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Tropilidene-1-thioether compound and synthetic method and application thereof

A technology for cycloheptatriene and compounds, which is applied in the field of cycloheptatriene-1-sulfide compounds and their synthesis, and achieves the effects of less side reactions, high conversion rate and mild reaction conditions

Inactive Publication Date: 2019-06-28
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the complexity and diversity of cycloheptatriene compounds, more efforts are needed to apply them to clinical diagnosis

Method used

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  • Tropilidene-1-thioether compound and synthetic method and application thereof
  • Tropilidene-1-thioether compound and synthetic method and application thereof
  • Tropilidene-1-thioether compound and synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 2

[0049] The synthesis of embodiment 2 cycloheptatriene-1-o-methylphenylene sulfide

[0050] Weigh 0.2mmol cycloheptatriene, 0.4mmol o-methylthiophenol, 0.22mmol DDQ and 2.5mL chloroform into a 15mL pressure-resistant reaction tube, add a magnetic stirrer, stir the reaction at 25°C for 5min, the chemical The equation is shown in equation (2).

[0051]After the reaction is over, carry out vacuum distillation at -0.090MPa and 40°C to remove chloroform, then use 50mL of dichloromethane to carry out vacuum filtration, and the obtained filtrate is to carry out vacuum distillation at -0.085MPa and 35°C to remove methylene chloride , and then carry out silica gel column chromatography purification with 200-300 mesh silica gel powder, the eluent is petroleum ether, to obtain cycloheptatriene-1-o-methylphenylsulfide, and its yield is 70%.

[0052] image 3 and Figure 4 It is the NMR characterization spectrum of cycloheptatriene-1-o-methylphenylene sulfide. in, image 3 Cycloheptatr...

Embodiment 3

[0055] The synthesis of embodiment 3 cycloheptatriene-1-m-bromophenylene sulfide

[0056] Weigh 0.2mmol cycloheptatriene, 0.4mmol m-bromothiophenol, 0.22mmol DDQ and 2.5mL chloroform into a 15mL pressure-resistant reaction tube, add a magnetic stirrer, and stir the reaction at 25°C for 5min. The chemical equation As shown in formula (3).

[0057] After the reaction is over, carry out vacuum distillation at -0.090MPa and 40°C to remove chloroform, then use 50mL of dichloromethane to carry out vacuum filtration, and the obtained filtrate is to carry out vacuum distillation at -0.085MPa and 35°C to remove methylene chloride , and then carry out silica gel column chromatography purification with 200-300 mesh silica gel powder, and the eluent is petroleum ether to obtain cycloheptatriene-1-m-bromophenylene sulfide with a yield of 72%.

[0058] Figure 5 and Figure 6 It is the NMR characterization collection of cycloheptatriene-1-m-bromophenylene sulfide, wherein, Figure 5 Cyc...

Embodiment 7

[0079] The synthesis of embodiment 7 cycloheptatriene-1-(3,4-dimethyl) phenylene sulfide

[0080]Weigh 0.2mmol cycloheptatriene, 0.4mmol 3,4-dimethylthiophenol, 0.22mmol DDQ and 2.5mL chloroform into a 15mL pressure-resistant reaction tube, add a magnetic stirrer, and stir the reaction at 25°C 5min, please refer to formula 7 for the chemical equation of this embodiment.

[0081] After the reaction is over, carry out vacuum distillation at -0.090MPa and 40°C to remove chloroform, then use 50mL of dichloromethane to carry out vacuum filtration, and the obtained filtrate is to carry out vacuum distillation at -0.085MPa and 35°C to remove methylene chloride , and then carry out silica gel column chromatography purification with 200-300 mesh silica gel powder, the eluent is petroleum ether: ethyl acetate = 100:1, to obtain cycloheptatriene-1-(3,4-dimethyl)benzenesulfide ether in 45% yield.

[0082] Figure 13 and Figure 14 It is the NMR spectrum of cycloheptatriene-1-(3,4-dime...

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Abstract

The invention belongs to the technical field of organic synthesis and discloses a tropilidene-1-thioether compound and a synthetic method and an application thereof. The tropilidene-1-thioether compound is prepared by adding tropilidene, a phenolic compound and an oxidizing agent into a solvent to react at 20-30 DEG C and purifying the product. The oxidizing agent is 2,3-dichloro-5,5-dicyano-1,4-benzoquinone. The structural formula of the phenolic compound is R-SH, and the molecular structure of the tropilidene-1-thioether compound is as shown in a formula (I), wherein R is alkyl or aryl. Theprepared tropilidene-1-thioether compound is free of side actions and high in conversion ratio, and the yield can reach 60-89%. The chemical structure of the tropilidene-1-thioether compound is diverse and has various bioactivities such as bacterial inhibition, virus prevention, tumor prevention, insecticiding, inflammation prevention and an enzyme inhibitor.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and more specifically relates to a cycloheptatriene-1-sulfide compound and its synthesis method and application. Background technique [0002] The chemical structures of cycloheptatriene and its phenolic ketone compounds are diverse, and most of them have various biological activities such as antibacterial, antiviral, antitumor, insecticidal, anti-inflammatory and enzyme inhibitors. At present, great progress has been made in chemical synthesis and properties, biological activity, biosynthesis and metabolism. However, due to the complexity and diversity of structures of cycloheptatriene compounds, more efforts are needed to apply them to clinical diagnosis. Contents of the invention [0003] In order to solve the deficiencies and shortcomings in the above-mentioned prior art, the primary purpose of the present invention is to provide a cycloheptatriene-1-sulfide compound. [0004] A...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/14C07C321/30C07C323/09C07D213/70C07B45/06
Inventor 吴佳微陈丹瑶颜建萍陈迁霍延平
Owner GUANGDONG UNIV OF TECH