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A kind of imine derivative containing alkyne group and its preparation method and application

A technology of derivatives and imines, applied in the field of imine derivatives containing alkynyl groups and their preparation, can solve the problems of difficult synthesis of compounds, and achieve the effect of high practicability

Active Publication Date: 2022-04-19
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, compounds containing an alkynyl moiety at the γ-position of the imine nitrogen atom are difficult to synthesize, even through the coupling reaction of an alkyl halide containing an imine moiety with an alkynylation reagent, which is very challenging.

Method used

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  • A kind of imine derivative containing alkyne group and its preparation method and application
  • A kind of imine derivative containing alkyne group and its preparation method and application
  • A kind of imine derivative containing alkyne group and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] In this example, (E)-2-(3-(triisopropylsilyl)-2-propyn-1-yl)cyclohexyl-2-en-1-one O-methyl oxime ether (1a) The preparation, its reaction formula is as follows:

[0059]

[0060] Under air atmosphere, imine compound 2a (13.9 mg, 0.1 mmol), dichloro(pentamethylcyclopentadienyl) iridium (III) dimer (2.0 mg), bistri Silver fluoromethanesulfonyl imide (5.8 mg), lithium carbonate (14.8 mg) and silver acetate (33.4 mg) were injected with a syringe containing alkyne compound 3a (54.0 mg, 0.3 mmol) in 1,2-dichloroethene Alkanes solution (1.0mL) was placed in a reactor at 120°C for 24 hours, and the reaction was determined to be complete by thin-layer chromatography analysis. After the reaction solution was filtered through diatomaceous earth, it was concentrated by rotary evaporation with 400 mesh silica gel to make a dry powder, and then The reaction product was separated by column chromatography, 5 grams of 400-mesh silica gel, and the developing agent was petroleum ether...

Embodiment 2

[0064] In this example, (E)-2-(3-(triisopropylsilyl)-2-propyn-1-yl)cyclohexyl-2-en-1-one O-ethyl oxime ether (1b) The preparation, its reaction formula is as follows:

[0065]

[0066] Under air atmosphere, imine compound 2b (15.3 mg, 0.1 mmol), dichloro(pentamethylcyclopentadienyl) iridium (III) dimer (2.0 mg), bistri Silver fluoromethanesulfonyl imide (5.8 mg), lithium carbonate (14.8 mg) and silver acetate (33.4 mg) were injected with a syringe containing alkyne compound 3a (54.0 mg, 0.3 mmol) in 1,2-dichloroethene Alkanes solution (1.0mL) was placed in a reactor at 120°C for 24 hours, and the reaction was determined to be complete by thin-layer chromatography analysis. After the reaction solution was filtered through diatomaceous earth, it was concentrated by rotary evaporation with 400 mesh silica gel to make a dry powder, and then The reaction product was separated by column chromatography, 5 grams of 400-mesh silica gel, and the developing agent was petroleum ether ...

Embodiment 3

[0070] In this example, (Z)-5-methyl-2-(3-(triisopropylsilyl)-2-propyn-1-yl)cyclohexyl-2-en-1-one O-methyl The preparation of oxime ether (1c), its reaction formula is as follows:

[0071]

[0072] Under air atmosphere, imine compound 2c (15.3 mg, 0.1 mmol), dichloro(pentamethylcyclopentadienyl) iridium (III) dimer (2.0 mg), bistri Fluoromethanesulfonylimide silver salt (5.8 mg), lithium carbonate (14.8 mg) and silver acetate (33.4 mg) were injected by syringe containing alkyne compound 3b (78 mg, 0.3 mmol) in 1,2-dichloroethane The solution (1.0mL) was placed in the reactor at 120°C for 24 hours, and the reaction was confirmed by thin-layer chromatography. After the reaction solution was filtered through diatomaceous earth, it was concentrated by rotary evaporation with 400-mesh silica gel to make a dry powder, and then used The reaction product was separated by column chromatography, 5 grams of 400-mesh silica gel, and the developing agent was petroleum ether and ethyl a...

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Abstract

The invention belongs to the technical field of organic synthesis, and in particular relates to an alkynyl-containing imine derivative and a preparation method and application thereof. The present invention provides an alkynyl-containing imine derivative. The structural formula of the alkynyl-containing imine derivative is shown in formula (I), wherein, R 1 R 2 , R 3 and R 4 One or R independently selected from hydrogen, C1-C20 hydrocarbon group, C5-C30 aryl group, C5-C30 substituted aryl group or functional group 2 with R 4 Forming cycloalkyl or substituted cycloalkyl, R 5 To replace silicon.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to an alkynyl-containing imine derivative and a preparation method and application thereof. Background technique [0002] In synthetic chemistry, in order to pursue a more green, efficient and step-economical synthesis method, the alkyl Csp 3 The direct functionalization of -H bonds has received increasing attention. However, in order to implement a lazy Csp 3 The position selectivity and reactivity of the -H bond have both, and this type of conversion often uses bidentate ligands to achieve high efficiency of the reaction. However, these pre-introduced bidentate ligands are often difficult to remove and expensive, which also limits the practicability of this type of reaction. [0003] As a class of nitrogen-containing compounds that use amines to protect carbonyl compounds, imines are characterized by easy synthesis and conversion; more importantly, imines ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/08
CPCC07F7/081
Inventor 李先纬饶建行
Owner GUANGDONG UNIV OF TECH