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Method for synthesizing anthracene fluorescent dye

A technology for fluorescent dyes and anthracenes, which is applied in the field of biochemical synthesis, can solve the problems of difficult preparation of key intermediates, limited reaction conditions, and low synthesis yields, avoiding the use of organometallic compounds, simple preparation, and cheap and readily available raw materials. Effect

Inactive Publication Date: 2020-05-29
CYGNUS BIOSCI BEIJING CO LTD
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  • Abstract
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Problems solved by technology

However, its synthesis yield is relatively low, and the reaction conditions are relatively limited
The present invention adopts a new method for synthesizing anthracene fluorescent dyes to solve the problems of difficult preparation of key intermediates and low yield when synthesizing anthracene fluorescent dyes; at the same time, the raw materials required by the new synthetic route are cheap and easy to obtain, and the reaction conditions are more efficient. Mild, reducing the risk of reaction operation, and less harmful to the environment during the experiment process and experimental treatment

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  • Method for synthesizing anthracene fluorescent dye
  • Method for synthesizing anthracene fluorescent dye
  • Method for synthesizing anthracene fluorescent dye

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preparation example Construction

[0057] The invention discloses a method for synthesizing anthracene compounds, which is characterized in that it comprises:

[0058] (1) Take m-halogenated phenol or substituted m-halogenated phenol; dissolve in methanol aqueous solution of concentrated hydrochloric acid; add paraformaldehyde, heat to 40-60 degrees Celsius, and react for 10-40 hours; separate the product to obtain diphenylmethane Derivatives; i.e. first intermediates;

[0059] (2) reacting the first intermediate product with tert-butyldimethylchlorosilane to obtain a diphenylmethane derivative with a phenolic hydroxyl protecting group TBS; the second intermediate product;

[0060] (3) reacting the second intermediate product with n-butyllithium to obtain an organic lithium salt, and reacting it with the dihalogenated compound 2,2-dibromopropane to obtain an anthracene derivative, that is, the third intermediate product;

[0061] (4) oxidizing the third intermediate product with potassium permanganate to obtai...

Embodiment 1

[0067] The synthesis of COOH-PO fluorescent dye is shown in Synthetic Route 2;

[0068]

[0069] 1) Synthesis of compound 4,4'-methylenebis(3-bromophenol)2: weigh compound 1 (10g, 57.8mmol), dissolve in 40% methanol and water (1:1) solution of concentrated hydrochloric acid, add polymer Formaldehyde (360 mg, 4 mmol) was used to heat the reaction solution to 50°C for 24 hours. After most of the methanol in the water was spun off from the reaction solution, brine was added, extracted with dichloromethane, and the solvent was spun off and purified by column chromatography to obtain 3.6 g of oily compound 2.

[0070] 1H NMR (300MHz, CDCl3) δ8.95(s, 2H), 7.22(dt, J=7.5, 1.1Hz, 2H), 7.01(d, J=1.5Hz, 2H), 6.75(dd, J=7.5, 1.5Hz,2H),4.02(t, J=1.0Hz,2H).13C NMR(75MHz,CDCl3)δ156.32,131.75,127.53,125.48,118.98,118.58,42.17.HRMS:Caled for C13H11Br2O2(M+H), 358.0290, Found m / z 358.0291.

[0071]

[0072] 2) Synthesis of compound bis(2-bromo-4-((tert-butyldimethylsilyl)oxy)phenyl)me...

specific Embodiment example 2

[0091] The synthesis of COOH-TM fluorescent dye is shown in Synthetic Route 3

[0092]

[0093] 1 compound 4,4'-methylenebis (3-bromophenol) 2 synthesis:

[0094] Weigh compound 1 (10g, 57.8mmol), dissolve in methanol and water (1:1) solution of 40% concentrated hydrochloric acid, react at room temperature for 20 minutes, add paraformaldehyde (360mg, 4mmol) and heat the reaction solution to 50 °C, react for 24 hours. After most of the methanol in the water was spun off from the reaction solution, brine was added, extracted with dichloromethane, and the solvent was spun off and purified by column chromatography to obtain 3.6 g of oily compound 2.

[0095] 1H NMR (300MHz, CDCl3) δ8.95(s, 2H), 7.22(dt, J=7.5, 1.1Hz, 2H), 7.01(d, J=1.5Hz, 2H), 6.75(dd, J=7.5, 1.5Hz,2H),4.02(t, J=1.0Hz,2H).13C NMR(75MHz,CDCl3)δ156.32,131.75,127.53,125.48,118.98,118.58,42.17.HRMS:Caled for C13H11Br2O2(M+H), 358.0290, Found m / z 358.0291.

[0096]

[0097] 2 Compound bis(2-bromo-4-((tert-but...

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Abstract

The invention provides a method for synthesizing an anthracene fluorescent dye, which is used for solving the problems of difficult preparation of a key intermediate and low yield when the anthracenefluorescent dye is synthesized. The method has the advantages of easily available raw materials, mild reaction conditions and reduced operation risk. The synthesis method mainly comprises the following six steps: reacting m-halogenated phenol or substituted m-halogenated phenol with formaldehyde in an acidic solution, and purifying to obtain a diphenylmethane derivative, namely a first intermediate product; converting the phenolic hydroxyl group of the first intermediate product into methyl ether or silyl ether to obtain a diphenylmethane derivative with phenolic hydroxyl group protecting groups, namely a second intermediate product; converting the second intermediate product into an organic lithium salt, and reacting the organic lithium salt with a dihalogenated compound to generate an anthracene derivative, namely a third intermediate product; oxidizing the third intermediate product to obtain an anthrone compound, namely a fourth intermediate product; reacting the fourth intermediate product with a Grignard reagent to obtain a fifth intermediate product; and removing the phenolic hydroxyl protecting groups to obtain the fluorescent dye.

Description

technical field [0001] The invention relates to a method for synthesizing anthracene fluorescent dyes in the near-infrared band, and belongs to the field of biochemical synthesis. It is especially suitable for the synthesis of anthracene compounds and heteroatom-containing anthracene compounds. Background technique [0002] With the rapid development of high-throughput sequencing technology in recent years, compared with traditional Sanger sequencing, the biggest advantage is that it can read massive sequence information at the same time. Although the accuracy is not as good as traditional sequencing methods, due to massive data analysis, information beyond the sequence itself can be obtained, such as gene expression, copy number variation, and more accurate readout is an important direction for the development of high-throughput sequencing. [0003] The fluorogenic sequencing method is also widely used in high-throughput sequencing, and fluorogenic sequencing uses terminal...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B1/04C09B6/00
CPCC09B1/04C09B6/00
Inventor 张甲强段海峰陈子天
Owner CYGNUS BIOSCI BEIJING CO LTD
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