Compound of thioketal, synthetic method, and application in synthesizing pheromone of southern Diabrotica in optical purity

A synthesis method and compound technology, applied in the direction of organic chemistry and the like, can solve problems such as poor attraction of southern corn rootworm, and achieve the effects of fewer reaction steps, high yield and reduced pollution

Inactive Publication Date: 2007-10-10
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In 1982, Guss et al. successfully identified and synthesized a western corn rootworm sex pheromone: propionate-8-methyl-2-n-decyl ester, which is effective against western corn rootworm, northern corn rootworm and Mexican corn rootworm. Male adults are very attractive, but less so to southern corn rootworms (J. Chem. Ecol. 1982, 8, 545)

Method used

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  • Compound of thioketal, synthetic method, and application in synthesizing pheromone of southern Diabrotica in optical purity
  • Compound of thioketal, synthetic method, and application in synthesizing pheromone of southern Diabrotica in optical purity
  • Compound of thioketal, synthetic method, and application in synthesizing pheromone of southern Diabrotica in optical purity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Synthesis of Example 1 Compound 2a

[0032]

[0033] A three-necked flask equipped with a constant pressure dropping funnel was treated with anhydrous and anaerobic treatment, added lactone 4 (342.5 mg, 2.67 mmol), 20 mL of absolute anhydrous ether, cooled to -78 ° C, and added dropwise 1.7 mL of MeLi ( 1.6M in Et 2 (0), stirred for 30 minutes after the completion of the dropwise addition, rose to room temperature, and TLC detected that the raw material disappeared, and the reaction system was poured into cold saturated NH 4 Quenched in Cl solution, separated the organic phase, back-extracted the aqueous phase with ether (2×15mL), combined the organic phases, washed with saturated brine, and anhydrous Na 2 SO 4 Dry and spin dry under reduced pressure, and the crude product is directly used in the next reaction.

[0034] The crude product obtained above was dissolved in 10 mL of dry CH 2 Cl 2 , add propanedithiol (0.4mL, 433mg, 4mmol), then ...

Embodiment 2

[0037] Synthesis of Example 2 Compound 2b

[0038]

[0039] A three-necked bottle equipped with a constant pressure dropping funnel, treated with anhydrous and anaerobic treatment. Compound 2a (1.17 g, 4.95 mmol) was dissolved in 35 mL of dry CH 2 Cl 2 , then add Et 3 N (1.1mL, 759mg, 7.5mmol), MsCl (0.6mL, 859mg, 7.5mmol) was added dropwise under ice-cooling. After 3 hours, TLC detected that the reaction was complete. Add 10 mL of water to quench the reaction, separate the organic phase, and the aqueous phase with CH 2 Cl 2 Back extraction (1×15mL), combined organic phases, washed with saturated brine, anhydrous Na 2 SO 4 Drying, spin-drying under reduced pressure, and flash column chromatography gave 1.48 g of a colorless oily substance 2b with a yield of 95%.

[0040] Compound 2b: C 12 h 24 o 3 S 3 ;FW312;

[0041] 1 H NMR (300MHz, CDCl 3 )δ: 4.22(t, J=6.9Hz, 2H), 3.00(s, 3H), 2.86-2.82(m, 4H), 1.98-1.86(m, 4H), 1.78-1.70(m, 2H), 1.61 ...

Embodiment 3

[0042] Synthesis of Example 3 Compound 2c

[0043]

[0044] A three-necked bottle equipped with a constant pressure dropping funnel, treated with anhydrous and anaerobic treatment. Compound 2a (1.17 g, 4.95 mmol) was dissolved in 35 mL of dry CH 2 Cl 2 , then add Et 3 N (1.1mL, 759mg, 7.5mmol), TsCl (1.43g, 7.5mmol) was added dropwise under ice-cooling. After 3 hours, TLC detected that the reaction was complete. Add 10 mL of water to quench the reaction, separate the organic phase, and the aqueous phase with CH 2 Cl 2 Back extraction (1×15mL), combined organic phases, washed with saturated brine, anhydrous Na 2 SO 4 Drying, spin-drying under reduced pressure, and flash column chromatography gave 1.85 g of a colorless oily substance 2c with a yield of 96%.

[0045] Compound 2c: C 18 h 28 o 3 S 3 ;FW 388;

[0046] 1 H NMR (300MHz, CDCl 3 )δ: 8.01(d, J=7.2Hz, 2H), 7.72(d, J=6.5Hz, 2H), 4.12(d, J=6.6Hz, 2H), 2.83-2.78(m, 4H), 2.43( s, 3H), 2...

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Abstract

This invention relates to a method for synthesizing novel chain molecules with thioketal structure, which can be used to synthesize optical pure sex pheromone of Diahrotica undecimpunctata (R)-10-methyl-2-tridecanone. The method has such advantages as few steps, easy operation and high yield.

Description

technical field [0001] The invention relates to a class of thioketal compounds and their synthesis method, which can be used to synthesize optically pure southern corn rootworm sex pheromone (R)-10-methyl-2-tridecanone. The method of the invention is used to synthesize the optically pure southern corn rootworm sex pheromone (R)-10-methyl-2-tridecanone, which has shorter steps, simpler operation and higher yield than the method in the existing literature. technical background [0002] The superfamily Diabroticites, belonging to the order Coleoptera, includes a wide variety of pest groups that damage field crops. Both adults and larvae are herbivorous, feeding on roots, stems, leaves, flowers, etc. of plants. Many species cause serious harm to crops, vegetables, forest trees, fruit trees, and pastures. For example, the world-renowned pest potato beetle belongs to the Chrysophyte family. The larvae of various types of beetles seriously damage corn crops, such as the Southern ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D339/06C07C49/04
Inventor 田伟生王子坤李伯玉许启海
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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