CN101302197A - 4- azido-1,8-naphthalimide compound and preparation thereof - Google Patents
4- azido-1,8-naphthalimide compound and preparation thereof Download PDFInfo
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- CN101302197A CN101302197A CNA2008100400210A CN200810040021A CN101302197A CN 101302197 A CN101302197 A CN 101302197A CN A2008100400210 A CNA2008100400210 A CN A2008100400210A CN 200810040021 A CN200810040021 A CN 200810040021A CN 101302197 A CN101302197 A CN 101302197A
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Abstract
The invention relates to a 4-azido-1,8-naphthalimide compound and a method for preparing the same. The structural formula of the compound is as follows: in the invention, an azide group is introduced into a 1,8-naphthalimide compound, which enriches the study on the structural photoelectron transfer of 1,8-naphthalimide compound, and contributes to the wide applications of the 4-azido-1,8-naphthalimide compound as a stable intermediate product with certain activity in a variety of fields. The method of the invention can produce 4-azido-1,8-naphthalimide compound with high yield rate.
Description
Technical field
The present invention relates to a kind of 4-nitrine-1,8-naphthalimide compound and preparation method thereof.
Background technology
Organic fluorescence materials is applied in extensive fields, and simplified summary has the following aspects:
1. organic fluorescent pigment and coating;
2. the fluorescence dye used of plastics and regenerated fiber;
3. optical whitening agent;
4. organic scintillator;
5. the flaw detection of rocket, steamer and main equipment;
6. the organic fluorescence source in chemistry and the electrochemiluminescence body;
7. fluorescence chemical analysis;
8. the fluorescent tracing of biology and medical science;
9. the fluorescence source of aspect such as military affairs.
1,8-naphthalimide fluorescent dyestuff is the very important fluorescence dye of a class, because of it has lovely luster, and fluorescence intensive characteristics, and be widely used in fluorescence dye and white dyes.In addition, also be used for metal fluorescent inspection, solar collector, liquid crystal, organic light-guide material.Therefore, the research of relevant such dyestuff is very active, and application prospect is boundless.In recent years, such dyestuff particularly is widely used in biotechnology research as functional pigmented its range of application of just constantly expanding.There are some researches show, because 1, the 8-naphthalimide is the good fluorescence color bodies of a class, as it being transformed into the reactive dyestuffs that contain hydrazides and vinyl sulfone(Remzaol active group, under suitable pH and temperature, single-minded selectivity is arranged, and can be used for the interior dyeing of born of the same parents of viable cell owing to it is nontoxic microorganism is painted.At present, the azido-substitution reaction of No. 4 positions not yet the someone attempt.
Summary of the invention
One of purpose of the present invention is to provide a kind of 4-nitrine-1,8-naphthalimide compound.
Two of purpose of the present invention is to provide the preparation method of this compounds.
For achieving the above object, reaction mechanism of the present invention is:
Wherein, R
1Be H, C
1～C
32Alkyl, aryl, PEG200～4000 or 2-carboxyl methylene radical;
The structural formula of described aryl is:
Wherein A, B, C, D, E are: H, C
1～C
5Alkyl, nitro, halogen, hydroxyl, amino, aldehyde radical or carboxyl;
The structural formula of described 2-carboxyl methylene radical is:
R wherein
4Alkyl, nitro, Cl, Br, F, I, hydroxyl, amino, aldehyde radical, carboxyl, hydrocinnamyl or phenyl for H, C1～C5;
R
2, R
3For: the alkyl of H, C1～C5, nitro, Cl, Br, F, I, hydroxyl, amino, aldehyde radical, carboxyl, hydrocinnamyl or phenyl.
According to above-mentioned reaction mechanism, the present invention adopts following technical scheme:
A kind of 4-nitrine-1, the 8-naphthalimide compound is characterized in that the structural formula of this compound is:
Wherein, R
1Be H, C
1～C
32Alkyl, aryl, PEG200～4000 or 2-carboxyl methylene radical;
The structural formula of described aryl is:
Wherein A, B, C, D, E are: H, C
1～C
5Alkyl, nitro, halogen, hydroxyl, amino, aldehyde radical or carboxyl;
The structural formula of described 2-carboxyl methylene radical is:
R wherein
4Alkyl, nitro, Cl, Br, F, I, hydroxyl, amino, aldehyde radical, carboxyl, hydrocinnamyl or phenyl for H, C1～C5;
R
2, R
3For: the alkyl of H, C1～C5, nitro, Cl, Br, F, I, hydroxyl, amino, aldehyde radical, carboxyl, hydrocinnamyl or phenyl.
