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Enantioselective synthesis method of chiral (3Z, 9Z)-6, 7-epoxy octadecadiene

A technology of epoxy octadecadiene and synthesis method, which is applied in the direction of organic chemical method, botany equipment and method, preservation of human or animal body, etc., and can solve problems such as difficult storage, difficult preparation, instability, etc.

Active Publication Date: 2017-05-17
HEFEI JIUYI AGRI DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The disadvantage of this method is that the intermediate 1,2-dibromobutene used is difficult to prepare and is extremely unstable and difficult to store. The synthetic intermediate 2,3-epoxy-5-yne-tetradecyl alcohol trifluoromethanesulfonate has properties It is lively and prone to reactions such as elimination, which is not conducive to the subsequent reaction, and the reaction often needs to be carried out at low temperature

Method used

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  • Enantioselective synthesis method of chiral (3Z, 9Z)-6, 7-epoxy octadecadiene
  • Enantioselective synthesis method of chiral (3Z, 9Z)-6, 7-epoxy octadecadiene
  • Enantioselective synthesis method of chiral (3Z, 9Z)-6, 7-epoxy octadecadiene

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Experimental program
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Effect test

Embodiment 1

[0101] step 1) Synthesis of (2R,3S,5Z)-2,3-epoxy-5-octen-1-ol(4)

[0102] Under a nitrogen atmosphere, mix 200 mg of calcium hydride with 500 mg of silica gel, add dichloromethane (25 mL) solvent and tetraisopropyl titanate (3.0 mL, 10 mmol), stir at -30 ° C, and then add D-( -)-diethyl tartrate (2.27g, 11mmol) in dichloromethane (10mL) solution, (2Z,5Z)-octadien-1-ol (3) (1.26g, 10mmol) in dichloromethane (5mL ) solution, tert-butanol peroxide (3.7mL, 20mmol, 5.5M in n-Nonane), and react at -30°C for 2 days. After quenching the reaction with 30mL of 10% aqueous citric acid solution, the temperature was raised, and the liquids were separated. The aqueous phase was extracted with dichloromethane (2×20mL), and the combined organic phases were washed with saturated brine (3×30mL), and washed with Dried over sodium sulfate, filtered and concentrated to obtain the crude product compound 4, which was directly carried out to the next reaction without purification.

[0103] Step...

Embodiment 2

[0130] step 1) Synthesis of (2R,3S,5Z)-2,3-epoxy-5-octen-1-ol(4)

[0131] Under the protection of nitrogen atmosphere, to 500mg Dichloromethane (25mL) solvent and tetraisopropyl titanate (3.0mL, 10mmol) were added to the molecular sieve, stirred at -30°C, and D-(-)-diethyl tartrate (2.27g, 11mmol) was added in sequence Dichloromethane (10mL) solution, (2Z,5Z)-octadien-1-ol (3) (1.26g, 10mmol) in dichloromethane (5mL) solution, peroxy tert-butanol (3.7mL, 20mmol , 5.5M in n-Nonane), followed by reaction at -30°C for 2 days. After the reaction was quenched with 10% citric acid aqueous solution, the temperature was raised, and the liquids were separated. The aqueous phase was extracted with dichloromethane, and the combined organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated to obtain crude The product compound 4 was directly carried out to the next reaction without purification.

[0132] Step 2) Synthesis of (2R,3...

Embodiment 3

[0159] step 1) Synthesis of (2R,3S,5Z)-2,3-epoxy-5-octen-1-ol(4)

[0160] Under the protection of nitrogen atmosphere, to 500mg Dichloromethane (25mL) solvent and tetraisopropyl titanate (3.0mL, 10mmol) were added to the molecular sieve, stirred at -30°C, and D-(-)-diethyl tartrate (2.27g, 11mmol) was added in sequence Dichloromethane (10mL) solution, (2Z,5Z)-octadien-1-ol (3) (1.26g, 10mmol) in dichloromethane (5mL) solution, peroxy tert-butanol (3.7mL, 20mmol , 5.5M in n-Nonane), followed by reaction at -30°C for 2 days. After the reaction was quenched with 10% citric acid aqueous solution, the temperature was raised, and the liquids were separated. The aqueous phase was extracted with dichloromethane, and the combined organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated to obtain crude The product compound 4 was directly carried out to the next reaction without purification.

[0161] Step 2) Synthesis of (2R,3...

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Abstract

The invention discloses an enantioselective synthesis method of chiral (3Z, 9Z)-6, 7-epoxy octadecadiene, and belongs to the technical field of tea geometrid control. The invention provides a high-efficiency and high-stereoselectivity synthesis method of a leavoisomer and a dextroisomer of a tea geometrid sex pheromone by taking easily-obtained (2Z, 5Z)-octadien-1-ol (3) as a starting raw material. The enantioselective synthesis method is simple in step operation; purification is simple, and in many steps, purification is not required and next-step reaction can be directly performed; used reagents are commonly-used cheap easily-obtained reagents; the route is relatively short; the synthesis method is suitable for large-scale production. Through EAG (antennal potential) and a wind tunnel experiment, the invention further preliminarily judges that leavoisomer 1 has higher tea geometrid trapping capability, while the dextroisomer 2 basically has no tea geometrid trapping activity. By the enantioselective synthesis method, asymmetric synthesis of an optically active sex pheromone is expected to be widely applied to agricultural green control.

Description

technical field [0001] The invention relates to an enantioselective synthesis method of chiral (3Z,9Z)-6,7-epoxy octadecadadiene, and belongs to the technical field of tea geometrid control. Background technique [0002] Tea geometrids belong to Lepidoptera, Geometriidae, and Ennominae, also known as arch worms, worms, and hanging silkworms. They are the main pests of tea gardens in Zhejiang, Jiangsu, and Anhui regions in my country. The generation number varies with the climatic conditions of the year, and there are 5 to 7 generations a year. When the outbreak occurs, the damage is extremely serious. The leaves and buds of the entire tea tree are all eaten up, leaving only the branches and veins, which look like fire, resulting in reduced tea production. More than 60%, and can lead to the consequences of premature aging of tea trees, poor cold resistance, and susceptibility to freezing damage in winter. Tea geometrids have a greater impact on tea yield, quality and tea tre...

Claims

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Application Information

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IPC IPC(8): C07D301/26C07D301/00C07D303/04A01N43/20A01N27/00A01P19/00
CPCY02P20/55C07D301/26A01N27/00A01N43/20C07B2200/07C07D301/00C07D303/04A01N2300/00
Inventor 宛晓春俞杰杨云秋郭峰
Owner HEFEI JIUYI AGRI DEV