Chiral tetraaryl-substituted methane and its preparation method

A chiral and aryl technology, applied in the field of chiral tetraaryl substituted methane and its preparation, can solve the problems of limited types and synthesis of aryl methane, and achieve the effects of good yield, environmental friendliness, simple and practical operation

Active Publication Date: 2021-02-12
HKUST SHENZHEN RES INST
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Problems solved by technology

[0003] The object of the present invention is to provide a chiral tetraaryl substituted methane and its preparation method, aiming to solve the technical problem of limited types and synthesis of existing aryl methane

Method used

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  • Chiral tetraaryl-substituted methane and its preparation method
  • Chiral tetraaryl-substituted methane and its preparation method
  • Chiral tetraaryl-substituted methane and its preparation method

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[0023] On the other hand, the embodiment of the present invention also provides a preparation method of chiral tetraaryl-substituted methane, comprising the following steps:

[0024] dissolving the compound represented by formula II and the compound represented by formula III in a solvent, and performing a synthesis reaction under the condition of a chiral phosphoric acid catalyst to obtain the compound represented by formula I;

[0025]

[0026] Among them, in the above compounds, Ar 1 、Ar 2 、Ar 3 and Ar 4 are independently selected from any one of aryl, heteroaryl, substituted aryl and substituted heteroaryl, and Ar 1 、Ar 2 、Ar 3 and Ar 4 different from each other.

[0027] In the above-mentioned preparation method provided by the embodiment of the present invention, the compound shown in formula II, that is, triaryl-substituted methanol and the compound shown in formula III, that is, aryl nucleophile are used to react under the condition of chiral phosphoric acid ...

Embodiment 1

[0039]

[0040] Using Ar 1 For 4-hydroxyphenyl, Ar 2 is 2-methoxyphenyl, Ar 3 The phenyl triaryl carbinol and 2-methylpyrrole are used as reaction raw materials, and the reaction is carried out with a chiral phosphoric acid catalyst. The specific implementation process is as follows:

[0041] Dissolve triarylmethanol (61.2mg, 0.2mmol) and 2-methylpyrrole (32.4mg, 0.4mmol) in 1,2-dichloroethane (3.6mL), and cool the mixture to 0°C, slowly drop A solution of chiral phosphoric acid (14.9 mg, 0.015 mmol) in 1,2-dichloroethane (0.4 mL) was added. After that, it was placed at 0°C and stirred for 48 hours. Its reaction equation is as follows:

[0042]

[0043] The reaction solution was directly applied to silica gel column chromatography to obtain 71.7 mg of the target product Ia as a pale yellow foamy solid, with a calculated yield of 97%.

[0044] After the preparation of this step is completed, in order to further verify that the purified compound is indeed the target ...

Embodiment 2

[0053]

[0054] Using Ar 1 For 4-hydroxyphenyl, Ar 2 For 2-benzo[1,3]-dioxolanyl, Ar 3 The phenyl triaryl carbinol and 2-methylpyrrole are used as reaction raw materials, and the reaction is carried out with a chiral phosphoric acid catalyst. The specific implementation process is as follows:

[0055] Dissolve triarylmethanol (64.0mg, 0.2mmol) and 2-methylpyrrole (32.4mg, 0.4mmol) in 1,2-dichloroethane (3.6mL), and cool the mixture to 0°C, slowly drop A solution of chiral phosphoric acid (14.9 mg, 0.015 mmol) in 1,2-dichloroethane (0.4 mL) was added. After that, it was placed at 0°C and stirred for 48 hours.

[0056] The reaction solution was directly applied to silica gel column chromatography to obtain 72.1 mg of the target product Ib as a pale yellow foamy solid, with a calculated yield of 94%.

[0057] After the preparation of this step is completed, in order to further verify that the purified compound is indeed the target product to be prepared in this example, t...

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Abstract

The invention belongs to the technical field of synthetic chemistry, and in particular relates to a chiral tetraaryl-substituted methane and a preparation method thereof. The general structural formula of the chiral tetraaryl-substituted methane is formula I in the description: in the general structural formula shown in formula I, Ar 1 、Ar 2 、Ar 3 and Ar 4 are independently selected from any one of aryl, heteroaryl, substituted aryl and substituted heteroaryl, and Ar 1 、Ar 2 、Ar 3 and Ar 4 different from each other. The chiral tetraaryl-substituted methane has a special molecular shape and stereo configuration, which makes it have special pharmaceutical properties and has great prospects in the development of new drugs, and this preparation method overcomes the inability to achieve in the fields of chemistry and drug synthesis. Directly catalyzing the construction of chiral tetraaryl quaternary carbon centers is a difficult problem in the synthesis of chiral tetraaryl methane structures. At the same time, the preparation method is simple and practical, with good yield. The preparation process is green and economical, environmentally friendly and easy to industrialize. .

Description

technical field [0001] The invention belongs to the technical field of synthetic chemistry, and in particular relates to a chiral tetraaryl-substituted methane and a preparation method thereof. Background technique [0002] Aryl-substituted methane has attracted extensive attention in the fields of organic materials, life sciences, and supramolecular chemistry due to its applications in optical devices, functional material frameworks, drug release, and protein translocation detection. However, the current limited synthesis methods of arylmethanes also greatly restrict their application development in the fields of synthesis and drug development. Contents of the invention [0003] The object of the present invention is to provide a chiral tetraaryl-substituted methane and its preparation method, aiming to solve the technical problem of limited types and synthesis of the existing aryl methane. [0004] For realizing above-mentioned purpose of the invention, the technical sc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/333C07D405/06C07D207/335C07D409/06C07D209/12
CPCC07B2200/07C07D207/333C07D207/335C07D209/12C07D405/06C07D409/06
Inventor 孙建伟李星光
Owner HKUST SHENZHEN RES INST
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