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Novel chemical total synthesis preparation method for coronalon

A technology of total synthesis and corona ketone, which is applied in the field of chemical total synthesis preparation of corona ketone Coronalon, can solve problems such as troublesome post-processing, high cost of corona ketone, harsh reaction conditions, etc., and achieves easy operation, low cost and reliable The effect of mild control and reaction conditions

Inactive Publication Date: 2012-05-02
SOUTH CHINA BOTANICAL GARDEN CHINESE ACADEMY OF SCI
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AI Technical Summary

Problems solved by technology

However, the current total synthesis method using tetrahydronaphthalene as the starting material to synthesize crownone through five-step chemical reactions has a serious and almost insurmountable bottleneck step, that is, the first step conversion reaction conditions starting from tetrahydronaphthene Harsh: This step requires long-term high-temperature reaction and needs to be heated to nearly 200°C with ultra-vacuum vacuum distillation and other measures to obtain the initial product, and the post-processing is extremely troublesome, even if this step is carried out on a small scale in the laboratory and the corresponding product The yield is also only about 30% (references: Eur.J.Org.Chem., 2001, 1663-1668), which makes the efficiency of the whole synthetic route extremely low, and the result is that the target compound is generally obtained by this route The cost of crown ketone is still very high

Method used

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  • Novel chemical total synthesis preparation method for coronalon

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment 1: Synthetic identification of intermediate 4-(4-ethylbenzene)-4-carbonyl-butyric acid (2)

[0020] Take 10g of succinic anhydride and 27.5g of anhydrous aluminum trichloride, add it to 200ml of dichloromethane and pre-stir at room temperature for 30 minutes, then continue stirring at room temperature, slowly drop 10.6g of ethylbenzene into the reaction solution and react for 2 hours, the reaction is complete After that, dichloromethane was distilled off under reduced pressure at 40°C, and then 250 ml of ether was added under ice bath conditions, and then about 200 grams of ice was added to the reaction vessel to hydrolyze the solid under the ether layer until it was separated from ether to achieve extraction, and the obtained ether solution After drying over anhydrous sodium sulfate and filtering, the diethyl ether was distilled off under reduced pressure to directly obtain 16.9 g of a white crystalline product (product 2) (yield 82%). Spectrum analysis confi...

Embodiment 2

[0021] Embodiment 2: Synthesis and identification of intermediate 4-(4-ethylbenzene)-butyric acid (3)

[0022] In 200ml ethylene glycol solvent, add 10.3g intermediate product 2 (4-(4-ethylbenzene)-4-carbonyl-butyric acid, obtained by embodiment 1) and 7.5ml 98% concentration of hydrazine hydrate (H 2 NNH 2 ·H 2O) and 9.5g of potassium hydroxide (KOH), heated and stirred at 130°C for reflux for 2 hours, heated and stirred at 195°C for 10 hours, cooled to room temperature after the reaction was completed, then diluted the reaction solution with 210ml of cold water and washed with 12N concentrated hydrochloric acid About 35ml was acidified to acidity, and then extracted twice with diethyl ether (200ml×2). The resulting diethyl ether extraction solution was dried, filtered and evaporated to remove the solvent under reduced pressure to directly obtain 8.4g of a white solid product (product 3), with a yield of 87.5% , spectral analysis confirms that gained compound 3 is 4-(4-ethy...

Embodiment 3

[0023] Example 3: Synthesis and identification of intermediate 7-ethyl-3,4-dihydronaphthalene (4)

[0024] Dissolve 8.0g of compound 3 (4-(4-ethylbenzene)-butyric acid, obtained in Example 2) into 8ml (about 13.5g) of 98% concentrated sulfuric acid and stir to dissolve, then heat to 80°C and react with stirring for 1.5 hours , then pour the reaction solution into 50ml of ice water to dilute and add about 22g of NaHCO 3 Neutralize the sulfuric acid, then extract with 30ml of normal hexane, the obtained normal hexane extract is dried, and the solvent is distilled off under reduced pressure to directly obtain 6.1g (yield 84%) of light yellow oily product (compound 4), and spectral analysis confirms that the obtained compound 4 is It is 7-ethyl-3,4-dihydronaphthalene (4), and the spectral data are as follows: 1 H-NMR (CDCl 3 ,500MHz)δ H : 1.23(t, J=7.5Hz, 3H), 2.10(tt, J 1 =6.5Hz,J 2 =6.5Hz, 2H), 2.64(m, 4H), 2.91(m, 2H), 7.15(d, J=8.0Hz, 1H), 7.29(dd, J 1 =8.0Hz,J 2 =2.0Hz...

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Abstract

The invention discloses a novel chemical total synthesis preparation method for coronalon. The method comprises the following steps of: reacting ethyl benzene with butanedioic anhydride to generate 4-(4-ethyl benzene)-4-carbonyl-butyric acid; reducing the 4-(4-ethyl benzene)-4-carbonyl-butyric acid with a hydrazine hydrate to obtain 4-(4-ethyl benzene)-butyric acid; performing dehydration and ring concentration on the 4-(4-ethyl benzene)-butyric acid to form 7-ethyl-3,4-dihydronaphthalenone; reducing and dehydrating the 7-ethyl-3,4-dihydronaphthalenone to generate 7-ethyl-3,4-dihydronaphthalene; performing oxidation-induced double bond loop opening on the 7-ethyl-3,4-dihydronaphthalenone to obtain 2-(2-carboxyl ethyl)-5-ethyl-benzoic acid; and dehydrating and cyclizing the 2-(2-carboxyl ethyl)-5-ethyl-benzoic acid to obtain 6-ethyl-4-carboxyl-indenone; and condensing the 6-ethyl-4-carboxyl-indenone with isoleucine methyl ester hydrochloride to generate molecular coronalon serving as a target product. The novel chemical total synthesis preparation method for coronalon disclosed by the invention is more economical and effectively, and conditions are created for promoting the practicability of coronalon serving as an ideal inductive agent for plant potential high-value active ingredients.

Description

Technical field: [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a new method for the chemical total synthesis of Coronalon. Background technique: [0002] Plant active secondary metabolites are a treasure trove of medicines and pesticides for human beings. However, the content of many plant (medicinal, etc.) It enables people to realize effective exploration, development and utilization of them. Research on new induction techniques that can effectively improve the synthesis and accumulation of plant active ingredients has its practical and important needs, and the discovery and development of ideal inducers is the key to advancing this process. [0003] Plant active secondary metabolites are closely related to plant defense functions, and their biosynthetic accumulation can be largely activated by the activation of plant-related defense responses, in which the information transmission of signaling molecules plays a crucial role...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/84C07C231/02
Inventor 谭建文周忠玉颜健张梅王晶
Owner SOUTH CHINA BOTANICAL GARDEN CHINESE ACADEMY OF SCI
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