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Trifluoromethyl-containing spiro [4, 5] decane compound and preparation method thereof

A technology of trifluoromethyl compounds, which is applied in the field of spiro[4,5]decane compounds and their preparation, can solve the problems of large iron reserves and achieve the effects of good tolerance, green reaction conditions and low cost

Active Publication Date: 2021-12-10
TIANJIN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Iron has large reserves in nature, and is less harmful to the environment and human body. Compared with copper, it is more economical and green. However, there are few reports on the method of activating Togni’s reagent with iron to construct compounds containing trifluoromethyl groups.

Method used

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  • Trifluoromethyl-containing spiro [4, 5] decane compound and preparation method thereof
  • Trifluoromethyl-containing spiro [4, 5] decane compound and preparation method thereof
  • Trifluoromethyl-containing spiro [4, 5] decane compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] 4-methyl-8-oxo-4- (2,2,2-trifluoroethyl) spiro ring [4.5] -6,9-diene-2,2-dimethyl diethyl ester (A) :

[0058]

[0059] In an inert atmosphere, acetylacetonate (21.28 mg, 0.06 mmol), 2,2'-bond pyridine (18.72 mg, 0.12 mmol) and 1,2-dichloroethane (5 mL) were added to 25 ml of reaction tube. , React at room temperature for 0.5 hours; add phenol derivative (96 mg, 0.3 mmol) and tert-butoxide (16.8 mg, 0.15 mmol) were heated to 60 ° C for 1 hour; then the trifluoromethyl source III (148.5 mg, 0.45 mmol) was added to 80 ° C, and the reaction 24 Up to the phenol derivative II reaction. The reaction was quenched with 2 M hydrochloric acid, washed, separated to obtain an organic phase, and the aqueous phase was extracted with dichloromethane, combined with an organic phase, dried over anhydrous sodium sulfate, remove the organic solvent, then purified by column chromatography A trifluoromethyl-containing snail is obtained [4,5] decane compound (formula a).

[0060] The product is...

Embodiment 2

[0063] 4-methyl-8-oxo-4- (2,2,2-trifluoroethyl) spiro loop [4.5] -6,9-diene-2,2-dimethyl dimethyl (B) :

[0064]

[0065] In an inert atmosphere, chloride (7.6 mg, 0.06 mmol), triaphic (27.96 mg, 0.12 mmol) and dichloromethane (5 ml) were added to 25 mL of reaction tube, and at room temperature for 1 hour; Add phenol derivative (87.6 mg, 0.3 mmol) and 2,6-di-tert-butylpyridine (28.65 mg, 0.15 mmol) were heated to 80 ° C for 2 hours; then add trifluoromethyl source IV (142.2 mg, 0.45 mmol), warmed From 100 ° C, the reaction was 12 hours until the phenol derivative II reaction was complete. The reaction was quenched with 2 m aqueous citric acid, washed, separated to obtain an organic phase, and the aqueous phase was extracted with dichloromethane, combined with an organic phase, dried over anhydrous sodium sulfate, remove the organic solvent, and then preciphematically After purification, a trifluoromethyl-containing snail [4,5] decane compound (formula B) is obtained.

[0066] T...

Embodiment 3

[0069] 4-methyl-8-oxo-4- (2,2,2-trifluoroethyl) spiro ring [4.5] -6,9-diene-2,2-dimethylene diisopropyl (C ):

[0070]

[0071] In an inert atmosphere, Fe (OTF) 2 (21.24 mg, 0.06 mmol), N-methylpyrrolidone (11.88 mg, 0.12 mmol) and dichloromethane (5 ml) were added to 25 ml of reaction tubes, reacted at room temperature for 2 hours; add phenol derivative (104.4 mg, 0.3 mmol) and N, N-diisopropylethylamine (19.35 mg, 0.15 mmol) were raised to 30 ° C for 3 hours; then the trifluoromethyl source IV (142.2 mg, 0.45 mmol), The temperature was raised to 40 ° C, and the reaction was 36 hours until the phenol derivative II reaction was complete. The reaction was added to the saturated aqueous solution of sodium carbonate. After obtaining a trifluoromethyl solution [4,5] decane compound (formula C).

[0072] The product was white solid, the yield was 97%, and the melting point was 83-85 ° C.

[0073] The characterization data of the product is: 1 H NMR (400MHz, CDCL 3 Δ6.98 (DD, J = 10....

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Abstract

The invention discloses a trifluoromethyl-containing spiro [4, 5] decane compound and a preparation method thereof, and the preparation method comprises the following steps: (1) in an inert atmosphere, dissolving a catalyst and a ligand in an organic solvent at room temperature to react; (2) adding a phenol derivative and alkali, and reacting at a certain temperature; and (3) adding a trifluoromethyl source, and controlling the reaction temperature and time until the phenol derivative reacts completely. The preparation method of the trifluoromethyl-containing spiro [4, 5] decane compound provided by the invention has the characteristics of low cost, good repeatability, environmental friendliness and the like, and the prepared trifluoromethyl-containing spiro [4, 5] decane compound is not only an important organic synthesis building block, but also an important skeleton of natural products and active ingredients.

Description

Technical field [0001] The present invention belongs to the field of organic material synthesis, and more particularly to a trifluoromethyl-containing screw [4,5] decane compound and a preparation method thereof. Background technique [0002] The fluorine-containing spiro-containing compound is not only an important organic synthetic block, but also an important skeleton of natural products and active ingredients. Since the trifluoromethyl group has a unique property, it can significantly alter the stability, lipidity, and bioavailability of the molecule in the organic molecule, and therefore, it is highly efficient and sustainable to the molecule to introduce trifluoro. The reaction of the base group has important research value in the field of medicine, materials. The spiro [4,5] decane is a complex cyclic molecule having a three-dimensional structure, which is widely present in the natural product and the biologically active ingredient. Introducing trifluoromethyl groups into ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/757C07C69/84C07C67/343
CPCC07C69/757C07C69/84C07C67/343C07C2602/50Y02P20/584
Inventor 韩贵芳刘阳平宋玉光赵一霖王雪
Owner TIANJIN MEDICAL UNIV
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