CN110483422A - The compound of one 3- hydroxyl -5,10- dimethylphenazine -2- formaldehyde - Google Patents
The compound of one 3- hydroxyl -5,10- dimethylphenazine -2- formaldehyde Download PDFInfo
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- CN110483422A CN110483422A CN201910855629.7A CN201910855629A CN110483422A CN 110483422 A CN110483422 A CN 110483422A CN 201910855629 A CN201910855629 A CN 201910855629A CN 110483422 A CN110483422 A CN 110483422A
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- dimethylphenazine
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 10
- GBAZHZRVGBVQKQ-UHFFFAOYSA-N 3-hydroxy-5,10-dimethylphenazine-2-carbaldehyde Chemical compound OC=1C(=CC=2N(C3=CC=CC=C3N(C=2C=1)C)C)C=O GBAZHZRVGBVQKQ-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 239000007850 fluorescent dye Substances 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 150000002988 phenazines Chemical class 0.000 description 2
- 238000012805 post-processing Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/46—Phenazines
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
本发明公开一个3‑羟基‑5,10‑二甲基吩嗪‑2‑甲醛的化合物，其结构式为：该结构合成路线简单，具有强供电子能力，荧光强度大等优点，作为一种全新的结构，可以作为有机化学中间体，也可做荧光染料应用，具有良好的应用前景。
The invention discloses a compound of 3-hydroxy-5,10-dimethylphenazine-2-carbaldehyde, and its structural formula is: The structure has the advantages of simple synthetic route, strong electron donating ability, high fluorescence intensity, etc. As a brand-new structure, it can be used as an organic chemical intermediate, and can also be used as a fluorescent dye, and has a good application prospect.
Description
技术领域technical field
本发明属于化学合成领域，具体涉及一个3-羟基-5,10-二甲基吩嗪-2-甲醛的化合物。The invention belongs to the field of chemical synthesis, in particular to a compound of 3-hydroxy-5,10-dimethylphenazine-2-carbaldehyde.
背景技术Background technique
吩嗪是一类重要的精细化学中间体，对有机化学研究者来说并不陌生。它广泛的存在于有机天然产物中并且具有较好的生物活性,含有天然骨架的吩嗪类化合物的合成过程简单,分子结构的功能化比较容易。该类化合物具有多个配位点和较大的共轭体系，对于很多化学反应有重要作用。研发吩嗪类药物成为近年来发展的一个重点。Phenazines are an important class of fine chemical intermediates and are no strangers to organic chemistry researchers. It exists widely in organic natural products and has good biological activity. The synthesis process of phenazine compounds containing natural skeleton is simple, and the functionalization of molecular structure is relatively easy. Such compounds have multiple coordination sites and larger conjugated systems, and play an important role in many chemical reactions. The research and development of phenazine drugs has become a focus of development in recent years.
发明内容SUMMARY OF THE INVENTION
本发明目的之一是提供一个3-羟基-5,10-二甲基吩嗪-2-甲醛的化合物，该方法反应操作简便且产率高。其结构如下HYJ：One of the objects of the present invention is to provide a compound of 3-hydroxy-5,10-dimethylphenazine-2-carbaldehyde, which has simple reaction operation and high yield. Its structure is as follows HYJ:
其合成路线为：Its synthetic route is:
具体合成方法：(a)将对苯醌(0.432g，4mmol)溶解于5mL无水乙醇中，再缓慢加入邻苯二胺(0.432g,4mmol)，在室温下反应2小时后，将反应液旋干后通过柱层析纯化得淡黄色固体(0.53g,产率67.4％)。(b)将化合物1(0.15g,0.76mmol)溶解在5mL乙腈中，加入3mL的碘甲烷溶液,而后加入碳酸钠(0.21g，1.98mmol)、保险粉(1.74g，10mmol)、四丁基硫酸氢铵(0.1g,0.295mmol)，在85℃下反应5h后，把反应体系倒入20mL的冰水中，用二氯甲烷萃取得到有机相，用无水硫酸钠干燥，旋干得到油状棕色产物2(0.12g,产率70％)(c)向三氯氧磷滴加无水DMF混合反应，有粉红色溶液生成时，将化合物2溶于5mL无水DMF中，滴加进反应液中，升温至70℃反应6h后，把反应体系倒入20mL的冰水中，调节pH至中性用二氯甲烷萃取得到有机相，用无水硫酸钠干燥，旋干纯化得到红色化合物HYJ(0.09g，产率75％)。Specific synthesis method: (a) p-benzoquinone (0.432g, 4mmol) was dissolved in 5mL of absolute ethanol, and then slowly added o-phenylenediamine (0.432g, 4mmol), after 2 hours of reaction at room temperature, the reaction solution was After spin drying, it was purified by column chromatography to obtain a pale yellow solid (0.53 g, yield 67.4%). (b) Compound 1 (0.15g, 0.76mmol) was dissolved in 5mL of acetonitrile, 3mL of iodomethane solution was added, and then sodium carbonate (0.21g, 1.98mmol), sodium hydrosulfite (1.74g, 10mmol), tetrabutyl Ammonium hydrogen sulfate (0.1 g, 0.295 mmol) was reacted at 85 °C for 5 h, the reaction system was poured into 20 mL of ice water, extracted with dichloromethane to obtain an organic phase, dried over anhydrous sodium sulfate, and spin-dried to obtain an oily brown Product 2 (0.12g, yield 70%) (c) Add dropwise anhydrous DMF to phosphorus oxychloride to mix the reaction, when a pink solution is formed, compound 2 is dissolved in 5mL of anhydrous DMF, and added dropwise to the reaction solution After the reaction was heated to 70 °C for 6 h, the reaction system was poured into 20 mL of ice water, adjusted to neutral pH, and extracted with dichloromethane to obtain the organic phase, dried over anhydrous sodium sulfate, and spin-dried to purify to obtain a red compound HYJ (0.09 g, 75% yield).
本发明提供了提供一个3-羟基-5,10-二甲基吩嗪-2-甲醛的化合物，该方法反应操作简单，后处理方便且产率高。作为一种全新的醛，可以作为有机化学中间体，也可以作为荧光染料使用。The invention provides a compound of 3-hydroxy-5,10-dimethylphenazine-2-carbaldehyde. The method has simple reaction operation, convenient post-processing and high yield. As a brand-new aldehyde, it can be used as an intermediate in organic chemistry and also as a fluorescent dye.
附图说明Description of drawings
图1为本发明所制备的3-羟基-5,10-二甲基吩嗪-2-甲醛的氢谱。Fig. 1 is the hydrogen spectrum of 3-hydroxy-5,10-dimethylphenazine-2-carbaldehyde prepared by the present invention.
图2为本发明所制备的3-羟基-5,10-二甲基吩嗪-2-甲醛的碳谱。Fig. 2 is the carbon spectrum of 3-hydroxy-5,10-dimethylphenazine-2-carbaldehyde prepared by the present invention.
具体实施实例Specific implementation example
实施例1：目标分子的合成Example 1: Synthesis of Target Molecules
化合物1的合成Synthesis of Compound 1
将对苯醌(0.432g，4mmol)溶解于5mL无水乙醇中，再缓慢加入邻苯二胺(0.432g,4mmol)，在室温下反应2小时后，用旋转蒸发仪将反应液旋干后，通过柱层析纯化得淡黄色固体1，产率为67.4％。P-benzoquinone (0.432g, 4mmol) was dissolved in 5mL of absolute ethanol, and o-phenylenediamine (0.432g, 4mmol) was slowly added, and reacted at room temperature for 2 hours, and the reaction solution was spin-dried with a rotary evaporator. , which was purified by column chromatography to obtain pale yellow solid 1 in a yield of 67.4%.
化合物2的合成Synthesis of Compound 2
将化合物1(0.15g,0.76mmol)溶解在5mL乙腈中，加入3mL的碘甲烷溶液,而后依次加入碳酸钠(0.21g，1.98mmol)、保险粉(1.74g，10mmol)、四丁基硫酸氢铵(0.1g,0.295mmol)，充分搅拌均匀后在85℃下反应5h后，把反应体系倒入20mL的冰水中，用二氯甲烷萃取得到有机相，用无水硫酸钠干燥，旋干得到油状棕色产物2，产率为70％。Compound 1 (0.15g, 0.76mmol) was dissolved in 5mL of acetonitrile, 3mL of iodomethane solution was added, and then sodium carbonate (0.21g, 1.98mmol), sodium hydrosulfite (1.74g, 10mmol), tetrabutyl hydrogen sulfate were added successively Ammonium (0.1 g, 0.295 mmol), fully stirred and reacted at 85 °C for 5 h, poured the reaction system into 20 mL of ice water, extracted with dichloromethane to obtain an organic phase, dried with anhydrous sodium sulfate, and spin-dried to obtain Oily brown product 2 in 70% yield.
