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A kind of synthetic method of ring bridged spiroindanone compounds

A synthesis method and compound technology are applied in the preparation of organic compounds, the preparation of carbon-based compounds, chemical instruments and methods, etc., which can solve the problems of low yield, long reaction time, and small expansion range of substrates, and achieve high yield. , Easy to operate, environment-friendly effect

Active Publication Date: 2020-04-07
YANGZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] 1,3-indandione can be used to synthesize spiroindanone compounds, but due to the particularity of 1,3-indandione substrate, derivatization is relatively difficult, and the methods reported in the literature exist to varying degrees Some problems, such as the use of strong acid, strong basic solvent, longer reaction time, lower yield, small substrate expansion range, etc.

Method used

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  • A kind of synthetic method of ring bridged spiroindanone compounds
  • A kind of synthetic method of ring bridged spiroindanone compounds
  • A kind of synthetic method of ring bridged spiroindanone compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: Preparation of 4b'-hydroxyl-17'-phenyl-4b', 14c'-dihydro-15' with the following structural formula H -Spiro[indene-2,16'-[4c,14b]ethylbisindene[1,2- a :1',2'- c ]fluorene]-1,3,5',10',15'-pentaone:

[0023]

[0024] Add 0.053g (0.5mmol) of benzaldehyde and 0.321g (2.2mmol) of 1,3-indandione into a 50 mL round bottom flask, then add 20 mL of ethanol, and then add 0.101g (1.0mmol) of triethylamine, The domino reaction was carried out under the condition of heating to reflux (78°C) for 5 hours.

[0025] After the reaction, the solvent was evaporated and concentrated, and purified by silica gel column chromatography using a mixed solvent of ethyl acetate and petroleum ether to obtain pure 4b'-hydroxy-17'-phenyl-4b',14c'-dihydro- 15' H -Spiro[indene-2,16'-[4c,14b]ethylbisindene[1,2- a :1',2'- c ]fluorene]-1,3,5',10',15'-pentone, the isolated yield was 71%.

[0026] The structural characterization data are as follows:

[0027] 1 H NMR (400 MHz, DMSO- d ...

Embodiment 2

[0028] Example 2: Preparation of 4b'-hydroxyl-17'-(2-methoxyphenyl)-4b',14c'-dihydro-15' with the following structural formula H -Spiro[indene-2,16'-[4c,14b]ethylbisindene[1,2- a :1',2'- c ]fluorene]-1,3,5',10',15'-pentaone:

[0029]

[0030] In a 50 mL round bottom flask, add 0.068g (0.5mmol) m-methoxybenzaldehyde, 0.365g (2.5mmol) 1,3-indandione, then add 15 mL methanol, and then add 0.127g (1.5mmol) Triethylamine, carry out domino reaction under the condition of 50 ℃ for 8 hours.

[0031] After the reaction, the solvent was evaporated and concentrated, and purified by silica gel column chromatography using a mixed solvent of ethyl acetate and petroleum ether to obtain 4b'-hydroxy-17'-(2-methoxyphenyl)-4b',14c '-Dihydro-15' H -Spiro[indene-2,16'-[4c,14b]ethylbisindene[1,2- a :1',2'- c ]fluorene]-1,3,5',10',15'-pentone, the isolated yield was 74%.

[0032] The structural characterization data are as follows:

[0033] 1 H NMR (400 MHz, DMSO- d 6 ) δ: 8.59 (d, J ...

Embodiment 3

[0034] Example 3: Preparation of 4b'-hydroxy-17'-(2-chlorophenyl)-4b',14c'-dihydro-15' with the following structural formula H -Spiro[indene-2,16'-[4c,14b]ethylbisindene[1,2- a :1',2'- c ]fluorene]-1,3,5',10',15'-pentaone:

[0035]

[0036] Add 0.070g (0.5mmol) m-chlorobenzaldehyde, 0.292g (2.0mmol) 1,3-indandione into a 50 mL round bottom flask, add 15 mL methanol, and add 0.127g (1.5mmol) piperidine Pyridine, the domino reaction was carried out at 40°C for 10 hours.

[0037] After the reaction, the solvent is evaporated and concentrated, and purified by silica gel column chromatography using a mixed solvent of ethyl acetate and petroleum ether to obtain 4b'-hydroxy-17'-(2-chlorophenyl)-4b',14c' -dihydro-15' H -Spiro[indene-2,16'-[4c,14b]ethylbisindene[1,2- a :1',2'- c ]fluorene]-1,3,5',10',15'-pentaketone, the isolated yield was 68%,

[0038] The structural characterization data are as follows:

[0039] 1 H NMR (400 MHz, DMSO- d 6 ) δ: 8.63 (d, J = 8.0 Hz, 1H...

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Abstract

A method for synthesizing ring-bridged spiroindanone compounds, belonging to the technical field of organic synthesis, in the presence of a solvent and a catalyst, a domino reaction occurs between an aromatic aldehyde and a multimolecular 1,3-indandione, and the reaction ends Then carry out silica gel column chromatography with a mixed solvent of ethyl acetate and petroleum ether to obtain ring-bridged spiroindanone compounds. Wherein, the solvent is ethanol or methanol; the catalyst is triethylamine, piperidine, triethylenediamine or 1,8-diazabicycloundec-7-ene. The invention has the advantages of wide expansion range of substrates, easy-to-obtain raw materials, simple operation, and can be synthesized without transition metal catalysts.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis. Background technique [0002] 1,3-Indandione has a nucleophilic methylene group and an electrophilic carbonyl group, and it is easier to undergo polymolecular condensation reactions (Jacob, K.; Sigalov, M,; et al. Self-Condensation of 1,3-Indandione: A Reinvestigation . [J]. Eur. J. Org. Chem. 2000, 2047-2055). The trimer of 1,3-indandione has a large conjugated system and has many applications in the field of optoelectronic materials. In 2012, Martín's research group reported the synthesis of 1,3-indanedione trimer and its derivatives as bowl-shaped electron donors for photovoltaic materials to absorb solar energy (Isla, H.; Martín, N.; et al. Bowl-shape electron donors with absorptions in the visible range of the solar spectrum and their supramolecular assemblies with C 60 [J]. Chem. Sci. , 2012, 3 , 498-508). [0003] Spiroindanone compounds also widely exist in biologicall...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/72C07C49/747C07C49/67C07C49/755C07C49/697C07C201/12C07C205/45C07D213/50
CPCC07C45/64C07C45/67C07C45/72C07C201/12C07D213/50C07C49/747C07C49/67C07C49/755C07C49/697C07C205/45
Inventor 颜朝国石荣国韩莹孙晶
Owner YANGZHOU UNIV