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1-tetralone spirocyclodiene, its synthesis method and its application

A kind of technology of tetralinone spiro and tetralinone, applied in chemical instrument and method, compound of periodic table 4/14 group element, carbon-based compound preparation and other directions, can solve the problem of 1-tetralinone spiro that has not yet been reported in the literature. The problems such as the synthesis method of cyclodiene, to achieve the effects of being conducive to large-scale production and promotion, the preparation method is simple, and easy to obtain

Inactive Publication Date: 2018-07-27
ANYANG INST OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] However, only the synthesis of the above-mentioned 1-tetralone spirocyclic compound has been reported at present, and there is no bibliographical report 1-tetralone spirocyclic diene and its synthetic method

Method used

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  • 1-tetralone spirocyclodiene, its synthesis method and its application
  • 1-tetralone spirocyclodiene, its synthesis method and its application
  • 1-tetralone spirocyclodiene, its synthesis method and its application

Examples

Experimental program
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Effect test

Embodiment 1

[0048] The preparation of embodiment 1 1-tetralone spiro diene

[0049] (1) Add 5mmol of 2-butenal, 5.5mmol of tert-butyldimethyltrifluoromethanesulfonate and 7.5mmol of triethylamine in a 100mL round-bottomed flask, then add 15mL of dichloromethane, at 45°C Under reaction for 48 hours, after the end of the reaction, add saturated aqueous solution of sodium bicarbonate to quench the reaction, then wash with water, then wash with saturated brine, wherein the volume of saturated aqueous solution of sodium bicarbonate, water and brine is 10mL, then the organic phase is directly Spin-dried to obtain the tert-butylsilyl-protected diene shown in the following formula, with a calculated yield of 96%;

[0050]

[0051] (2) 5mmol 2-methylene-1-tetralone and 1mmol zinc trifluoromethanesulfonate are added to the reaction tube, and the nitrogen is pumped through the double row tube for three times, then 15mL of toluene is added, and then 10mmol of the step ( The tert-butyldimethylsily...

Embodiment 2

[0052] The preparation of embodiment 2 1-tetralone spiro diene

[0053] (1) In a 100mL round bottom flask, add 10mmol of 2-butenal, 12mmol of tert-butyldimethyltrifluoromethanesulfonate and 20mmol of triethylamine respectively, then add 30mL of dichloromethane, at 50°C Reacted for 42 hours. After the reaction was over, add a saturated aqueous solution of sodium bicarbonate to quench the reaction, then wash with water, and then wash with saturated brine, wherein the saturated aqueous solution of sodium bicarbonate used, the volume of water and brine is 30mL, and then the organic phase is directly Spin-dried to obtain the tert-butylsilyl-protected diene shown in the following formula, with a calculated yield of 95%;

[0054]

[0055] (2) Add 5mmol 2-methylene-1-tetralone and 0.75mmol zinc trifluoromethanesulfonate into the reaction tube, pump and change nitrogen three times through the double row tube, then add 15mL toluene, and then add 12.5mmol The tert-butyldimethylsilyl-...

Embodiment 3

[0056] Example 3 Preparation of 1-tetralone spirodiene

[0057] (1) In a 100mL round bottom flask, add 15mmol of 2-butenal, 19.5mmol of tert-butyldimethyltrifluoromethanesulfonate and 37.5mmol of triethylamine, then add 45mL of dichloromethane, at 60 ℃ for 36 hours, after the reaction, quench the reaction by adding saturated aqueous solution of sodium bicarbonate, then wash with water, and then wash with saturated brine, wherein the volumes of saturated aqueous solution of sodium bicarbonate, water and brine are 60mL, and then the organic phase Spin dry directly to obtain the tert-butyldimethylsilyl-protected diene shown in the following formula, with a calculated yield of 94%;

[0058]

[0059] (2) Add 5mmol 2-methylene-1-tetralone and 0.5mmol zinc trifluoromethanesulfonate into the reaction tube, pump and change nitrogen three times through the double row tube, then add 15mL toluene, and finally add 15mmol step The tert-butyldimethylsilyl-protected diene obtained in (1) ...

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Abstract

The invention relates to 1-tetralone spiro-diene as well as a synthetic method and an application thereof. 1-tetralone spiro-diene is represented by formula (1), and the compound can be used for synthesizing more types of 1-tetralone spiro-framework compounds. 1-tetralone spiro-diene is prepared by the steps of adding 2-crotonaldehyde, tert-butyldimethylsilyl triflate and triethylamine into dichloromethane for reaction so as to obtain a reaction system containing tert-butyl dimethyl silicon protected diene, adding 2-methylene-1-tetralone and zinc trifluoromethanesulfonate into a reaction container, adding an aromatic hydrocarbon solvent under the protection of inert gas, and adding prepared tert-butyl dimethyl silicon protected diene for reaction, so as to finally obtain 1-tetralone spiro-diene. A preparation method of 1-tetralone spiro-diene is simple, the cost is low, and the consumption of catalysts is low.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to 1-tetralone spirodiene, its synthesis method and its application. Background technique [0002] Tetralone compounds are very important pharmaceutical intermediates, for example, 5,8-dimethoxy-2-tetralone is a key intermediate for the synthesis of antineoplastic drug amrubicin, 4-(3,4- Dichlorophenyl)-1-tetralone is an intermediate for the synthesis of the antidepressant sertraline, and 6-isopropyl-5-methoxy-2-tetralone is the raw material for the synthesis of tripterine . Therefore, the development and application of tetralone and its related compounds are of great significance. [0003] The spirocycle is the basic framework of many biologically active natural products, such as insect pheromones, steroidal saponins, and polyantibiotics. In recent years, the basic structure of the helical ring with special biological activity has become a research hotspot. The develo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/675C07C45/69
CPCC07C45/69C07C49/675C07F7/188
Inventor 郁有祝郭玉华卫爱民杨立国苏文辉黄建平张允王鑫邱明艳牛永生
Owner ANYANG INST OF TECH
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