3-(4-carbazole-9-yl-phenyl)-1-ferrocenyl-acetone and preparing method thereof

A ferrocene-based, -1- technology, applied in chemical instruments and methods, metallocene, organic chemistry, etc., can solve the problems of high equipment requirements, time-consuming and labor-consuming, complicated operation, etc., and achieve high reactivity, shorten The effect of response time and simple operation process

Inactive Publication Date: 2015-11-18
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The traditional method of synthesizing chalcone is a liquid-phase synthesis method, generally using ethanol as a solvent. The traditional synthesis method is complex in operation, high in equipment requirements, long in time, time-consuming and labor-intensive, and has a very low yield
However, the synthesis of chalcones containing carbazole groups has become a new field of research. At present, there is no report in the literature that the grinding method is used to combine the two through chemical methods, in order to obtain the superposition of their properties.

Method used

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  • 3-(4-carbazole-9-yl-phenyl)-1-ferrocenyl-acetone and preparing method thereof
  • 3-(4-carbazole-9-yl-phenyl)-1-ferrocenyl-acetone and preparing method thereof
  • 3-(4-carbazole-9-yl-phenyl)-1-ferrocenyl-acetone and preparing method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] 1) Add 0.35 mmol acetylferrocene, 0.42 mmol 4-carbazol-9-yl-benzaldehyde, 0.42 mmol NaOH and 0.42 mmol K to a dry mortar 2 CO 3 , grind at room temperature for 15 minutes until uniform, to obtain a mixture;

[0034] 2) The mixture was incubated and reacted for 30 minutes at a temperature of 80°C. After the mixture was naturally cooled, it was washed with ethanol with a volume concentration of 95%, suction filtered, and the filter cake was recrystallized with absolute ethanol to obtain 3-(4- Carbazol-9-yl-phenyl)-1-ferrocenyl-acetone, the yield reached 97.5%.

[0035] image 3 For the infrared spectrum of the obtained 3-(4-carbazol-9-yl-phenyl)-1-ferrocenyl-acetone, from image 3 As can be seen in the 3050cm -1 The stronger absorption vibration peaks are the stretching vibration absorption peak of benzene ring C-H and the vibration absorption peak of H on the unsaturated C=C double bond; at 1660cm -1 The left and right are the vibrational absorption peaks of C=O; du...

Embodiment 2

[0038] 1) Add 0.35 mmol acetylferrocene, 0.42 mmol 4-carbazol-9-yl-benzaldehyde, 0.385 mmol NaOH and 0.385 mmol K to a dry mortar 2 CO 3 , grind at room temperature for 10 minutes until uniform, to obtain a mixture;

[0039] 2) The mixture was incubated and reacted for 20 minutes at a temperature of 85°C. After the mixture was naturally cooled, it was washed with ethanol with a volume concentration of 92%, suction filtered, and the filter cake was recrystallized with absolute ethanol to obtain 3-(4- Carbazol-9-yl-phenyl)-1-ferrocenyl-acetone in a yield of 97%.

Embodiment 3

[0041] 1) Add 0.35 mmol acetylferrocene, 0.42 mmol 4-carbazol-9-yl-benzaldehyde, 0.40 mmol NaOH and 0.40 mmol K to a dry mortar 2 CO 3 , grind at room temperature for 20 minutes until uniform, to obtain a mixture;

[0042] 2) The mixture was incubated and reacted for 40 minutes at a temperature of 82°C. After the mixture was naturally cooled, it was washed with ethanol with a volume concentration of 90%, suction filtered, and the filter cake was recrystallized with absolute ethanol to obtain 3-(4- Carbazol-9-yl-phenyl)-1-ferrocenyl-acetone, the yield reached 97.5%.

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Abstract

The invention provides 3-(4-carbazole-9-yl-phenyl)-1-ferrocenyl-acetone and a preparing method thereof. Acetyl ferrocene, 4-carbazole-9-yl-benzaldehyde, NaOH and K2CO3 are added into a dry reaction vessel, ground uniformly and subjected to a heat preserving reaction, and a product is treated to obtain the 3-(4-carbazole-9-yl-phenyl)-1-ferrocenyl-acetone. According to the method, acetyl ferrocene and 4-carbazole-9-yl-benzaldehyde are used as raw materials, NaOH and K2CO3 are used as catalysts, and a solid-phase solvent-free method is adopted for preparing the 3-(4-carbazole-9-yl-phenyl)-1-ferrocenyl-acetone; according to the method, reaction time is short, solvent is not needed, the operation process is simple, the reaction condition is mild, the requirement for equipment is low, post-treatment is simple, reaction is complete, the yield reaches over 97%, and the prepared 3-(4-carbazole-9-yl-phenyl)-1-ferrocenyl-acetone has a good antibacterial effect.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and particularly relates to 3-(4-carbazol-9-yl-phenyl)-1-ferrocenyl-acetone and a preparation method thereof. Background technique [0002] Carbazole is a very important nitrogen-containing aromatic heterocyclic compound with high biological activity, low toxicity, good coordination ability and variable structure. It is used in medicine (anticancer, antibacterial, antihistamine , anti-oxidation, anti-inflammation, nerve suppression, etc.), dyes, materials and other fields have broad application prospects. In recent years, the introduction of carbazole groups into different molecules in order to synthesize new compounds with special properties has been attracting attention from chemical researchers. of favor. [0003] Chalcones and their derivatives are products of cross-aldol condensation of aromatic aldehydes and ketones, and contain substituent groups such as C=O, -OH, and -X (halogen), makin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/02
CPCC07F17/02
Inventor 刘玉婷王金玉尹大伟吴倩倩杨丽莎彭雪蕾冉春梅曹双瑜
Owner SHAANXI UNIV OF SCI & TECH
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