HYJ的合成Synthesis of HYJ
向三氯氧磷(1mL)滴加进10mL无水DMF混合反应，有粉红色溶液生成时，将化合物2溶于5mL无水DMF中，滴加进反应液中，升温至70℃反应6h后，把反应体系倒入20mL的冰水中，调节pH至中性。用二氯甲烷萃取得到有机相，用无水硫酸钠干燥，旋干纯化得到红色化合物HYJ，产率为75％。Phosphorus oxychloride (1 mL) was added dropwise to 10 mL of anhydrous DMF and mixed for reaction. When a pink solution was formed, compound 2 was dissolved in 5 mL of anhydrous DMF, added dropwise to the reaction solution, heated to 70 °C and reacted for 6 h. , the reaction system was poured into 20 mL of ice water, and the pH was adjusted to neutral. The organic phase was obtained by extraction with dichloromethane, dried over anhydrous sodium sulfate, and purified by spin drying to obtain a red compound HYJ with a yield of 75%.
1H NMR(400MHz,DMSO)δ10.86(s,1H),9.85(d,J＝16.7Hz,1H),9.65(s,1H),7.36(d,J＝8.1Hz,1H),6.90(s,1H),6.69–6.58(m,2H),6.09(s,1H),3.15–2.98(m,6H)。1H NMR(400MHz, DMSO)δ10.86(s,1H),9.85(d,J=16.7Hz,1H),9.65(s,1H),7.36(d,J=8.1Hz,1H),6.90(s , 1H), 6.69–6.58 (m, 2H), 6.09 (s, 1H), 3.15–2.98 (m, 6H).
13C NMR(400MHz,DMSO)δ190.71,160.67,146.14,143.70,135.47,129.86,129.69,129.16,114.75,110.90,110.34,110.15,99.96,33.12,32.91。13C NMR (400MHz, DMSO) δ 190.71, 160.67, 146.14, 143.70, 135.47, 129.86, 129.69, 129.16, 114.75, 110.90, 110.34, 110.15, 99.96, 33.12, 32.91.
本发明提供了提供一个3-羟基-5,10-二甲基吩嗪-2-甲醛的化合物，该方法反应操作简单，后处理方便且产率高。作为一种全新的醛，可以作为有机化学中间体，也可以作为荧光染料使用。The invention provides a compound of 3-hydroxy-5,10-dimethylphenazine-2-carbaldehyde. The method has simple reaction operation, convenient post-processing and high yield. As a brand-new aldehyde, it can be used as an intermediate in organic chemistry and also as a fluorescent dye.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN117701028A (en) * | 2022-10-18 | 2024-03-15 | 华东理工大学 | Near-infrared II region small molecule dyes with large Stokes shift and their synthesis methods |
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| US5998617A (en) * | 1997-04-02 | 1999-12-07 | Gentex Corporation | Electrochromic compounds |
| CN109293493A (en) * | 2018-10-29 | 2019-02-01 | 清华大学 | Novel benzhydryl compounds with inhibitory activity against Mycobacterium tuberculosis |
| CN110212203A (en) * | 2019-05-22 | 2019-09-06 | 南京大学 | A kind of organic flow battery of basic hydroxide group azophenlyene class and preparation method |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5998617A (en) * | 1997-04-02 | 1999-12-07 | Gentex Corporation | Electrochromic compounds |
| CN109293493A (en) * | 2018-10-29 | 2019-02-01 | 清华大学 | Novel benzhydryl compounds with inhibitory activity against Mycobacterium tuberculosis |
| CN110212203A (en) * | 2019-05-22 | 2019-09-06 | 南京大学 | A kind of organic flow battery of basic hydroxide group azophenlyene class and preparation method |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN117701028A (en) * | 2022-10-18 | 2024-03-15 | 华东理工大学 | Near-infrared II region small molecule dyes with large Stokes shift and their synthesis methods |
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Application publication date: 20191122 |