A nitrogen-containing tri-substituted olefin compound, a preparation method and application thereof

Abstract

The application discloses a nitrogen-containing tri-substituted olefin compound, a preparation method and application thereof, and relates to a compound of formula I and pharmaceutically acceptable salts thereof: The synthesis method of the compound has the advantages of no transition metal catalysis, easy availability of reaction raw materials, simple reaction system, wide application range of substrates, high yield and the like. The test paper sheet of the nitrogen-containing tri-substituted olefin compound can detect malononitrile in an environmental system, and is expected to detect emitted malononitrile in a chemical plant system, and has potential application in the field of public safety.

Description

Technical Field

[0001] This invention relates to the field of material detection technology, and in particular to a nitrogen-containing trisubstituted olefin compound, its preparation method, and its application. Background Technology

[0002] In recent years, the construction of trisubstituted olefin probe molecules has attracted widespread attention from researchers. Based on the structure of the substituents on the olefin double bond, trisubstituted olefin probe molecules can be broadly classified into the following categories: triaryl (heterocyclic) substituted olefin molecules, trisubstituted olefin molecules with a cyano group attached to the double bond, and trisubstituted olefin molecules with a heteroatom attached to the double bond. Currently, trisubstituted olefin probe molecules with a heteroatom attached to the olefin double bond can be applied to fields such as picric acid detection, in vivo cell imaging, and the detection of toxic mercury ions. However, there are no literature reports on the detection of malononitrile by trisubstituted olefin probe molecules.

[0003] Malononitrile is an important chemical raw material with excellent solubility in various solvents (such as organic solvents and water). As the simplest dinitrile, malononitrile has high reactivity and is widely used in pharmaceutical production and industrial chemistry. However, malononitrile is also a dangerous cyanide-causing agent. When dissolved in aquatic environments, it pollutes water bodies. After entering human and animal tissues and being metabolized, it is completely converted into HCN, thereby inhibiting aerobic glycolysis and respiration in the brain, kidneys, and liver, and further causing serious diseases. Ultimately, it causes irreversible damage to the human body. Excessive emissions of malononitrile from chemical plants can pollute water bodies and the surrounding environment, and its toxicity may gradually accumulate along the food chain. Therefore, the detection of malononitrile has received considerable attention from researchers in recent years. Compounds with aldehyde groups in their molecular structure often undergo Knoevenagel condensation reactions with malononitrile. Therefore, utilizing the color change that occurs when aldehyde groups react with malononitrile could potentially enable naked-eye detection of malononitrile. Summary of the Invention

[0004] The present invention aims to at least solve one of the aforementioned technical problems existing in the prior art. Therefore, the object of the present invention is to provide a nitrogen-containing trisubstituted olefin compound, its preparation method, and its application.

[0005] To achieve the above objectives, the technical solution adopted by the present invention is as follows:

[0006] In a first aspect, the present invention provides compounds of formula I and pharmaceutically acceptable salts thereof:

[0007]

[0008] in, It contains an N-containing heterocyclic group.

[0009] In some embodiments of the present invention, the N-containing heterocyclic group comprises a cyclic system of 5 to 18-membered monocyclic or polycyclic heterocycles having one or more saturated or unsaturated rings and containing 1 to 5 nitrogen atoms.

[0010] In some embodiments of the present invention, the N-containing heterocyclic group includes unsaturated 3-6 membered heterocyclic groups containing 1-4 nitrogen atoms, such as pyrroloyl, pyrrolinyl, imidazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyrazinyl, triazolyl (e.g., 1,2,4-triazolyl) or tetrazolyl; saturated 3-6 membered heterocyclic groups containing 1-4 nitrogen atoms, such as pyrroloalkyl, imidazoalkyl (e.g., imidazomethyl, imidazoethyl), piperidinyl or piperazinyl; and unsaturated fused heterocyclic groups containing 1-5 nitrogen atoms, such as indolyl, isoyindolyl, inazinyl, benzimidazolyl, quinolinyl, isoquinolinyl, inazolyl, benzotriazolyl or tetrazolpyrazinyl.

