Preparation method of quinone compound

A technology of compounds and quinones, which is applied in the field of preparation of quinones, can solve the problems of single preparation methods of quinones, and achieve the effect of cheap raw materials, easy availability of raw materials, and simple reaction conditions

Active Publication Date: 2021-12-03
SHANGHAI TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The technical problem to be solved by the present invention is that the preparation method of the existing qu...

Method used

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  • Preparation method of quinone compound
  • Preparation method of quinone compound
  • Preparation method of quinone compound

Examples

Experimental program
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Effect test

Embodiment 1

[0202]

[0203] In a dry 100mL flask, add a magnetic stirrer, 1.36g (10mmol, 1 equivalent) of 2,3-dimethyl-p-benzoquinone, 2,6-dimethyl-3,5-di(ethoxyacyl )-1,4-dihydropyridine 126mg (0.5mmol, 0.05 equivalent), dry chlorobenzene 50mL, 1-chloro-3-methyl-2-butene (isoamyl chloride) 1.73g (16.5mmol, 1.65 equivalent ), 237 mg (1.5 mmol, 0.15 equivalents) of 2-methyl-2-nonanol. After the solid is dissolved, add 0.8 g of commercially available 60% sodium hydride-mineral oil mixture (about 0.5 g of sodium hydride, about 2 equivalents) to the reaction flask, and then connect an air condenser to the round bottom flask to replace nitrogen And continue to blow nitrogen bubbles in the reaction system. The flask was heated to 80°C and the reaction was stirred for 48 hours. Thereafter, the reaction solution was placed in a centrifuge tube and centrifuged at 10,000 rpm for 2 minutes, and the supernatant was taken and subjected to column chromatography with petroleum ether: ethyl acetate ...

Embodiment 2

[0205]

[0206] In a dry 10mL flask, add a magnetic stirrer, 2,6-dimethyl-p-benzoquinone 68mg (0.5mmol, 1 equivalent), 2,6-dimethyl-3,5-di(ethoxyacyl )-1,4-dihydropyridine 6.3mg (0.025mmol, 0.05 equivalent), dry chlorobenzene 2.5mL, 1-chloro-3-methyl-2-butene (isoamyl chloride) 87mg (0.83mmol, 1.66 equivalent), 2-methyl-2-nonanol 23.7 mg (0.15 mmol, 0.3 equivalent). After the solid dissolves, add 40 mg of commercially available 60% sodium hydride-mineral oil mixture (containing about 24 mg of sodium hydride, 2 equivalents) to the reaction flask, then connect an air condenser to the round bottom flask, replace nitrogen and continue to pass through the flask. Nitrogen bubbles in the reaction system. The flask was heated to 80°C and the reaction was stirred for 48 hours. Thereafter, the reaction solution was placed in a centrifuge tube and centrifuged at 10,000 rpm for 2 minutes, and the supernatant was taken and subjected to column chromatography with petroleum ether: ethyl...

Embodiment 3～31

[0208] After the types and amounts of each raw material in the above-mentioned embodiment 2 were changed, embodiments 3-31 were formed. See the table below for the types and dosage changes of the materials described:

[0209]

[0210]

[0211]

[0212] Note: The equivalents in the above table are based on 2,6-dimethyl-p-benzoquinone as 1 equivalent. HE = 2,6-dimethyl-3,5-di(ethoxyacyl)-1,4-dihydropyridine; HQ = 1,4-hydroquinone.

[0213] K 2 CO 3 The pKa of sodium phenoxide is 10.25, which is slightly higher than that of sodium phenoxide (9.98).

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Abstract

The invention discloses a preparation method of a quinone compound. The invention provides the preparation method of the quinone compound, the preparation method comprises the following step: in the presence of alkali, carrying out condensation reaction on a compound as shown in a formula II and a compound as shown in a formula III to obtain the quinone compound as shown in a formula I, the alkalinity of the alkali is stronger than that of sodium phenate. The method is easy to operate and suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of quinone compounds. Background technique [0002] Benzoquinones have unique structural and functional characteristics, widely exist in nature and play important roles. Coenzyme Q10, vitamin K, plastoquinone and other compounds containing quinone functional groups are electron transfer carriers in eukaryotic respiration, photosynthesis and other biochemical processes. Studies have shown that coenzyme Q10 and vitamin K family are indispensable vitamins in the human body and have positive effects on organs and tissues such as the heart and bones. However, the food sources of these vitamins are limited, so chemical synthesis is an important source of them, and the successful synthesis method The market potential is huge. [0003] The classic method of synthesizing quinone compounds generally starts with raw materials such as phenol and aryl ether, and carries out side chain modification through functionaliz...

Claims

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Application Information

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IPC IPC(8): C07C46/00C07C50/06C07C50/08C07C50/14C07C50/28C07C50/32
CPCC07C46/00C07C2601/16C07C2602/10C07C50/06C07C50/08C07C50/14C07C50/28C07C50/32Y02P20/55
Inventor 李智张子宁
Owner SHANGHAI TECH UNIV
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