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A kind of preparation method of novel 5-allyl cyclopentenone and product thereof

A technology of allyl cyclopentenone and enynyl ester, applied in the field of preparation of novel 5-allyl cyclopentenone, which can solve the problems of poor selectivity, uncontrollable high yield of products, etc.

Inactive Publication Date: 2021-05-18
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

And the preparation method of existing 5-allyl cyclopentenone has many disadvantages: the selectivity is poor, the high yield of the product that can't control reaction obtains 5-allyl cyclopentenone, so cyclopentenone asymmetrically introduces alkene Propyl still a big problem

Method used

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  • A kind of preparation method of novel 5-allyl cyclopentenone and product thereof
  • A kind of preparation method of novel 5-allyl cyclopentenone and product thereof
  • A kind of preparation method of novel 5-allyl cyclopentenone and product thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027]

[0028] Under nitrogen protection, add 25 mL of anhydrous THF to a 100 mL dry eggplant-shaped bottle, add 2-methyl-1-butene-3-yne (1.43 mL, 15 mmol), start stirring at -78 ° C, and add dropwise n-Butyllithium (6.00mL, 15mmol), add benzaldehyde (1.02mL, 10mmol) after 1.5h, stir for 2h, add allyl chloroformate (2.13mL, 15mmol), continue stirring for 30min, TLC monitors the reaction, the reaction After the end, it was quenched with saturated ammonium chloride solution, extracted with ethyl acetate (20mL*2), the organic phase was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and rotary evaporated using a Heidolph rotary evaporator after suction filtration. The rotating speed is 200rpm, the temperature is 40°C, the vacuum degree is 0.06Mpa, and the processing time is 15min. Then, 1a (1.99g, 7.8mmol, yield 78%) was isolated by 200-300 mesh silica gel column chromatography, the eluent was ethyl acetate:petroleum ether=2:100.

[00...

Embodiment 2

[0033]

[0034] Under nitrogen protection, add bistriphenylphosphine palladium dichloride (140.3mg, 0.2mmol) and cuprous iodide (76.2mg, 0.4mmol) into a dry 100mL eggplant-shaped bottle, add 20mL THF, and start at room temperature Stir. Add 3 mL of diisopropylamine, then dissolve 1-phenyl-1-propynyl alcohol (1.32 g, 10 mmol) in 10 mL of THF into the reaction vessel, and finally add 6-iodo-1-phenyl-6-heptene- 1-Keto (4.71 g, 12 mmol), TLC monitored the reaction. After the reaction was completed, it was quenched with saturated ammonium chloride solution, extracted with ethyl acetate (20mL*2), the organic phase was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then evaporated using a Heidolph rotary evaporator after suction filtration. The rotating speed is 200rpm, the temperature is 40°C, the vacuum degree is 0.06Mpa, and the processing time is 10min. Then through 200-300 mesh silica gel column chromatography, the eluent is ethy...

Embodiment 3

[0040]

[0041] Under nitrogen protection, add bistriphenylphosphine palladium dichloride (140.3mg, 0.2mmol) and cuprous iodide (76.2mg, 0.4mmol) into a dry 100mL eggplant-shaped bottle, add 20mLTHF, and start stirring at room temperature . Add 3 mL of diisopropylamine, then dissolve 1-phenyl-1-propynyl alcohol (1.32 g, 10 mmol) in 10 mL of THF and add to the reaction vessel, and finally add iodide (N-(4-iodopent-4-en-1 -yl)-4-methyl-N-phenylbenzenesulfonamide) (5.29g, 12mmol), TLC monitored the reaction. After the reaction was completed, it was quenched with saturated ammonium chloride solution, extracted with ethyl acetate (20mL*2), the organic phase was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then evaporated using a Heidolph rotary evaporator after suction filtration. The rotating speed is 200rpm, the temperature is 40°C, the vacuum degree is 0.06Mpa, and the processing time is 10min. Then through 200~300 mesh silica ...

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Abstract

The invention discloses a preparation method of novel 5-allyl cyclopentenone and its product. It includes: first, sequentially add molecular sieves, anhydrous dichloroethane, enynyl ester, (acetonitrile) [(2-biphenyl) di-tert-butylphosphine] gold (I) hexafluoroantimonate, and stir under normal temperature and pressure 3 hours; Next, add tetrakis (triphenylphosphine) palladium, stir at normal temperature and pressure for 2 hours, then concentrate the reaction solution by rotary evaporation, and obtain the target product 5-allyl cyclopentenone by silica gel column chromatography. The whole reaction is carried out at normal temperature and pressure, with mild conditions and low energy consumption. The whole reaction is carried out in a "one-pot" gold-palladium co-catalysis method, without the need to separate intermediates, and has good atom economy. The range of reaction substrates is wide, not only simple enynate compounds can be applied, but also natural products can be modified. The 5‑allylcyclopentenone compound developed by research and development has potential biological activity, and its drug activity can be tested for subsequent drug screening.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a preparation method of novel 5-allyl cyclopentenone and a product thereof. Background technique [0002] Allyl cyclopentenone has important physiological activities and widely exists in drug molecules and spices. It is an important alkaloid and a key intermediate of drug molecules, such as 2-allyl-4-hydroxy-2-cyclopentene Ketone is a key intermediate in the synthesis of prostaglandin drug 4-thio-PGIL, which can be obtained by rearrangement of 5-allyl-4-hydroxy-2-cyclopentene, and has important physiological activity and medicinal value. [0003] The potential biological activity of 5-allyl cyclopentenone compounds has attracted widespread attention of scientists, and has great synthetic significance. And the preparation method of existing 5-allyl cyclopentenone has many disadvantages: the selectivity is poor, the high yield of the product that can't contr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/00C07C49/597C07C51/00C07C51/373C07C303/36C07C311/17C07D209/12C07D211/96
CPCC07C45/00C07C49/597C07C51/00C07C51/373C07C303/36C07C311/17C07D209/12C07D211/96C07C2601/10C07C2601/14
Inventor 饶卫东陈翠丽周媛媛陈先枭凌媛尹栋梁
Owner NANJING FORESTRY UNIV
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