1,2,3,4-Tetrahydronaphthalene compound and its preparation method and application

A compound, tetrahydronaphthalene technology, applied in the field of organic compound synthesis, can solve problems such as limited application range, harsh preparation conditions, and unfriendly environment, and achieve the effect of shortening the reaction route, requiring low reaction conditions, and reducing environmental pollution pressure

Active Publication Date: 2021-07-20
PEKING UNIV SHENZHEN GRADUATE SCHOOL
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The invention provides a 1,2,3,4-tetrahydronaphthalene compound and a preparation method thereof to solve the problem of harsh preparation conditions, low yield and complex process of existing 1,2,3,4-tetrahydronaphthalene compounds. Technical problems such as unfriendly environment and limited application range

Method used

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  • 1,2,3,4-Tetrahydronaphthalene compound and its preparation method and application
  • 1,2,3,4-Tetrahydronaphthalene compound and its preparation method and application
  • 1,2,3,4-Tetrahydronaphthalene compound and its preparation method and application

Examples

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preparation example Construction

[0097] In one embodiment, the preparation method of the 1,2,3,4-tetrahydronaphthalene compound comprises the following steps:

[0098] S01: respectively provide the styrene compound A and the olefin compound B represented by the following structural formula:

[0099]

[0100] S02: Add the styrene compound A and the olefin compound B into a reaction system containing a visible light catalyst, a co-catalyst and a solvent to react at a temperature of -80-100°C to obtain the following structure represented by (I) The 1,2,3,4-tetrahydronaphthalene compounds shown,

[0101]

[0102]Specifically, in the above step S01, R in the molecular structural formula of styrene compound A 1 , R 2 , R 5 , R 6 , R 7 , R 8 The represented group is as above in the invention embodiment 1,2,3,4-tetrahydronaphthalene compound molecular structure general formula (I) in R 1 , R 2 , R 5 , R 6 , R 7 , R 8 The groups represented are the same.

[0103] R in the molecular structure formula...

Embodiment 1

[0136] Example 1 provides 1-(4-methoxyphenyl)-4-methyl-1,2,3,4-tetrahydronaphthalene and its preparation method.

[0137] The structural formula of the 1-(4-methoxyphenyl)-4-methyl-1,2,3,4-tetrahydronaphthalene is shown in the following molecular structural formula I1:

[0138]

[0139] Its preparation steps are as follows:

[0140] In a dry 10 mL test tube, add mesitylene-substituted acridinium salt visible light catalyst (0.01 mmol, 0.1 eq), diphenyl disulfide co-catalyst (0.01 mmol, 0.1 eq) and 2 mL of anhydrous dichloroethane, argon Replace three times, add 0.3mmola-methylstyrene, replace with argon three times again, seal the reaction test tube and stir at room temperature for 10 min. Dissolve p-methoxystyrene benzene (0.1mmol, 1.0eq) in 2mL of anhydrous dichloroethane, and slowly add it into the reaction system, while adding it, irradiate it with two blue LEDs with a power of 15w, add and react The time is 10h. After the reaction was completed, the filtrate was spi...

Embodiment 2

[0143] Example 2 provides 1-(4-methoxyphenyl)-4-ethyl-1,2,3,4-tetrahydronaphthalene and its preparation method. The structural formula of the 1-(4-methoxyphenyl)-4-ethyl-1,2,3,4-tetrahydronaphthalene is shown in molecular structural formula I2 below:

[0144]

[0145] Its preparation method refers to the preparation method of 1-(4-methoxyphenyl)-4-methyl-1,2,3,4-tetrahydronaphthalene in Example 1, the difference is that a-ethylstyrene (0.3mmol) instead of a-methylstyrene, the filtrate was spin-dried, and separated by column chromatography to obtain the target product as a colorless oily liquid with a yield of 77% and a dr value of 1:1.

[0146] The product I2 prepared is subjected to characterization data analysis, and the result is: 1 HNMR (300MHz, Chloroform-d) δ7.29(td, J=8.5, 1.5Hz, 1H), 7.19(tt, J=7.8, 2.1Hz, 1H), 7.12–6.98(m, 3H), 6.87(qd ,J=5.8,5.2,2.0Hz,3H), 4.09(t,J=11.1,7.0Hz,1H),3.82(s,3H),2.83(ddq,J=19.4,9.8,5.3Hz,1H), 2.24(dddd,J=12.6,8.7,5.6,2.8Hz,1H),2.10–...

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Abstract

The invention discloses a 1,2,3,4-tetrahydronaphthalene compound, a preparation method and application thereof. Described 1,2,3,4-tetrahydronaphthalene compound molecular structure general formula is as described in formula (I), and described 1,2,3,4-tetrahydronaphthalene compound preparation method comprises styrene compound Steps such as carrying out reaction in A, olefin compound B, visible light catalyst, co-catalyst and solvent. The 1,2,3,4-tetrahydronaphthalene compound of the present invention has a tetralin basic skeleton substituted by an electron-withdrawing group and an electron-donating group, and can be widely used in the synthesis and preparation of pharmaceutical intermediates, especially polycyclic compounds. Preparation of functional materials. The preparation method has simple process, low requirements on reaction conditions, safe and controllable reaction process, high atom utilization rate and production efficiency, and at the same time, the regioselectivity and stereoselectivity of the product are efficiently ensured, and the product is pollution-free.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and specifically relates to a 1,2,3,4-tetrahydronaphthalene compound and a preparation method and application thereof. Background technique [0002] Polycyclic compounds refer to a class of compounds that contain multiple ring units in their molecular structure. Polycyclic compounds are not only extremely important pharmaceutical fragments and intermediates, but also potential biologically active molecules. Starting from polycyclic products and modifying them with known chemical means is an important part of the research and development of new drug molecules. [0003] Among them, 1,2,3,4-tetrahydronaphthalene compounds are important ones among polycyclic compounds. 1,2,3,4-Tetrahydronaphthalene compounds are important building blocks for the synthesis of pharmaceutical intermediates, especially heterocyclic compounds and the preparation of functional materials. The classic m...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C41/30C07C43/21C07C43/225C07C17/275C07C25/22
CPCC07C17/275C07C25/22C07C41/30C07C43/21C07C43/225
Inventor 黄湧王雷锋陈杰安
Owner PEKING UNIV SHENZHEN GRADUATE SCHOOL
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