CN109232428A - A kind of pyrazolyl azophenol compound and its synthesis, derivative - Google Patents

A kind of pyrazolyl azophenol compound and its synthesis, derivative Download PDF

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Publication number
CN109232428A
CN109232428A CN201811257615.7A CN201811257615A CN109232428A CN 109232428 A CN109232428 A CN 109232428A CN 201811257615 A CN201811257615 A CN 201811257615A CN 109232428 A CN109232428 A CN 109232428A
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pyrazolyl
azophenol
phenol
methyl
pyrazoles
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CN109232428B (en
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李涛
张召阳
贺逸昕
周颖
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Shanghai Jiaotong University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/38—Nitrogen atoms

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  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The present invention relates to a kind of pyrazolyl azophenol compound and its synthesis, derivative.Specially 4- ((1- methyl-1 H- pyrazoles -4- base) diazenyl) phenol, structure are as follows:The synthetic method of 4- ((1- methyl-1 H- pyrazoles -4- base) diazenyl) phenol is simple, and a variety of azobenzene optical Response functional moleculars with long half-lift Z isomers can be derived by phenolic hydroxyl group.Compared with prior art, pyrazolyl azophenol raw materials of compound proposed by the invention is easy to get, and synthesis technology is simple, and yield is high, is readily mass-produced.The etherificate and esterification of the compound are classical organic reactions, have mild condition, the high advantage of yield.In short, the present invention provides convenient and fast approach for the development and utilization of long half-lift Z isomers azobenzene optical Response functional molecular.

