CN108947945A - A kind of 1,3- dihydroisobenzofuran derivative and its synthetic method and application - Google Patents

A kind of 1,3- dihydroisobenzofuran derivative and its synthetic method and application Download PDF

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CN108947945A
CN108947945A CN201810991246.8A CN201810991246A CN108947945A CN 108947945 A CN108947945 A CN 108947945A CN 201810991246 A CN201810991246 A CN 201810991246A CN 108947945 A CN108947945 A CN 108947945A
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dihydroisobenzofuran
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analog derivative
aryl
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CN108947945B (en
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赵育磊
张正
王宗康
司志姚
傅德斌
刘旭
郑丽君
李曼
李慧婷
孟占乾
刘璐
李�瑞
吴楠
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Qufu Normal University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
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    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
    • G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
    • G01N21/64—Fluorescence; Phosphorescence

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Abstract

The invention discloses a kind of formulas (I) 1,3- dihydroisobenzofuran derivative and its synthetic method, using the amine ketene compounds of ortho position alkynyl substituted as raw material, under the action of catalyst, synthesis obtains formula (I) 1,3- dihydroisobenzofuran derivative.Preparation method of the present invention has many advantages, such as that reaction condition is mild, reaction is insensitive to air, raw material is simple and easy to get, substrate universality is good, post-processing is easy, yield is outstanding, environmentally friendly.The present invention also provides application of formula (I) the 1,3- dihydroisobenzofuran analog derivative in fluorescence probe.