[0011] In some embodiments of the present invention, the compound of formula I is selected from the following compounds:

[0012]

[0013] A second aspect of the present invention provides a method for preparing the compound of formula I, comprising the following steps:

[0014]

[0015] Compound of Formula II With Formula III compounds The reaction yields compound I;

[0016] Where X is a halogen atom; The definition is as described above.

[0017] In some embodiments of the present invention, the halogen atom includes at least one of F, Cl, Br, and I.

[0018] In some embodiments of the present invention, the molar ratio of compound II to compound III is 1:2 to 2.5.

[0019] In some embodiments of the present invention, the catalyst for the reaction comprises an inorganic base; the inorganic base comprises at least one of CsF, K2CO3, Na2CO3, and NaHCO3.

[0020] In some embodiments of the present invention, the solvent for the reaction includes at least one of DMF, DMSO, and THF.

[0021] In some embodiments of the present invention, the reaction temperature is 25°C to 35°C and the reaction time is 16h to 28h.

[0022] In some embodiments of the present invention, the preparation method of the compound of formula I further includes purifying the reaction product; the purification process includes extraction, separation to obtain an organic layer, washing the organic layer, drying, and column chromatography; the specific operations of the purification process include: extracting the reaction product with ethyl acetate and separating it, combining the organic layers, washing the organic layers sequentially with saturated ammonium chloride and saturated brine, drying with anhydrous sodium sulfate, and evaporating under reduced pressure to obtain a crude product, and analyzing the crude product by column chromatography to obtain the compound of formula I.

[0023] A third aspect of the invention provides a probe comprising the compound of formula I.

[0024] In some embodiments of the present invention, the concentration of the compound of formula I is 1 × 10⁻⁶. -6 M~1.0M; e.g., 1×10 - 4 M~0.1M.

[0025] In some embodiments of the present invention, the probe further includes a substrate on which the compound of formula I is loaded.

[0026] In some embodiments of the present invention, the substrate includes at least one of test paper and filter paper.

[0027] In a fourth aspect, the present invention provides a method for detecting malononitrile, comprising using a compound of formula I and / or the probe described herein to detect malononitrile.

[0028] In some embodiments of the present invention, the method for detecting malononitrile includes visual inspection after contacting the compound of Formula I and / or the probe with malononitrile.

[0029] In some embodiments of the present invention, the visual inspection specifically refers to: observing the color change of the detection system; preferably, the color change includes a change from no edge to yellow; preferably, the intensity of the yellow can also reflect the malononitrile content in the detection system, specifically, the more obvious the yellow, the higher the malononitrile content; preferably, the time for the color change to occur is 1 second to 300 minutes; preferably, the time for the color change to occur can reflect the malononitrile content in the detection system, specifically, the shorter the color change time, the higher the malononitrile content.

[0030] In some embodiments of the present invention, the concentration range of the malononitrile includes 0.0001M to 10M; such as 0.001M to 0.1M.

[0031] In a fourth aspect, the invention proposes the application of the compound of Formula I and / or the probe described herein in the detection of malononitrile.

[0032] The beneficial effects of this invention are:

[0033] (1) This invention synthesizes a series of novel nitrogen-containing trisubstituted olefin compounds, and the synthesized compounds are then subjected to… 1 HNMR, 13 The structure was characterized by C NMR, ESI-HRMS and X-ray single crystal diffraction analysis to clarify its structure.

[0034] (2) The synthesis method of the compound of the present invention selects a suitable inorganic base and achieves the reaction by nucleophilic substitution of halobutenaldehyde (such as 3,4-dibromo-5-hydroxy-2(5H)-furanone) and nitrogen-containing heterocyclic compound. It does not require transition metal catalysis, the reaction raw materials are readily available, and it has the advantages of simple reaction system, wide range of substrates and high yield. At the same time, it enriches the small molecule library of novel trisubstituted olefins with nitrogen-containing structure.

