obtain diphenyldiazomethane; diphenyldiazomethane was reacted with 1.8g methyl acrylate in ethyl acetate solvent at 50°C for 1.5 h, after the reaction was over, the ethyl acetate solvent was distilled off under reduced pressure at room temperature, and then recrystallized with 95% ethano...

Embodiment 2

[0030] The present embodiment provides a kind of chloromethyl 2,2-diphenylcyclopropanecarboxylate, and its structural formula is:

[0031]

[0032] Get 3.64g of benzophenone and 10ml of 50% hydrazine hydrate in 100ml of ethyl acetate solvent at 70 ℃ reflux 2.5h, cooling crystallization after the end of the reaction to obtain benzophenone hydrazone; Add 1.82g of manganese dioxide to the ethyl ester solution, stir at 60°C for 1.2h, and distill off the ethyl acetate solvent under reduced pressure at room temperature after the reaction, and then redissolve the residue in ethyl acetate , and distilled off the ethyl acetate solvent again under reduced pressure to obtain diphenyldiazomethane; react diphenyldiazomethane with 2.4g chloromethyl acrylate in ethyl acetate solvent at 40°C for 1.5h, and the reaction ends After that, the ethyl acetate solvent was distilled off under reduced pressure at room temperature, and then recrystallized with 95% ethanol to obtain 5.53 g of the targ...

Embodiment 3

[0034] This embodiment provides a kind of ethyl 2,2-diphenylcyclopropanecarboxylate, its structural formula is:

[0035]

[0036] The synthetic method of this compound comprises: get 3.64g benzophenone and 5ml 70% hydrazine hydrate in 100ml ethyl acetate at 80 ℃ reflux 3h, cooling crystallization after reaction finishes and obtains benzophenone hydrazone; To benzophenone hydrazone Add 1.74g of manganese dioxide to the anhydrous ethyl acetate solution, and stir at 40°C for 1.5h. After the reaction is over, the ethyl acetate solvent is distilled off under reduced pressure at room temperature, and then the residue is redissolved in In ethyl acetate, the ethyl acetate solvent was distilled off under reduced pressure again to obtain diphenyldiazomethane; diphenyldiazomethane was reacted with 2.23g ethyl acrylate in ethyl acetate solvent at 65°C for 1.5h After the reaction, the ethyl acetate solvent was distilled off under reduced pressure at room temperature, and then recrystall...

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Abstract

The present invention provides a 2,2-diphenylcyclopropyl compound, which has a chemical name 2,2-diphenyl methyl cyclopropanecarboxylate compound, wherein the structure formula is defined in the specification, and the group R in the structure formula represents C1-C4 short-chain alkane, cycloalkane, halogenated alkane or halogenated cycloalkane. The present invention further provides a synthesis method of the 2,2-diphenylcyclopropyl compound, wherein the system method comprises: synthesizing Benzophenone hydrazone, synthesizing diphenyldiazomethane, and synthesizing the target product. According to the present invention, the three-membered ring of the 2,2-diphenyl methyl cyclopropanecarboxylate compound contains a chiral center, which can be used as a chiral precursor to introduce the chiral carbon atom into the reaction product so as to provide more possibility for the development of active compounds; and the synthesis method is simple, easy to operate, and suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of drug synthesis, and in particular relates to a 2,2-diphenylcyclopropyl compound and a synthesis method thereof. Background technique [0002] The cyclopropane structure widely exists in natural products and drug molecules, and has good biological activity. For example, sponge extract has antitumor activity, pyrethroids have insecticide activity, coronatine has plant growth regulation activity, cyproconazole is a widely used agricultural fungicide, ciprofloxacin is a broad-spectrum and efficient anti-inflammatory agent Drug, ciprosulfuron-methyl is herbicide in paddy field. Due to its rigid planar structure, special bond angles, and multiple chiral centers, the cyclopropane skeleton has gradually attracted the attention of the physical organic chemistry community in recent years. [0003] Cyclopropane compounds not only have a variety of biological activities, but also have high activity due to the unstable three-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/753C07C67/343C07C251/86C07C249/16C07C245/14
CPCC07C67/343C07C249/16C07C245/14C07C2601/02C07B2200/07C07C251/86C07C69/753
Inventor 邓照西
Owner ZHENGZHOU INST OF CHIRAL DRUGS RES CO LTD
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