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Scopoletin labeled by stable isotope and synthetic method for scopoletin

A stable isotope and isotope labeling technology, which is applied in the direction of isotope introduction of heterocyclic compounds, organic chemistry methods, organic chemistry, etc., can solve the problems of isotope-labeled scopoletin research and no reports, etc., and achieve high product yield and easy operation Effects that are easy to implement and synthesize with simple steps

Active Publication Date: 2016-08-24
ZHENGZHOU TOBACCO RES INST OF CNTC +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

After reviewing the literature, there are few studies on isotope-labeled scopoletin, and stable isotope-labeled scopoletin-2- 13 The synthesis of C has not been reported so far

Method used

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  • Scopoletin labeled by stable isotope and synthetic method for scopoletin
  • Scopoletin labeled by stable isotope and synthetic method for scopoletin
  • Scopoletin labeled by stable isotope and synthetic method for scopoletin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] (1) Isotope-labeled acetic acid reacts with thionyl chloride at a molar ratio of 1:1.5 to generate isotopically-labeled acetyl chloride. The reaction temperature is 60°C for 3 hours, and the fraction at 45°C is distilled.

[0035] (2) In the organic solvent dichloromethane, 2,4-dihydroxy-5-methoxybenzaldehyde reacts with isotope-labeled acetyl chloride (commercial products can also be used directly) in a molar ratio of 3:1 to produce 2- Aldehyde-4-methoxy-5-hydroxyphenylacetate, the concentration of the reaction system (equivalent to the concentration of 2,4-dihydroxy-5-methoxybenzaldehyde in the system) is 0.25M, and the reaction temperature is 20 o C; the reaction time was 17 h; after the reaction, 0.1M hydrochloric acid was added to the reaction mixture to quench the reaction, extracted with dichloromethane, and the obtained crude product was separated and purified by column chromatography to obtain the isotope labeled 2-aldehyde phenyl-4-methoxy-5-hydroxyacetate. ...

Embodiment 2

[0038] (1) The isotope-labeled acetic acid reacts with thionyl chloride at a molar ratio of 1:2.1 to generate isotopically-labeled acetyl chloride. The reaction temperature is 80°C for 2 hours, and the fraction at 43°C is distilled.

[0039] (2) In the organic solvent tetrahydrofuran, 2,4-dihydroxy-5-methoxybenzaldehyde reacts with isotope-labeled acetyl chloride in a molar ratio of 3:2 to generate 2-aldehyde-4-methoxy-5- Phenyl hydroxyacetate, the concentration of the reaction system (equivalent to the concentration of 2,4-dihydroxy-5-methoxybenzaldehyde in the system) is 0.1M, and the ratio is the reaction temperature of 50 oC; the reaction time was 12 h; after the reaction was completed, 1M sulfuric acid was added to the reaction mixture to quench the reaction, extracted with tetrahydrofuran, and the obtained crude product was separated and purified by column chromatography to obtain the isotope labeled 2-aldehyde-4 -Methoxy-5-hydroxyphenylacetate.

[0040] (3) In the org...

Embodiment 3

[0042] (1) Isotope-labeled acetic acid reacts with thionyl chloride at a molar ratio of 1:1.1 to generate isotopically-labeled acetyl chloride. The reaction temperature is 70°C for 3 hours, and the fraction at 51°C is distilled.

[0043] (2) In the organic solvent chloroform, 2,4-dihydroxy-5-methoxybenzaldehyde reacts with isotope-labeled acetyl chloride in a molar ratio of 3:1.4 to generate 2-aldehyde-4-methoxy-5- Phenyl hydroxyacetate, the concentration of the reaction system (equivalent to the concentration of 2,4-dihydroxy-5-methoxybenzaldehyde in the system) is 3M, and the reaction temperature is 35 o C; the reaction time is 20 hours; after the reaction is completed, 2M nitric acid is added to the reaction mixture to quench the reaction, extracted with chloroform, and the obtained crude product is separated and purified by column chromatography to obtain the isotope label 2-aldehyde-4 -Methoxy-5-hydroxyphenylacetate.

[0044] (3) In the organic solvent chloroform, the is...

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Abstract

The invention belongs to the synthesis field of isotope labeled compound synthesis, and particularly relates to scopoletin labeled by stable isotope and a synthetic method for the scopoletin. The synthetic method is characterized in that scopoletin labeled acetylchloride-2-13 C is taken as a raw material, and the scopoletin labeled acetylchloride-2-13C reacts with 2,4-dihydroxyl-5-methoxybenzaldehyde to generate 2-aldehyde-4-methoxy-5-hydroxyl phenyl acetate; under the action of a basic catalyst, scopoletin-2-13C is generated through Perkin reaction. The synthetic method is simple in synthesis step, is gentle in reaction condition, is simple and convenient in operation, is high in product yield being 26% or higher, is capable of effectively synthesizing an isotope labeled coumarin derivative, so that a novel way is provided for synthesizing the isotope labeled coumarin derivative. Certain innovation and unique research significance are achieved on organic synthetic method.

Description

technical field [0001] The invention belongs to the field of isotope-labeled compound synthesis, in particular to a preparation of stable isotope-labeled scopolamine-2- 13 Synthesis of C. This compound is an important building block for the preparation of isotopically labeled coumarin derivatives. Background technique [0002] Scopolamine belongs to the class of coumarin compounds, which is a kind of important organic heterocyclic compounds with benzopyrone as the parent structure modification. This type of compound is widely found in a variety of Chinese herbal medicines. Due to its special lactone structure, it has a wide range of pharmacological activities. In addition to its heat-clearing, analgesic, antibacterial and anti-inflammatory effects, it is used in some vascular diseases such as vasodilation and anticoagulation. It also has significant curative effect and certain anticancer activity. [0003] Isotope-labeled compounds have important applications as tracer re...

Claims

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Application Information

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IPC IPC(8): C07D311/16
CPCC07B59/002C07B2200/05C07D311/16
Inventor 李炎强彭小敏张攀科薛华珍王田田杨贯羽宗永立
Owner ZHENGZHOU TOBACCO RES INST OF CNTC
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