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2,2-di(1H-indole-3-yl)-2H-acenaphthene-1-ketone compound and preparation method thereof

A technology of ketone compounds and compounds, which is applied in the field of organic chemical synthesis, can solve problems such as cumbersome operating procedures, unfavorable industrial production, and low yield, and achieve the effects of simple operating procedures, low equipment requirements, and reduced production costs

Active Publication Date: 2014-07-23
山东金鹏德盛斋扒鸡有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Obviously, the method yield is low, and the operation procedure is loaded down with trivial details, is unfavorable for industrialized production

Method used

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  • 2,2-di(1H-indole-3-yl)-2H-acenaphthene-1-ketone compound and preparation method thereof
  • 2,2-di(1H-indole-3-yl)-2H-acenaphthene-1-ketone compound and preparation method thereof
  • 2,2-di(1H-indole-3-yl)-2H-acenaphthene-1-ketone compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043]

[0044] In a 50mL round-bottom flask, add 91mg acenaphthenequinone (MW=182, 0.5mmol), 117mg indole (MW=117, 1.0mmol), 11.6mg camphorsulfonic acid (CSA) (MW=232, 0.05mmol), 5 mL of absolute ethanol, the reaction solution was stirred at 80°C under reflux for 15 minutes (the reaction progress was monitored by TLC, developing solvent: 60-90 petroleum ether: ethyl acetate = 2:1, volume ratio). After the reaction was completed, the reaction solution was cooled to room temperature, 5 mL of distilled water was added, a yellow solid powder was precipitated, suction filtered, washed twice with 1 mL of cold absolute ethanol, and vacuum-dried to obtain 197.0 mg of the product with a yield of 99%. The purity measured by HPLC was: 99.5%. 1 H NMR (500 MHz, DMSO -d 6 ): δ 10.98 (s, 2H, NH), 8.37 (d, J = 8.0 Hz, 1H), 8.04–7.97 (m, 2H), 7.91–7.88 (m, 1H), 7.71–7.68 (m, 1H), 7.55 (d, J = 6.7 Hz, 1H), 7.35 (d, J = 8.0 Hz, 2H), 7.02–6.99 (m, 4H), 6.85 (s, 2H), 6.74 (t, J = 7.4...

Embodiment 3

[0048] Comparative example, other operations are the same as in Example 1. The reaction solution was stirred at 40° C. for 15 minutes, and processed according to Example 1 to obtain 189.1 mg of the product with a yield of 95%.

Embodiment 4

[0050] Comparative example, other operations are the same as in Example 1. The reaction solution was stirred at 60° C. for 15 minutes, and processed according to Example 1 to obtain 193.0 mg of the product with a yield of 97%.

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Abstract

The invention relates to a 2,2-di(1H-indole-3-yl)-2H-acenaphthene-1-ketone compound and a preparation method thereof, and belongs to the technical field of organic chemical synthesis. The preparation method comprises the following steps: reacting in an anhydrous alcohol solvent in the presence of a sulfonic acid compound by taking acenaphthequinone and an indole compound as raw materials, cooling a reaction liquid to reach a room temperature after the reaction is completely carried out; adding distilled water into the reaction liquid so as to separate out yellow solid powder; carrying out suction filtration on the yellow solid powder and washing the yellow solid powder with absolute ethyl alcohol; and carrying out vacuum drying so as to obtain the 2,2-di(1H-indole-3-yl)-2H-acenaphthene-1-ketone compound. The method carried out by taking the anhydrous alcohol as a solvent and the sulfonic acid compound as a catalyst is simple and easy in raw material obtainment, low equipment requirement, moderate in reaction condition, good in catalytic effect as well as simple and convenient to operate. The yield of the obtained compound can reach above 97%; and the purity of the obtained compound can reach above 99%. The 2,2-di(1H-indole-3-yl)-2H-acenaphthene-1-ketone compound, the structure of which is authenticated by the nuclear magnetic resonance, is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, in particular to a kind of 2,2-bis(1 H -indol-3-yl)-2 H -Acenaphthene-1-one compound and its preparation method. Background technique [0002] In the fields of pharmacy, medicine and biochemistry, indole derivatives are a series of important heterocyclic compounds. Among them, bisindolylmethanes (BIAs) extracted from many terrestrial or marine natural products such as tunicates and sponges exhibit diverse pharmacological activities and have been widely used in the treatment of fibromyalgia, chronic fatigue, irritable bowel syndrome, etc. Studies have shown that these substances can also effectively inhibit the proliferation and spread of estrogen-dependent and independent breast tumor cells. Therefore, the synthesis of bisindolylmethanes (BIAs) has always been an important research direction in the field of organic chemistry. [0003] According to the information, it is fo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/12
CPCC07D209/12
Inventor 沈田华宋庆宝党海波
Owner 山东金鹏德盛斋扒鸡有限公司
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