Method for synthesizing dihydrofuran containing 1, 3-indandione spiro skeleton by using micro-channel reaction device

A technology of microchannel reaction and indanedione spiro, which is applied in chemical instruments and methods, chemical/physical/physical chemical reactors, chemical/physical/physical chemical processes, etc., can solve the problem of low reaction efficiency, long reaction time, reaction The steps are cumbersome and other problems, to achieve the effect of speeding up the reaction rate, green reaction conditions, and shortening the reaction time

Pending Publication Date: 2021-01-12
NANJING ADVANCED BIOLOGICAL MATERIALS & PROCESS EQUIP INST CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Purpose of the invention: the present invention aims at the deficiencies of the prior art, and provides a method for synthesizing dihydrofuran containing a 1,3-indanedione spiro ring skeleton by using a microchannel reaction device, so as to solve the cumbersome reaction steps in the prior art, Long reaction time, low reaction efficiency and other problems, simple and efficient synthesis of dihydrofuran containing 1,3-indanedione spiro ring skeleton without the use of metal catalysts

Method used

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  • Method for synthesizing dihydrofuran containing 1, 3-indandione spiro skeleton by using micro-channel reaction device
  • Method for synthesizing dihydrofuran containing 1, 3-indandione spiro skeleton by using micro-channel reaction device
  • Method for synthesizing dihydrofuran containing 1, 3-indandione spiro skeleton by using micro-channel reaction device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Dissolve 1mmol (0.234g) of 2-benzylidene indene-1,3-dione and 0.2mmol (0.074g) of tetrabutylammonium iodide in 10ml of γ-valerolactone, and the resulting mixed solution is denoted as Solution A; 1.2mmol (0.23g) of ethyl benzoylacetate, 3mmol (0.44g) of tert-butyl peroxide are dissolved in 10ml of γ-valerolactone, and the resulting mixed solution is designated as solution B, and then Solution A and solution B are pumped into the microchannel reaction device according to the flow volume ratio of 1:1, and the flow rate is 0.5mL / min respectively, and enter the microchannel reactor after being mixed by the Y-type mixer (the polytetrafluoroethylene The inner diameter of the tube is 0.5 mm, and the volume of the polytetrafluoroethylene tube is 10 mL) at 120° C. for 10 min. The organic phase was obtained from the discharge of the microreactor, concentrated in vacuo to obtain the crude product, and separated by column chromatography with a developing agent with a ratio of petrol...

Embodiment 2

[0045] Dissolve 1mmol (0.264g) of 2-(4-methoxybenzylidene)-1H-indene-1,3(2H)-dione, 0.2mmol (0.074g) of tetrabutylammonium iodide in 10ml of In γ-valerolactone, the resulting mixed solution is designated as solution A; 1.2 mmol (0.23 g) of ethyl benzoyl acetate and 3 mmol (0.44 g) of tert-butyl peroxide are dissolved in 10 ml of γ-valerolactone In the ester, the resulting mixed solution is recorded as solution B, and then solution A and solution B are pumped into the microchannel reaction device according to the flow volume ratio of 1:1, the flow rate is 0.5mL / min, and enter the microchannel reaction after being mixed by a Y-shaped mixer. React at 120° C. for 10 min in a microreactor (the inner diameter of the polytetrafluoroethylene tube of the microreactor is 0.5 mm, and the volume of the polytetrafluoroethylene tube is 10 mL). The organic phase was obtained from the discharge of the microreactor, concentrated in vacuo to obtain the crude product, which was separated by deve...

Embodiment 3

[0047] Dissolve 1mmol (0.268g) of 2-(3-chlorobenzylidene)-1H-indene-1,3(2H)-dione, 0.2mmol (0.074g) of tetrabutylammonium iodide in 10ml of γ - In valerolactone, the resulting mixed solution is denoted as solution A; 1.2mmol (0.23g) of ethyl benzoylacetate, 3mmol (0.44g) of tert-butyl peroxide are dissolved in 10ml of γ-valerolactone , the resulting mixed solution is recorded as solution B, then solution A and solution B are pumped into the microchannel reaction device according to the flow volume ratio of 1:1, the flow rate is 0.5mL / min, and enter the microchannel reactor after being mixed by a Y-type mixer In the medium (the inner diameter of the polytetrafluoroethylene tube of the microreactor is 0.5 mm, and the volume of the polytetrafluoroethylene tube is 10 mL), react at 120° C. for 10 min. The organic phase was obtained from the discharge of the microreactor, concentrated in vacuo to obtain the crude product, and separated by column chromatography with a developing agen...

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Abstract

The invention discloses a method for synthesizing a dihydrofuran compound containing a 1, 3-indandione spiro skeleton as shown in a formula III by using a micro-channel reaction device, which comprises the following steps: by using a 2-benzylidene-1, 3-indandione compound I and a benzoyl ethyl acetate compound II as reaction raw materials, carrying out continuous reaction by using the micro-channel reaction device to prepare the dihydrofuran compound containing a 1, 3-indandione spiro skeleton. The micro-channel reaction device comprises a feeding pump, a micro-mixer and a micro-reactor whichare sequentially connected through a pipeline. Compared with the prior art, the new dihydrofuran containing the 1, 3-indandione spiro skeleton is prepared by taking the 2benzylidene 1, 3-indandione compound as the substrate for the first time, and the method avoids multi-component reaction, uses a non-metal catalyst and a low-toxicity solvent, and is a quick, efficient, green and environment-friendly synthetic product, wherein R1 is selected from halogenated benzene, C1-C4 alkyl benzene, C1-C4 alkoxy benzene, nitrobenzene, furan or naphthalene, and R2 is selected from halogenated benzene, C1-C4 alkyl benzene, C1-C4 alkoxy benzene, nitrobenzene, furan, thiophene, pyridyl or naphthalene.

Description

technical field [0001] The invention belongs to the technical field of dihydrofuran synthesis, and in particular relates to a method for synthesizing dihydrofuran containing a spiro-ring 1,3-indanedione structure by using a microchannel reaction device. Background technique [0002] The 2,3-dihydrofuran skeleton is an important class of heterocyclic compounds, which are ubiquitous in many natural products with biological activity. In addition, it is also an important class of synthetic intermediates. Many compounds containing this structural unit have a wide range of pharmaceutical activities, including antibacterial, anti-inflammatory, anti-cardiovascular and cerebrovascular diseases, anti-cancer, anti-Parkinson's disease, etc. Therefore, researchers have carried out long-term research on the method of synthesizing these compounds. [0003] At present, the preparation method of dihydrofuran mainly contains: (1) 1,3-dicarbonyl compound and unsaturated carbonyl compound are ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/94B01J19/00
CPCB01J19/0093C07D307/94
Inventor 郭凯张磊徐高晨方正邱江凯李玉光季栋其他发明人请求不公开姓名
Owner NANJING ADVANCED BIOLOGICAL MATERIALS & PROCESS EQUIP INST CO LTD
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