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Diarylmethane compounds as well as preparation method and application thereof

A technology for diarylmethane and compound, which is applied in the field of organic compound synthesis, can solve the problems of harsh preparation conditions, complicated process, low yield and the like, and achieves the effect of strengthening application

Active Publication Date: 2019-07-16
PEKING UNIV SHENZHEN GRADUATE SCHOOL
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of the present invention is to overcome the above-mentioned deficiencies of the prior art, and provide a kind of diarylmethane compound and preparation method thereof, to solve the problem of harsh preparation conditions, low yield, complex process and environmental pollution of existing diarylmethane compounds. Technical issues such as friendliness and limited application range

Method used

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  • Diarylmethane compounds as well as preparation method and application thereof
  • Diarylmethane compounds as well as preparation method and application thereof
  • Diarylmethane compounds as well as preparation method and application thereof

Examples

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preparation example Construction

[0110] On the other hand, on the basis of the above-mentioned diarylmethane compound of the present invention, the embodiment of the present invention also provides a preparation of the diarylmethane compound of the above molecular structure general formula (I) method. The method comprises the steps of:

[0111] S01: respectively provide benzyl halogenated hydrocarbons or benzyl alcohol sulfonate compound A, boric acid or boric anhydride compound B represented by the following structural formula:

[0112] A. B.

[0113] S02: Add the sulfonate compound A of the benzyl halogenated hydrocarbons or benzyl alcohol, the boric acid or boric anhydride compound B into the reaction system containing small organic molecule catalysts, alkaline reagents, and solvents at 30-110 Under ℃ of temperature, react, obtain following structure general formula as the diarylmethane compounds shown in (I):

[0114]

[0115] Specifically, in the above step S01, R in the molecular structural fo...

Embodiment 1

[0136] This embodiment provides 1-(4-methoxybenzyl)-2,4-dimethylbenzene and a preparation method thereof. The structural formula of the 1-(4-methoxybenzyl)-2,4-dimethyl is shown in the following molecular structural formula I1:

[0137]

[0138] Its preparation steps are as follows:

[0139] Add 2-methoxy-10-(4-methoxyphenyl)-10H-phenothiazine catalyst (0.1mmol, 0.2eq), potassium pyrophosphate (1.0mmol, 2.0eq) into a dry 10mL sealed tube , 4-methoxyphenylboronic acid (0.75mmol, 1.5eq) and 0.5mL of anhydrous acetonitrile, replaced by argon three times, added 0.5mmol 2-(chloromethyl)-1,4-dimethylbenzene, again argon After three replacements, the reaction test tube was sealed and stirred at 110°C for a reaction time of 48 hours.

[0140] After the reaction was completed, the filtrate was spin-dried and separated by column chromatography to obtain the target product as a colorless oily liquid with a yield of 66%.

[0141] Correlation representation analysis, the result is: ...

Embodiment 2

[0144] This example provides a kind of 4-(4-methoxybenzyl)-1,1'-biphenyl and its preparation method. The structural formula of the 4-(4-methoxybenzyl)-1,1'-biphenyl is shown in the following molecular structural formula I2:

[0145]

[0146]Its preparation method refers to the preparation method of 1-(4-methoxybenzyl)-2,4-dimethylbenzene in Example 1, the difference is that 4-chloromethyl-1,1'-biphenyl ( 0.5 mmol) to replace 2-(chloromethyl)-1,4-dimethylbenzene, the filtrate was spin-dried, and separated by column chromatography to obtain the target product as a white solid with a yield of 74%.

[0147] The product I2 prepared is subjected to characterization data analysis, and the result is: 1 H NMR (400MHz, CDCl 3 )δ7.65–7.60(m,2H),7.60–7.55(m,2H),7.51–7.44(m,2H),7.41–7.35(m,1H),7.33–7.29(m,2H),7.23– 7.17(m,2H),6.95–6.88(m,2H),4.02(s,2H),3.84(s,3H). 13 C NMR (101MHz, CDCl 3 )δ158.04,141.04,140.74,138.96,133.14,129.91,129.21,128.73,127.21,127.07,127.02,113.95,55.28,40...

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Abstract

The invention discloses diarylmethane compounds as well as a preparation method and application thereof. The diarylmethane compounds have a molecular structural general formula as defined by a generalformula (I) in the description. The preparation method of the diarylmethane compounds comprises the steps of adding a benzyl halogenated hydrocarbon compound A and an arylboronic acid B into a reaction system containing an organic small-molecular catalyst, an alkali reagent and a solvent, and performing a reaction to prepare the compounds. The diarylmethane compounds provided by the invention contain electron withdrawing groups and an electron-donating group substituted diarylmethane basic structure, and can be widely used for synthesis of pharmaceutical intermediates, particularly polysubstituted methane compounds, and preparation of functional materials; and the preparation method has a simple process and low requirements for reaction conditions, the reaction process is safe and controllable, the atomic utilization rate and production efficiency are high, the regioselectivity and stereoselectivity of the products are efficiently ensured, a frontier science small-molecule organocatalysis concept is introduced, and the method is friendly to the environment.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a diarylmethane compound, a preparation method thereof and an application of the diarylmethane compound. Background technique [0002] Diarylmethane compounds refer to a class of compounds in which two aromatic substituents are simultaneously connected to the same substituting carbon atom. Diarylmethane compounds not only widely exist in biologically active compounds such as natural products, drug molecules and intermediates, but also are widely used in industrial production, such as dyes, heat transfer fluids, solvents, etc. Therefore, the synthesis of such compounds is an important content of current organic chemistry. [0003] Traditional synthesis methods of diarylmethanes include Friedel–Crafts reaction, reduction reaction of diaryl ketone or diaryl carbinol, and Suzuki cross-coupling reaction catalyzed by transition metals. But there are man...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/205C07C43/225C07C41/30C07C253/30C07C255/54C07C67/343C07C69/92C07C319/20C07C323/18C07C209/68C07C211/54C07C15/30C07C43/275C07F7/18C07D209/08C07D215/227C07D231/12C07D209/12C07C69/712C07J1/00
CPCC07C43/205C07C43/225C07C43/2055C07C255/54C07C69/92C07C323/18C07C211/54C07C15/30C07C43/275C07D209/08C07D215/227C07D231/12C07D209/12C07C69/712C07J1/0011C07F7/1804
Inventor 黄湧陈杰安和志奇
Owner PEKING UNIV SHENZHEN GRADUATE SCHOOL
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