Isochroman derivative and enzymatic synthesis method and application thereof

A synthetic method, the technology of isochroman, which is applied in the field of isochroman derivatives and their enzyme-catalyzed synthesis, can solve the problems of complicated operation and heavy pollution, and achieve the effects of simple operation, improved conversion rate and mild reaction

Active Publication Date: 2021-07-02
HUAZHONG UNIV OF SCI & TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In view of the above defects or improvement needs of the prior art, the present invention provides an enzyme-catalyzed synthesis method of isochroman derivatives, the purpose of which is to obtain high value-added Different colors are combined, thus solving the shortcomings of the existing technology such as complex operation and large pollution

Method used

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  • Isochroman derivative and enzymatic synthesis method and application thereof
  • Isochroman derivative and enzymatic synthesis method and application thereof
  • Isochroman derivative and enzymatic synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Add 2,3-dihydroxybenzoic acid (0.3mmol, 46.2mg), 4-tert-butylstyrene (0.15mmol, 27.5uL), MnxEFG (0.01mol%), hydrogen peroxide to a 10ml reaction flask in sequence (0.75mmol, 75uL), deionized water (1mL), acetonitrile (1mL), hydrochloric acid (0.3mmol, 13uL) magnetically stirred at room temperature for 48 hours, after the conversion of the substrate, ethyl acetate was added to the reaction system to extract (3mL *4), the organic phases were combined and dried with anhydrous sodium sulfate, filtered and concentrated in vacuo to obtain a crude product. The obtained crude product was purified and separated by column chromatography to obtain a white solid product with an isolated yield of 77%.

[0034] The synthetic route of embodiment 1 is as follows:

[0035]

[0036] The proton nuclear magnetic resonance spectrum of the target product obtained in Example 1 is as follows.

[0037] 1 H NMR (400MHz, CDCl 3 ):11.06(s,1H),7.91–7.77(m,1H),7.46(d,J=8.4Hz,2H),7.41(d,J=8.4H...

Embodiment 2

[0040] Add 2,3-dihydroxybenzoic acid (0.3mmol, 46.2mg), 4-fluoro-α-methylstyrene (0.15mmol, 20.2uL), MnxEFG (0.01mol% ), hydrogen peroxide (0.75mmol, 75uL), deionized water (1mL), acetonitrile (1mL), hydrochloric acid (0.3mmol, 13uL) were magnetically stirred at room temperature for 48 hours, and ethyl acetate was added to the reaction system after the conversion of the substrate Extract (3mL*4), combine the organic phases and dry over anhydrous sodium sulfate, filter and concentrate in vacuo to obtain the crude product. The obtained crude product was purified and separated by column chromatography to obtain a white solid product with an isolated yield of 66%.

[0041] The synthetic route of embodiment 2 is as follows:

[0042]

[0043] The proton nuclear magnetic resonance spectrum of gained target product is as follows:

[0044] 1 H NMR (400MHz, CDCl 3):10.99(s,1H),7.42-7.40(m,2H),7.07–7.01(m,3H),6.65(d,J=5.6Hz,1H),3.44(d,J=10.8Hz,1H) ,3.32(d,J=10.8Hz,1H),1.77(s,3H)....

Embodiment 3

[0046] Add 2,3-dihydroxybenzoic acid (0.3mmol, 46.2mg), 4-methyl-α-methylstyrene (0.15mmol, 21.9uL), MnxEFG (0.01mol %), hydrogen peroxide (0.75mmol, 75uL), deionized water (1mL), acetonitrile (1mL), hydrochloric acid (0.3mmol, 13uL) were magnetically stirred at room temperature for 48 hours, and ethyl acetate was added to the reaction system after the conversion of the substrate Ester extraction (3mL*4), the organic phases were combined and dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to obtain the crude product. The obtained crude product was purified and separated by column chromatography to obtain a white solid product with an isolated yield of 81%.

[0047] The synthetic route of embodiment 3 is as follows:

[0048]

[0049] The proton nuclear magnetic resonance spectrum of gained target product is as follows:

[0050] 1 H NMR (400MHz, CDCl 3 ):11.04(s,1H),7.30(d,J=8.0Hz,2H),7.13(d,J=8.0Hz,2H),7.04(d,J=8.0Hz,1H),6.64(d,J =8.0Hz,1H),5.54(...

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Abstract

The invention belongs to the technical field of fine chemical synthesis, and particularly relates to an isochroman derivative and an enzymatic synthesis method and application thereof. According to the enzymatic synthesis method, 2, 3-dihydroxybenzoic acid and styrene compounds are taken as substrates, multi-copper oxidase is taken as a catalyst, and the isochroman derivatives are obtained through reaction. The isochroman compound with high added value is obtained from cheap and easily available chemical raw materials through the oxidative coupling reaction catalyzed by using the multi-copper oxidase as the catalyst, and the method is mild in reaction, low in cost, simple to operate, green and environment-friendly.

Description

technical field [0001] The invention belongs to the technical field of fine chemical synthesis, and in particular relates to an isochroman derivative and an enzyme-catalyzed synthesis method and application thereof. Background technique [0002] Isochroman compounds are natural benzolides, which widely exist in many natural products and drug molecules, and have a wide range of biological activities, including antibacterial, anti-inflammatory and anti-tumor effects. In the past two decades, the synthesis of isochroman compounds is inseparable from the use of transition metals, and the required conditions are relatively harsh. In addition, transition metal catalysts are usually expensive and not environmentally friendly. Therefore, the green and efficient synthesis of isochromans has attracted extensive attention from synthetic chemists and pharmacologists. [0003] Enzyme-catalyzed biosynthesis methods have developed rapidly in recent years. Enzyme-catalyzed synthesis has th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P17/06C07D311/76C07D409/04
CPCC12P17/06C07D311/76C07D409/04
Inventor 钟芳锐郭欢
Owner HUAZHONG UNIV OF SCI & TECH
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