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2-cyclohexyl-5-(1,1- dimethyl octyl) phenol and synthesizing method thereof

A technology of dimethyloctyl and synthesis methods, which is applied in the directions of active ingredients of hydroxyl compounds, chemical instruments and methods, drug combinations, etc., to achieve the effects of high yield, short synthesis route and easy industrial production

Inactive Publication Date: 2010-05-26
WUHAN SYNCHALLENGE UNIPHARM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] 2-Cyclohexyl-5-(1,1-dimethyloctyl)phenol has no literature report on its synthesis and application, so our company is the first to synthesize and report

Method used

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  • 2-cyclohexyl-5-(1,1- dimethyl octyl) phenol and synthesizing method thereof
  • 2-cyclohexyl-5-(1,1- dimethyl octyl) phenol and synthesizing method thereof
  • 2-cyclohexyl-5-(1,1- dimethyl octyl) phenol and synthesizing method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0017] Example 1: Synthesis of 2-benzyloxy-1-cyclohexyl-4-(1,1-dimethyloctyl)benzene

[0018] In a well-dried 500ml reaction flask, 60g 2-benzyloxy-1-bromo-4-(1,1-dimethyloctyl)benzene was dissolved in 300ml dichloromethane. Under the protection of argon gas, Add 65g of n-butyllithium dropwise within 30 minutes at -25°C, increase the temperature in the reaction to about 30°C after the addition is complete, react at this temperature for 30 minutes, cool to -20°C, and then add 20g dropwise to the reactor The mixed solution of cyclohexene and 20g of dichloromethane, continue to stir the reaction for 40min, after the reaction is over, add 60ml of 1N dilute hydrochloric acid, wash the organic phase twice with water, and then use saturated NaHCO 3 Wash with aqueous solution and collect the organic phase. The solvent was removed from the organic phase by rotary evaporation, and 48 g of pale yellow oil was obtained after evaporation to dryness.

Embodiment 2

[0019] Example 2: Synthesis of 2-benzyloxy-1-(3'-methoxycyclohexyl)-4-(1,1-dimethyloctyl)benzene

[0020] In a well-dried 500ml reaction flask, dissolve 60g 2-benzyloxy-1-bromo-4-(1,1-dimethyloctyl)benzene in 300ml ether. Under the protection of argon, 100g of n-butyllithium was added dropwise within 30 minutes at ℃. After the addition, the temperature in the reaction was increased to about 30°C, reacted at this temperature for 45 minutes, cooled to -25°C, and then 25g methoxy was added dropwise to the reactor The mixed solution of cyclohexene and 25g ether, continue to stir the reaction for 60min, after the reaction is over, add 90ml of 1N dilute hydrochloric acid, wash the organic phase twice with water, and then use saturated NaHCO 3 Wash with aqueous solution and collect the organic phase. The solvent was removed from the organic phase by rotary evaporation, and 51 g of light yellow oil was obtained after evaporation to dryness.

Embodiment 3

[0021] Example 3: Synthesis of 2-benzyloxy-1-(3'-cyclohexyloxycyclohexyl)-4-(1,1-dimethyloctyl)benzene

[0022] In a well-dried 500ml reaction flask, 60g 2-benzyloxy-1-bromo-4-(1,1-dimethyloctyl)benzene was dissolved in 300ml dichloromethane. Under the protection of nitrogen gas, Add 80g n-butyllithium dropwise within 30 minutes at 10°C. After the dropwise addition, increase the internal temperature of the reaction to about 30°C, react at this temperature for 50 minutes, cool to -30°C, and then drop 110g ring into the reactor. The mixed solution of hexyloxycyclohexene and 110g of dichloromethane, continue to stir the reaction for 60min, after the reaction is over, add 60ml of dilute hydrochloric acid, wash the organic phase twice with water, and then use saturated NaHCO 3 Wash with aqueous solution and collect the organic phase. The solvent was removed from the organic phase by rotary evaporation, and 60 g of light yellow oil was obtained after evaporation to dryness.

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Abstract

The invention relates to a 2-cyclohexyl-5-(1,1-dimethyl octyl) phenol and a synthesizing method thereof. 2-benzyloxy-1-bromine-4-(1,1-dimethyl octyl) benzene carries out addition reaction to obtain 2-benzyloxy-1-(cyclohexyl or 3'-alkoxy cyclohexyl)-4-(1,1-dimethyl octyl) benzene, and the 2-benzyloxy-1-(cyclohexyl or 3'-alkoxy cyclohexyl)-4-(1,1-dimethyl octyl) benzene is hydrogenated to carry outbenzyl removing reaction to obtain the 2-cyclohexyl-5-(1,1-dimethyl octyl) phenol. The invention has short synthesizing route, simple method and higher yield and is easy for industrialized production. The 2-cyclohexyl-5-(1,1-dimethyl octyl) phenol has liquid crystal performance and excellent antibiosis inflammation eliminating effect, can be used as one of liquid crystal composition components ofa liquid crystal display, has the inhibiting effect on porphyromonas gingialis, streptococcus, spider-shaped selenomonas, and the like and can be used for preparing a mouth cleaning agent and a medicament for preparing oral cavity diseases.

Description

Technical field [0001] The present invention relates to 2-cyclohexyl-5-(1,1-dimethyloctyl)phenol and a synthesis method thereof. Background technique [0002] With the continuous discovery of biologically active substances and uses of long-chain alkyl-substituted phenol derivatives, the application of such compounds is currently one of the active research topics in the field of medical applications. Studies have shown that these compounds can inhibit the proliferation of a variety of tumor cell lines, have broad-spectrum anti-tumor, anti-oxidation, improve cardiomyocyte contractility, regulate cholesterol biosynthesis, reduce human skin pigmentation, inhibit tyrosinase, and brighten It has multiple effects on skin and inflammation. The common features of these derivatives are the phenol derivatives with bifunctional groups containing long-chain alkyl substituents. Because of their bifunctional groups, they have broad applications in the synthesis of new drugs, electronic chemica...

Claims

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Application Information

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IPC IPC(8): C07C39/17C07C37/50C09K19/30A61K31/05A61P1/02A61P31/04A61K8/33A61Q11/00
Inventor 张淑娴汤兴国廖明授杜小兰廖春花
Owner WUHAN SYNCHALLENGE UNIPHARM INC
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