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Stereoselective synthetic method for tea geometrid sex pheromone

A technology of stereoselectivity and synthesis method, applied in the production of bulk chemicals, organic chemistry, etc., can solve the problems of high price, difficult purification, poor selectivity, etc., and achieve high enantioselectivity, simple separation and high yield Effect

Active Publication Date: 2013-02-06
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The disadvantage of this method is that the starting material (2Z,5Z)-octadiene-1-ol is expensive and difficult to synthesize, and the alkenyl Grignard reagent is difficult to prepare, and the yield of the last coupling reaction is low, the selectivity is poor, and the purification More difficult, difficult to achieve a large number of synthesis

Method used

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  • Stereoselective synthetic method for tea geometrid sex pheromone
  • Stereoselective synthetic method for tea geometrid sex pheromone
  • Stereoselective synthetic method for tea geometrid sex pheromone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Step 1 Synthesis of (Z)-4-chloro-2-buten-1-ol (2)

[0042] Dissolve cis-2-butene-1,4-diol (1) (22g, 250mmol) in tetrahydrofuran (120mL) solvent, add pyridine (22mL, 275mmol) at 0°C, drop through constant pressure dropping funnel Thionyl chloride (20 mL, 275 mmol) was added, raised to room temperature, and stirred for 1 day. After the reaction was quenched by adding 50 mL of ice water dropwise, the liquid was separated and the aqueous phase was extracted with diethyl ether (3×30 mL). The organic phases were combined, washed with 10% sodium hydroxide solution (30mL), saturated sodium bicarbonate solution (30mL) and saturated brine (20mL), dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and purified to obtain compound 2 (18.5g, 70%). Colorless liquid, b.p.78-82°C (13mmHg). 1 H NMR (400MHz, CDCl 3 )δ2.58(s,1H),4.10(d,J=7.0Hz,2H),4.24(d,J=5.6Hz,2H),5.70-5.80(m,2H)ppm; 13 C NMR (100MHz, CDCl 3 ) δ39.0, 57.9, 127.3, 133.1ppm; MS (ESI) ...

Embodiment 2

[0062] Step 1 Synthesis of (Z)-4-chloro-2-buten-1-ol (2)

[0063] Dissolve cis-2-butene-1,4-diol (1) in ether solvent, add pyridine at 0°C, add thionyl chloride dropwise through a constant pressure dropping funnel, rise to room temperature, and stir for 1 day . After the reaction was quenched by adding ice water dropwise, the mixture was allowed to stand for liquid separation, and the aqueous phase was extracted with diethyl ether. The combined organic phases were dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and purified to obtain a colorless liquid 2 (68%).

[0064] Step 2 Synthesis of (Z)-2-en-5-yne tetradec-1-alcohol (3)

[0065] Anhydrous potassium carbonate, cuprous iodide, and sodium iodide were added to N,N-dimethylacetamide solvent, 1-decyne was added at room temperature, stirred for 1 h, compound 2 was added dropwise, and stirred at room temperature for 6 h. After stopping the reaction, filter, concentrate under reduced pressu...

Embodiment 3

[0083] Step 1 Synthesis of (Z)-4-chloro-2-buten-1-ol (2)

[0084] Dissolve cis-2-butene-1,4-diol (1) in tetrahydrofuran solvent, add pyridine at room temperature, add thionyl chloride dropwise through a constant pressure dropping funnel, raise the temperature to 65°C, and stir for 10 hours. After adding ice water to quench the reaction, let stand to separate the layers, and extract the aqueous phase with diethyl ether. The combined organic phases were dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and purified to obtain compound 2 (66%).

[0085] Step 2 Synthesis of (Z)-2-en-5-yne tetradec-1-alcohol (3)

[0086] Anhydrous cesium carbonate, cuprous iodide, and sodium iodide were added to N,N-dimethylformamide solvent, 1-decyne was added at room temperature, stirred for 1 h, compound 2 was added dropwise, and stirred at room temperature for 8 h. After stopping the reaction, filter, concentrate under reduced pressure, dilute with water, and ...

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Abstract

The invention discloses a stereoselective synthetic method of tea geometrid sex pheromone and relates to a stereoselective synthetic method of propylene epoxide compounds. The tea geometrid sex pheromone is I [dextrorotation-(3Z, 9Z, 6R, 7S)-6, 7-epoxy octadecadiene] and an enantiomer II [sinistrogyration-(3Z, 9Z, 6S, 7R)-6, 7-epoxy octadecadiene]. According to the invention provides the stereoselective synthetic method of tea geometrid sex pheromone provided by the invention, cis-2-butene-1, 4-glycol (1) is taken as raw material, the efficiency, the yield and the enantioselectivity are high, the operation and the separation are simple, the yield is high, the using reagents are all commonly used, so that the tea geometrid sex pheromone is cheap and easy to obtain, a protecting group does not need to be used, and the preparation procedures are few, so that the tea geometrid sex pheromone is suitable for batch production.

Description

technical field [0001] The present invention relates to a stereoselective synthesis method of propylene oxide compounds, especially a method for synthesizing tea geometrid sex pheromone I [dextrorotatory-(3Z,9Z,6R,7S)-6,7-epoxyoctadecyl Carbadiene] and its enantiomer II [L-(3Z,9Z,6S,7R)-6,7-epoxy octadecadiene]. Background technique [0002] Tea geometrid, also known as arch worm, is one of the main leaf-eating pests of tea trees. It mainly eats the young leaves of tea trees. The output is mainly distributed in Zhejiang, Jiangsu, Anhui, Hunan, Hubei, Jiangxi, Fujian and other provinces. In recent years, the damage has been serious in Fujian tea areas. When a large number of them occur, the entire tea garden will be eaten up, resulting in a reduction of more than 60% of tea production, and seriously affecting the quality of finished tea. In addition to tea trees, the insect can also harm soybeans, cowpeas, sesame, sunflower, and Polygonum, causing significant economic losse...

Claims

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Application Information

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IPC IPC(8): C07D303/04C07D301/00
CPCY02P20/55
Inventor 郑剑峰梁攀黄培强
Owner XIAMEN UNIV
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