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1,3-dihydroxy-3,7-dimethyl-6-octen-2-one synthesis method

A synthesis method, dihydroxyl technology, applied to compounds of elements of group 4/14 of the periodic table, chemical instruments and methods, hydrolysis to prepare carbonyl compounds, etc., can solve problems such as many steps

Active Publication Date: 2017-02-01
EAST CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] 2) In 2009, Chauhan et al. reported the total synthesis of (S)-CPD starting from chiral substrates. This route has many steps, thus requiring a lot of time and effort to separate the corresponding intermediate products

Method used

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  • 1,3-dihydroxy-3,7-dimethyl-6-octen-2-one synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-10

[0055] Embodiment 1-10: use TMSCN as cyanide source (table 1):

[0056]

[0057] General operation procedure 1: In a dry 100mL three-necked flask, sequentially add catalyst I, raw material 1 (5.04g, 40mmol), solvent (40mL), and then slowly add TMSCN (6.0mL, 48mmol). The reaction process is monitored by thin-layer chromatography. After the corresponding raw material 1 is consumed, the reaction solution is slowly added dropwise under stirring to a container containing (methanol: 20mL; CH 2 Cl 2 : 60mL; in the Erlenmeyer flask of acid 1), after the dropwise addition, add saturated sodium chloride solution (50mL) again. The obtained two-phase solution was separated with a separatory funnel, the obtained organic phase was washed once with saturated sodium chloride solution (50 mL), and then the solvent was removed by rotary evaporation to obtain a colorless oily liquid. Next, the obtained oily liquid was dissolved in tetrahydrofuran (40mL), base I (50mmol) was added under stir...

Embodiment 11～15

[0063] Embodiment 11~15: use HCN as cyanide source (table 2):

[0064]

[0065] General operating procedure 2: In a 100mL three-neck flask with an absorption device of dry ice and sodium hydroxide, add catalyst I, raw material 1 (5.04g, 40mmol), solvent (40mL) in sequence, and then slowly feed HCN (g ). The reaction process was monitored by thin layer chromatography. After the corresponding starting material 1 was consumed, the solvent was removed by rotary evaporation to obtain a colorless oily liquid. Next, the obtained oily liquid was dissolved in tetrahydrofuran (40mL), base I (50mmol) was added under stirring, the resulting solution was cooled at -10°C for 10min, and then 4 was added slowly. After the dropwise addition, the reaction solution was placed in After stirring at room temperature for 2 h, it was quenched with saturated sodium bicarbonate solution (50 mL). Then, the mixture obtained after removing the solvent by rotary evaporation was subjected to column chr...

Embodiment 16～20

[0070] Embodiment 16~20: use NaCN or KCN as cyanide source (table 3):

[0071]

[0072] General operation procedure 3: In a 100mL three-neck flask equipped with an absorption device of dry ice and sodium hydroxide, add catalyst Ⅰ, raw material 1 (5.04g, 40mmol), solvent (40mL) in sequence, and then add NaCN or KCN. The reaction process was monitored by thin-layer chromatography. After the corresponding raw material 1 was consumed, the solvent was removed by suction filtration and rotary evaporation to obtain a colorless oily liquid. Next, the obtained oily liquid was dissolved in tetrahydrofuran (40mL), base I (50mmol) was added under stirring, the resulting solution was cooled at -10°C for 10min, and then 4 (50mmol) was slowly added. After the dropwise addition, The reaction solution was stirred at room temperature for 2 h and quenched with saturated sodium bicarbonate solution (50 mL). Then, the mixture obtained after removing the solvent by rotary evaporation was subjec...

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Abstract

The present invention discloses new 1,3-dihydroxy-3,7-dimethyl-6-octen-2-one synthesis method, which comprises racemic synthesis and enantioselective synthesis. According to the present invention, commercially available 6-methyl-5-hepten-2-one (CAS:110-93-0) is adopted as a starting material, two one-pot series connection reaction systems are adopted, simple operations are performed, the separation purification of the intermediate is effectively avoided, the high-yield racemic synthesis of the 1,3-dihydroxy-3,7-dimethyl-6-octen-2-one is achieved, and the asymmetric synthesis method for enantioselective synthesis of (R)-1,3-dihydroxy-3,7-dimethyl-6-octen-2-one and (S)-1,3-dihydroxy-3,7-dimethyl-6-octen-2-one is developed. The present invention further discloses an intermediate compound.

Description

technical field [0001] The invention belongs to the technical field of organic compound technology application, and specifically relates to a novel synthesis method of 1,3-dihydroxy-3,7-dimethyl-6-octen-2-one, which includes racemization synthesis, enantiometry selective synthesis. Background technique [0002] The Colorado potato beetle is a global pest that causes billions of dollars in damages every year. Previously, insecticides were mainly relied on to control its infestation, but as the Colorado potato beetle has evolved resistance to almost every insecticide used, this has prompted the search for new strategies to control the Colorado potato beetle. Potato beetle damage. Insect pheromone is a relatively simple, safe and environmentally friendly alternative to insecticides. Recent studies have shown that the pheromone (S)-1,3-dihydroxy-3,7-dimethyl-6-octen-2-one [(S)-CPD] secreted by male Colorado potato beetles can effectively attracts both sexes of the Colorado p...

Claims

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Application Information

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IPC IPC(8): C07C45/42C07C49/24
CPCC07C45/42C07F7/188C07C49/24
Inventor 周剑曾兴平
Owner EAST CHINA NORMAL UNIVERSITY
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