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A kind of method of synthesizing indenoid compound

A technology of compounds and acids, which is applied in the field of synthesizing indenes, can solve the problems of easy occurrence of danger, harsh reaction conditions, and harmful by-products, and achieve the effects of wide applicability, mild reaction system, and high conversion rate

Active Publication Date: 2022-05-17
SHANGHAI BOOK CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The reaction conditions are harsh, prone to danger, and the by-products are harmful

Method used

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  • A kind of method of synthesizing indenoid compound
  • A kind of method of synthesizing indenoid compound
  • A kind of method of synthesizing indenoid compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] The present embodiment performs the preparation of 2- (o- tolyl (trimethylsilyl) methylene) -1H-indene-1,3(2H)-dione. The specific operation is as follows:

[0051]

[0052] In nitrogen, 2-(3-Methylsilyl)propionyl)benzylnitrile (0.1 mmol), 2-methylphenylboronic acid (0.25 mmol), [RhOH(COD)] 2 ] 2 (2.5mmol%), 1,4-dioxane (2ml) and water (0.05ml) are added to the magnet-filled Shrek tube. React at 60 °C, monitor the reaction using TLC plates, wait until 2-(3-methylsilyl)propionyl)benzyl)benzyl nitrile react completely, stop heating and cool the reaction to room temperature. The resulting mixture was filtered through a sand core funnel, washed with dichloromethane (10 ml, 3-5 times), and then the solvent was evaporated with a rotary evaporator at low pressure to give a crude product. The crude product was purified by silica gel column chromatography to obtain the desired product, 2-(o-tolyl(trimethylsilyl)methylene)-1H-indene-1, 3(2H)-dione, the product was a yellow oily liq...

Embodiment 2

[0058] The present embodiment performs the preparation of 2- ((2-methoxyphenyl) (trimethylsilyl) methylene) -1H-indene-1,3(2H)-dione. The specific operation is as follows:

[0059]

[0060] Under nitrogen, 2-(3-Methylsilyl)propionyl)benzylnitrile (0.1 mmol), 2-methoxyphenylboronic acid (0.25 mmol), [RhOH(COD)] 2 ] 2 (2.5mmol%), 1,4-dioxane (2ml) and water (0.05ml) are added to the magnet-filled Shrek tube. React at 60 °C, monitor the reaction using TLC plates, wait until 2-(3-methylsilyl)propionyl)benzyl)benzyl nitrile react completely, stop heating and cool the reaction to room temperature. The resulting mixture was filtered through a sand core funnel, washed with dichloromethane (10 ml, 3-5 times), and then the solvent was evaporated with a rotary evaporator at low pressure to give a crude product. The crude product was purified by silica gel column chromatography to obtain the desired product, 2-(((2-methoxyphenyl) (trimethylsilyl) methylene)-1H-indene-1, 3(2H)-dione, the pro...

Embodiment 3

[0066] The present embodiment performs the preparation of 2- (naphthalen-1-yl (trimethylsilyl) methylene) -1H-indene-1, 3(2H)-dione. The specific operation is as follows:

[0067]

[0068] In a nitrogen environment, 2-(3-Methylsilyl)propionyl)benzylnitrile (0.1 mmol), naphthoronic acid (0.25 mmol), [RhOH(COD)] 2 ] 2(2.5mmol%), 1,4-dioxane (2ml) and water (0.05ml) are added to the magnet-filled Shrek tube. React at 60 °C, monitor the reaction using TLC plates, wait until 2-(3-methylsilyl)propionyl)benzyl)benzyl nitrile react completely, stop heating and cool the reaction to room temperature. The resulting mixture was filtered through a sand core funnel, washed with dichloromethane (10 ml, 3-5 times), and then the solvent was evaporated with a rotary evaporator at low pressure to give a crude product. The crude product was purified by silica gel column chromatography to obtain the desired product, 2-(naphthalen-1-yl(trimethylsilyl)methylene)-1H-indene-1, 3(2H)-dione, the product ...

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Abstract

The invention relates to a method for synthesizing indenoid compounds. The method uses metal rhodium to catalyze the reaction of 2-(3-(silyl) propionyl)benzonitrile compounds and phenylboronic acid compounds. Step 1: Add 2‑(3‑(silyl) propionyl) benzonitrile compound, hydroxy (cyclooctadiene) rhodium (I) dimer and phenylboronic acid into a drying tube with magnets; step 2. Slowly add an organic solvent under a nitrogen atmosphere, and stir the reaction at 60 ° C. After the 2-(3-(silyl) propionyl) benzonitrile derivative is completely reacted, stop the reaction and cool to room temperature; step 3, the The mixture obtained in step 2 is filtered, washed, separated and purified to obtain. The indenoid derivatives were successfully synthesized with high yield. Compared with other methods for synthesizing indenoid derivatives, the operation is simple and convenient, and can be suitable for the synthesis of large sterically hindered indenoid derivatives. In addition, no toxic substances are added or produced during the reaction process, and no alkaline reagents need to be added.

Description

Technical field [0001] The present invention belongs to the field of organic chemistry, specifically relates to a method of synthesizing indine compounds. Background [0002] Indene is an aromatic hydrocarbon, colorless transparent oily liquid at room temperature, extracted from tar kerosene with a boiling point of 182.44 °C, which can be used to produce indyl-gumarone resin. From the structural formula, it can be considered that the benzene ring is formed by the combination of cyclopentadiene, so it can also be called benzocyclopentadiene. Indine is an important class of organic compounds that are the products of extraction and separation from tar kerosene. Indyne molecules are not aromatic, placed in the air will become black, indole molecules in the cyclopentadiene contains a lively methylene, can occur a variety of substitution reactions. Conventional synthesis methods enable epochs by b block through activated carbon at 625 °C, or tetrahydronaphthalene by SiO at 670 °C 2 -A...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/08
CPCC07F7/081C07F7/083Y02P20/584
Inventor 岳燕妮邓学祖
Owner SHANGHAI BOOK CHEM CO LTD
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