[0035] (3) The test strip containing nitrogen-containing trisubstituted olefin compounds in this invention can detect malononitrile in environmental systems, and is expected to detect malononitrile emissions in chemical plant systems, and has potential applications in the field of public safety. Attached Figure Description

[0036] Figure 1 This is an X-ray single-crystal diffraction pattern of compound 6 in Example 6 of the present invention.

[0037] Figure 2 This is the Blank control group for the test strip in Example 7 of the present invention.

[0038] Figure 3 The results of the test strip containing compound 4 in Example 7 of this invention for the detection of malononitrile are shown.

[0039] Figure 4 The results of the test strip containing compound 4 in Example 7 of this invention for detecting low concentrations of malononitrile are shown.

[0040] Figure 5 This is the Blank control group for the test strip in Example 8 of the present invention.

[0041] Figure 6 The results of the test strip containing compound 5 in Example 8 of this invention for the detection of malononitrile are shown.

[0042] Figure 7 The results of the test strip containing compound 5 in Example 8 of this invention for detecting low concentrations of malononitrile are shown.

[0043] Figure 8 This is the Blank control group for the test strip in Example 9 of the present invention.

[0044] Figure 9 The results of the test strip containing compound 6 in Example 9 of this invention for the detection of malononitrile are shown.

[0045] Figure 10 The results of the test strip containing compound 6 in Example 9 of this invention for detecting low concentrations of malononitrile are shown. Detailed Implementation

[0046] The present invention will be further described in detail below through specific embodiments. Unless otherwise specified, the raw materials, reagents, or apparatus used in the embodiments and comparative examples are all available from conventional commercial sources or can be obtained by existing technical methods. Unless otherwise specified, the test or experimental methods are conventional methods in the art.

[0047] Example 1

[0048] In this embodiment, compound 1 (chemical name: 3,3-bis(1H-pyrazole-1-yl)propenal) was prepared, and the specific process was as follows:

[0049] 2.5 mmol of pyrazole was added to a 25 mL round-bottom flask, and 3 mL of DMF was added to dissolve it. After stirring at room temperature for 10 minutes, 1.0 mmol of 3,4-dibromo-5-hydroxy-2(5H)-furanone and 4.0 mmol of cesium fluoride were added to the flask, and the reaction was carried out at 35 °C for 24 hours. After the reaction was completed, the reaction was quenched with 15 mL of water, and then extracted with ethyl acetate (15 mL × 3), and the layers were separated. The organic layers were combined and washed successively with saturated ammonium chloride and saturated brine. The organic layers were dried over anhydrous sodium sulfate and evaporated under reduced pressure to obtain the crude product. The crude product was separated by column chromatography to give compound 1, a yellow waxy substance (55.2 mg, 67%).

[0050] The structural formula and related characterization data of compound 1 are shown below:

[0051]

[0052] 1 H NMR (600MHz, CDCl3), δ, ppm: 6.49-6.52 (m, 2H, = CH-2, ArH-5), 6.58-6.61 (m, 1H, ArH-8), 7.38 (d, J = 3.0Hz,, 1H, ArH-4), 7.78(d,J=2.4Hz,1H,ArH-6),7.82(d,J=1.2Hz,1H,ArH-7),7.89(d,J=1.2Hz,1H,ArH-9),9.53(d,J=7.2Hz,1H,CHO-1);

[0053] 13C NMR (150MHz, CDCl3), δ, ppm: 108.9 (C-2), 109.9 (C-8), 110.7 (C-5), 130.2 (C-7), 133.4 (C-4), 143.8 (C-9), 144.7 (C-6), 147.0 (C-3), 189.7 (C-1);

[0054] ESI-HRMS,m / z:Calcd for C9H8N4O[M+H] + ,189.0770,found:189.0768.