Description

A kind of 1,3- dihydroisobenzofuran derivative and its synthetic method and application
Technical field
The invention belongs to organic compound synthesize field, and in particular to one kind 1,3- dihydroisobenzofuran analog derivative and Its synthetic method and application.
Background technique
1,3- dihydroisobenzofuran compound is a kind of important organic compound, is many natural products and function point The essential building blocks of son, can be used for organic synthesis intermediate, there is weight in terms of the synthesis of drug, natural products and functional molecular The application value wanted, but the efficient construction method about the class formation is less.Therefore, people are for 1,3- dihydroisobenzofuran The study on the synthesis of compound starts to give more and more concerns.Such as under the action of noble metal, alkali and other salts, warp Multistep synthesizes to obtain 1,3- dihydroisobenzofuran derivative.Such as: document [1] Shang, X.S.；Li,N.T.；Guo,Z.Q.； Liu,P.N.Dyes and Pigments 2016,132,167.[2]Sekine,K.；Takayanagi,A.；Kikuchi,S.； Yamada,T.Chem.Commun.2013,49,11320.[3]Zhang,W.-Z.；Yang,M.-W.；Yang,X.-T.；Shi, L.-L.；Wang,H.-B.；Lu,X.-B.Org.Chem.Front.2016,3,217.[4]Li,D.Y.；Shang,X.S.； Chen,G.R.；Liu,P.N.Org.Lett.2013,15,3848.[5]Li,D.Y.；Shi,K.J.；Mao,X.F.；Chen, G.R.；Liu, P.N.J.Org.Chem.2014,79,4602. but the prior art, which exist, to be needed using noble metal catalyst, raw material Synthesize cumbersome, the disadvantages of needing high temperature, substrate limited.
Summary of the invention
The object of the present invention is to provide a kind of preparation methods of novel 1,3- dihydroisobenzofuran derivative, provide one Kind nonmetal catalyzed, reaction condition it is mild, low cost, environment amenable 1,3- dihydroisobenzofuran derivative and its Synthetic method.
The present invention also provides a kind of preparation methods of formula (I) 1,3- dihydroisobenzofuran derivative, with ortho position alkynyl Under the action of catalyst for raw material, it is derivative that synthesis obtains formula (I) 1,3- dihydroisobenzofuran to substituted amine ketene compounds Object.Preparation method of the present invention is mild with reaction condition, reaction is insensitive to air, raw material is simple and easy to get, substrate universality is good, The advantages that post-processing is easy, yield is outstanding, environmentally friendly.
The present invention provides a kind of novel 1,3- dihydroisobenzofuran analog derivative, shown in structure such as formula (I):
In formula (I), R1For aryl, alkyl；R2For aryl, silicon substrate, hydrogen atom；R3For hetero atom, alkyl, aryl substituent.
The present invention also provides a kind of new synthetic method of formula (I) 1,3- dihydroisobenzofuran analog derivative, specifically: with The amine ketene compounds of ortho position alkynyl substituted are raw material, under air conditions, organic solvent and catalyst are added, mild A period of time is reacted under reaction temperature, a step catalyzes and synthesizes to obtain formula (I) 1,3- dihydroisobenzofuran analog derivative, reacts Shown in process such as formula (II):
In formula (II), R1For aryl, alkyl；
R2For aryl, silicon substrate, hydrogen atom；
R3For hetero atom, alkyl, aryl substituent；
It is highly preferred that R1For 4- aminomethyl phenyl, 4- methoxyphenyl, phenyl, 4- chlorphenyl, 4- bromophenyl, 2- naphthalene 2.6- diisopropyl phenyl, 4- tert-butyl-phenyl, tert-butyl；
R2For 3,4,5- trimethoxyphenyl, 2- naphthalene, 4- chlorphenyl, trimethyl silicon substrate, hydrogen atom；
R3For methyl, methoxyl group, halogenic substituent.
Preferably, the amine ketene compounds of ortho position alkynyl substituted are the ortho position alkynyl substituted that electron-withdrawing group is connected on aryl Amine ketenes；The amine ketenes of the ortho position alkynyl substituted of electron-donating group is connected on aryl；The adjacent alkynes that alkyl, hetero atom or silicon substrate replace Base amine ketenes.
Preferably, catalyst is the composition of tetrabutyl ammonium fluoride (TBAF), tetrabutylammonium bromide and cesium fluoride, more preferably Ground, catalyst are tetrabutyl ammonium fluoride.
Preferably, the molar ratio of the amine ketene compounds and catalyst of raw material ortho position alkynyl substituted is 10:1~1:1, more Preferably, the molar ratio of the amine ketenes and tetrabutyl ammonium fluoride of ortho position alkynyl substituted is 10:2.
Preferably, the organic solvent is one of tetrahydrofuran (THF) and ethyl acetate, it is highly preferred that described molten Agent is tetrahydrofuran (THF).
Preferably, the reaction temperature is 25 DEG C or 35 DEG C, it is highly preferred that reaction temperature is 35 DEG C.
Preferably, the reaction time is 15 minutes to 3 hours, it is highly preferred that the reaction time is 2 hours.
Preferably, the reaction is not necessarily to inert gas shielding, without using heavy metal catalyst.
