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Preparation method of allene compound

A compound and alkyl technology, applied in the field of preparation of allene compounds, can solve the problems of difficulty in utilization, short life, lack of convenient methods, etc., and achieve the effects of good stereoselectivity and wide substrate adaptability

Active Publication Date: 2020-03-20
FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the 1,4-addition of 1,3-enynes to polysubstituted allenes via free radical pathways has hardly been reported.
As far as we know, allenyl radicals are difficult to exploit in organic synthesis mainly due to the lack of easy methods to generate them and their short lifetime
The capture of allenyl radicals by intramolecular cyclization has been reported by Zard et al., but few examples have been reported on the synthesis of allenes via the pathway of allenyl radical intermediates, especially the intermolecular reactions.

Method used

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  • Preparation method of allene compound
  • Preparation method of allene compound
  • Preparation method of allene compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055]

[0056]In this example, the compound represented by the general formula 1-2 was prepared according to the following preparation method and proportion: under the protection of nitrogen, add CuTc (0.01mmol), 1,10-phenanthroline (0.013mmol) into a 25mL reaction tube , evacuated, replaced with nitrogen three times, added acetonitrile (1 mL), and stirred at room temperature for 30 minutes. Add 1,3-enyne (0.2mmol), NFSI (0.3mmol) and TMSCN (0.3mmol) represented by formula 1-1 into the reaction tube, and react at room temperature for 12 hours. After the reaction is completed, dilute with ethyl acetate, The silica gel was quickly filtered, and the solvent was removed by a rotary evaporator under reduced pressure, followed by column chromatography to separate the obtained product sample as the compound of the general formula 1-2.

[0057] The compound shown in general formula 1-2 has following structure:

[0058]

Embodiment 2

[0060]

[0061] In this example, the compound represented by the general formula 2-2 was prepared according to the following preparation method and proportion: under the protection of nitrogen, add CuTc (0.01mmol), 1,10-phenanthroline (0.013) into a 25mL reaction tube , evacuated, replaced with nitrogen three times, added acetonitrile (1 mL), and stirred at room temperature for 30 minutes. Add 1,3-enyne (0.2mmol), NFSI (0.3mmol) and TMSCN (0.3mmol) shown in formula 2-1 into the reaction tube, and react at 50 degrees Celsius for 12 hours. After the reaction is completed, dilute with ethyl acetate , quickly filtered through silica gel, and the solvent was removed by a rotary evaporator under reduced pressure, and separated by column chromatography, and the product sample obtained was designated as compound 2-2. The compound shown in general formula 2-2 has following structure:

[0062]

[0063]

Embodiment 3

[0065]

[0066] In this example, the compound shown in the general formula 3-2 was prepared according to the following preparation method and proportion: under the protection of nitrogen, the Cu(OAc) 2 (0.025mmol, 5mol%), 1,10-phenanthroline (0.0325mmol, 6.5mol%) were added to a 25mL reaction tube, dichloromethane (2mL) was added, and stirred at room temperature for 30 minutes. Add 1,3-enyne (0.5mmol, 1.0eq), peroxide (1.5mmol, 3.0eq), TMSCN (1.5mmol, 3eq) shown in Formula 3-1 into the reaction tube, and react at 50°C After 12 hours, after the completion of the reaction, dilute with ethyl acetate, quickly filter through silica gel, remove the solvent under reduced pressure with a rotary evaporator, and separate by column chromatography to obtain a product sample as compound 3-2.

[0067] The compound shown in general formula 3-2 has following structure:

[0068]

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Abstract

The invention belongs to the field of organic synthetic chemistry, particularly relates to a preparation method of an allene compound, and provides a preparation method of a compound represented by aformula I, a racemate, a stereoisomer and a tautomer thereof, wherein the method comprises: carrying out a reaction on a compound represented by a formula III or a compound represented by a formula IVor a compound represented by a formula V, a compound represented by a formula II and SiR3-CN in the presence of a copper salt and 1,10-phenanthroline to obtain a compound represented by a formula I-1.

Description

technical field [0001] The invention belongs to the field of organic synthetic chemistry, and in particular relates to a preparation method of an allene compound. Background technique [0002] Allenes are a class of important organic synthesis intermediates containing 1,2-propadiene functional groups, and are widely used in various organic reactions. Therefore, the research on the synthesis of allene compounds has important theoretical significance and practical value. [0003] In recent years, researchers have extensively studied the difunctionalization of alkenes or alkynes by free radicals. However, the 1,4-addition of 1,3-enynes to polysubstituted allenes via free radical pathways has hardly been reported. As far as we know, the main reasons why allenyl radicals are difficult to utilize in organic synthesis are the lack of easy methods to generate them and their short lifetime. The capture of allenyl radicals by intramolecular cyclization has been reported by Zard et ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/49C07C255/35C07C255/37C07C255/40C07C255/41C07C309/82C07D333/24C07C303/40C07C253/00C07C303/22
CPCC07C255/35C07C255/37C07C255/40C07C255/41C07C309/82C07C311/49C07D333/24C07C2601/02C07C2601/08C07C2601/14C07C2603/18
Inventor 鲍红丽邓威力朱晓韬冯薇薇
Owner FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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