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Hemi-cucurbituril C33H39O3N9 containing aniline structure and synthesis method thereof

A technology of C33H39O3N9 and C33H39O3N, which is applied in the field of semimelon ring C33H39O3N9 and its synthesis, to achieve the effect of easy operation and low cost

Active Publication Date: 2021-10-22
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, there is no synthetic method that can introduce the aniline structure into the semicucurbitan ring as a basic unit

Method used

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  • Hemi-cucurbituril C33H39O3N9 containing aniline structure and synthesis method thereof
  • Hemi-cucurbituril C33H39O3N9 containing aniline structure and synthesis method thereof
  • Hemi-cucurbituril C33H39O3N9 containing aniline structure and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Embodiment 1: Synthesis of intermediate 3,5 bis-(bromomethyl)nitrobenzene (3):

[0056] The compound 5-nitrobenzene-1,3-dioic acid (1) (59.7mmol, 12.66g, 1eq) was weighed and dissolved in THF (100mL), stirred until completely dissolved, and the solution was cooled to 0°C. NaBH 4 (208.95mmol, 7.94g, 3.5eq) was added to the solution in batches, and when the solution stopped bubbling, slowly added BF 3 ·Et 2 O (0.208mol, 28.4mL, 3.5eq) was added dropwise to the reaction liquid within 1h, the temperature was allowed to rise to room temperature naturally, and the reaction was kept at this temperature for more than 16h, after the reaction was completed. The reaction solution was cooled to 0° C., and the reaction solution was carefully quenched with aqueous sodium hydroxide (1 mol / L, 200 mL), and the reaction solution was stirred for 3 h to be completely quenched. Part of the solvent was spun off from the reaction solution with a rotary evaporator. The suspension was extra...

Embodiment 2

[0057] Example 2: Synthesis of intermediate 3,5-bis((methylene)(imidazolidin-2-one)-5-nitrobenzene) (4):

[0058] Hemiglycoside (174mmol, 15g, 10.77eq) was weighed and dissolved in DMF (45mL), compound 3 (16.2mmol, 5g, 1eq) was added to the reaction solution, and stirred overnight at 100°C. Spot the plate to monitor the reaction. After the reaction is complete, spin the DMF to dryness, pour the suspension into 100mL water, extract the aqueous phase with dichloromethane three times or more, combine the organic phases, wash with water and brine, and wash with Na 2 SO 4 dry. Filter and spin dry to obtain a crude oily liquid. The crude product was purified by silica gel column chromatography (EtOAc:CH 3 OH=10:1) to obtain a white solid product with a yield of 25.1%.

Embodiment 3

[0059] Example 3: Synthesis of intermediate 3,5-bis((methylene)(imidazolidin-2-one)-5-nitrobenzene) (4):

[0060] Weigh hemiglycoside (174mmol, 15g, 10.77eq), tetrabutylammonium bromide (0.387mmol, 0.13g, 0.3eq), sodium iodide (0.52mmol, 0.08g, 0.4eq) dissolved in DMF (45mL) , compound 3 (16.2mmol, 5g, 1eq) was added to the reaction solution and stirred overnight at 100°C. Spot the plate to monitor the reaction. After the reaction is complete, spin the DMF to dryness, pour the suspension into 100mL water, extract the aqueous phase with dichloromethane three times or more, combine the organic phases, wash with water and brine, and wash with Na 2 SO 4 dry. Filter and spin dry to obtain a crude oily liquid. The crude product was purified by silica gel column chromatography (EtOAc:CH 3 OH=10:1) to obtain a white solid product with a yield of 24.3%.

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Abstract

The invention discloses a hemi-cucurbituril C33H39O3N9 containing an aniline structure. The chemical name of the hemi-cucurbituril C33H39O3N is 3<5>, 7<5>, 11<5>-triamino-1, 5, 9 (1, 3)-triimidazoline-3, 7, 11 (1, 3)-triphenylmethyldodecatriene-1<2>, 5<2>, 9<2>-triketone. The synthesis method of the C33H39O3N9 comprises the following steps of: obtaining 3, 5-bis-(hydroxymethyl) nitrobenzene from 5-nitrobenzene-1, 3-diacid, generating3, 5-bis-(bromomethyl) nitrobenzene, generating 3, 5-bis ((methylene) (imidazolidine-2-ketone) 5-nitrobenzene), generating 1, 3-bis (3-(bromomethyl)-5-nitrobenzene) imidazolidine-2-ketone, generating 3<5>, 7<5>, 11<5>-trinitro-1, 5, 9 (1, 3)-triimidazoline-3, 7, 11 (1, 3)-triphenylmethyldodecatriene-1<2>, 5<2>, 9<2>-triketone, and generating 3<5>, 7<5>, 11<5>-triamido-1, 5, 9 (1, 3)-triphenylmethyldodecatriene-3, 7, 11 (1, 3)-triphenylmethyldodecatriene-1<2>, 5<2>, 9<2>-triketone. The C33H39O3N9 can be used as a detector of Fe < 3 + >; and the detector can also be used as a detector for nitrophenol substances. The synthesis method has the characteristics of simplicity, rapidness, easiness in operation, low cost and the like.

Description

technical field [0001] The invention relates to the field of organic synthesis in the field of chemistry, in particular to a semicucurbitan C containing aniline structure 33 h 39 o 3 N 9 and its synthesis method. Background technique [0002] Semicucurbitan is a macrocyclic compound composed of methylene bridged ethylene urea (semiglycoside urea) monomers. Since it was first synthesized and reported by Yuji Miyahara in 2004, a series of modified semicucurbital macrocyclic compounds have been synthesized so far. Cyclic compounds, such as cyclohexyl half melon ring, bamboo half melon ring, biotin half melon ring, etc. The synthesis of new semicucurbit rings is an eternal and challenging research content in supramolecular chemistry; most of the basic skeletons based on semicucurbit rings are derived from the structural unit hemiglycosides of semicucurbit rings, thereby synthesizing modified The hemiglucoside urea, and then reacted with formaldehyde under acidic conditions ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22C09K11/06G01N21/64
CPCC07D487/22C09K11/06G01N21/643G01N21/6428C09K2211/1074G01N2021/6432
Inventor 刘懋龙秋梦曾庆凯汪丽游玉婷袁晓婷
Owner GUIZHOU UNIV
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