[0055] Example 2

[0056] In this embodiment, compound 2 (chemical name: 3,3-bis(1H-1,2,4-triazol-1-yl)propenal) was prepared. The specific process is as follows:

[0057] 2.5 mmol of 1,2,4-triazole was added to a 25 mL round-bottom flask, and 3 mL of DMF was added to dissolve it. After stirring at room temperature for 10 minutes, 1.0 mmol of 3,4-dibromo-5-hydroxy-2(5H)-furanone and 4.0 mmol of cesium fluoride were added to the flask, and the reaction was carried out at 35 °C for 24 hours. After the reaction was completed, the reaction was quenched with 15 mL of water, and then extracted with ethyl acetate (15 mL × 3), and the layers were separated. The organic layers were combined and washed successively with saturated ammonium chloride and saturated brine. The organic layers were dried over anhydrous sodium sulfate and evaporated under reduced pressure to obtain the crude product. The crude product was separated by column chromatography to give compound 2, a yellow waxy substance (51.0 mg, 62%).

[0058] The structural formula and related characterization data of compound 2 are shown below:

[0059]

[0060] 1 H NMR (600MHz, CDCl3), δ, ppm: 6.74 (d, J = 7.2Hz, 1H, = CH-2), 8.17 (s, 1H, ArH-6), 8.22 ( s,1H,ArH-4),8.30(s,1H,ArH-7),8.55(s,1H,ArH-5),9.65(d,J=6.6Hz,1H,CHO-1);

[0061] 13 C NMR (150MHz, CDCl3), δ, ppm: 113.7 (C-2), 140.0 (C-6), 144.1 (C-4), 146.8 (C-3), 154.4 (C-7), 154.6 (C-5), 187.9 (C-1);

[0062] ESI-HRMS,m / z:Calcd for C7H6N6O[M+H] + ,191.0675,found:191.0673.

[0063] Example 3

[0064] In this embodiment, compound 3 (chemical name: 3,3-bis(1H-benzimidazol-1-yl)propenal) was prepared, and the specific process was as follows:

[0065] 2.5 mmol of benzimidazole was added to a 25 mL round-bottom flask, and 3 mL of DMF was added to dissolve it. After stirring at room temperature for 10 minutes, 1.0 mmol of 3,4-dibromo-5-hydroxy-2(5H)-furanone and 4.0 mmol of cesium fluoride were added to the flask, and the reaction was carried out at 35 °C for 24 hours. After the reaction was completed, the reaction was quenched with 15 mL of water, and then extracted with ethyl acetate (15 mL × 3), and the layers were separated. The organic layers were combined and washed successively with saturated ammonium chloride and saturated brine. The organic layers were dried over anhydrous sodium sulfate and evaporated under reduced pressure to obtain the crude product. The crude product was separated by column chromatography to give compound 3, a yellow waxy substance (121.1 mg, 86%).

[0066] The structural formula and related characterization data of compound 3 are shown below:

[0067]

[0068] 1 H NMR (600MHz, CDCl3), δ, ppm: 6.40 (d, J = 7.2Hz, 1H, ArH-15), 6.77 (d, J = 7.8Hz, 1H,=CH-2),6.87(d,J=8.4Hz,1H,ArH-8),7.21-7.24(m,2H,ArH-7,14),7.33-7 .37(m,2H,ArH-6,13),7.82(d,J=7.8Hz,1H,ArH-12),7.89(d,J=7.2Hz,1H,Ar H-5),7.94(s,1H,ArH-17),8.20(s,1H,ArH-10),9.55(d,J=7.8Hz,1H,CHO-1);

[0069] 13C NMR (150MHz, CDCl3), δ, ppm: 110.7 (C-2), 111.3 (C-12), 112.4 (C-5), 121.6 (C-15), 121.6 (C-8), 125.0 (C-14), 125.1 (C-7), 125.8 (C-13),125.9(C-6),131.5(C-11),133.1(C-4),141.0(C-17),141.6(C-10),142.7(C-16),143.7(C-9),144.6(C-3),187.9(C-1);

[0070] ESI-HRMS, m / z: Calculated for C 17 H 12 N4O[M+H] + ,289.1083,found:289.1080.

