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Electrochemical synthesis method and application of D-nucleoside compound

A synthesis method and compound technology are applied in the field of electrochemical synthesis of D-nucleoside cooling agents to achieve the effects of enriching tobacco aroma, reducing substance consumption and reducing side reactions

Active Publication Date: 2022-02-01
CHINA TOBACCO YUNNAN IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is aimed at the limitation of current traditional chemical synthesis method of menthyl ether cooling agent, and provides a kind of preparation method of novel menthyl ether cooling agent

Method used

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  • Electrochemical synthesis method and application of D-nucleoside compound
  • Electrochemical synthesis method and application of D-nucleoside compound
  • Electrochemical synthesis method and application of D-nucleoside compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1: (-)-L-menthyl-D-nucleoside

[0033] Substrate 150mg (1mmol) D-ribose and 156mg (1mmol) (-)-L-menthol are standard substrates, under constant current conditions (J=15mA / cm 2 ), without separating the electrolyzer, to NH 4 Br is the supporting electrolyte, CH 3 CN / H 2 When O was used as the electrolyte and the Pt electrode was used as both the anode and the cathode, the reaction was carried out at room temperature for 5 hours. After extraction, the target product was obtained by column chromatography with a yield of 85%.

[0034] The product structure is as figure 2 .

[0035] The NMR spectrum of the product obtained is as follows:

[0036] α-Pyranose

[0037] 1 H NMR (CD 3 COCD 3 ,500MHz)δ=4.72(d,1H,J=3.0Hz,CH),3.88-3.74(m,3H,2xCH,CH 2 ),3.66-3.60(m,2H,CH,CH 2 ), 3.38(td, 1H, J=4.4, 10.7, CH), 2.34(ddd, 1H, J=14.0, 7.4, 2.7Hz, CH), 2.25-2.19(m, 2H, 2xCH), 1.72-1.02( m,6H,2xCH,2xCH 2 ),0.94-0.89(m,6H,2xCH 3 ),0.80(d,J=3.0Hz,3H,CH 3 )

[0038] ...

Embodiment 2

[0043] Example 2: Cyclopentyl-D-nucleosides

[0044] Substrate 150mg (1mmol) D-ribose and 26mg (1mmol) cyclopentanol were standard substrates, under constant current conditions (J=15mA / cm 2 ), without separating the electrolyzer, to NH 4 Br is the supporting electrolyte, CH 3 CN / H 2 When O was used as the electrolyte and the Pt electrode was used as both the anode and the cathode, the reaction was carried out at room temperature for 5 hours. After extraction, column chromatography separated the target product with a yield of 90%.

[0045] The product structure is as follows image 3 .

[0046] The NMR spectrum of the product obtained is as follows:

[0047] α-Pyranose

[0048] 1 H-NMR (CD 3 OD,500MHz)δ=4.77(d,1H,J=3.6Hz,CH),4.22-4.28(m,1H,CH),3.86-3.74(m,2H,CH,CH 2 ),3.65-3.59(m,2H,CH,CH 2 ),3.50(m,1H,CH),1.9-1.5(m,8H,4xCH2).

[0049] 13 C-NMR (CD 3 OD,126MHz)δ=100.2,80.4,73.1,69.9,68.9,64.4,33.9,32.5,24.1,23.9.

[0050] β-Pyranose

[0051] 1 H-NMR (D 2 O,500M...

Embodiment 3

[0054] Example 3: 2-Bromoethyl-D-ribopyranoside

[0055] Substrate 150mg (1mmol) D-ribose and 125mg (1mmol) 2-bromoethanol were standard substrates, under constant current conditions (J=15mA / cm 2 ), without separating the electrolyzer, to NH 4 Br is the supporting electrolyte, CH 3 CN / H 2 When O was used as the electrolyte and the Pt electrode was used as both the anode and the cathode, the reaction was carried out at room temperature for 5 hours. After extraction, column chromatography separated the target product with a yield of 78%.

[0056] The product structure is as follows Figure 4 .

[0057] The NMR spectrum of the product obtained is as follows:

[0058] α-Pyranose

[0059] 1 H-NMR (CD 3 OD,500MHz)δ=4.7(d,1H,J=2.9Hz,CH),4.02-3.96(m,1H,CH),3.86(m,1H,CH 2 ),3.86-3.76(m,3H,CH,CH 2 ),3.71-3.66(m,1H,CH 2 ),3.64-3.59(m,1H,CH),3.45(t,2H,J=6.1Hz,CH 2 ).

[0060] 13 C-NMR (CD 3 OD,126MHz)δ=100.6,72.4,70.1,69.8,68.5,64.7,31.4.β-Pyranose

[0061] 1 H-NMR (CD 3...

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Abstract

The invention discloses an electrochemical synthesis method of a D-nucleoside compound and application of the D-nucleoside compound in cigarettes, wherein D-ribose and an alcohol are synthesized into the D-nucleoside compound under electrochemical catalysis, and the specific synthesis method is as follows: in an air environment, the D-ribose and the alcohol are taken as substrates, an inorganic salt is taken as an electrolyte, dehydration condensation is carried out in a reaction solvent. The reaction formula is disclosed in the invention. The D-nucleoside compound prepared by the preparation method disclosed by the invention is added into cigarettes and tobacco products as a cigarette additive, so that the aroma amount is increased, the cigarette aroma is enriched, the cigarette smoking quality is improved, and the smoking comfort is improved. Particularly, the D-ribose menthyl ether compound ((-)-L-menthyl-D-nucleoside) prepared by the preparation method disclosed by the invention is used as a cooling agent to be added into cigarettes and tobaccos, so that the smoking quality of the cigarettes is improved, and the throat is cleared and benefited.

Description

technical field [0001] The invention belongs to the technical field of tobacco additives, in particular to a novel electrochemical synthesis method of a D-nucleoside cooling agent capable of improving smoking quality, clearing throat and clearing throat. Background technique [0002] In daily life, compounds that can produce a cooling sensation on the sense of smell, skin, and mouth are usually called cooling agents, the most well-known and commonly used is menthol, but because it has a strong mint flavor when used in high concentrations , bitter taste, and also cause a burning sensation, which affects its use in some fields, so fragrance chemists have been looking for menthol substitutes or derivatives in the past few decades, and there have been many The few compounds that are considered safe are used in food, tobacco, medicine, daily chemical and other industries, including various derivatives containing menthyl and derivatives without menthyl. The relatively successful a...

Claims

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Application Information

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IPC IPC(8): C25B3/07C25B3/20A24B3/12A24B15/30
CPCC25B3/07C25B3/20A24B3/12A24B15/30
Inventor 刘春波唐石云刘志华韩莹夏建军李振杰蒋薇徐艳群司晓喜朱瑞芝杨继申钦鹏郭成金何沛向能军桂清文
Owner CHINA TOBACCO YUNNAN IND