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Synthesis of the Aggregated Pheromone (e)-cis-6,7-epoxy-2-nonenal

A technology for aggregating pheromone and pink-necked longhorn beetle is applied in the field of new synthesis of natural product pheromone components, which can solve the problems of harsh conditions, expensive raw materials, unsuitable for industrial production, etc., and achieves the effect of mild conditions and simple operation.

Active Publication Date: 2020-06-16
江苏宁录科技股份有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Its raw material is more expensive, and condition is harsh, is not suitable for industrialized production (K.Mori.Pheromone synthesis.Part 263:Synthesis of the racemate and theenantiomers of (E)-cis-6,7-epoxy-2-nonenal, the male-produced pheromone of the red-necked longhorn beetle, Aromia bungii. Tetrahedron, 2018, 74, 1444-1448)

Method used

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  • Synthesis of the Aggregated Pheromone (e)-cis-6,7-epoxy-2-nonenal

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: Add p-toluenesulfonic acid monohydrate (2.3g, 12mmol) to a tetrahydrofuran / dichloromethane mixed solution (220mL) of 1,4 butanediol (13.0g, 144mmol), cool to 0°C, drop Add 3,4-dihydro-2H-pyran (10.8 mL, 120 mmol) and stir at room temperature for 6 h. TLC detection, after the reaction, quenched with water, extracted with dichloromethane, combined the organic phases, dried over anhydrous sodium sulfate, concentrated under reduced pressure, purified by column chromatography to obtain a colorless liquid 3 (15.56g, yield 75% ). 1 H NMR(400MHz, CDCl 3 ): δ4.53(t,J=3.5Hz,1H),3.76-3.81(m,1H),3.69-3.73(m,1H),3.57(t,J=6.0Hz,2H),3.43-3.46( m,1H),3.34-3.37(m,1H),2.98(s,1H),1.72-1.76(m,1H),1.61-1.65(m,5H),1.44-1.53(m,4H); 13 C NMR(100MHz, CDCl 3 ): δ99.8, 67.5, 62.4, 62.3, 30.6, 29.8, 26.4, 25.3, 19.5.

Embodiment 2

[0028] Example 2: Add pyridinium p-toluenesulfonate (0.31g, 1.2mmol) to 1,4-butanediol (1.3g, 14.4mmol) in tetrahydrofuran dichloromethane mixed solution (22mL), after cooling to 0°C, 3,4-Dihydro-2H-pyran (1.1 mL, 12 mmol) was added dropwise, and the mixture was stirred at room temperature for 6 h. TLC detection, after the completion of the reaction, quenched by adding water, extracted with dichloromethane, combined the organic phases, dried over anhydrous sodium sulfate, concentrated under reduced pressure, purified by column chromatography to obtain a colorless liquid 3 (1.5g, yield 70% ). Compared with Example 1, the p-toluenesulfonic acid monohydrate was changed to p-toluenesulfonic acid pyridine salt, and other conditions remained unchanged. Product 1 H NMR and 13 CNMR is completely consistent with Example 1.

Embodiment 3

[0029] Example 3: Add p-toluenesulfonic acid monohydrate (0.23g, 12mmol) to 1,4-butanediol (1.08g, 12mmol) in tetrahydrofuran dichloromethane mixed solution (22mL), after cooling to 0°C, drip Add 3,4-dihydro-2H-pyran (1.1mL, 12mmol) and stir at room temperature for 6h. TLC detection, after the reaction, quenched by adding water, extracted with dichloromethane, combined the organic phases, dried over anhydrous sodium sulfate, concentrated under reduced pressure, purified by column chromatography to obtain a colorless liquid 3 (1.3g, yield 62% ). Compared with Example 1, the equivalent weight of 1,4-butanediol is reduced, and other conditions remain unchanged. Product 1 H NMR and 13 The C NMR is completely consistent with Example 1.

[0030] Step 2: Preparation of 4-((tetrahydro-2H-pyran-2-yl)oxy)butyraldehyde (4)

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Abstract

The invention relates to a synthesis method of aggregation pheromone (E)-cis-6, 7-epoxy-2-nonenal of Aromia bungii, which belongs to the field of pharmaceutical synthesis. The synthesis method comprises the following steps: taking 1, 4-butanediol as a raw material, singly protecting diol with DHP (dihexylphthalate) and then oxidizing TEMPO (tetramethylpiperidine oxide) into 4-((tetrahydro-2H-pyran-2-base) oxy) butyraldehyde; performing a Wittig reaction, so as to obtain (Z)-2-(hepta-4- alkene-1-base-oxy) tetrahydro-2H-pyran; removing the protection of the DHP and oxidizing TEMPO, so as to obtain (Z)-4-heptenal; performing a Wittig reaction, so as to obtain (2E, 6Z)-nona-2, 6-heptadienal; finally, performing epoxidation, so as to obtain the aggregation pheromone (E)-cis-6, 7-epoxy-2-nonenalof the Aromia bungii. The total yield is 6.5%. In the synthesis method, the 1, 4-butanediol with low cost is taken as the starting raw material; the synthesis method has the advantages of being simple in operation and mild in conditions, therefore, the synthesis method is suitable for large-scale preparation.

Description

Technical field [0001] The invention relates to a new synthetic method of natural product pheromone components, in particular to a synthetic method of Aromia bungii aggregation pheromone (E)-cis-6,7-epoxy-2-nonenal , It has insect attraction, non-toxic and harmless, and belongs to the field of drug synthesis. Background technique [0002] Aromia bungii (Coleoptera: Cerambycidae) is a wood beetle native to China, Korea, Mongolia, and eastern Russia. It has recently invaded Japan, Italy, Germany and other countries, and has also been found in the United States, the United Kingdom, Australia and other countries. It mainly parasitizes trees of the genus Prunus, including some economic fruit trees, such as cherry trees, cherry trees, peach trees, plum trees and apricot trees. It is one of only four species in the world. Like many geranium beetles, the developing larvae feed on the nutrient-rich phloem, cambium, and outer sapwood, and live through the winter as larvae, sometimes for...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D303/32C07D301/14
CPCC07D301/14C07D303/32
Inventor 何佳怡陈志立赵帅夏冉吴林盛侯苏童周骏涛陈新
Owner 江苏宁录科技股份有限公司
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