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2H-chromene derivative containing perfluoroalkyl group, and synthetic method thereof

A technology of perfluoroalkyl and derivatives, applied in organic chemistry and other fields, can solve the problems of complicated operation, cumbersome reaction steps, and difficulty in obtaining raw materials, and achieve the effects of environmental friendliness, high atom economy, and easy operation

Inactive Publication Date: 2016-10-12
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] Summarizing the synthesis methods so far, it is not difficult to see that in the past 2 H -In the synthesis method of chromene derivatives, strong base or metal is often needed as a catalyst; or the raw materials are difficult to obtain, and the raw materials must be synthesized first, and then the next reaction is carried out, which makes the reaction steps cumbersome and complicated. Both reactions have their disadvantages

Method used

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  • 2H-chromene derivative containing perfluoroalkyl group, and synthetic method thereof
  • 2H-chromene derivative containing perfluoroalkyl group, and synthetic method thereof
  • 2H-chromene derivative containing perfluoroalkyl group, and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Add salicylaldehyde (122 mg, 1 mmol), methyl trifluoromethylpropiolate (152~182 mg, 1~1.2 mmol) into a round bottom flask, L -Proline (11.5~34.5 mg, 0.1~0.3 mmol), methanol (3 mL) as solvent, heated to 70~90°C for 18~30 hours, cooled to room temperature, spin-dried the solvent, and separated by column chromatography Pure product. white solid. Yield 82%.

[0024] Structural formula:

[0025]

[0026] Chinese name: 2-hydroxy-2-(trifluoromethyl)-2 H -Methyl chromene-3-carboxylate

[0027] English name: Methyl 2-hydroxy-2-(trifluoromethyl)-2 H -chromene-3-carboxylate

[0028] Molecular weight: 274.05

[0029] Appearance: white solid

[0030] Melting point: 70.7.6-73.0 °C

[0031] H NMR spectrum (500MHz, CDCl 3, Internal standard: TMS): δ : 3.75 (s, 3H), 7.02 (d, J = 8.0Hz, 1H), 7.06-7.09 (m, 1H), 7.40-7.44 (m, 1H), 7.52-7.54 (m, 1H), 7.97 (s,1H), 9.05 (s, 1H) ppm;

[0032] C NMR spectrum (125MHz, CDCl 3 , internal standard: TMS): δ: 53.1, 95.3 (q, 2 ...

Embodiment 2

[0035] Add 2-hydroxy-3-methoxybenzaldehyde (152 mg, 1 mmol), methyl trifluoromethylpropiolate (152~182 mg, 1~1.2 mmol) into a round bottom flask, L -Proline (11.5~34.5 mg, 0.1~0.3 mmol), methanol (3 mL) as solvent, heated to 70~90°C for 18~30 hours, cooled to room temperature, spin-dried the solvent, and separated by column chromatography Pure product. Pale yellow solid. Yield 75%.

[0036] Structural formula:

[0037]

[0038] Chinese name: 2-hydroxy-8-methoxy-2-(trifluoromethyl)-2 H -Methyl chromene-3-carboxylate

[0039] English name: Methyl 2-hydroxy-8-methoxy-2-(trifluoromethyl)-2 H -chromene-3-carboxylate

[0040] Molecular weight: 304.06

[0041] Appearance: pale yellow solid

[0042] Melting point: 85.4-97.0 °C

[0043] H NMR spectrum (500MHz, CDCl 3, Internal standard: TMS): δ : 3.75 (s, 3H), 3.81 (s, 3H),7.00 (t, J = 7.8 Hz, 1H), 7.09-7.11 (m, 1H), 7.14-7.16 (m, 1H), 7.92 (s, 1H), 9.05 (s, 1H) ppm;

[0044] C NMR spectrum (125MHz, CDCl 3 , inte...

Embodiment 3

[0047]Add 2-hydroxy-3-bromobenzaldehyde (200 mg, 1 mmol), methyl trifluoromethylpropiolate (152~182 mg, 1~1.2 mmol) into a round bottom flask, L -Proline (11.5~34.5 mg, 0.1~0.3 mmol), methanol (3 mL) as solvent, heated to 70~90°C for 18~30 hours, cooled to room temperature, spin-dried the solvent, and separated by column chromatography Pure product. Pale yellow solid. Yield 66%.

[0048] Structural formula:

[0049]

[0050] Chinese name: 8-bromo-2-hydroxy-2-(trifluoromethyl)-2 H -Methyl chromene-3-carboxylate

[0051] English name: Methyl 8-bromo-2-hydroxy-2-(trifluoromethyl)-2 H -chromene-3-carboxylate

[0052] Molecular weight: 351.96

[0053] Appearance: pale yellow solid

[0054] Melting point: 106.9-108.8 °C

[0055] H NMR spectrum (500MHz, CDCl 3, Internal standard: TMS): δ : 3.77 (s, 3H), 7.03 (t, J = 7.8Hz, 1H), 7.56-7.57 (m, 1H), 7.69-7.71 (m, 1H), 8.00 (s, 1H), 9.38 (s, 1H)ppm;

[0056] C NMR spectrum (125MHz, CDCl 3 , internal standard: TMS):...

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Abstract

The present invention relates to a kind of containing perfluoroalkyl 2 H Chromene derivatives and synthetic methods thereof, the structure of the compound is: Wherein, R is H, methoxy, bromo, methyl or nitro; RF is trifluoromethyl or pentafluoroethyl. The method of the present invention is synthesized by two-component one-pot method, compared with the method of original report, this method uses L -Proline as a green and mild organic catalyst to synthesize perfluoroalkyl-containing 2 H -Chromene derivatives have the advantages of high atom economy, environmental friendliness, easy operation and mild conditions. The reaction uses anhydrous methanol as a solvent, which has little environmental pollution. High regioselectivity and good yield. Therefore, this method is the synthesis of perfluoroalkyl-containing 2 H - Efficient new approach to chromene derivatives.

Description

technical field [0001] The present invention relates to a kind of containing perfluoroalkyl 2 H -Chromene derivatives and methods for their synthesis. Background technique [0002] Multifunctional substituted chromene (benzopyran) derivatives are a very important class of compounds due to their wide range of biological and pharmacological activities, such as antispasmodics, diuretics, anticoagulants, antitumor and antiallergic etc., so that it has been widely valued by people. Among them, 2 H -Chromene derivatives are the basic framework of a series of natural products and drugs with potential biological and pharmacological activities, so design simple and effective methods to synthesize2 H -Chromene derivatives have certain scientific significance. [0003] However, how to synthesize rings economically and efficiently is still a hotspot in synthesis. Judging from many published research results, although there are many different multifunctional groups with novel str...

Claims

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Application Information

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IPC IPC(8): C07D311/12C07D311/14C07D311/16C07D311/18
CPCC07D311/12C07D311/14C07D311/16C07D311/18
Inventor 严旭峰韩靖陈杰张慧曹卫国
Owner SHANGHAI UNIV
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