Method for difluoroalkylation after fatty amine deamination

A technology of difluoroalkyl and aliphatic amine, applied in the field of difluoroalkylation after deamination of aliphatic amine, can solve the problems of no literature report, few literature reports, etc., and achieve excellent functional group compatibility and excellent reaction diversity , the effect of mild reaction conditions

Active Publication Date: 2020-11-06
ZUNYI MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented process describes methods for making certain types of chemicals called difuorenylmethanes through addition of specific molecules like fluoresceine onto an alkenoimide derivative containing two different substituents on one side thereof. These modifications result in improved properties compared to previous versions made without these modifying agents.

Problems solved by technology

This patented technical problem addressed by the inventors relating to introducing difluorochloroketone (DFC) onto different types of chemical structures has been highlighted during recent years due to its importance in controlling various properties such as solubility or reactivity with other substances involved in industrial processes like polymer production. However, previous researchers were unable to find any specific type of difluohnerylation process suitable for studying natural products containing certain nitrogen atom(N).

Method used

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  • Method for difluoroalkylation after fatty amine deamination
  • Method for difluoroalkylation after fatty amine deamination
  • Method for difluoroalkylation after fatty amine deamination

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preparation example Construction

[0037] The product prepared by the preparation method of the present invention can be separated and purified by various methods, and the methods include: thin layer chromatography, column chromatography and the like. The above purification methods are conventional methods in this area. For example, when using thin-layer chromatography and column chromatography, the developing agent used can be a single solvent or a mixed solvent, such as petroleum ether or ethyl acetate-petroleum ether. mixed solvents, etc.

[0038] The above-mentioned features mentioned in the present invention, or the features mentioned in the embodiments can be combined arbitrarily. All the features disclosed in the specification of this case can be used in combination with any combination, and each feature disclosed in the specification can be replaced by any alternative feature that provides the same, equivalent or similar purpose. Therefore, unless otherwise specified, the disclosed features are only ge...

Embodiment 1-18

[0042]

[0043] Into a 25mL reaction tube, add 990.5mg (2.5mmol, 1 equivalent) of compound B, inject 2.5mL of absolute ethanol, 297.5mg (3mmol, 1.2 equivalent) of compound A-1, and heat and stir at 90°C for 5 hours to obtain compound C-1.

[0044] In the reaction tube of 25mL, add 47.7mg (0.1mmol, 1 equivalent) compound C-1, 1.8mg (2mol%) [Ir (dtbbpy) (ppy) 2 ]PF 6 , after argon replacement three times, add the corresponding solvent in the following table, inject 54.1 mg (0.2 mmol, 2 equivalents) of compound D, and under blue light irradiation, heat and stir at 50 ° C for 24 hours to obtain compound E-1, the yield of fluorine spectrum See the table below. 1 HNMR (400MHz, CDCl 3 )δ8.08(d, J=8.0Hz, 2H), 7.62(t, J=7.4Hz, 1H), 7.49(t, J=7.8Hz, 2H), 2.30–2.18(m, 1H), 1.84– 1.80(m,4H),1.70–1.66(m,1H),1.34–1.16(m,5H). 19 F NMR (376MHz, CDCl 3 )δ-108.56 (d, J=14.7Hz, 2F). Compound E-1 is a new compound.

[0045]

[0046]

Embodiment 19-21

[0048]

[0049] In a 25mL reaction tube, add 47.7mg (0.1mmol, 1 equivalent) of compound C-1, the corresponding catalyst [PC] (2.0mol%) in the table below, and add 0.25mL N,N-di Methylacetamide (DMA) and 0.75mL ethylene glycol dimethyl ether (DME), injected 54.1mg (0.2mmol, 2 equivalents) of compound D, under blue light irradiation, heated and stirred at 50°C for 24 hours to obtain compound E- 1. The yield of fluorine spectrum is shown in the table below. 1 H NMR (400MHz, CDCl 3 )δ8.08(d, J=8.0Hz, 2H), 7.62(t, J=7.4Hz, 1H), 7.49(t, J=7.8Hz, 2H), 2.30–2.18(m, 1H), 1.84– 1.80(m,4H),1.70–1.66(m,1H),1.34–1.16(m,5H). 19 F NMR (376MHz, CDCl 3 )δ-108.56 (d, J=14.7Hz, 2F). Compound E-1 is a new compound.

[0050]

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Abstract

The invention discloses a method for difluoroalkylation after fatty amine deamination in the field of organic synthesis. Particularly the method comprises the following steps: by taking simple and easily available fatty amine represented by a formula A as a raw material, reacting the fatty amine with pyranyl tetrafluoroborate represented by a formula B under a heating or room temperature conditionto obtain alkyl pyridinium represented by a formula C; and under the illumination condition, obtaining various difluoroalkyl substituted alkanes, cycloalkanes and derivatives thereof with high yieldby selecting commercially available [Ir(dtbbpy)(ppy)2]PF6 as a catalyst and difluoroenol silyl ether D as a difluoroalkylation reagent. According to the invention, the method is simple and convenientto operate, simple and mild in reaction condition, excellent in functional group compatibility and suitable for large-scale production and synthesis; and fluorine-containing amino acid with potentialapplication value can be obtained through the catalytic synthesis method, and various difluoroalkyl-containing compounds with novel structures and important significance in the fields of medicines, pesticides and materials can be easily obtained through further conversion of the obtained product.

Description

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Claims

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Application Information

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Owner ZUNYI MEDICAL UNIVERSITY
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