Description

A kind of pyrazolyl azophenol compound and its synthesis, derivative
Technical field
The present invention relates to a kind of azobenzene compound and its synthesis, more particularly, to a kind of pyrazolyl azophenol compound And its it synthesizes, is derivative.
Background technique
Azobenzene is a kind of classical photochromic molecules, they can be converted under ultraviolet light from E (trans-) configuration For Z (cis-) configuration, and replying under visible light illumination from Z configuration is E configuration.Since this reversible photoisomerization reacts, Azobenzene compound provides wide space to develop light-operated functional material and device, in photoswitch, optical drive, energy Attention is received in multiple technologies field with information storage etc..
For major applications, the stability of isomers is most important.But in general, the Z of azobenzene compound Isomers stablize it is poor, can rapidly heat reply be E isomer.Although can be adjusted by substituent group, there is length partly to decline The azobenzene compound of phase Z isomers is still very rare.Document (J.Am.Chem.Soc.2014,136,11878- 11881) pyrazolyl azobenzene compound 1- methyl-(phenyl-diazenyl) -1H- pyrrole of overlength half-life period a kind of is reported Azoles, its Z isomers have the stability of superelevation, and the long half time under room temperature (25 DEG C) was up to 1000 days.But due to this point Unsubstituted on the phenyl ring of son, is not easy to derive, and limits exploitation with long half-lift Z isomers azobenzene molecule and answers With.
Summary of the invention
In order to overcome existing long half-lift azobenzene compound 1- methyl -4- (phenyl-diazenyl) -1H- pyrazoles not Easily derivative disadvantage, the present invention provide a kind of pyrazolyl azophenol compound and its synthetic method and derivative.
The purpose of the present invention can be achieved through the following technical solutions:
The present invention provides a kind of pyrazolyl azophenol compound, specially 4- ((1- methyl-1 H- pyrazoles -4- base) phenodiazine Alkenyl) phenol, structure is as follows:
4- ((1- methyl-1 H- pyrazoles -4- base) diazenyl) phenol, can be regarded as 1- methyl -4- (phenyl diazene Base) -1H- pyrazoles phenolic hydroxyl group substituent.
The synthetic method of 4- ((1- methyl-1 H- pyrazoles -4- base) diazenyl) phenol is simple, and can be spread out by phenolic hydroxyl group Bear a variety of azobenzene optical Response functional moleculars with long half-lift Z isomers.
The present invention also provides the synthetic methods of the pyrazolyl azophenol compound, comprising the following steps:
Diazotising is carried out to 4- amino -1- methylpyrazole first, then utilizes the coupling reaction of aryl diazonium salts and phenol Obtain target compound 4- ((1- methyl-1 H- pyrazoles -4- base) diazenyl) phenol.
Synthetic route is as follows:
The present invention also provides the applications of the pyrazolyl azophenol compound, by the 4- ((1- methyl-1 H- pyrrole Azoles -4- base) diazenyl) phenol phenolic hydroxyl group etherificate or esterification, derive the ethers or esters of pyrazolyl azophenol Derivative.
Reaction equation is as follows:
The present invention also provides a kind of etherification reaction of pyrazolyl azophenol, etherifying reagent is with the organic of halogenic substituent Reagent RCH2X, wherein X=Cl, Br, I, R include but is not limited to H, alkyl, aryl or other possible organic groups,
Following product structure is obtained after reaction:
In above formula, R includes but is not limited to H, alkyl, aryl or other possible organic groups.
The present invention also provides a kind of esterification of pyrazolyl azophenol, esterifying reagent is with the organic of active acyl Reagent obtains following product structure after reaction:
Wherein, R includes but is not limited to alkyl, aryl or other possible organic groups.
The organic reagent with active acyl includes carboxylic acid, acyl chlorides and acid anhydrides etc..
The present invention also provides a kind of ether derivative of pyrazolyl azophenol, structure is as follows:
Wherein, R includes but is not limited to H, alkyl, aryl or other possible organic groups.
The present invention also provides a kind of ester derivative of pyrazolyl azophenol, structure is as follows:
Wherein, R includes but is not limited to alkyl, aryl or other possible organic groups.
On the one hand pyrazolyl azophenol compound proposed by the invention has overlength half-life period azobenzene molecule 1- The precursor structure of methyl -4- (phenyl-diazenyl) -1H- pyrazoles, the phenolic hydroxyl group on the other hand with easy progress chemical derivatization, Therefore it can be used as precursor to derive to obtain the azobenzene optical Response functional molecular with long half-lift Z isomers.Into one Step ground, the present invention are prepared for the azobenzene of two serial long half-lift Z isomers by simply etherificate and esterification Molecule.
Pyrazolyl azophenol raw materials of compound proposed by the invention is easy to get, and synthesis technology is simple, and yield is high, is easy amount It produces.The etherificate and esterification of the compound are classical organic reactions, have mild condition, the high advantage of yield.In short, The present invention provides convenient and fast approach for the development and utilization of long half-lift Z isomers azobenzene optical Response functional molecular.
Detailed description of the invention
Fig. 1 is embodiment 1,2 gained compound pyrazolyl azophenol compound 4- ((1- methyl-1 H- pyrazoles -4- base) Diazenyl) phenol nuclear magnetic spectrum；
Fig. 2 is 3 gained etherification derivative 4- of embodiment ((4- methoxyphenyl) diazenyl) -1- methyl-1 H- pyrazoles Nuclear magnetic spectrum；
Fig. 3 is 4 gained etherification derivative 4- of embodiment ((4- (allyloxy) phenyl) diazenyl) -1- methyl-1 H- pyrrole The nuclear magnetic spectrum of azoles；
Fig. 4 is 5 gained esterification derivative 4- of embodiment ((1- methyl-1 H- pyrazoles -4- base) diazenyl) phenylacetate Nuclear magnetic spectrum.
