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2-nitrovinyl cyclopropane compound and synthesis method thereof

A technology of ethylene cyclopropane and nitroethylene, applied in the field of 2-nitrovinyl cyclopropane compounds and their synthesis, can solve the problems of less research on the nitration reaction of alkenyl cyclopropane, and achieve high yield and good application Foreground, environment-friendly effect

Active Publication Date: 2021-07-16
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The modification of natural compounds has always been a research hotspot for chemists, so the research on the nitration reaction of such compounds is also very meaningful, but there are few studies on the nitration reaction of alkenyl cyclopropane

Method used

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  • 2-nitrovinyl cyclopropane compound and synthesis method thereof
  • 2-nitrovinyl cyclopropane compound and synthesis method thereof
  • 2-nitrovinyl cyclopropane compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] In this embodiment, a kind of diethyl 2-(trans-2-nitrovinyl)cyclopropane-1,1-dicarboxylate has the structural formula:

[0063]

[0064] The synthetic method of 2-(trans-2-nitrovinyl)cyclopropane-1,1-dicarboxylate of this embodiment has the following steps:

[0065] Under a nitrogen atmosphere, 6.4 grams of 2-vinylcyclopropane-1,1-diethyl dicarboxylate (30 mmol), 21.7 grams of copper nitrate trihydrate (90 mmol), 14.9 grams of potassium iodide (90 mmol) were added to a 500 ml three-necked flask. ), 150 milliliters of 1,4-dioxane, heated to 65° C.; track the reaction with thin layer chromatography, and react until the raw materials disappear after 2 hours;

[0066] After the reaction, the reaction system was cooled to room temperature, and the solvent was removed to obtain a crude product; using a developer with a volume ratio of petroleum ether and ethyl acetate of 20:1, the obtained crude product was directly separated and purified by column chromatography to obtain...

Embodiment 2

[0073] This embodiment is basically the same as Embodiment 1, especially in that:

[0074] In this embodiment, a dimethyl 2-(trans-2-nitrovinyl)cyclopropane-1,1-dicarboxylate has the structural formula:

[0075]

[0076] The synthesis method of 2-(trans-2-nitrovinyl)cyclopropane-1,1-dicarboxylic acid dimethyl ester in this embodiment has the following steps:

[0077] Under a nitrogen atmosphere, 5.5 grams of 2-vinylcyclopropane-1,1-dicarboxylic acid dimethyl ester (30 mmol), 21.7 grams of copper nitrate trihydrate (90 mmol), 14.9 grams of potassium iodide (90 mmol) were added to a 500 ml three-necked flask. ), 150 milliliters of 1,4-dioxane, heated to 65° C.; track the reaction with thin layer chromatography, and react until the raw materials disappear after 2 hours;

[0078] After the reaction, the reaction system was cooled to room temperature and the solvent was removed to obtain a crude product; using a developer with a volume ratio of petroleum ether and ethyl acetate...

Embodiment 3

[0086] This embodiment is basically the same as the previous embodiment, and the special features are:

[0087] In this embodiment, a kind of dibenzyl 2-(trans-2-nitrovinyl)cyclopropane-1,1-dicarboxylate has the structural formula:

[0088]

[0089] The synthesis method of 2-(trans-2-nitrovinyl)cyclopropane-1,1-dibenzyl dicarboxylate in this embodiment has the following steps:

[0090]Under a nitrogen atmosphere, 10.1 g of 2-vinylcyclopropane-1,1-dibenzyl dicarboxylate (30 mmol), 21.7 g of copper nitrate trihydrate (90 mmol), 14.9 g of potassium iodide (90 mmol) were added to a 500 ml three-necked flask. ), 150 milliliters of 1,4-dioxane, heated to 65° C.; track the reaction with thin layer chromatography, and react until the raw materials disappear after 2 hours;

[0091] After the reaction, the reaction system was cooled to room temperature, and the solvent was removed to obtain a crude product; using a developer with a volume ratio of petroleum ether and ethyl acetate o...

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Abstract

The invention discloses a synthesis method of a 2-nitrovinyl cyclopropane compound. The structural formula of the 2-nitrovinyl cyclopropane compound is shown in the description, wherein R1 is hydrogen, a methoxycarbonyl group, an ethoxycarbonyl group, a benzoyloxycarbonyl group, cyclopropane methoxycarbonyl group, an allyl ester group, an isopropyl ester group, a tert-butyl ester group, a methylsulfonyl group, a benzenesulfonyl group or a benzoyloxymethyl group; R2 is hydrogen, a methoxycarbonyl group, an ethoxycarbonyl group, a benzoyloxycarbonyl group, a cyclopropane methoxycarbonyl group, an allyl ester group, an isopropyl ester group, a tert-butyl ester group, a methylsulfonyl group, a benzenesulfonyl group or a benzoyloxymethyl group; and R3 is hydrogen or p-toluenesulfonyl. According to the method, raw materials are simple and easy to obtain, copper nitrate trihydrate is adopted as a nitro source for reaction, and high reaction activity is shown under catalysis of potassium iodide; and the reaction process is simple to operate, mild in condition, environment-friendly and high in yield. New compounds can be synthesized by applying the method provided by the invention, the new compounds have potential medicinal value, and the method has a good application prospect in industrial production.

Description

technical field [0001] The invention relates to a nitroolefin, in particular to a 2-nitrovinyl cyclopropane compound and a synthesis method thereof. Background technique [0002] Nitroalkenes widely exist in nature, and they are also important intermediates in drug synthesis. See literature: Barrett, A.G.M. et al. Chem. Rev. 1986, 86, 751-762. Since the nitro group is a strong electron-withdrawing group, nitroalkenes are alkenes with strong electron-deficient properties. Nitroolefin itself has two functional groups of nitro group and carbon-carbon double bond, which leads to a variety of reactions, such as conjugate addition reaction, Diels-Alder reaction and so on. At the same time, the nitro group can also undergo a variety of transformations, such as conversion to oxime, hydroxylamine, and amine in the reduction reaction, and conversion to aldehydes and ketones in the Nef reaction. An important intermediate of its derivatives. [0003] Nitroalkenes also play an import...

Claims

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Application Information

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IPC IPC(8): C07C205/55C07C309/66C07C309/71C07C201/08C07C303/30
CPCC07C205/55C07C309/66C07C309/71C07C2601/02Y02P20/55
Inventor 刘秉新周立涛许斌刘天琪王辉
Owner SHANGHAI UNIV
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