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Ferrocene derivative as well as synthesis method and application thereof

A technology of ferrocene derivatives and synthesis methods, applied in the field of organic chemistry synthesis, can solve problems such as detection signal and sensitivity limitation

Active Publication Date: 2022-04-15
RESEARCH INSTITUTE OF TSINGHUA UNIVERSITY IN SHENZHEN +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The ferrocene derivatives disclosed in the related art have good prospects in the application of labeled nucleotides, but they can only modify the 5' end of the nucleotide, which still has certain limitations for improving the detection signal and sensitivity

Method used

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  • Ferrocene derivative as well as synthesis method and application thereof
  • Ferrocene derivative as well as synthesis method and application thereof
  • Ferrocene derivative as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0105] This embodiment has prepared a kind of divalent ferrocene derivative, and specific process is:

[0106] (1) Dissolve 0.5g (4.27mmol) of 6-amino-1-hexanol in 25mL of anhydrous tetrahydrofuran, add 2.1g (9.81mmol, 2.31eq) of ferroceneformaldehyde at room temperature and stir, and then take triacetoxy Sodium borohydride 2.3g (10.90mmol, 2.5eq) was added to the system in batches and reacted overnight. After the reaction was detected by thin-layer chromatography (TLC), it was quenched with 30 mL of saturated sodium carbonate solution, extracted with 50 mL of ethyl acetate, then washed with 20 mL of saturated brine and high-purity water successively, and the organic phase was dried over anhydrous sodium sulfate. Concentration, sample mixing and column chromatography gave 1.8 g of 6-N,N-bisferrocenylmethylamino-1-hexanol (dark brown solid), with a yield of 85%.

[0107] The parameters of the structure of 6-N,N-bisferrocenemethylamino-1-hexanol verified by proton nuclear magne...

Embodiment 2

[0112] This embodiment has prepared a kind of tetravalent ferrocene derivative, and specific process is:

[0113] (1) Dissolve 0.5g (3.42mmol) of L-lysine in 25mL of anhydrous tetrahydrofuran, add 3.37g (15.73mmol, 4.6eq) of ferroceneformaldehyde at room temperature and stir, and then take triacetoxy borohydrogenation Sodium 3.62g (17.10mmol, 5eq) was added to the system in batches and reacted overnight. After the reaction was detected by thin-layer chromatography (TLC), it was quenched with 30 mL of saturated sodium carbonate solution, extracted with 50 mL of ethyl acetate, then washed with 20 mL of saturated brine and high-purity water successively, and the organic phase was dried over anhydrous sodium sulfate. Concentration, sample mixing and column chromatography gave 2.7 g of 2,6-N,N-di-bis-ferrocenylmethylaminocaproic acid (dark brown solid), with a yield of 84%.

[0114] (2) Take 0.5 g of 2,6-N,N-di-bis-ferrocenylmethylaminocaproic acid obtained in step (1), dissolve i...

Embodiment 3

[0118] This embodiment has prepared a kind of octavalent ferrocene derivative, and specific process is:

[0119] (1) Dissolve 0.5 g (983 μmol) of 6-hydroxyhexyl-2,3,4,6-tetra-O-propylamino-β-D-glucopyranoside in 25 mL of anhydrous tetrahydrofuran, and add di 1.94g (9.4mmol, 9.2eq) of ferrocene formaldehyde was stirred, and then 2.1g (9.83mmol, 10eq) of sodium triacetoxyborohydride was added to the system in batches and reacted overnight. After the reaction was detected by thin-layer chromatography (TLC), it was quenched with 30 mL of saturated sodium carbonate solution, extracted with 50 mL of ethyl acetate, then washed with 20 mL of saturated brine and high-purity water successively, and the organic phase was dried over anhydrous sodium sulfate. Concentrate, mix sample column chromatography and obtain 6-hydroxyhexyl-2,3,4,6-N,N,N,N-tetra-bisferrocene-O-propylamino-β-D-glucopyranoside ( Dark brown solid) 1.5 g, yield 73%.

[0120] (2) Take the 6-hydroxyhexyl-2,3,4,6-N,N,N,N-...

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Abstract

The invention belongs to the field of organic chemical synthesis, and discloses a ferrocene derivative as well as a synthesis method and application thereof. The ferrocene derivative disclosed by the invention comprises at least one of a divalent ferrocene derivative, a tetravalent ferrocene derivative, an octavalent ferrocene derivative or a tetravalent ferrocene derivative. In the oligonucleotide molecule, the succinimide ester of the ferrocene derivative can be modified on amino groups of nucleotides at different sites to perform multiple labeling on the oligonucleotide molecule, and at the moment, the oligonucleotide molecule has a ferrocene group. Ferrocene has good electrochemical activity, so that the target nucleotide molecule can be used as an electrochemical sensing indicator in electrochemical detection, can effectively improve the detection sensitivity and the signal intensity, and also has a wide application prospect in the field of gene detection.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, and in particular relates to a ferrocene derivative and its synthesis method and application. Background technique [0002] Ferrocene, also known as dicyclopentadienyl iron, is a "sandwich" sandwich compound formed by two cyclopentadienyl anions and one ferrous ion. The special sandwich structure of ferrocene makes it have outstanding aromaticity, it is not easy to undergo addition reaction and reduction reaction, but it is particularly prone to electrophilic substitution reaction, and derivatives containing ferrocenyl functional groups are synthesized, and the reaction The activity is much higher than that of benzene. [0003] Based on the low toxicity, unique electrochemical activity and photochemical properties, special redox properties and superior stability of ferrocene and its derivatives, ferrocene derivatives can be used in the preparation of modified electrodes, functional mate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/02C07H1/00C07H23/00C12Q1/6806G01N27/26
CPCY02P20/55
Inventor 何筠杨照亮秦龙田晖
Owner RESEARCH INSTITUTE OF TSINGHUA UNIVERSITY IN SHENZHEN
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