Specific embodiment
Below with reference to specific drawings and examples, the present invention is described in detail.
Embodiment 1
The small lot of pyrazolyl azophenol compound 4- ((1- methyl-1 H- pyrazoles -4- base) diazenyl) phenol synthesizes (yield is less than 0.73g)
Synthetic route is as follows:
4- amino -1- methylpyrazole (0.39g, 4mmol, 1eq.) is added in 10mL deionized water, it is dense to add 2mL Hydrochloric acid (12.2mol/L, 25mmol) is cooled to 0 DEG C, and cold sodium nitrite (0.33g, 4.8mmol, the 1.2eq.) water of 10mL is added dropwise Solution stirs 15min.Be added dropwise again the cold phenol of 20mL (0.45g, 4.8mmol, 1.2eq.), sodium hydroxide (0.48g, 12mmol) with sodium carbonate (1.3g, 12mmol) mixed aqueous solution, continue to stir 30min.Then it filters, washes, drying obtains Yellow solid product (0.73g, 90.4%).1H NMR(500MHz,CDCl3)δ7.98(s,1H),7.92(s,1H),6.91(d,J =8.9Hz, 2H), 5.30 (s, 1H), 3.97 (s, 3H)；UV-Vis(EA):λmax=342.0nm；M.P.192.1-196.7℃.
Embodiment 2, pyrazolyl azophenol compound 4- ((1- methyl-1 H- pyrazoles -4- base) diazenyl) phenol it is big Batch synthesis (yield 5.2g)
Synthetic route is as follows:
4- amino -1- methylpyrazole (2.91g, 30mmol, 1eq.) is added in 60mL deionized water, 14mL is added Concentrated hydrochloric acid (12.2mol/L, 170mmol) is cooled to 0 DEG C, and the cold sodium nitrite (3.3g, 48mmol, 1.6eq.) of 60mL is added dropwise Aqueous solution stirs 15min.Be added dropwise again the cold phenol of 120mL (3.38g, 36mmol, 1.2eq.), sodium hydroxide (3.2g, 80mmol) with sodium carbonate (8.48g, 80mmol) mixed aqueous solution, continue to stir 30min.Then it filters, washes, drying obtains Yellow solid product (5.2g, 85.8%).1H NMR(500MHz,CDCl3)δ7.98(s,1H),7.92(s,1H),6.91(d,J =8.9Hz, 2H), 5.30 (s, 1H), 3.97 (s, 3H)；UV-Vis(EA):λmax=342.0nm；M.P.192.1-196.7℃.
Embodiment 3, pyrazolyl azophenol etherification derivative 4- ((4- methoxyphenyl) diazenyl) -1- methyl-1 H- The synthesis of pyrazoles
Synthetic route is as follows:
By 4- ((1- methyl-1 H- pyrazoles -4- base) diazenyl) phenol (505mg, 2.5mmol, 1eq.), potassium tert-butoxide (365mg, 3.25mmol, 1.3eq.) and iodomethane (3.55g, 25mmol, 10eq.) are in 10mL N,N-dimethylformamide 40 DEG C of return stirrings 2h, TLC monitor reaction process (PE:EA=5:1).After reaction plus elutriation goes out solid, filters, washing. Filter cake is dissolved with ethyl acetate, and anhydrous sodium sulfate is dry, and column chromatography for separation (PE:EA=5:1) finally obtains yellow crystals (366mg, 68%).1H NMR(400MHz,CDCl3) δ 7.98 (s, 1H), 7.92 (s, 1H), 7.78 (d, J=9.0Hz, 2H), 6.98 (d, J=9.0Hz, 2H), 3.96 (s, 3H), 3.87 (s, 3H)；UV-Vis(CH3CN):λmax=342.0nm； M.P.113.5-114.8℃。
Embodiment 4, pyrazolyl azophenol etherification derivative 4- ((4- (allyloxy) phenyl) diazenyl) -1- first The synthesis of base -1H- pyrazoles
Synthetic route is as follows:
By 4- ((1- methyl-1 H- pyrazoles -4- base) diazenyl) phenol (505mg, 2.5mmol, 1eq.), potassium tert-butoxide The bromo- 1- propylene (3.0g, 25mmol, 10eq.) of (365mg, 3.25mmol, 1.3eq.) and 3- is in 10mL N, N- dimethyl formyl 65 DEG C of return stirrings 2h, TLC monitor reaction process (PE:EA=5:1) in amine.System is down to room temperature after reaction, adds elutriation Solid out filters, washing.Filter cake is dissolved with ethyl acetate, and anhydrous sodium sulfate is dry, column chromatography for separation (PE:EA=5:1), most Yellow crystals (496mg, 82%) is obtained eventually.1H NMR(400MHz,CDCl3)δ7.98(s,1H),7.91(s,1H),7.77(d,J =9.0Hz, 2H), 6.99 (d, J=9.0Hz, 2H), 6.07 (ddd, J=22.5,10.5,5.3Hz, 1H), 5.44 (dd, J= 17.3,1.5Hz, 1H), 5.31 (dd, J=10.5,1.3Hz, 1H), 4.60 (d, J=5.3Hz, 2H), 3.95 (s, 3H)；UV- Vis(CH3CN):λmax=342.5nm；M.P.102.4-103.7℃.
Implementation case 5, pyrazolyl azophenol esterification derivative 4- ((1- methyl-1 H- pyrazoles -4- base) diazenyl) acetic acid The synthesis of phenyl ester
Synthetic route is as follows:
Under nitrogen protection, by 4- ((1- methyl-1 H- pyrazoles -4- base) diazenyl) phenol (101mg, 0.5mmol, It 1eq.) is dissolved in 5mL tetrahydrofuran, injects triethylamine (83 μ L, 0.6mmol, 1.2eq.), chloroacetic chloride is injected in ice-water bath (177 μ L, 2.5mmol, 5eq.), then 48h is stirred at room temperature, TLC monitors reaction process (PE:EA=5:2).After reaction Saturated ammonium chloride solution quenching reaction is added, is extracted with ethyl acetate, anhydrous sodium sulfate is dry, column chromatography for separation (PE:EA=5: 2) yellow crystals (98mg, 80.3%), is finally obtained.1H NMR(400MHz,CDCl3)δ8.00(s,1H),7.96(s,1H), 7.82 (d, J=8.9Hz, 2H), 7.21 (d, J=8.9Hz, 2H), 3.98 (s, 3H), 2.33 (s, 3H)；UV-Vis(CH3CN): λmax=331.5nm；M.P.107.2-110.0℃.
Embodiment 6, the half-life measurement method of pyrazolyl azophenol derivative, is described as follows:
The test method reference literature (J.Am.Chem.Soc.2014,136,11878-11881) of overlength half-life period.Specifically Method is, using DMSO as solvent, using Z → E of the UV-Vis absorption spectrometry measurement azobenzene derivatives at 65,75 and 85 DEG C The rate constants k (following first-order kinetics) of reaction recycles Arrhenius equation to calculate the rate obtained at 25 DEG C normal Number k, and then obtain the half-life period of Z isomers at 25 DEG C.The result of the corresponding product of embodiment 3-5 is as shown in the table, they Half-life period was some months to more than ten month, presented the property of overlength half-life period.
Rate constant and half-life period of the 1. embodiment derivative Z isomers of table at 25 DEG C
The above description of the embodiments is intended to facilitate ordinary skill in the art to understand and use the invention. Person skilled in the art obviously easily can make various modifications to these embodiments, and described herein general Principle is applied in other embodiments without having to go through creative labor.Therefore, the present invention is not limited to the above embodiments, ability Field technique personnel announcement according to the present invention, improvement and modification made without departing from the scope of the present invention all should be of the invention Within protection scope.

