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1-phenyl-4-penten-1-one derivative and its synthesis method and application

A synthesis method and derivative technology, applied in the field of 1-phenyl-4-penten-1-one derivatives and their synthesis, can solve the problems of severe reaction conditions, cumbersome operation, difficult selectivity control, etc., and achieve high Effects of regioselectivity, high step economy, and high atom economy

Active Publication Date: 2021-10-15
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the prior art, due to problems such as low substrate activity, lack of catalysts, difficult selectivity control, severe reaction conditions, and poor functional group compatibility, the existing synthesis methods for such compounds have high costs, low yields, Complicated operation and other disadvantages

Method used

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  • 1-phenyl-4-penten-1-one derivative and its synthesis method and application
  • 1-phenyl-4-penten-1-one derivative and its synthesis method and application
  • 1-phenyl-4-penten-1-one derivative and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] In a 50ml round bottom flask, add rhodium acetate (0.01mmol), allylpalladium chloride (0.05mmol), 4,5-bisdiphenylphosphine-9,9-dimethylxanthene (0.1 mmol) and under nitrogen protection, cinnamyl methyl carbonate (1 mmol), methanol (1 mmol) were dissolved in 15 ml of dichloromethane and poured into a round bottom flask. Dissolve 2-diazoacetophenone (1.5 mmol) in 5 ml of dichloromethane, pour it into a round bottom flask with a peristaltic pump within 2 hours, and continue the reaction for 0.5 hours after the dropwise addition. After distilling off the solvent under reduced pressure, it was purified by column chromatography (petroleum ether: ethyl acetate = 200:1) to obtain pure product 10a. The yield was 74%. nuclear magnetic resonance 1 HNMR, 13 The C NMR spectrum is shown in FIG. 1 .

[0054] 10a: 1 H NMR (400MHz, CDCl 3 )δ8.05(d, J=7.6Hz, 2H), 7.56(t, J=7.4Hz, 1H), 7.45(t, J=7.6Hz, 2H), 7.32–7.22(m, 4H), 7.17( t,J=7.0Hz,1H),6.40(d,J=15.8Hz,1H),6.25(dd,J=15.2,7....

Embodiment 2

[0059] In a 50ml round bottom flask, add rhodium acetate (0.01mmol), allylpalladium chloride (0.05mmol), 4,5-bisdiphenylphosphine-9,9-dimethylxanthene (0.1 mmol) and under nitrogen protection, allyl methyl carbonate (1 mmol), methanol (1 mmol) were dissolved in 15 ml of dichloromethane and poured into a round bottom flask. Dissolve 2-diazoacetophenone (1.5 mmol) in 5 ml of dichloromethane, pour it into a round bottom flask with a peristaltic pump within 2 hours, and continue the reaction for 0.5 hours after the dropwise addition. After distilling off the solvent under reduced pressure, it was purified by column chromatography (petroleum ether:ethyl acetate=200:1) to obtain pure product 10b. The yield was 62%. nuclear magnetic resonance 1 HNMR, 13 The C NMR spectrum is shown in FIG. 2 .

[0060] 10b: 1 H NMR (400MHz, CDCl 3 )δ7.97(d, J=7.3Hz, 2H), 7.51(t, J=7.4Hz, 1H), 7.40(t, J=7.7Hz, 2H), 5.89–5.66(m, 1H), 5.10– 4.96(m,2H),4.49(dd,J=7.1,5.7Hz,1H),3.31(s,3H),2.58–2.39(m...

Embodiment 3

[0065] In a 50ml round bottom flask, add rhodium acetate (0.01mmol), allylpalladium chloride (0.05mmol), 4,5-bisdiphenylphosphine-9,9-dimethylxanthene (0.1 mmol) and under nitrogen protection, (E)-3-(4-methoxyphenyl)allyl methyl carbonate (1 mmol), methanol (1 mmol) were dissolved in 15 ml of dichloromethane and poured into a round bottom flask. Dissolve 2-diazoacetophenone (1.5 mmol) in 5 ml of dichloromethane, pour it into a round bottom flask with a peristaltic pump within 2 hours, and continue the reaction for 0.5 hours after the dropwise addition. After distilling off the solvent under reduced pressure, it was purified by column chromatography (petroleum ether: ethyl acetate = 200:1) to obtain pure product 10c. The yield was 73%. nuclear magnetic resonance 1 H NMR, 13 The C NMR spectrum is shown in FIG. 3 .

[0066] 10c: 1 H NMR (400MHz, CDCl 3 )δ7.96(d, J=7.7Hz, 2H), 7.48(t, J=7.3Hz, 1H), 7.37(t, J=7.5Hz, 2H), 7.15(d, J=8.4Hz, 2H) ,6.72(d,J=8.3Hz,2H),6.26(d,J=15.8...

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Abstract

The invention discloses a 1-phenyl-4-penten-1-one derivative represented by formula (1) and a synthesis method thereof, using diazo compounds, allyl alcohol derivatives and alkyl alcohols as raw materials, The 1-phenyl-4-penten-1-one derivative is obtained by using metal palladium, metal rhodium and an organic phosphine ligand as catalysts in an organic solvent through one-step reaction. The synthesis method of the 1-phenyl-4-pentene-1-ketone derivative of the present invention has the advantages of high atom economy, high regioselectivity, low catalyst consumption, simple and safe operation, and the obtained 1-phenyl-4 ‑Penten‑1‑one derivatives are important chemical and pharmaceutical intermediates.

Description

technical field [0001] The invention belongs to the technical fields of synthetic medicine and chemical industry, and mainly relates to a 1-phenyl-4-penten-1-one derivative and its synthesis method and application. Background technique [0002] The 1-phenyl-4-penten-1-one derivative has good biological activity, and at the same time it plays an important role in the construction of natural products and drugs, and is an important intermediate in organic synthesis and drug synthesis. Structural molecules with 1-phenyl-4-penten-1-one derivatives have strong antioxidant capacity, antibacterial and anticancer effects, etc. In the prior art, due to problems such as low substrate activity, lack of catalysts, difficult selectivity control, severe reaction conditions, and poor functional group compatibility, the existing synthesis methods for such compounds have high costs, low yields, There are disadvantages such as cumbersome operation. Contents of the invention [0003] The in...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/84C07C205/45C07F7/08A61P35/00
CPCA61P35/00C07C49/84C07C205/45C07F7/081
Inventor 胡文浩寿家毅吴逸昕董素珍邢栋
Owner EAST CHINA NORMAL UNIV
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