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Method for synthesizing (R)-cacopsylla pyricola sex pheromone

A technology of psyllid and pheromone, which is applied in the field of new synthesis-sex pheromone of psyllid, can solve problems such as difficulty in amplification, cumbersome reaction steps, and lengthy routes

Inactive Publication Date: 2021-06-22
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Although the synthesis research of (R)-pear psyllid sex pheromone has been reported in the literature, there are many problems such as long route, harsh reaction conditions, cumbersome reaction steps, and difficulty in amplification. Therefore, chemists need to develop new, environmentally friendly A Simple, Efficient, and Easy-to-Scale-Up Method for Synthesizing (R)-Psyllium Psyllium Sex Pheromone

Method used

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  • Method for synthesizing (R)-cacopsylla pyricola sex pheromone
  • Method for synthesizing (R)-cacopsylla pyricola sex pheromone
  • Method for synthesizing (R)-cacopsylla pyricola sex pheromone

Examples

Experimental program
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Effect test

Embodiment 1

[0025] (R)-4-Benzyl-3-n-tetradecanoyl Synthesis of oxazolidinone (2)

[0026] At 0°C, DCM (20 mL), n-tetradecanoic acid 1 (2.28 g, 10 mmol) and 3-5 drops of DMF were sequentially added into a 100 mL three-neck flask, and mixed well. Then oxalyl chloride (1.90 g, 15 mmol) was slowly added dropwise. The reaction was stirred for 1 h at 0 °C. After TLC monitors that the reaction is complete, stop the reaction. Concentrate under reduced pressure to remove the reaction solvent to obtain crude n-tetradecanoyl chloride as light yellow solid.

[0027] At room temperature, sequentially add THF (20mL) and (R)-4-benzyl Oxazolidinone (1.45g, 8.25mmol), stirred well. Sodium hydride (0.50 g, mass fraction 60%, 12.3 mmol) was slowly added at 0° C., the mixture was warmed up to room temperature, and stirred for 2 h. The crude product of n-tetradecyl chloride was added at room temperature, and the stirring reaction was continued for 3h. After TLC monitors that the reaction is complete,...

Embodiment 2

[0029] (R)-4-Benzyl-3-((R)-2-methyltetradecanoyl) Synthesis of oxazolidinone (3)

[0030] Under argon protection, add in a 250mL three-necked bottle at room temperature Solution of oxazolidinone amide 3 (3.87 g, 10 mmol) in THF (80 mL). The solution was cooled to -78°C, NaHMDS (7.12 mL, 2.0M THF solution, 14.25 mmol) was added dropwise within 15 min, and the mixture was stirred for 1 h. At 78°C, iodomethane (7.34g, 3.22mL, 52mmol) was slowly added dropwise, and the stirring reaction was continued for 3h. After TLC monitors that the reaction is complete, stop the reaction. with saturated NH 4 Cl solution (75 mL) was used to quench the reaction, and the layers were separated. The aqueous phase was extracted with ethyl acetate (3 x 75 mL), and the organic phases were combined. The organic phase was washed with saturated NaCl solution (300 mL), anhydrous NaCl 2 SO 4 Dry and concentrate under reduced pressure to obtain crude product. The crude product was purified by sil...

Embodiment 3

[0032] Synthesis of (R)-2-methyl-1-tetradecyl alcohol (4)

[0033] Add in a 250mL three-necked bottle at room temperature Oxazolidinone amide 3 (8.90g, 22.16mmol) and THF (80mL), stirred and dissolved. Under ice-bath cooling, sodium borohydride (3.35 g, 88.65 mmol) aqueous solution (10 mL) was added dropwise within 30 min. The temperature of the reaction solution was raised to room temperature, and the stirring reaction was continued for 3 h. After TLC monitors that the reaction is complete, stop the reaction. Adjust the pH to 6 with 2.5M hydrochloric acid, and separate the liquids. The aqueous layer was extracted with ethyl acetate (3 x 30 mL), and the organic phases were combined. The organic phase was sequentially washed with saturated NaHCO 3 Aqueous solution (20mL) was washed with saturated NaCl solution (20mL), anhydrous NaCl 2 SO 4 Dry and concentrate under reduced pressure to obtain crude product. The crude product was purified by silica gel column chromatogra...

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Abstract

The invention belongs to the technical field of green pesticides, and discloses a novel method for synthesizing (R)-cacopsylla pyricola sex pheromone. The method comprises the steps: by taking n-tetradecanoic acid 1 as an initial raw material, firstly reacting with oxalyl chloride to generate n-tetradecanoyl chloride, and then reacting with (R)-4-benzyl-2-oxazolidinone to generate oxazolidinone amide 2; reacting with CH3I in the presence of NaHMDS to generate oxazolidinone amide 3 with one or more methyl groups, and reducing the oxazolidinone amide 3 into chiral alcohol 4 through sodium borohydride; carrying out bromination, and reacting with PPh3 to generate quaternary phosphonium salt 6; and finally carrying out Wittig reaction and catalytic hydrogenation to prepare the (R)-cacopsylla pyricola sex pheromone, namely (R)-13-methylheptacosanoic acid. The chiral methyl is constructed by using an Evans chiral induction method, and the method has the advantages of simple synthetic route, mild reaction conditions, easiness in amplification and the like.

Description

technical field [0001] The invention relates to the technical field of green pesticides, in particular to a new method for synthesizing (R)-sex pheromone of pear psyllid. Background technique [0002] The pear psyllid (Cacopsylla pyricola) is an important pest that harms pear trees. It mainly sucks the juice from the tender green tissues of pear trees and secretes honeydew to induce sooty spot disease, which affects the quality and yield of pears (Yan Wentao; Zhang Huaijiang; Yue Qiang; Qiu Guisheng; Sun Lina; Wang Yasi . Fruit Tree Practical Technology and Information 2020, 31. Horton, D.R.; Cooper, W.R.J. Insect. Sci. 2017, 17, 1.). The sex pheromone of pear psyllid is secreted and released by the gonads of adult female moths, and has the physiological activity of attracting males (Victoria Soroker, S.T., Ally R. et al J. Insect. Behav. 2004, 17, 613). In 2009, Guédot et al. identified for the first time that the main active ingredient of the sex pheromone in Psyllium psy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C5/03C07C9/22
CPCC07B2200/07C07C1/34C07C5/03C07C17/16C07C29/147C07C2523/44C07D263/26C07F9/5442C07C9/22C07C11/02C07C19/075C07C31/125
Inventor 边庆花袁谷城钟江春杨宇雄周云王敏
Owner CHINA AGRI UNIV
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