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Lactone compound

A technology for esters and derivatives, applied to the field of lactone derivatives, can solve the problems of low yield, uncontrollable selectivity, and no acquisition, and achieve the effect of protecting the ecological environment and meeting sustainable development.

Inactive Publication Date: 2012-01-25
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Methylenecyclopropanes and CO 2 Although the reaction has been reported more than 20 years ago, no greater progress has been made because the yield is too low and its selectivity cannot be controlled [(e) Inoue, Y.; Hibi, T.; Satake, M.; Hashimoto, H.J.Chem.Soc., Chem.Commun.1979, 982-983; (f) Binger, P.; Weintz, H.J.Chem.Ber.1984, 117, 654-665]

Method used

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Embodiment 1

[0043] The synthetic steps of embodiment 1 lactone derivatives

[0044] Synthesis of lactone derivative 2: Add MCP 1 (0.2 mmol), Pd 2 (dba) 3 (0.04mmol), with fresh distilled toluene as solvent (2mL), then add PCy 3 (0.16mmol) and DMSO (0.2mL); wherein MCPs represents methylenecyclopropane; dba represents dibenzylidene acetone; Cy represents tricyclohexylphosphine; DMSO represents dimethylsulfoxide. Bubble with carbon dioxide balloon for two minutes, place the reaction test tube in the autoclave, fill with carbon dioxide to 4.05x10 6 Under Pa atmospheric pressure, after heating to 120 ℃ and stirring for 36 hours, cooling, releasing gas slowly, opening the autoclave, performing fast column chromatography (SiO 2 , the eluent is ethyl acetate / petroleum ether=1 / 30) to obtain the corresponding product 2.

[0045] Product 2a: colorless oil; IR(CH 2 Cl 2 ):v 3019, 2922, 2858, 1764, 1670, 1514, 1447, 1351, 1154, 1113, 1031, 902cm -1 ; 1 H NMR (300MHz, CDCl 3 , TMS): δ1.60-1.6...

Embodiment 2

[0062] The synthetic steps of embodiment 2 (±)-Nobaco

[0063] Synthesis of compound 1q: under argon protection, phosphonium salt 3.24g (7.0mmol), NaH0.88g (21.6mmol) (60%), ketone 1.19g (9.72mmol), newly treated THF ( 10mL). React under reflux for 10 hours. Suction filtration (300-400 mesh silica gel), the solid was washed several times with an appropriate amount of petroleum ether, and the filtrate was separated by column chromatography to obtain methylenecyclopropane 1q (0.67 g, 56%).

[0064] Synthesis of compound 2q: Add 1q (0.2 mmol), Pd 2 (dba) 3 (0.04mmol), with fresh distilled toluene as solvent (2mL), then add PCy 3 (0.16mmol) and DMSO (0.2mL); wherein MCPs represents methylenecyclopropane; dba represents dibenzylidene acetone; Cy represents tricyclohexylphosphine; DMSO represents dimethylsulfoxide. Bubble with carbon dioxide balloon for two minutes, place the reaction test tube in the autoclave, fill with carbon dioxide to 4.05x10 6 Under Pa atmospheric pressu...

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Abstract

The invention relates to a lactone derivative. The spirocyclic lactone derivative is synthesized by performing insertion reaction of carbon dioxide on naphthenic hydrocarbon-containing methylene cyclopropane under the action of a palladium catalyst. The reaction can be performed successfully in spite of using various aromatic rings, various alkyl groups or hydrogen as substituent groups on naphthenic bases in various methylene cyclopropane substrates to generate a corresponding lactone derivative with medium to high yield and a product having a spirocyclic framework, wherein the conventional researches prove that the substrates have various high bioactivities and pharmacological activities. Simultaneously, the compound has high modification property, can be used for conveniently transforming various functional groups and has potential application value.

Description

technical field [0001] The invention relates to a lactone derivative. The lactone derivative is obtained by using methylene cyclopropane and carbon dioxide to undergo insertion reaction on cyclopropane under the catalysis of palladium, and then realizes the fixation of carbon dioxide. Background technique [0002] Cyclic lactone compounds can be used industrially in medicine, pesticide and veterinary medicine. It can be used as a solvent for agricultural chemicals, polymers and dyes, printing, and petrochemical extraction. Using lactone as raw material, it can also produce spices, pharmaceutical intermediates, rust removers, etc. [0003] Simultaneously, the synthesis of compounds with cyclic lactones in natural products has attracted the interest of many chemists, such as Bakkenolide A, (+)-norbakkenolide A [(a) Srikrishna.A.; Nagaraju, A.S.J.Chem.Soc., Chem. Commum.1993, 285-288], this kind of compound has certain biological activity, has anti-inflammatory effect and imm...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/94B01J31/24
Inventor 蒋敏施敏
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI