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A kind of preparation method of the neolignan compound of benzotetrahydrofuran

A technology of benzotetrahydrofuran and compounds, which is applied in the field of preparation of neolignan compounds, can solve the problems of cumbersome one step, not suitable for acid-sensitive substrates, and high cost of the second catalyst, and achieve the effect of low cost

Inactive Publication Date: 2019-09-24
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The first step of the prior art is cumbersome, the second catalyst of the prior art is expensive, the third condition of the prior art is relatively severe, and sensitive to water and oxygen, and the reaction is carried out in a strongly acidic medium, which is not suitable for acid-sensitive substrates. It is necessary to study the preparation method of new benzotetrahydrofuran-like new lignan compounds

Method used

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  • A kind of preparation method of the neolignan compound of benzotetrahydrofuran
  • A kind of preparation method of the neolignan compound of benzotetrahydrofuran
  • A kind of preparation method of the neolignan compound of benzotetrahydrofuran

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Embodiment 1

[0028] A preparation method of a benzotetrahydrofuran-like neolignan compound, comprising the following steps:

[0029] Add 32.4mg (0.3mmol) BQ, 363.9mg (0.9mmol) Ce(SO 4 ) 2 4H 2 O and 216.7mg (1.8mmol) MgSO 4 Then add 3ml of toluene, and finally add 2.1mmol of isopropenylbenzene; stir and react at room temperature for 24 hours; after the reaction is completed, use a diatomaceous earth sand core funnel to filter, spin dry, and separate on a column to obtain a pure product.

[0030] Table 1 is under the condition of embodiment 1, adjusts the amount of substance of each raw material, obtains the product yield situation:

[0031] Table 1:

[0032]

[0033] The product of embodiment 1 is made proton nuclear magnetic resonance spectrum and carbon nuclear magnetic resonance spectrum, obtains respectively figure 1 with figure 2 , it can be deduced that the chemical formula of the product is:

[0034]

Embodiment 2

[0036] R in the chemical formula 1 Replaced by F, and the rest of the preparation conditions were unchanged, and the product was subjected to proton nuclear magnetic resonance spectrum and carbon nuclear magnetic resonance spectrum to obtain image 3 with Figure 4 , it can be deduced that the chemical formula of the product is:

[0037]

Embodiment 3

[0039] R in the chemical formula 1 Replaced by a methyl group, the rest of the preparation conditions remain unchanged, and the product is subjected to a proton nuclear magnetic resonance spectrum and a carbon nuclear magnetic resonance spectrum to obtain Figure 5 with Image 6 , it can be deduced that the chemical formula of the product is:

[0040]

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Abstract

The invention provides a preparation method of a neolignan compound of benzotetrahydrofurans. The method comprises the following steps: adding p-benzoquinone (BQ), Ce(SO4)2.4H2O and MgSO4 into a reaction container, then adding methylbenzene, finally adding olefin, and carrying out a stirring reaction for 20 to 28 hours at room temperature; using a kieselguhr sand core funnel to filter after the reaction is ended, and carrying out separation on columns after spin-drying, so that a pure product can be obtained. The preparation method is simple and convenient, low in cost, mild in conditions and high in tolerance to water and oxygen, the yield can reach 80% or more, the preparation method is a novel synthetic method for the neolignan compound of benzotetrahydrofurans, and active exploration is provided for the application of the compound.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of benzotetrahydrofuran-based neolignan compounds. Background technique [0002] Lignans widely exist in plants in nature and are natural products formed by oxidative polymerization of phenylpropanoid units (C6-C3C). It has attracted the attention of pharmacologists and chemists because of its structural diversity and wide range of biological activities. It is found in more than 70 species of plants in various locations, and is even found in plant secretions, human and animal urine. Benzotetrahydrofuran-like neolignans are an important component of lignans, but their synthesis methods are seldom reported. [0003] Prior art 1: Monte group reduced benzofuranone to benzotetrahydrofuran by reduction method: [0004] [0005] Existing technology 2: Ellman's group uses Wilkinson catalyst to directly activate the C-H bond, and then treats it with hydrochloric...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/04
Inventor 火星方济中
Owner LANZHOU UNIVERSITY