A kind of yield of the new synthetic method of described formula (I) the 1,3- dihydroisobenzofuran analog derivative be > 95% (with When TBAF is catalyst).
The present invention also provides a kind of formula (I) 1,3- dihydroisobenzofuran analog derivatives to answer in terms of fluorescent molecular probe With.
Preferably, it can be used for the building of organic synthesis intermediate and fluorescent molecular probe skeleton, such probe can be used for two The detection of valence copper ion and cyanide ion content.
Preferably, it can be used for the fluorescent functional material system with 1,3- dihydroisobenzofuran analog derivative for crucial skeleton It is standby.
In a specific embodiment, in preparation method of the present invention, with tetrabutyl ammonium fluoride (TBAF) for catalyst, such as Shown in following formulas (II):
Wherein, R1For aryl；R2For aryl；R3For alkyl.
Wherein, the catalyst is tetrabutyl ammonium fluoride (TBAF).
Wherein, the amine ketenes of ortho position alkynyl substituted: tetrabutyl ammonium fluoride molar ratio is 5:1.
Wherein, the solvent is tetrahydrofuran (THF).
Wherein, reaction temperature is 35 DEG C.Reaction time is 2 hours.The yield of the synthetic method is > 95%.
In a specific embodiment, the synthetic method of the present invention 1,3- dihydroisobenzofuran is being urged under air In the presence of agent tetrabutyl ammonium fluoride (TBAF), the amine ketenes of ortho position alkynyl substituted is dissolved in solvent appropriate and is warming up to 35 DEG C, it reacts 2 hours, after separating-purifying, obtains formula (I) 1,3- dihydroisobenzofuran analog derivative.
The present invention also proposes the 1,3- dihydroisobenzofuran analog derivative using the synthesis of above-mentioned preparation method.Formula (I) 1, 3- dihydroisobenzofuran analog derivative be present invention firstly provides noval chemical compound, until so far, having no relevant report.Its Shown in structure such as formula (I):
Wherein, R1For aryl, alkyl；R2For aryl, silicon substrate；Preferably, R1For 4- aminomethyl phenyl, 4- methoxyphenyl, benzene Base, 4- chlorphenyl, 4- bromophenyl, 2- naphthalene 2.6- diisopropyl phenyl, 4- tert-butyl-phenyl, tert-butyl；
R2For 3,4,5- trimethoxyphenyl, 2- naphthalene, 4- chlorphenyl, trimethyl silicon substrate；
R3For methyl, methoxyl group, halogenic substituent.R3For hetero atom, alkyl, aryl substituent.
The invention also provides formula (I) 1,3- dihydroisobenzofuran analog derivatives in fluorescent molecular probe and natural products In application.Furan derivative proposed by the present invention is the primary structure building block of many natural products and fluorescent functional molecule, It can be used for the building research of organic synthesis intermediate and fluorescent molecular probe.
The present invention includes the following advantages: without using heavy metal catalyst, non-metallic catalyst tetrabutyl ammonium fluoride used (TBAF) cheap and easy to get, the amine ketene compounds of raw material ortho position alkynyl substituted are convieniently synthesized, react insensitive to air, reaction Mild condition, substrate universality is good, and post-processing is easy, and yield is outstanding, environmentally friendly.For functional material, especially with 1,3- Dihydroisobenzofuran provides important reference for the preparation of the fluorescent material of crucial skeleton.
Specific embodiment
In conjunction with following specific embodiments, the present invention is described in further detail, and of the invention protects content not limit to In following embodiment.Without departing from the spirit and scope of the invention, those skilled in the art it is conceivable that variation and excellent Point is all included in the present invention, and using appended claims as protection scope.Implement process of the invention, condition, Reagent, experimental method etc. are among the general principles and common general knowledge in the art, this hair in addition to what is specifically mentioned below It is bright that there are no special restrictions to content.
In the method for the present invention, the amine ketene compounds of ortho position alkynyl substituted, the cyclisation under tetrabutyl ammonium fluoride catalysis Reaction, as shown in formula (II), under air, in the presence of catalyst tetrabutyl ammonium fluoride, by the amine ketenes of ortho position alkynyl substituted Compound is dissolved in tetrahydrofuran, at 35 DEG C or at room temperature, is reacted 15 minutes to 3 hours, after separating-purifying, is obtained formula (I) 1,3- dihydroisobenzofuran analog derivative:
Wherein, R1For aryl, alkyl；R2For aryl, silicon substrate, hydrogen atom；R3For alkyl, aryl, hetero atom substituents, halogen Plain replacing group.
Embodiment 1:
Trans- 2- ((suitable) -3- (suitable)-benzylidene) isobenzofuran -1 (three hydrogen)-methylene)-N- phenethyl -1- imines (IA) synthesis