[0071] Example 4

[0072] In this embodiment, compound 4 (chemical name: 3,3-bis(1H-imidazol-1-yl)propenal) was prepared. The specific process is as follows:

[0073] Add 2.5 mmol of imidazole to a 25 mL round-bottom flask and dissolve in 3 mL of DMF. After stirring at room temperature for 10 minutes, add 1.0 mmol of 3,4-dibromo-5-hydroxy-2(5H)-furanone and 4.0 mmol of cesium fluoride to the flask and react at 35 °C for 24 hours. After the reaction is complete, quench the reaction with 15 mL of water, then extract with ethyl acetate (15 mL × 3) and separate the layers. Combine the organic layers and wash them successively with saturated ammonium chloride and saturated brine. Dry the organic layers with anhydrous sodium sulfate and evaporate to dryness under reduced pressure to obtain the crude product. Separate the crude product by column chromatography to obtain compound 4, a white solid (64.0 mg, 78%) with a melting point of 146 °C–147 °C.

[0074] The structural formula and related characterization data of compound 4 are shown below:

[0075]

[0076] 1H NMR (600MHz, CDCl3), δ, ppm: 6.17 (d, J = 7.2Hz, 1H, = CH-2), 7.02-7.04 (m, 1H, ArH-8), 7.19-7.23 (m, 2H, Ar H-5,7),7.29-7.32(m,1H,ArH-4),7.64(s,1H,ArH-9),7.88(s,1H,ArH-6),9.43(d,J=7.2Hz,1H,CHO-1);

[0077] 13 C NMR (150MHz, CDCl3), δ, ppm: 111.7(C-2), 117.6(C-7), 120.7(C-4), 131.9(C-8), 132.5(C-5), 136.3(C-9), 139.0(C-6), 142.4(C-3), 187.7(C-1);

[0078] ESI-HRMS,m / z:Calcd for C9H8N4O[M+H] + ,189.0770,found:189.0768.

[0079] Example 5

[0080] In this embodiment, compound 5 (chemical name: 3,3-di(2-methyl-1H-imidazol-1-yl)propenal) was prepared, and the specific process was as follows:

[0081] 2.5 mmol of methylimidazole was added to a 25 mL round-bottom flask, and 3 mL of DMF was added to dissolve it. After stirring at room temperature for 10 minutes, 1.0 mmol of 3,4-dibromo-5-hydroxy-2(5H)-furanone and 4.0 mmol of cesium fluoride were added to the flask, and the reaction was carried out at 35 °C for 24 hours. After the reaction was completed, the reaction was quenched with 15 mL of water, and then extracted with ethyl acetate (15 mL × 3), and the layers were separated. The organic layers were combined and washed successively with saturated ammonium chloride and saturated brine. The organic layers were dried over anhydrous sodium sulfate and evaporated under reduced pressure to obtain the crude product. The crude product was separated by column chromatography to give compound 5, a white solid (33 mg, 80%) with a melting point of 166 °C–168 °C.

[0082] The structural formula and related characterization data of compound 5 are shown below:

[0083]

[0084] 1H NMR (600MHz, CDCl3), δ, ppm: 2.18 (s, 3H, CH3-11), 2.22 (s, 3H, CH3-7), 6.13 (d, J = 7.2Hz, 1H, = CH-2), 6.88 (d, J = 1.8Hz, 1H, Ar H-4),7.07(d,J=1.8Hz,1H,ArH-5),7.12(d,J=1.2Hz,1H,ArH-8),7.17(d,J=1.2Hz,1H,ArH-9),9.49(d,J=7.2Hz,1H,CHO-1);

[0085] 13 C NMR (150MHz, CDCl3), δ, ppm: 13.4 (C-11), 14.2 (C-7), 115.8 (C-2), 117.2 (C-8), 119.2 (C-4),122.0(C-9),130.1(C-5),143.5(C-10),145.9(C-6),146.4(C-3),188.4(C-1);

[0086] ESI-HRMS, m / z: Calculated for C 11 H 12 N4O[M+H] + ,217.1084,found:217.1081.

