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Paradol synthesis method

A synthesis method and a technology for zingerol, which are applied in chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, preparation of carbon-based compounds, etc., can solve the problem that compound 21 has a long reaction time, high cost, and is not suitable for industrialization. Production and other problems, to avoid absolute anaerobic conditions, low cost, stable structure

Active Publication Date: 2020-03-31
许昌远志生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The route is long, the cost is high, and the reaction time for preparing compound 21 is long, so it is not suitable for industrial production

Method used

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  • Paradol synthesis method
  • Paradol synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0093] Preparation of compound 3

[0094]

[0095] Add methoxymethylamine hydrochloride (20.0 g, 211 mmol, 1.0 eq.), dichloromethane (100 mL), chloroacetyl chloride aqueous solution (ca. 2.1 M H2O solution, 100 mL, 211 mmol, 1.0eq.), cooled to 0ºС in an ice bath, and added anhydrous potassium carbonate (138.21 g, 253 mmol, 1.2 eq.) in portions. After the addition was completed, the reaction was continued at room temperature for 12 h, detected by TLC. After the reaction was complete, the reaction solution was poured into 200 mL of water, and the aqueous phase was extracted with dichloromethane (50 mL×3). The organic phases were combined, dried over anhydrous sodium sulfate, the filtrate was collected by filtration, and spin-dried to obtain 32.3 g of a colorless transparent oil, with a yield of 93%. 1H NMR (400 MHz, CDCl3) δ 4.25 (s, 2H, CH2), 3.76 (s, 3H, NCH3), 3.24 (s, 3H, OCH3); 13C NMR (100 MHz, CDCl3) δ 167.62 (C=O ), 61.77,40.81, 32.58; HRMS (ESI): calcd. for C4H8ClN...

Embodiment 2

[0112] Preparation of compound 3

[0113]

[0114] Add methoxymethylamine hydrochloride (1.0 kg, 10.2 mol, 1.0 eq.), dichloromethane (4 L), chloroacetyl chloride aqueous solution (ca. 3 M H2O solution, 3.4 L, 10.2 mol, 1.0 eq.), cooled to -5 ℃ under ice bath, and added anhydrous potassium carbonate (1.7 kg, 12.2 mol, 1.2 eq.) in batches. After the addition was completed, the reaction was continued at room temperature for 12 h, and detected by TLC. After the reaction was complete, the reaction solution was poured into water (5 L), and the aqueous phase was extracted with dichloromethane (2 L×3). The organic phases were combined, dried over anhydrous sodium sulfate, the filtrate was collected by filtration, and spin-dried to obtain 1.3 kg of a colorless transparent oil, with a yield of 94%. HRMS (ESI): calcd. for C4H8ClNO2 [M+H]+, 138.0244; found 138.0278.

[0115] Preparation of Compound 4

[0116]

[0117] Add compound 3 (1.1 kg, 8.0 mol, 1.0 eq.) and triethyl phosphi...

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PUM

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Abstract

The invention discloses a complete synthesis method of a natural product paradol, the route being represented as the specification. The method employs feasible raw materials and simple operation, is high in yield and low in cost, is high in final product purity, is controllable in quality, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing zingerol (6-Paradol), which belongs to the fields of medicine synthesis technology and health food. Background technique [0002] Zingerol, chemical name: 1-(4-hydroxy-3-methoxyphenyl)-3-decanone, is a class of chemical substances present in the African cardamom plant Paradise pepper, its chemical structure is similar to ginger pepper elements are very similar. Current research shows that on the one hand, gingerol has the effect of significantly reducing blood sugar and blood lipids in the human body, and at the same time can promote the metabolism of the human body and has a good weight loss effect; on the other hand, the compound has little toxicity and irritation and has no side effects at present. related reports; therefore, zingerol has broad development prospects as a health product and functional food additive. [0003] At present, the preparation of zingerol as reported in the literature main...

Claims

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Application Information

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IPC IPC(8): C07C45/00C07C45/41C07C49/255C07C259/06C07C45/64C07C47/575C07F9/40
CPCC07C45/004C07C45/41C07C259/06C07C45/64C07F9/4006C07F9/4075C07C49/255C07C47/575
Inventor 周伟锋张智勇施翔张广燕吴迎春谢智宇
Owner 许昌远志生物科技有限公司
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