A kind ofly prepare above-mentioned 4-nitrine-1, the method of 8-naphthalimide compound, it is characterized in that this method has following steps: with 4-bromo-1, the 8-naphthalimide is dissolved among the DMF, drip the sodiumazide aqueous solution, temperature of reaction is 60～140 ℃, reacts 1～20 hour, obtains product with frozen water, mixing solutions recrystallization with DMF and water gets 4-nitrine-1, the 8-naphthalimide compound; Described 4-bromo-1, the mol ratio of 8-naphthalimide and sodiumazide is: 1: 1.
Azido group is a class active reactive group, thereby the compound that possesses azido group can both use as a kind of active intermediate in many reactions, the present invention is incorporated into 1 with azido group, in the 8-naphthalimide compound, not only enriched 1, the photoelectron transfer research that the 8-naphthalimide compound is structural, and make it be widely applied to multiple field as a kind of stable active intermediate product.The synthetic 4-nitrine-1 of method energy high yield of the present invention, the 8-naphthalimide compound.
Embodiment
Raw material 4-bromo-1 of the present invention, the preparation method of 8-naphthalimide sees also following reference:
1.Feng?L.，Cui，F.J.；Guo，L.Y.；Qian，X.H.；etal.Bioorganic?&?MedicinalChemistry，2007，15，5114.
2.Quaquebeke，E.V.；Mahieu，T.；Dumont，P.Journal?of?Medicinal?Chemistry，2007，50，4122.
3. Zhao is with rich, Hu Yongqiang, Zhao Defeng, Cheng Lvbai, dyestuffs industries, 1997,34,13.
4.Liisa?D.；Van?V.；Tom?E.；Patrick?J.F.；etal.Journal?of?Medicinal?Chemistry，2007，50，102327.
Embodiment one: get N-butyl-4-bromo-1,8-naphthalimide 1mol, be dissolved among the DMF of 50ml, drip the sodiumazide aqueous solution (the 1mol sodiumazide is dissolved in the water of 2ml) in 1 hour, temperature of reaction is 80 ℃, reacts 6 hours, obtains product with frozen water, mixing solutions recrystallization with DMF and water gets pure products, productive rate 95%.This product structure formula is:
Title: N-butyl-4-nitrine-1,8-naphthalimide
Color: yellow
Fusing point: 114.5-115.0 ℃
IR(KBr，cm-1)：v?2957，2933，2871，2138，1699，1658，1386，1354，1286，1234，784。1H?NMR(500MHz，CDCl3)：δ?8.66(dd，1J＝7.5Hz，2J＝1Hz，1H)，8.60(d，J＝1Hz，1H)，8.46(dd，1J＝8.5Hz，2J＝1Hz，1H)，7.76(dd，1J＝8.5Hz，2J＝7.5Hz，1H)，7.49(d，J＝8Hz，1H)，4.20(t，J＝7.5Hz，2H)，1.71-1.77(m，2H)，1.44-1.51(m，2H)，1.00(t，J＝7Hz，3H)。
MS：m/z(％)：294(M
+，19)，266(M-N
2，100)。
Ultimate analysis: Found, %:C 64.97, and N 19.00, and H 4.70; Calculated, %:C 65.31, and N 19.05, H 4.76.
Embodiment two: get N-dodecyl-4-bromo-1,8-naphthalimide 1mol, be dissolved among the DMF of 50ml, drip the sodiumazide aqueous solution (the 1mol sodiumazide is dissolved in the water of 2ml) in the 1H, temperature of reaction is 100 ℃, reacts 4 hours, obtains product with frozen water, mixing solutions recrystallization with DMF and water gets pure products, productive rate 80%.
This product structure formula is:
Title: N-dodecyl-4-nitrine-1,8-naphthalimide
Color: yellow
Fusing point: 59.4-59.8 ℃
(KBr，cm
-1)：v?2954，2922，2851，2125，1699，1659，1586，1559，1386，1353，1291，1235，781。
1H?NMR(500MHz，CDCl
3)：δ8.65(d，J＝7.5Hz，1H)，8.60(d，J＝8Hz，1H)，8.45(d，J＝8.5Hz，1H)，7.76(d，J＝7Hz，1H)，7.49(d，J＝8Hz，1H)，4.18(t，J＝7.5Hz，2H)，1.72-1.77(m，2H)，1.27-1.45(m，18H)，0.90(t，J＝6.5Hz，3H)。
MS：m/z(％)：406(M
+，8)，378(M-N
2，100)。
Ultimate analysis: Found, %:C 70.29, and N 13.62, and H 7.01.Calculated，％：C?70.94，N?13.79，H?7.39。
Embodiment three: get N-hexadecyl-4-bromo-1,8-naphthalimide 1mol, be dissolved among the DMF of 50ml, drip the sodiumazide aqueous solution (the 1mol sodiumazide is dissolved in the water of 2ml) in the 1H, temperature of reaction is 100 ℃, reacts 8 hours, obtains product with frozen water, mixing solutions recrystallization with DMF and water gets pure products, productive rate 85%.