[0087] Example 6

[0088] In this embodiment, compound 6 (chemical name: 3,3-di(2-ethyl-1H-imidazol-1-yl)propenal) was prepared. The specific process is as follows:

[0089] 2.5 mmol of ethylimidazole was added to a 25 mL round-bottom flask, and 3 mL of DMF was added to dissolve it. After stirring at room temperature for 10 minutes, 1.0 mmol of 3,4-dibromo-5-hydroxy-2(5H)-furanone and 4.0 mmol of cesium fluoride were added to the flask, and the reaction was carried out at 35 °C for 24 hours. After the reaction was completed, the reaction was quenched with 15 mL of water, and then extracted with ethyl acetate (15 mL × 3), and the layers were separated. The organic layers were combined and washed successively with saturated ammonium chloride and saturated brine. The organic layers were dried over anhydrous sodium sulfate and evaporated under reduced pressure to obtain the crude product. The crude product was separated by column chromatography to give compound 6, a white solid (90.3 mg, 85%) with a melting point of 107 °C–108 °C.

[0090] The structural formula and related characterization data of compound 6 are shown below:

[0091]

[0092] 1 H NMR (600MHz, CDCl3), δ, ppm: 1.22 (t, J = 7.2Hz, 3H, CH3-8), 1.26 (t, J = 7.2Hz, 3H, CH3-13), 2.31-2.37 (m, 4H, CH2-7, 12), 6.06 (d, J = 7.2Hz, 1H, = CH-2), 6.80(d,J=1.8Hz,1H,ArH-4),7.04(d,J=1.8Hz,1H,ArH-5),7.09(d,J=1.2Hz,1H,ArH-9),7.13(d,J=1.2Hz,1H,ArH-10),9.42(d,J=7.2Hz,1H,CHO-1);

[0093] 13 C NMR (150MHz, CDCl3), δ, ppm: 11.5 (C-13), 11.6 (C-8), 20.5 (C-12), 21.1 (C-7), 116.1 (C-2), 119.2 ( C-9),122.2(C-4),129.7(C-10),129.8(C-5),143.4(C-11),150.6(C-6),151.1(C-3),188.5(C-1);

[0094] ESI-HRMS, m / z: Calculated for C 13 H 16 N4O[M+H] + ,245.1397,found:245.1394.

[0095] The X-ray single-crystal diffraction pattern of compound 6 is attached. Figure 1 As shown.

[0096] The results of proton nuclear magnetic resonance (NMR) spectroscopy, carbon nuclear magnetic resonance (NMR) spectroscopy, high-resolution mass spectrometry (HRMS) and X-ray single-crystal diffraction (XRD) showed that the structure of compound 6 was consistent with the expected structure.

[0097] Example 7

[0098] This embodiment describes the detection of malononitrile, and the specific process is as follows:

[0099] Compound 4 was prepared into different concentrations (10). -1 M~10 -4 A solution of M) was prepared and made into test strips (white). Then, malononitrile was dissolved in dichloromethane to prepare a solution with a concentration of 10. -1 Solution of M. Then, a set of test strips made from compound 4 were placed in an environment free of malononitrile (Blank control). Figure 2In one group, test strips made from compound 4 were placed in the same sealed space as a solution of malononitrile in dichloromethane, and the phenomena were observed. Figure 3 After approximately 40 minutes of exposure to both compounds, the test strips turned yellow, with the yellow color becoming less pronounced at lower concentrations of compound 4. The Blank control test strip, which was not exposed to malononitrile, showed no color change. Even after diluting the malononitrile concentration 100-fold, the color change was still observed on the test strips. Figure 4 However, this will take approximately 200 minutes.