Claims (8)

1. a kind of pyrazolyl azophenol compound, which is characterized in that be specially 4- ((1- methyl-1 H- pyrazoles -4- base) phenodiazine Alkenyl) phenol, structure is as follows:
2. the synthetic method of pyrazolyl azophenol compound described in a kind of claim 1, which is characterized in that including following step It is rapid:
Diazotising is carried out to 4- amino -1- methylpyrazole first, is then obtained using the coupling reaction of aryl diazonium salts and phenol Target compound 4- ((1- methyl-1 H- pyrazoles -4- base) diazenyl) phenol.
3. the application of pyrazolyl azophenol compound described in a kind of claim 1, which is characterized in that by the 4- ((1- Methyl-1 H- pyrazoles -4- base) diazenyl) phenol phenolic hydroxyl group etherificate or esterification, derive pyrazolyl azophenol Ethers or ester derivative.
4. a kind of etherification reaction of pyrazolyl azophenol, which is characterized in that etherifying reagent is organic examination with halogenic substituent Agent RCH2X, wherein X=Cl, Br, I, R include but is not limited to H, alkyl, aryl or other organic groups,
Following product structure is obtained after reaction:
In above formula, R includes but is not limited to H, alkyl, aryl or other organic groups.
5. a kind of esterification of pyrazolyl azophenol, which is characterized in that esterifying reagent is organic examination with active acyl Agent obtains following product structure after reaction:
Wherein, R includes but is not limited to alkyl, aryl or other organic groups.
6. a kind of esterification of pyrazolyl azophenol according to claim 5, which is characterized in that the active acyl of band The organic reagent of base includes but is not limited to carboxylic acid, acyl chlorides and acid anhydrides.
7. a kind of ether derivative of pyrazolyl azophenol, which is characterized in that its structure is as follows:
Wherein, R includes but is not limited to H, alkyl, aryl or other organic groups.
8. a kind of ester derivative of pyrazolyl azophenol, which is characterized in that its structure is as follows:
Wherein, R includes but is not limited to alkyl, aryl or other organic groups.
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CN113912543A (en) * 2021-10-11 2022-01-11 上海交通大学 Pyrazolyl azoaniline-based light-operated small-molecule adhesive

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CN113912543B (en) * 2021-10-11 2022-12-23 上海交通大学 Pyrazolyl azoaniline-based light-operated small-molecule adhesive

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