This product structure formula is:
Title: N-hexadecyl-4-nitrine-1,8-naphthalimide
Color: yellow
Fusing point: 35.5-36.1 ℃
IR(KBr，cm
-1)：v?2959，2920，2850，2125，1699，1660，1586，1353，781。
1H?NMR(500MHz，CDCl
3)：δ8.64(d，J＝7Hz，1H)，8.58(d，J＝8Hz，1H)，8.43(d，J＝8Hz，1H)，7.75(d，J＝8Hz，1H)，7.47(d，J＝8Hz，1H)，4.17(t，J＝8Hz，2H)，1.70-1.76(m，2H)，1.26-1.43(m，26H)，0.89(t，J＝7Hz，3H)。
MS：m/z(％)：462(M
+，8)，434(M-N
2，100)。
Ultimate analysis: Found, %:C 72.57, and N 11.99, and H 8.12.Calculated，％：C?72.73，N?12.12，H?8.23。
Embodiment five: get N-(2-chloro-3-butyl phenyl)-4-bromo-1,8-naphthalimide 1mol, be dissolved among the DMF of 50ml, drip the sodiumazide aqueous solution (the 1mol sodiumazide is dissolved in the water of 2ml) in the 1H, temperature of reaction is 80 ℃, reacted 6 hours, and obtained product, get pure products with the mixing solutions recrystallization of DMF and water with frozen water.This product structure formula is:
Title: N-(2-chloro-3-butyl phenyl)-4-nitrine-1, the 8-naphthalimide
Color: yellow
Embodiment six: get N-(1-butyl-acetate)-4-bromo-1,8-naphthalimide 1mol, be dissolved among the DMF of 50ml, drip the sodiumazide aqueous solution (the 1mol sodiumazide is dissolved in the water of 2ml) in the 1H, temperature of reaction is 80 ℃, reacted 2 hours, and obtained product, get pure products with the mixing solutions recrystallization of DMF and water with frozen water.
This product structure formula is:
Title: N-(1-butyl-acetate)-4-nitrine-1, the 8-naphthalimide
Color: yellow
Embodiment seven: get N-PEG200-4-bromo-1,8-naphthalimide 1mol, be dissolved among the DMF of 50ml, drip the sodiumazide aqueous solution (the 1mol sodiumazide is dissolved in the water of 2ml) in the 1H, temperature of reaction is 80 ℃, reacted 15 hours, and obtained product, get pure products with the mixing solutions recrystallization of DMF and water with frozen water.
This product structure formula is:
Claim: N-PEG200-4-nitrine-1,8-naphthalimide
Color: yellow
Embodiment eight: get N-PEG3000-4-bromo-1,8-naphthalimide 1mol, be dissolved among the DMF of 50ml, drip the sodiumazide aqueous solution (the 1mol sodiumazide is dissolved in the water of 2ml) in the 1H, temperature of reaction is 80 ℃, reacted 12 hours, and obtained product, get pure products with the mixing solutions recrystallization of DMF and water with frozen water.
This product structure formula is:
Title: N-PEG3000-4-nitrine-1,8-naphthalimide
Color: yellow
Embodiment nine: get N-butyl-5-phenyl-4-bromo-1,8-naphthalimide 1mol, be dissolved among the DMF of 50ml, drip the sodiumazide aqueous solution (the 1mol sodiumazide is dissolved in the water of 2ml) in the 1H, temperature of reaction is 80 ℃, reacted 6 hours, and obtained product, get pure products with the mixing solutions recrystallization of DMF and water with frozen water.This product structure formula is:
Title: N-butyl-5-phenyl-4-nitrine-1,8-naphthalimide
Color: yellow
Embodiment ten: get N-phenyl-2-carboxyl-4-bromo-1,8-naphthalimide 1mol, be dissolved among the DMF of 50ml, drip the sodiumazide aqueous solution (the 1mol sodiumazide is dissolved in the water of 2ml) in the 1H, temperature of reaction is 80 ℃, reacted 4 hours, and obtained product, get pure products with the mixing solutions recrystallization of DMF and water with frozen water.
This product structure formula is:
Title: N-phenyl-2-carboxyl-4-nitrine-1,8-naphthalimide
Color: yellow.