(inert gas shielding is not necessarily to) under air, and into 10 milliliters of bottles, the amine alkene that ortho position phenylacetylene base replaces is added Ketone (0.4mmol), tetrahydrofuran (4mL), tetrabutyl ammonium fluoride (0.08mmol, 80uL, 1mol/L in THF) are warming up to 35 DEG C Reaction 2 hours, obtains target product (IA), yellow solid, separation yield 99%, mp:106-108 DEG C.
Product nuclear magnetic data:1H NMR(500MHz,DMSO-d6): δ 8.80 (d, J=9.5Hz, 1H), 8.09 (d, J= 7.8Hz, 1H), 8.00 (d, J=7.8Hz, 1H), 7.85 (d, J=7.5Hz, 2H), 7.68-7.65 (m, 1H), 7.61-7.58 (m, 1H), 7.46-7.42 (m, 4H), 7.30-7.23 (m, 4H), 6.71 (s, 1H), 6.59 (d, J=9.5Hz, 1H)；13C NMR (125MHz,DMSO-d6): δ 159.74,154.93,152.26,150.31,134.34,134.23,131.65,131.07, 130.02,129.32,128.98,128.82,127.19,125.70,121.91,120.83,120.49,102.11,99.72.
Product high resolution mass spectrum data: HRMS (ESI) calcd for C23H18NO[M+H]+:324.1383,found 324.1385.
Embodiment 2:
Trans- 2- ((suitable) -3- (suitable)-benzylidene) isobenzofuran -1 (three hydrogen)-methylene)-N- is to methoxybenzene second The synthesis of base -1- imines (IB)
(inert gas shielding is not necessarily to) under air, and into 10 milliliters of bottles, methoxy-substituted ortho position phenylacetylene is added Base amine ketenes (0.4mmol), tetrahydrofuran (4mL), tetrabutyl ammonium fluoride (0.04mmol, 40uL, 1mol/L in THF) heating It reacts 3 hours, obtains target product (IB), yellow solid, separation yield 99%, mp:118-120 DEG C to 35 DEG C.
Product nuclear magnetic data:1H NMR(500MHz,DMSO-d6): δ 8.81 (d, J=9.5Hz, 1H), 8.05 (d, J= 7.5Hz, 1H), 7.98 (d, J=8.0Hz, 1H), 7.86 (d, J=7.5Hz, 2H), 7.66-7.63 (m, 1H), 7.60-7.55 (m, 1H), 7.46-7.43 (m, 2H), 7.30-7.26 (m, 3H), 7.01-6.99 (m, 2H), 6.68 (s, 1H), 6.55 (d, J= 9.5Hz,1H),3.79(s,3H)；13C NMR(125MHz,DMSO-d6):δ158.92,157.81,152.67,150.39, 145.06,134.32,134.22,131.43,131.20,129.99,128.95,128.84,127.11,122.12,121.76, 120.48,114.59,101.78,100.03,55.31.
Product high resolution mass spectrum data: HRMS (ESI) calcd for C24H20NO2[M+H]+:354.1489,found 354.1491.
Embodiment 3:
Trans- 2- ((suitable) -3- (suitable)-benzylidene) isobenzofuran -1 (three hydrogen)-methylene)-N- is to chlorobenzene ethyl -1- The synthesis of imines (IC)
(inert gas shielding is not necessarily to) under air, and into 10 milliliters of bottles, the ortho position phenylacetylene base amine that chlorine replaces is added Ketenes (0.4mmol), tetrahydrofuran (4mL), tetrabutylammonium bromide (referred to as: TBAB, 0.08mmol, 25.8mg) and cesium fluoride (0.8mmol, 121.5mg) is warming up to 35 DEG C and reacts 2 hours, obtains target product (IC), yellow solid, separation yield is 72%, mp:149-451 DEG C.
Product nuclear magnetic data:1H NMR(500MHz,DMSO-d6): δ 8.79 (d, J=9.5Hz, 1H), 8.09 (d, J= 7.8Hz, 1H), 8.01 (d, J=7.8Hz, 1H), 7.86 (d, J=7.6Hz, 2H), 7.69-7.66 (m, 1H), 7.61-7.58 (m, 1H), 7.48-7.43 (m, 4H), 7.30-7.27 (m, 3H), 6.72 (s, 1H), 6.58 (d, J=9.5Hz, 1H)；13C NMR (125MHz,DMSO-d6): δ 160.18,155.71,151.06,150.27,134.43,134.17,131.79,131.00, 130.06,129.88,129.24,129.07,128.87,127.26,122.65,122.00,120.52,102.37,99.55.
Product high resolution mass spectrum data: HRMS (ESI) calcd for C23H17ClNO[M+H]+:358.0993,found 358.0995.
Embodiment 4:
The conjunction of trans- 2- ((suitable) -3- methylene isobenzofuran -1 (three hydrogen)-methylene)-N- phenethyl -1- imines (ID) At
(inert gas shielding is not necessarily to) under air, and into 10 milliliters of bottles, the neighbour that trimethyl silicon substrate (TMS) replaces is added Position phenylacetylene base amine ketenes (0.4mmol), tetrahydrofuran (4mL), tetrabutyl ammonium fluoride (0.4mmol, 400uL, 1mol/L in THF it) reacts 15 minutes for 25 DEG C, obtains target product (ID), yellow solid, separation yield 99%, mp:72-74 DEG C.
Product nuclear magnetic data:1H NMR(500MHz,DMSO-d6): δ 8.67 (d, J=12.1Hz, 1H), 8.04 (d, J= 9.1Hz, 1H), 7.92 (d, J=9.2Hz, 1H), 7.65-7.58 (m, 2H), 7.40-7.36 (m, 2H), 7.22-7.18 (m, 3H), 6.47 (d, J=12.1Hz, 1H), 5.29 (d, J=3.3Hz, 1H), 5.06 (d, J=3.4Hz, 1H)；13C NMR (125MHz,DMSO-d6):δ160.13,157.35,155.61,152.69,133.38,132.73,132.03,130.90, 129.62,126.06,122.20,121.56,121.25,99.44,86.67.
Product high resolution mass spectrum data: HRMS (ESI) calcd for C17H14NO[M+H]+:248.1070,found 248.1068.
Embodiment 5:
Trans- 2- ((suitable) -3- (suitable)-benzylidene) -5,6- dimethoxy isobenzofuran -1 (three hydrogen)-methylene)-N- The synthesis of phenethyl -1- imines (IE)
(inert gas shielding is not necessarily to) under air, and into 10 milliliters of bottles, the ortho position benzene second that bi-methoxy replaces is added Alkynylamine ketenes (0.4mmol), ethyl acetate (4mL), tetrabutyl ammonium fluoride (0.08mmol, 80uL, 1mol/L in THF) rise Temperature is reacted 3 hours to 35 DEG C, is obtained target product (IE), yellow solid, separation yield 95%, mp:201-203 DEG C.
Product nuclear magnetic data: 1H NMR (500MHz, DMSO-d6): δ 8.76 (d, J=9.6Hz, 1H), 7.80 (d, J= 7.5Hz,2H),7.63(s,1H),7.56(s,1H),7.44-7.39(m,4H),7.26-7.21(m,4H),6.59(s,1H), 6.51 (d, J=9.6Hz, 1H)；13C NMR(125MHz,DMSO-d6): δ 160.23,155.03,152.86,152.44, 151.46,150.68,134.62,129.29,128.82,128.65,128.15,126.77,125.43,124.14,120.81, 103.20,102.09,100.69,98.38,56.10.
Product high resolution mass spectrum data: HRMS (ESI) calcd for C25H22NO3[M+H]+:384.1594,found 384.1596。

