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Method of reducing beta-CF3 substituted alpha,beta-unsaturated ketones

A -CF3, unsaturated technology, applied in the α field, can solve the problems of unrealized technology and low reaction efficiency, and achieve the effects of shortening the synthesis process technology route, high reaction yield, and improving synthesis efficiency

Active Publication Date: 2019-04-05
SHANGHAI UNIV OF MEDICINE & HEALTH SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, two-step reactions are required to complete the selective reduction, and the reaction efficiency is low. On the other hand, the two-step reactions need to be completed under the catalysis of expensive transition metals (such as Ru, Rh and Ir metals).
[0005] Currently one-step construction of synthetic β-CF 3 The method of substituted α,β-unsaturated ketones is technically unrealizable

Method used

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  • Method of reducing beta-CF3 substituted alpha,beta-unsaturated ketones
  • Method of reducing beta-CF3 substituted alpha,beta-unsaturated ketones
  • Method of reducing beta-CF3 substituted alpha,beta-unsaturated ketones

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] In a 15mL reaction flask, add 2.0ml of toluene, and then add β-CF shown in the following formula (1) 3 Substituted α,β-unsaturated ketone (69.4mg, 0.25mmol), benzylamine (107μl, 0.75mmol) and metal cobalt perchlorate hexahydrate (2.0mg, 0.005mmol), the molar ratio of the three is 1: 3: 0.005;

[0027] Heat the reaction bottle in an oil bath, stir vigorously at 100°C for 24 hours, stop the reaction, add hydrochloric acid to acidify, and extract with ethyl acetate;

[0028] Get 1mL concentrated and spin-dried and use 1H-NMR to detect the reduced product (beta-CF shown in the following formula (1') 3 substituted saturated ketone), the yield of the reduced product was 89%.

[0029]

[0030] In the above formula (1), (E) represents the E configuration (stereoisomer), which means that the atoms or groups with large atomic numbers connected to the double bond are on different sides of the double bond plane. It is the same in the following examples.

Embodiment 2-10

[0032] The difference between embodiment 2-10 and embodiment 1 is: the β-CF shown in formula (1) 3 The substituted α, β-unsaturated ketone, benzylamine and hexahydrate cobalt perchlorate metal salt have different molar ratios. The rest of the reaction conditions and operations are exactly the same, and details will not be repeated.

[0033] The results of the three molar ratios and the yield of the reduced product in Examples 2-10 are shown in Table 1 below.

[0034] Table 1

[0035]

Embodiment 11

[0037] In a 15mL reaction bottle, add 2.0ml of toluene, and then add β-CF shown in the above formula (1) 3 Substituted α, β-unsaturated ketone (69.4mg, 0.25mmol), benzylamine (160μl, 1.13mmol) and zinc dichloride (0.68mg, 0.005mmol), the molar ratio of the three is 1:4.52:0.02;

[0038] Heat the reaction bottle in an oil bath, stir vigorously at 100°C for 24 hours, stop the reaction, add hydrochloric acid to acidify, and extract with ethyl acetate;

[0039] Get 1mL concentrated and spin-dried and use 1H-NMR to detect the reduced product (β-CF shown in the above formula (1') 3 substituted saturated ketone), the yield of the reduced product was 80%.

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Abstract

The invention relates to a method of reducing beta-CF3 substituted alpha,beta-unsaturated ketones. Benzylamine or substituted benzylamine is in the method for the first time as an intramolecular 1,5-hydrogen transfer agent; under promotion of Lewis acid metal salt, reduction of beta-CF3 substituted alpha,beta-unsaturated ketones is achieved through one-step reaction; the process route is shortened; synthetic efficiency is improved. In addition, the method has the advantages of high substrate applicability, high reaction yield, mild reaction conditions, good operational simplicity, and low synthetic cost.

Description

technical field [0001] The present invention relates to a kind of β-CF 3 The invention relates to a method for reducing substituted α, β-unsaturated ketones, which belongs to the technical field of organic chemical synthesis. Background technique [0002] Methods for the reduction of α,β-unsaturated carbonyl compounds, especially for the chemoselective reduction of carbonyl groups, are one of the most important topics in synthetic organic chemistry. [0003] About β-CF 3 For the selective reduction of the carbonyl group of substituted enones, the methods commonly used in the prior art are mainly catalytic hydrogenation with hydrogen, or catalytic transfer hydrogenation with alcohol or other expensive hydrogen sources. However, these methods usually require two-step construction to achieve . [0004] Not long ago, Yoko Hamada et al. published "Under metal-free conditions, alkali-promoted CF-containing 3 The isomerization of allyl alcohol to the corresponding saturated ket...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/813C07C45/62C07C49/84C07C49/233C07D307/46
CPCC07C45/62C07D307/46C07C49/813C07C49/84C07C49/233
Inventor 孔丽张万斌谢芳李雪薇吴小婷
Owner SHANGHAI UNIV OF MEDICINE & HEALTH SCI
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