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1,2-dicarbonyl compounds and synthesis method thereof

A synthesis method and compound technology, applied in the first field, can solve problems such as instability and many side reactions, and achieve the effects of good yield, simple synthesis method, and cheap and easy-to-obtain raw materials

Inactive Publication Date: 2019-07-16
EAST CHINA NORMAL UNIVERSITY
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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 compounds and synthesis method thereof
  • 1,2-dicarbonyl compounds and synthesis method thereof
  • 1,2-dicarbonyl compounds and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Synthesis of Compound 2a:

[0044]

[0045] Under nitrogen protection, α-hydroxyacetophenone (0.5mmol), S 8 (64.2 mg, 2.0 mmol, 4.0 equiv), KHCO 3 (100mg, 1.0mmol, 2.0equiv), TBAB (32.3mg, 0.1mmol, 20mol%) were added to the reaction tube with the magneton placed, evacuated for three times and then added H 2 O (4mmol, 20equiv) and solvent CPME (4mL), the reaction system was heated to 90 ° C for 10 hours, and after the conversion of α-hydroxyacetophenone was detected by spotting, add benzyl bromide (0.75mmol, 1.5equiv) to the system , continued to react for 2 hours, lowered to room temperature, added water to the system to dilute, then added ethyl acetate (10mL*3) to extract, dried over anhydrous sodium sulfate, filtered, concentrated, and separated by column chromatography to obtain a yellow solid 2a (90 %). 1 H NMR (400MHz, CDCl 3)δ8.14(d, J=8.2Hz, 2H), 7.65(t, J=7.4Hz, 1H), 7.49(t, J=7.8Hz, 2H), 7.40-7.27(m, 5H), 4.28( s, 2H). 13 C NMR (100MHz, CDCl 3 )δ191.9...

Embodiment 2

[0047] Synthesis of compound 2a':

[0048]

[0049] Under nitrogen protection, α-hydroxyacetophenone (3.0mmol), S 8 (12.0 mmol, 4.0 equiv), KHCO 3 (6.0mmol, 2.0equiv), TBAB (0.6mmol, 20mol%) was added to the reaction tube with the magneton placed, and after evacuating nitrogen for three times, add H 2 O (60mmol, 20equiv) and solvent CPME (20mL), the reaction system was heated to 90 ° C for 10 hours, and after the spot plate detection of α-hydroxyacetophenone was completely converted, ethyl bromide (6.0mmol, 2equiv) was added to the system , continued to react for 2 hours, lowered to room temperature, added water to the system to dilute, then added ethyl acetate (30mL*3) to extract, dried over anhydrous sodium sulfate, filtered, concentrated, and separated by column chromatography to obtain yellow oil 2a' (81%). 1 H NMR (400MHz, CDCl 3 )δ8.16-8.08(m, 2H), 7.68-7.62(m, 1H), 7.54-7.47(m, 2H), 3.06(q, J=7.4Hz, 2H), 1.37(t, J=7.4Hz , 3H). 13 C NMR (100MHz, CDCl 3 )δ193.0,...

Embodiment 3

[0051] Synthesis of compound 2b:

[0052]

[0053] Under nitrogen protection, α-hydroxyl 4-methylacetophenone (0.5mmol), S 8 (64.2 mg, 2.0 mmol, 4.0 equiv), KHCO 3 (100mg, 1.0mmol, 2.0equiv), TBAB (32.3mg, 0.1mmol, 20mol%) was added to the reaction tube with the magneton placed, and after evacuating nitrogen for three times, add H 2 O (4mmol, 20 equiv) and solvent CPME (4mL), the reaction system was heated to 90 ° C for 10 hours, after spot plate detection of α-hydroxyacetophenone complete conversion, add benzyl bromide (0.75mmol, 1.5equiv ), continued to react for 2 hours, lowered to room temperature, added water to the system to dilute, then added ethyl acetate (10mL*3) for extraction, dried over anhydrous sodium sulfate, filtered, concentrated, and separated by column chromatography to obtain a yellow solid 2b ( 72%). 1 H NMR (400 MHz, CDCl 3 )δ8.06(d, J=8.3Hz, 2H), 7.41-7.27(m, 7H), 4.28(s, 2H), 2.44(s, 3H). 13 CNMR (100MHz, CDCl 3 )δ192.2, 185.4, 146.2, 136.4, 13...

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Abstract

The invention discloses a synthesis method of new 1,2-dicarbonyl compounds. The 1,2-dicarbonyl compounds are represented by a formula (1), and the synthesis method comprises the steps: adopting alpha-hydroxyketone, a sulfur reagent and alkyl bromide as reaction raw materials, and performing a reaction in a solvent under the action of alkali and additives so as to obtain a series of the new 1,2-dicarbonyl compounds. The 1,2-dicarbonyl compounds are synthesized in one step by using the sulfur reagent as a sulfur source under the condition of no metal catalysis, and the disadvantage that unstableacyl chloride is utilized to synthesize 1,2-dicarbonyl compounds in a conventional method is overcome; and the synthesis method is simple, the raw materials are cheap and easily available, the substrate has wide universality, and the yield of 45-86% is good.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis and application, and relates to 1,2-dicarbonyl compounds and their synthesis method and application. Background technique [0002] 1,2-dicarbonyl compounds are a very important class of compounds, especially widely used in natural products and drug molecules. Therefore, the development of efficient, environmentally friendly, step-economical synthesis of 1,2-dicarbonyl compounds method is particularly important. [0003] The method of 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]...

Claims

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Application Information

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IPC IPC(8): C07C327/22C07D307/54C07D307/80C07D209/22C07C327/30C07C327/32
CPCC07C327/22C07C327/30C07C327/32C07D209/22C07D307/54C07D307/80
Inventor 姜雪峰王明代志洪
Owner EAST CHINA NORMAL UNIVERSITY
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