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Novel fluorocyclopentenone preparation method and product thereof

A technology of fluorocyclopentenone and substituted cyclopentenone, which is applied in the field of preparation of new fluorocyclopentenone, and achieves the effects of low energy consumption, wide range and high yield

Inactive Publication Date: 2018-07-13
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, how to efficiently and regioselectively introduce fluorine atoms into organic compounds remains a major challenge.

Method used

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  • Novel fluorocyclopentenone preparation method and product thereof
  • Novel fluorocyclopentenone preparation method and product thereof
  • Novel fluorocyclopentenone preparation method and product thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048]

[0049] Take a 25mL round bottom flask, add 6mL methyl tert-butyl ether, enynyl ester a (64mg, 0.3mmol), (acetonitrile)[(2-biphenyl)di-tert-butylphosphine] gold (I ) (5mg, 0.006mmol), N-fluorobisbenzenesulfonamide (189mg, 0.6mmol). Stir at 500 rpm for 24 hours at normal temperature and pressure. Then use a Heidolph rotary evaporator to rotate to evaporate, the rotation speed is 200rpm, the temperature is 40°C, the vacuum degree is 0.06Mpa, and the processing time is 10min. Then through 200~300 mesh silica gel column chromatography, the eluent is ethyl acetate:petroleum ether=5:100, and the target product A (49mg, 0.26mmol, yield 86%) is separated and obtained from the appearance, signal, noise of nuclear magnetic spectrum etc. can also reflect the high purity of the product).

[0050] 1 H NMR (400MHz, CDCl 3 ):δ7.67-7.65(m,2H),7.55-7.46(m,3H),6.58(m,1H),

[0051] 3.41-3.30(ddd,1H,J=19.8,18.0,1.6Hz),3.20-3.12(ddd,1H,J=12.0,10.4,1.7Hz),1.61(d,3H,J=22.8Hz).

[00...

Embodiment 2

[0055]

[0056] Take a 25mL round bottom flask, add 6mL methyl tert-butyl ether, enynyl ester b (76mg, 0.3mmol), (acetonitrile)[(2-biphenyl)di-tert-butylphosphine] gold (I ) (5mg, 0.006mmol), N-fluorobisbenzenesulfonamide (189mg, 0.6mmol). Stir at 500 rpm for 24 hours at normal temperature and pressure. Then use a Heidolph rotary evaporator to rotate to evaporate, the rotation speed is 200rpm, the temperature is 40°C, the vacuum degree is 0.06Mpa, and the processing time is 10min. Then by 200~300 mesh silica gel column chromatography, the eluent is ethyl acetate:petroleum ether=5:100, and the target product B (45mg, 0.20mmol, yield 65%) is isolated and obtained from the nuclear magnetic spectrum appearance, signal, noise etc. can also reflect the high purity of the product).

[0057] 1 H NMR (400MHz, CDCl 3 ):δ7.65-7.58(m,2H),7.52-7.43(m,3H),6.47(s,1H),3.49-3.39(ddd,1H,J=21.3,8.9,6.8Hz),2.27-2.12 (m,2H),1.99-1.85(m,1H),1.85-1.73(m,1H),1.58-1.41(m,2H),1.37-1.17(m,2H). ...

Embodiment 3

[0061]

[0062] Take a 25mL round bottom flask, add 6mL methyl tert-butyl ether, enynyl ester c (146mg, 0.3mmol), (acetonitrile)[(2-biphenyl)di-tert-butylphosphine]gold(I ) (5mg, 0.006mmol), N-fluorobisbenzenesulfonamide (189mg, 0.6mmol). Stir at 500 rpm for 24 hours at normal temperature and pressure. Then use a Heidolph rotary evaporator to rotate to evaporate, the rotation speed is 200rpm, the temperature is 40°C, the vacuum degree is 0.06Mpa, and the processing time is 10min. Then through 200~300 mesh silica gel column chromatography, the eluent is ethyl acetate:petroleum ether=25:100, isolate and obtain target product C (131mg, 0.28mmol, productive rate 94%, from nuclear magnetic spectrum appearance, signal, noise etc. can also reflect the high purity of the product).

[0063] 1 H NMR (400MHz, CDCl 3 ):δ7.68-7.61(m,2H),7.59-7.43(m,5H),7.32-7.25(m,5H),7.06-7.03(m,2H),6.56(d,1H,J=1.2Hz ),3.61(t,2H,J=6.8Hz),3.26-3.06(m,2H),2.44(s,3H),2.15-2.00(m,1H),1.97-1.79(m,1H),1...

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Abstract

The invention discloses a novel fluorocyclopentenone preparation method and a product thereof. The novel fluorocyclopentenone preparation method is characterized by comprising the following step: methyl tert-butyl ether, enynic ester, gold (acetonitrile)[(2-biphenyl)di-tert-butylphosphine] hexafluoroantimonate (I) and N-fluorobenzenesulfonimide are added to react, so that fluorocyclopentenone is obtained. The novel method for preparing a fluorocyclopentenone compound which is provided by the invention ensures that an enynic ester compound can be converted into the fluorocyclopentenone compound. The whole reaction is carried out under normal temperature and normal pressure, conditions are mild, and energy consumption is low. The whole reaction is carried out by utilizing a one-pot method, operation is easy, yield is high, and the purity of the product is 98 percent or more. The reaction substrate range is wide, and not only the simple enynic ester compound but also complex compounds containing natural product groups are applicable. The developed fluorocyclopentenone compound has potential bioactivity, and can become a drug by subsequent testing or modification.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a preparation method of a novel fluorocyclopentenone and a product thereof. Background technique [0002] Fluorine-containing compounds play an important role in many fields such as medicine, pesticides, and materials. However, naturally occurring fluorine-containing compounds are extremely rare, and most of them are artificially synthesized. 5-Fluorouracil acts as an anti-metabolite. After being converted into effective fluorouracil deoxynucleotide in the cell, it interferes with the conversion of deoxyribouridine into thymidylate by intracellular thymidylate synthase. DNA synthesis. Fluorouracil can also interfere with RNA synthesis. After intravenous administration, fluorouracil is widely distributed in body fluids and disappears from the blood within 4 hours. After it is converted into nucleotides, it is preferentially taken up by actively dividing t...

Claims

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Application Information

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IPC IPC(8): C07C45/00C07C49/697C07C303/40C07C311/16C07D209/08C07C67/313C07C69/738
CPCC07C45/00C07C49/697C07C67/313C07C69/738C07C303/40C07C311/16C07D209/08
Inventor 饶卫东陈先枭周媛媛尹栋梁凌媛
Owner NANJING FORESTRY UNIV
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