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1,2-dicarbonyl compound and synthesis method thereof

A synthesis method and compound technology, applied in 1 field, can solve the problems of instability and many side reactions, and achieve the effect of convenient and efficient construction

Inactive Publication Date: 2019-08-30
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the preparation method of α-carbonyl acid chloride not only uses polluting and irritating reagents, but also has many shortcomings such as instability and many side reactions.

Method used

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  • 1,2-dicarbonyl compound and synthesis method thereof
  • 1,2-dicarbonyl compound and synthesis method thereof
  • 1,2-dicarbonyl compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Synthesis of compound 2a:

[0058]

[0059] Biscarbonyl thioester 1a (0.2mmol), THF (2mL) was added to the reaction tube placed with the magneton, the rubber stopper was sealed, and ammonia gas was bubbled into it at room temperature for 15 minutes to continue the reaction for 3 hours, and then to the Bubble it once, spot plate detection, dilute with ethyl acetate after the reaction is complete, remove the organic solvent with a rotary evaporator, and then use a silica gel column to separate and purify by column chromatography to obtain the target biscarbonyl amide compound 2a with a yield of 79%, light yellow solid. 1 H NMR (400MHz, CDCl 3 )δ8.43-8.15(m, 2H), 7.79-7.58(m, 1H), 7.47(t, J=7.7Hz, 2H), 7.08(s, 1H), 6.48(s, 1H). 13 C NMR (100MHz, CDCl 3 )δ187.5, 164.2, 134.5, 132.9, 131.0, 128.5. MS (EI) m / z 149 (M + ).

Embodiment 2

[0061] Synthesis of compound 2b:

[0062]

[0063] Add biscarbonylthioester 1a (0.2mmol), D-phenylalaninol (0.2mmol) and THF (2mL) into a reaction tube with a magneton placed, react overnight at room temperature, spot plate detection and use after the reaction is complete Diluted with dichloromethane, removed the organic solvent with a rotary evaporator, and purified by column chromatography on a silica gel column to obtain the target biscarbonyl amide compound 2b with a yield of 85%, a white solid. 1 H NMR (400MHz, CDCl 3 )δ8.18(d, J=7.4Hz, 2H), 7.60(t, J=7.4Hz, 1H), 7.48-7.35(m, 3H), 7.34-7.21(m, 5H), 4.37-4.25(m , 1H), 3.72(ddd, J=16.1, 11.2, 4.3Hz, 2H), 3.03-2.89(m, 2H), 2.65(s, 1H). 13 C NMR (100MHz, CDCl 3 )δ187.9, 162.1, 137.2, 134.4, 133.1, 131.1, 129.2, 128.7, 128.4, 126.7, 63.5, 52.8, 37.0. MS (EI) m / z 283 (M + ).

Embodiment 3

[0065] Synthesis of compound 2c:

[0066]

[0067] Add biscarbonylthioester 1a (0.2mmol), octadecylamine (0.2mmol, 1.0equiv) and THF (2mL) into a reaction tube with a magneton placed, react overnight at room temperature, spot plate detection and use after the reaction is complete Diluted with dichloromethane, removed the organic solvent with a rotary evaporator, separated and purified by column chromatography on a silica gel column to obtain the target biscarbonyl amide compound 2c with a yield of 65%, a white solid. 1 H NMR (400MHz, CDCl 3 )δ8.37-8.29 (m, 2H), 7.61 (t, J = 7.4Hz, 1H), 7.46 (t, J = 7.8Hz, 2H), 7.12 (s, 1H), 3.37 (dd, J = 13.6 , 6.9Hz, 2H), 1.65-1.53(m, 2H), 1.36-1.17(m, 30H), 0.87(t, J=6.8Hz, 3H). 13 C NMR (100MHz, CDCl 3 )δ187.9, 161.7, 134.3, 133.4, 131.2, 128.4, 39.4, 31.9, 29.7, 29.6(3), 29.6(0), 29.5(4), 29.5, 29.3(3), 29.3, 29.2, 26.9, 22.7 , 14.1. HRMS (EI) Calcd for C 26 h 43 NO 2 401.3294, Found 401.3296.

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Abstract

The invention discloses a method for synthesizing a 1,2-dicarbonyl compound (1,2-dicarbonylamide or alpha-diketone compound), wherein 1,2-dicarbonyl thioester compounds used as 1,2-dicarbonyl reagentsreact with amine compounds or boric anhydride compounds under appropriate conditions to respectively synthesize a series of 1,2-dicarbonyl compounds. According to the present invention, the 1,2-dicarbonyl compound is obtained by using the stable 1,2-dicarbonyl thioester compound as the dicarbonylation reagent through one-step construction under mild conditions, such that the disadvantage that thetraditional method uses the unstable alpha-carbonyl acyl chloride to synthesize the 1,2-dicarbonyl compound is avoided.

Description

technical field [0001] The invention belongs to the technical field of synthesis and application of organic compounds, and relates to 1,2-dicarbonyl compounds and a synthesis method thereof. Background technique [0002] 1,2-Dicarbonyl compounds are a very important class of compounds, especially widely used in natural products and drug molecules. It is particularly important to develop a class of stable and widely used 1,2-dicarbonyl reagents. [0003] The method of synthesizing 1,2-dicarbonyl compounds is mainly through the transformation of α-carbonyl acid chloride. However, the preparation method of α-carbonyl acid chloride not only uses polluting and irritating reagents, but also has many shortcomings such as instability and many side reactions. Therefore, it is of great significance to develop a 1,2-dicarbonyl reagent that is chemically stable and has broad-spectrum applications. Contents of the invention [0004] In order to overcome the above-mentioned defects o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/02C07D295/192C07C319/20C07C321/14C07D209/20C07D207/16C07C45/67C07C49/84C07C321/20C07D317/26C07C49/76C07D307/46C07C67/343C07C69/738C07D401/12C07D209/12
CPCC07C45/673C07C67/343C07C231/02C07C319/20C07D207/16C07D209/12C07D209/20C07D295/192C07D307/46C07D317/26C07D401/12C07C235/78C07C321/14C07C49/84C07C321/20C07C49/76C07C69/738
Inventor 姜雪峰王明代志洪
Owner EAST CHINA NORMAL UNIV
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