Synthesis method of alpha-F-beta-OH-carbonyl compound

A technology of carbonyl compounds and synthesis methods, which is applied in the field of synthesis of α-F-β-OH-carbonyl compounds, can solve the problems of unsaturated ketone fluorination and hydroxylation, expensive transition metals, large fluorine-containing reagents, etc., and achieve Substrate applicability Economic and environmental protection, good substrate applicability, low cost effect

Active Publication Date: 2019-05-10
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The synthetic method of α-F-β-OH compound of above-mentioned report often needs the bigger fluorine-containing reagent of toxicity (triethylamine trihydrofluoride, pyridine hydrofluoride etc.), poor stability, harsh conditions
Fluorinated hydroxylations of alkenes or alkynes with N-F reagents often require expensive transition metals
In addition, none of the existing methods can realize the fluorination and hydroxylation of unsaturated ketones

Method used

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  • Synthesis method of alpha-F-beta-OH-carbonyl compound
  • Synthesis method of alpha-F-beta-OH-carbonyl compound
  • Synthesis method of alpha-F-beta-OH-carbonyl compound

Examples

Experimental program
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Effect test

Embodiment 1

[0029] Chalcone (1mmol, 208mg) and Selectfluor (1.0mmol, 247mg) were added to a 25mL single-port reaction flask, and a mixture of acetonitrile and water with a volume ratio of 20:1 was added as a reaction solvent (reaction solvent addition was 7.35mL ), warming up to 40°C for 12h. After the reaction, the reaction solution was washed with water, extracted with dichloromethane, and separated into an organic layer and an aqueous layer. After the organic layer was dried over anhydrous sodium sulfate, it was concentrated by vacuum distillation to remove the solvent to obtain a yellow oil. The yellow oil was separated by column chromatography, using a mixture of petroleum ether and ethyl acetate at a volume ratio of 20:1 as the eluent, collecting the eluate containing the target compound, distilling off the solvent and drying to obtain 112 mg of white solid 2-fluoro- 3-Hydroxy-1,3-diphenylpropan-1-one, the yield is 46%, the chemical structural formula is:

[0030]

[0031] Chara...

Embodiment 2

[0033] The reaction time was shortened to 8 h, and the other operating conditions were the same as in Example 1. Finally, 90 mg of white solid 2-fluoro-3-hydroxy-1,3-diphenylpropan-1-one was obtained with a yield of 37%.

Embodiment 3

[0035] The reaction solvent was replaced with a mixed solvent of acetonitrile and water with a volume ratio of 50:1, the amount of the reaction solvent added was 7.14 mL, and other operating conditions were the same as in Example 1, finally obtaining 122 mg of white solid 2-fluoro-3-hydroxyl-1, 3-Diphenylpropan-1-one, yield 50%.

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Abstract

The invention discloses a synthesis method of an alpha-F-beta-OH-carbonyl compound. The synthesis method comprises the following steps: dissolving an unsaturated ketone compound shown in formula (I) and an N-F reagent in a reaction solvent, reacting for 5 to 25 hours at the temperature of 30 to 100 DEG C, after the reaction is ended, performing the after-treatment for a reaction solution to obtainan alpha-F-beta-OH-carbonyl compound as shown in formula (II), wherein the reaction formula is shown as follows: (shown in the description) In formula (I) and (II), substituent groups R1 and R2 are respectively independently selected from phenyl, substituted phenyl, thienyl or furyl; and the substituent group of the substituted phenyl is at least one of C1 to C3 alkyl, C1 to C3 alkoxy, nitro, trifluoromethyl, fluorine, chlorine and bromine. The N-F reagent is used as a fluorine source and Lewis acid, no additional catalyst is used, so that the reaction is more environment-friendly, and the cost is lower; and the method for synthesizing the alpha-F-beta-OH-carbonyl compound provided in the invention has the advantages of easy availability of raw materials, mild reaction conditions, no needof other catalysts, good reaction selectivity, simplicity in operation and the like.

Description

technical field [0001] The present invention relates to the synthesis method of α-F-β-OH-carbonyl compound. Background technique [0002] Fluorine-containing organic compounds have good biological activity and stability, and are widely used in fine chemical fields such as drugs, pesticides, surfactants, and fluorocarbon coatings. attention from the world and academia. Studies have shown that fluorine-containing organic compounds have good biological activity, have remarkable effects in antibacterial, anti-inflammatory, anti-cancer and other aspects, and have a wide range of applications in the field of medicine. In recent years, the synthesis of α-F-β-OH compounds has received extensive attention and some progress has been made. [0003] Before the present invention, existing α-F-β-OH compound synthetic method mainly comprises following several kinds: [0004] (a) Fluorination and hydroxylation of alkenes by pyridinium hydrofluoride, such as literature: Org. Lett. 2018, 2...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/83C07C49/84C07C45/64C07C205/45C07C201/12C07D333/22C07D307/46
Inventor 周嘉第李坚军方叶王芳
Owner ZHEJIANG UNIV OF TECH
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