Claims (10)

1. one kind 1,3- dihydroisobenzofuran analog derivative, which is characterized in that shown in its structure such as formula (I):
In formula (I), R1For aryl, alkyl；R2For aryl, silicon substrate, hydrogen atom；R3For hetero atom, alkyl, aryl substituent.
2. a kind of synthetic method of formula (I) 1,3- dihydroisobenzofuran analog derivative, which is characterized in that with ortho position alkynyl substituted Amine ketene compounds be raw material, under air conditions, organic solvent and catalyst is added, it is anti-under mild reaction temperature Should for a period of time, a step catalyzes and synthesizes to obtain formula (I) 1,3- dihydroisobenzofuran analog derivative, reaction process such as formula (II) It is shown:
In formula (II), R1For aryl, alkyl；R2For aryl, silicon substrate, hydrogen atom；R3For hetero atom, alkyl, aryl substituent.
3. a kind of synthetic method of formula (I) according to claim 21,3- dihydroisobenzofuran analog derivative, feature It is, the amine ketene compounds of the ortho position alkynyl substituted are the amine alkene that the ortho position alkynyl substituted of electron-withdrawing group is connected on aryl Ketone；The amine ketenes of the ortho position alkynyl substituted of electron-donating group is connected on aryl；The adjacent alkynylamine alkene that alkyl, hetero atom or silicon substrate replace Ketone.
4. a kind of synthetic method of formula (I) according to claim 21,3- dihydroisobenzofuran analog derivative, feature It is, the catalyst is selected from the combination of tetrabutyl ammonium fluoride or tetrabutylammonium bromide and cesium fluoride.
5. a kind of synthetic method of formula (I) according to claim 21,3- dihydroisobenzofuran analog derivative, feature It is, the amine ketene compounds of raw material ortho position alkynyl substituted and the molar ratio of catalyst are 10:1~1:1.
6. a kind of synthetic method of formula (I) according to claim 21,3- dihydroisobenzofuran analog derivative, feature It is, the organic solvent is selected from one of tetrahydrofuran, ethyl acetate.
7. a kind of synthetic method of formula (I) according to claim 21,3- dihydroisobenzofuran analog derivative, feature It is, the reaction is not necessarily to inert gas shielding, without using heavy metal catalyst；The reaction temperature is 25 DEG C or 35 DEG C； The reaction time is 15 minutes to 3 hours.
8. a kind of formula (I) 1,3- dihydroisobenzofuran analog derivative according to claim 1-7 is in fluorescence point Application in terms of sub- probe.
9. a kind of formula (I) 1,3- dihydroisobenzofuran analog derivative according to claim 8 is in fluorescent molecular probe side Face application, which is characterized in that can be used for the building of organic synthesis intermediate and fluorescent molecular probe skeleton, such probe can be used for The detection of bivalent cupric ion and cyanide ion content.
10. a kind of formula (I) 1,3- dihydroisobenzofuran analog derivative according to claim 8 is in fluorescent molecular probe side Face application, which is characterized in that can be used for the fluorescent functional material with 1,3- dihydroisobenzofuran analog derivative for crucial skeleton Preparation.
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CN110669030B (en) * 2019-09-18 2021-05-18 曲阜师范大学 Isobenzofuran diester derivative and synthetic method thereof
CN113816843A (en) * 2021-08-17 2021-12-21 临沂大学 2-hydroxy-9-fluorenone derivative and synthesis method and application thereof
CN114736181A (en) * 2022-04-28 2022-07-12 河南大学 Synthesis method of visible light mediated acylated benzofuran derivative
CN114736181B (en) * 2022-04-28 2024-03-08 河南大学 Synthesis method of visible light mediated acylated benzofuran derivative

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