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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- compound
- dimethylphenazine
- hydroxyl
- formaldehyde
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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
Abstract
The present invention discloses the compound of 3- hydroxyl -5,10- dimethylphenazine -2- formaldehyde, structural formula are as follows:The structure synthetic route is simple, has many advantages, such as strong electron supplying capacity, and fluorescence intensity is big, as a kind of completely new structure, can be used as organic chemical intermediates, can also do fluorescent dye application, have a good application prospect.
Description
Technical field
The invention belongs to the field of chemical synthesis, and in particular to the change of 3- hydroxyl -5,10- dimethylphenazine -2- formaldehyde
Close object.
Background technique
Azophenlyene is a kind of important fine chemistry intermediate, not strange for organic chemistry researcher.It is extensive
It is present in organic natural products and there is preferable bioactivity, the synthesis of the azophenlyene class compound containing natural skeleton
Journey is simple, and the functionalization of molecular structure is easier.Such compound has multiple coordination sites and biggish conjugated system, for
Many chemical reactions play an important role.Research and development azophenlyene class drug becomes the emphasis developed in recent years.
Summary of the invention
One of the object of the invention is to provide the compound of 3- hydroxyl -5,10- dimethylphenazine -2- formaldehyde, this method
Operation is easy and yield is high.The following HYJ of its structure:
Its synthetic route are as follows:
Specific synthetic method: (a) 1,4-benzoquinone (0.432g, 4mmol) is dissolved in 5mL dehydrated alcohol, is slow added into
O-phenylenediamine (0.432g, 4mmol) is obtained after reacting 2 hours at room temperature, after reaction solution is spin-dried for by column chromatographic purifying yellowish
Color solid (0.53g, yield 67.4%).(b) compound 1 (0.15g, 0.76mmol) is dissolved in 5mL acetonitrile, 3mL is added
Iodomethane solution, then be added sodium carbonate (0.21g, 1.98mmol), sodium hydrosulfite (1.74g, 10mmol), tetrabutyl hydrogen sulfate
Ammonium (0.1g, 0.295mmol) pours into reaction system in the ice water of 20mL after reacting 5h at 85 DEG C, is extracted with dichloromethane
Organic phase is obtained, it is dry with anhydrous sodium sulfate, it is spin-dried for obtaining oily brown product 2 (0.12g, yield 70%) (c) to trichlorine oxygen
Anhydrous DMF hybrid reaction is added dropwise in phosphorus, and when having pink solution generation, compound 2 is dissolved in 5mL anhydrous DMF, is added dropwise into reaction
In liquid, after being warming up to 70 DEG C of reaction 6h, reaction system is poured into the ice water of 20mL, adjusting pH to neutrality is extracted with dichloromethane
Organic phase is obtained, it is dry with anhydrous sodium sulfate, it is spin-dried for purifying and obtains red compound HYJ (0.09g, yield 75%).
The present invention provides provide the compound of 3- hydroxyl -5,10- dimethylphenazine -2- formaldehyde, this method reaction
It is easy to operate, convenient post-treatment and yield height.As a kind of completely new aldehyde, it can be used as organic chemical intermediates, can also make
For fluorescent dye use.
Detailed description of the invention
Fig. 1 is the hydrogen spectrum of 3- hydroxyl -5,10- dimethylphenazine -2- formaldehyde prepared by the present invention.
Fig. 2 is the carbon spectrum of 3- hydroxyl -5,10- dimethylphenazine -2- formaldehyde prepared by the present invention.
Example is embodied
Embodiment 1: the synthesis of target molecule
The synthesis of compound 1
1,4-benzoquinone (0.432g, 4mmol) is dissolved in 5mL dehydrated alcohol, be slow added into o-phenylenediamine (0.432g,
4mmol), it after reacting 2 hours at room temperature, after being spin-dried for reaction solution with Rotary Evaporators, is obtained by column chromatographic purifying faint yellow
Solid 1, yield 67.4%.
The synthesis of compound 2
Compound 1 (0.15g, 0.76mmol) is dissolved in 5mL acetonitrile, the iodomethane solution of 3mL is added, then successively
Be added sodium carbonate (0.21g, 1.98mmol), sodium hydrosulfite (1.74g, 10mmol), 4-butyl ammonium hydrogen sulfate (0.1g,
0.295mmol), after reacting 5h at 85 DEG C after stirring, reaction system is poured into the ice water of 20mL, dichloromethane is used
Organic phase is obtained by extraction in alkane, dry with anhydrous sodium sulfate, is spin-dried for obtaining oily brown product 2, yield 70%.
The synthesis of HYJ
It is added dropwise to phosphorus oxychloride (1mL) into 10mL anhydrous DMF hybrid reaction, when having pink solution generation, by compound 2
It is dissolved in 5mL anhydrous DMF, is added dropwise into reaction solution, after being warming up to 70 DEG C of reaction 6h, reaction system is poured into the ice water of 20mL
In, pH is adjusted to neutrality.It is extracted with dichloromethane to obtain organic phase, it is dry with anhydrous sodium sulfate, it is spin-dried for purifying and obtains redization
Close object HYJ, yield 75%.
1H NMR (400MHz, DMSO) δ 10.86 (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。
The present invention provides provide the compound of 3- hydroxyl -5,10- dimethylphenazine -2- formaldehyde, this method reaction
It is easy to operate, convenient post-treatment and yield height.As a kind of completely new aldehyde, it can be used as organic chemical intermediates, can also make
For fluorescent dye use.
Claims (1)
1. the compound of 3- hydroxyl -5,10- dimethylphenazine -2- formaldehyde, structural formula are as follows:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910855629.7A CN110483422A (en) | 2019-09-11 | 2019-09-11 | The compound of one 3- hydroxyl -5,10- dimethylphenazine -2- formaldehyde |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910855629.7A CN110483422A (en) | 2019-09-11 | 2019-09-11 | The compound of one 3- hydroxyl -5,10- dimethylphenazine -2- formaldehyde |
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| CN110483422A true CN110483422A (en) | 2019-11-22 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN201910855629.7A Pending CN110483422A (en) | 2019-09-11 | 2019-09-11 | The compound of one 3- hydroxyl -5,10- dimethylphenazine -2- formaldehyde |
Country Status (1)
| Country | Link |
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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 | With the inhibition active novel benzhydryl class compound of 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 |
-
2019
- 2019-09-11 CN CN201910855629.7A patent/CN110483422A/en active Pending
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 | With the inhibition active novel benzhydryl class compound of 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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Application publication date: 20191122 |
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