Claims (2)
1. 4-nitrine-1, the 8-naphthalimide compound is characterized in that the structural formula of this compound is:
Wherein, R
1Be H, C
1～C
32Alkyl, aryl, PEG200～4000 or 2-carboxyl methylene radical;
The structural formula of described aryl is:
Wherein A, B, C, D, E are: H, C
1～C
5Alkyl, nitro, halogen, hydroxyl, amino, aldehyde radical or carboxyl;
The structural formula of described 2-carboxyl methylene radical is:
R wherein
4Alkyl, nitro, Cl, Br, F, I, hydroxyl, amino, aldehyde radical, carboxyl, hydrocinnamyl or phenyl for H, C1～C5; R
2, R
3For: the alkyl of H, C1～C5, nitro, Cl, Br, F, I, hydroxyl, amino, aldehyde radical, carboxyl, hydrocinnamyl or phenyl.
2. one kind prepares 4-nitrine-1 according to claim 1, the method of 8-naphthalimide compound, it is characterized in that this method has following steps: with 4-bromo-1, the 8-naphthalimide is dissolved among the DMF, drip the sodiumazide aqueous solution, temperature of reaction is 60～140 ℃, reacts 1～20 hour, obtains product with frozen water, mixing solutions recrystallization with DMF and water gets 4-nitrine-1, the 8-naphthalimide compound; Described 4-bromo-1, the mol ratio of 8-naphthalimide and sodiumazide are 1: 1; Described 4-bromo-1, the structural formula of 8-naphthalimide is:
Wherein, R
1Be H, C
1～C
32Alkyl, aryl, PEG200～4000 or 2-carboxyl methylene radical; The structural formula of described aryl is:
Wherein A, B, C, D, E are: H, C
1～C
5Alkyl, nitro, halogen, hydroxyl, amino, aldehyde radical or carboxyl;
The structural formula of described 2-carboxyl methylene radical is:
R wherein
4Alkyl, nitro, Cl, Br, F, I, hydroxyl, amino, aldehyde radical, carboxyl, hydrocinnamyl or phenyl for H, C1～C5; R
2, R
3For: the alkyl of H, C1～C5, nitro, Cl, Br, F, I, hydroxyl, amino, aldehyde radical, carboxyl, hydrocinnamyl or phenyl.
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|---|---|---|---|
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012094603A1 (en) * | 2011-01-06 | 2012-07-12 | Georgia State University Research Foundation, Inc. | Chemosensors for hydrogen sulfide |
| CN103923008A (en) * | 2014-04-15 | 2014-07-16 | 福州大学 | 1,8-naphthalimides derivative with fluorescent brightening property and preparation method thereof |
| CN104927045A (en) * | 2015-07-15 | 2015-09-23 | 湖南科技大学 | Sulfion sensor based on polyethylene glycol and preparation method and application thereof |
| CN115745888A (en) * | 2022-11-30 | 2023-03-07 | 河南省农业科学院农业质量标准与检测技术研究所 | Naphthalimide derivative fluorescent probe molecule for detecting sulfur nitrogen acid and preparation method and application thereof |
-
2008
- 2008-07-01 CN CNA2008100400210A patent/CN101302197A/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012094603A1 (en) * | 2011-01-06 | 2012-07-12 | Georgia State University Research Foundation, Inc. | Chemosensors for hydrogen sulfide |
| CN103299187A (en) * | 2011-01-06 | 2013-09-11 | 佐治亚州立大学研究基金会公司 | Chemosensors for hydrogen sulfide |
| US9175165B2 (en) | 2011-01-06 | 2015-11-03 | Georgia State University Research Foundation, Inc. | Chemosensors for hydrogen sulfide |
| CN103299187B (en) * | 2011-01-06 | 2016-01-06 | 佐治亚州立大学研究基金会公司 | The chemical sensor of sulfuretted hydrogen |
| CN103923008A (en) * | 2014-04-15 | 2014-07-16 | 福州大学 | 1,8-naphthalimides derivative with fluorescent brightening property and preparation method thereof |
| CN104927045A (en) * | 2015-07-15 | 2015-09-23 | 湖南科技大学 | Sulfion sensor based on polyethylene glycol and preparation method and application thereof |
| CN104927045B (en) * | 2015-07-15 | 2017-04-05 | 湖南科技大学 | A kind of sulfide ion sensor based on Polyethylene Glycol and its preparation method and application |
| CN115745888A (en) * | 2022-11-30 | 2023-03-07 | 河南省农业科学院农业质量标准与检测技术研究所 | Naphthalimide derivative fluorescent probe molecule for detecting sulfur nitrogen acid and preparation method and application thereof |
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Open date: 20081112 |