Method for preparing Asiatic corn borer sex pheromone from tridecane compound

A technology of corn borer sex and thirteen carbons, which is applied in the field of preparation of sex pheromones of Asian corn borer, can solve the problems that the cis-trans ratio is difficult to control, affects the wide application of the technology, and harsh reaction conditions

Active Publication Date: 2015-03-25
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0016] 1. Some routes or starting raw materials are expensive, or the reaction conditions are harsh, or the preparation route is too long, or the cis-trans ratio is not easy to control, and cannot meet the natural ratio and other prominent problems, which limit the application and large-scale production of this method and affect this technology. wide application of
[0017] 2. In some methods, the two components of cis and trans are prepared separately, and they can be used in the field after mixing in the later stage, which increases the difficulty of use

Method used

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  • Method for preparing Asiatic corn borer sex pheromone from tridecane compound
  • Method for preparing Asiatic corn borer sex pheromone from tridecane compound
  • Method for preparing Asiatic corn borer sex pheromone from tridecane compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Take 1.2210g (5mmol) of 1,13-tridecanedioic acid in a dry 150ml round bottom flask, add 50ml of anhydrous THF (tetrahydrofuran) to dissolve it, add 0.5690g (15mmol) of lithium aluminum hydride under the protection of ice bath and nitrogen, React at room temperature for 12 hours. After the reaction is over, add 10% (mass ratio) HCl solution dropwise under ice bath until the gas no longer escapes, suction filter, wash the filter cake 3 times with 20ml ethyl acetate, and use anhydrous MgSO for the filtrate 4 dry. After rotary evaporation, 1.0824 g of the crude white solid product, namely the crude product of 1,13-tridecanediol was obtained, and the yield was calculated in combination with the next step.

Embodiment 2

[0048] Take 1.0818g (5mmol) of 1,13-tridecanediol crude product in a 250ml round bottom flask, add 40ml cyclohexane to dissolve, stir to dissolve at 55℃, add dropwise to the reaction flask within 10 minutes and dissolve in 30ml water An aqueous solution of 23ml glacial acetic acid and 0.08ml concentrated sulfuric acid, react at 55°C for 10 hours, cool to room temperature, separate the liquids, first use 20ml saturated NaHCO for the organic phase 3 The solution was washed twice, and then washed twice with 20 ml of saturated brine, and the crude product was obtained by rotary evaporation. Purification by column chromatography (eluent: petroleum ether: diethyl ether=3:1, volume ratio) to obtain 0.8398 g of white solid 13-hydroxytridecan-1-ol acetate, with a total yield of 65 in 1-2 steps %.

Embodiment 3

[0050] Take 0.6466g (3mmol) of PCC (pyridine chlorochromate) into a 50ml round bottom flask, add 15ml of dichloromethane at room temperature to dissolve, add 0.5168g (2mmol) of 13-hydroxytridecan-1-ol into the reaction flask Acetate, stirred at room temperature, TLC monitoring, after 3 hours, the reaction was completed, suction filtration, 10ml anhydrous ether to wash the filter cake twice, the filtrate was rotary evaporated, the crude product was subjected to column chromatography (eluent: petroleum ether: ether = 8 (1, volume ratio) to obtain a colorless oily liquid product of 0.6466 g of 13-aldehyde tridec-1-ol acetate, with a yield of 95%.

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Abstract

The invention discloses a novel method for preparing asiatic corn borer sex pheromone from a tridecane compound which is taken as an initial raw material, and belongs to the technical field of agricultural plant protection. The invention provides a novel method for preparing asiatic corn borer sex pheromone from a tridecane compound which is taken as an initial raw material. In particular, the invention first proposes an innovative and unique '13C+1C' synthesis strategy for chemical synthesis of the asiatic corn borer sex pheromone. The method disclosed by the invention has the characteristics of low raw material cost, short synthesis route, simple synthesis condition, high total yield and the like, and is applicable to industrial production.

Description

Technical field [0001] The invention belongs to the technical field of agricultural plant protection, and specifically relates to a preparation method of Asian corn borer sex pheromone using 13-carbon compounds as starting materials. Background technique [0002] The Asian corn borer is the main pest in my country’s corn fields. Among various methods to control the Asian corn borer, the insect sex pheromone biological control method has high sensitivity, strong selectivity, non-toxic, no environmental pollution, no damage to natural enemies, and difficult It has advantages such as resistance to pesticides and conforms to the IPM (Integrated Pest Management) strategy. It is currently an internationally recognized green plant protection technology. It is of great significance for protecting agricultural production, ecological security and achieving sustainable agricultural development, and has been widely promoted and applied. [0003] Because the content of sex pheromone produced by ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/145C07C67/293
CPCC07C29/147C07C67/08C07C67/293C07C69/145C07C69/16C07C31/20
Inventor 张大伟刘伟潘洪玉杨鹏蒋龙杨国庆
Owner JILIN UNIV
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