[0100] Example 8

[0101] This embodiment describes the detection of malononitrile, and the specific process is as follows:

[0102] Compound 5 was prepared into different concentrations (10). -1 M~10 -4 The solution of M) was prepared into test strips, and then malononitrile was dissolved in dichloromethane to prepare a solution with a concentration of 10. -1 Solution of M. Then, a set of test strips made from compound 5 were placed in an environment free of malononitrile (Blank control). Figure 5 In one group, test strips made from compound 5 were placed in the same sealed space as a solution of malononitrile in dichloromethane, and the phenomena were observed. Figure 6 After approximately 30 minutes of exposure to both compounds, the test strips turned yellow, with the yellow color becoming less pronounced at lower concentrations of compound 5. The Blank control test strip, which was not exposed to malononitrile, showed no color change. Even after diluting the malononitrile concentration 100-fold, the color change was still observed on the test strips. Figure 7 However, the time required at this point is approximately 180 minutes.

[0103] Example 9

[0104] This embodiment describes the detection of malononitrile, and the specific process is as follows:

[0105] Compound 6 was prepared into different concentrations (10). -1 M~10 -4 The solution of M) was prepared into test strips, and then malononitrile was dissolved in dichloromethane to prepare a solution with a concentration of 10. -1 Solution of M. Then, a set of test strips made from compound 6 were placed in an environment free of malononitrile (Blank control). Figure 8 In one group, test strips made from compound 6 were placed in the same sealed space as a solution of malononitrile in dichloromethane, and the phenomena were observed. Figure 9After approximately 15 minutes of exposure to both, the test strips turned yellow, with the yellow color becoming less pronounced at lower concentrations of compound 6. The Blank compound 6 test strip, not exposed to malononitrile, showed no color change. Even after diluting the malononitrile concentration 100-fold, the color change was still observed on the test strips. Figure 10 However, it takes about 60 minutes.

[0106] In summary, the nitrogen-containing trisubstituted olefin compounds of this invention can be successfully synthesized in a one-step process without a metal catalyst. These compounds exhibit varying degrees of color change in the presence of malononitrile, and the higher the concentration of malononitrile, the deeper the color change of the test strip containing these compounds, and the shorter the time required. Therefore, these compounds can achieve effective detection of malononitrile in the environment.

[0107] The above embodiments are preferred embodiments of the present invention, but the embodiments of the present invention are not limited to the above embodiments. Any changes, modifications, substitutions, combinations, or simplifications made without departing from the spirit and principle of the present invention shall be considered equivalent substitutions and shall be included within the protection scope of the present invention.

Claims

1. Compound of Formula I: ； The compound of formula I is selected from the following compounds: 、 、 、 。 2. A method for preparing the compound of formula I as described in claim 1, characterized in that: Includes the following steps: Compound of Formula II With Formula III compounds The reaction yields compound I; Where X is a halogen atom; The definition is as described in the specific compound of claim 1; The catalyst for the reaction includes an inorganic base; the reaction temperature is 25℃~35℃.

3. A probe, characterized in that: Includes the compound of formula I as described in claim 1; the concentration of the compound of formula I is 1 × 10⁻⁶. -4 M~1.0M.

4. The probe according to claim 3, characterized in that: The probe also includes a substrate on which the compound of formula I is loaded.

5. A method for detecting malononitrile for non-disease diagnosis or treatment purposes, comprising using a compound of formula I as claimed in claim 1 and / or a probe as claimed in claim 3 or 4 to detect malononitrile.

6. The use of the compound of formula I as described in claim 1 and / or the probe as described in claim 3 or 4 in the detection of malononitrile for non-disease diagnostic or therapeutic purposes.

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