CN104447824A - Fluoro-boron diisoindole compounds and preparation method thereof - Google Patents

Fluoro-boron diisoindole compounds and preparation method thereof Download PDF

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CN104447824A
CN104447824A CN201310441927.4A CN201310441927A CN104447824A CN 104447824 A CN104447824 A CN 104447824A CN 201310441927 A CN201310441927 A CN 201310441927A CN 104447824 A CN104447824 A CN 104447824A
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compound
formula
boron
fluorine boron
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杨晓霞
陶晓春
蔡良珍
林智星
蔺卉
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East China University of Science and Technology
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Abstract

The invention relates to fluoro-boron diisoindole compounds and a preparation method thereof. Compared with the conventional fluoro-boron dipyrrole compounds, according to the fluoro-boron diisoindole compounds, pyrrole rings are directly replaced by isoindole rings, the conjugated range of pi bonds in a parent molecule is increased and thus the photochemical and physical properties of the compounds are changed, molecular absorption and emission wavelengths cause a 'red shift', the maximum ultraviolet absorption wavelength can reach 640nm-680nm and the maximum fluorescence emission wavelength is up to 670nm-713nm and the fluoro-boron diisoindole compounds are near-infrared fluorescent dyes.

Description

Fluorine boron two isoindoles compound and preparation method thereof
Technical field
Fluorine boron two isoindoles compound that the present invention relates to a kind of novel structure and preparation method thereof.
Background technology
Fluorine boron two azoles is, by boron bridged bond and methine bridged bond, two pyrroles's molecules are fixed in one plane formed compound, and its structure is shown below.
This compounds has very high molar absorptivity (usual ε >80000cm -1m -1) and fluorescence quantum yield, and there is good light stability, therefore have in fields such as fluorescence chemical sensor, solar cell photoreceptor, liquid crystal material, supermolecule polymers and study widely.Recently, there are reports, by the modification to fluorine boron two azole compounds structure, changes its optical property, makes it the research being applicable to photosensitizers or fluorescent probe.
O ' shea etc. reports a kind of azepine fluorine boron two azoles, it has near infrared absorbing wavelength, good phototoxicity is shown for tumour cell simultaneously, particularly the experiment of compound MDA-231 in nude mouse shows it and effectively can kill breast cancer cell (J Am Chem Soc, 2004,126:10619-10631; J Am Chem Soc, 2005,127:16360-16361; Brit J Cancer, 2009,101:1565-1573); Nagano etc. disclose a kind of fluorine boron two azoles replaced by iodine, and it has the quantum yield of higher singlet oxygen and long infrared absorption wavelength (630-670nm) (J AmChem Soc, 2005,127:12162-12163); Akkaya etc. provide a kind of Bodipy compounds replaced in pyrroles 5-position, and it has strong absorption at the treatment window of 650-680nm, and has good phototoxicity (Chem Commun, 2006,42:4398-4400 for K562 leukemia cell; Chem Commun, 2009,4956-4958).
But problems of the prior art are: want the absorption and the emission wavelength " red shift " that make existing fluorine boron two azoles, generally in parent molecule, introduce macromolecular conjugation group (as introduced multiple styrene group or phenylacetylene group etc.), cause the synthesis difficulty of this compounds to increase (the tediously long and productive rate of synthetic route is low etc.).In addition, fluorine boron two azoles that molecular weight is too large can affect its absorption in vivo, thus affects its biological activity.
Summary of the invention
The present inventor designs and has synthesized a kind of fluorine boron two isoindoles compound of novel structure.It is simple and be easy to the advantages such as synthesis (synthetic route is succinct) that described fluorine boron two isoindoles compound has structure.
Fluorine boron two isoindoles compound provided by the invention, compared to fluorine boron two azoles, direct isoindole ring instead of pyrrole ring, add π key conjugation scope in parent molecule, thus change photochemistry and the physicals of compound, make molecular absorption and emission wavelength " red shift ", uv-absorption maximum wavelength reaches 640nm ~ 680nm, maximum emission wavelength reaches 670nm ~ 713nm, is a class near infrared fluorescent dye.
In addition, owing to introducing halogen or halogen-containing substituting group (particularly fluorine or fluorine-containing substituting group) the invention provides in fluorine boron two isoindoles compound, it may change the absorption in vivo of described fluorine boron two isoindoles compound and transmission speed, and its physiological action is changed.
One object of the present invention is, provides a kind of fluorine boron two isoindoles compound of novel structure, and described fluorine boron two isoindoles compound is compound shown in formula I:
In formula I, R 1for halogen (F, Cl, Br or I) or halo C 1~ C 3alkyl; R 2and R 3independently be selected from: hydrogen (H) or C 1~ C 3a kind of in alkoxyl group.
Another object of the present invention is, provide the method for compound shown in a kind of preparation formula I, described method comprises the steps:
(1) step of 4-substituted-phenyl phenylhydrazine (shown in formula III compound) is prepared by 4-substituted ethyl benzoate (shown in formula II compound);
(2) step of N-[1-(aryl) ethylidene] fragrant formyl hydrazine (shown in formula V compound) is prepared by 4-substituted-phenyl phenylhydrazine (shown in formula III compound);
(3) step of (2-acetylphenyl) benzophenone (shown in formula VI compound) replaced is prepared by N-[1-(aryl) ethylidene] fragrant formyl hydrazine (shown in formula V compound);
(4) step of two isoindole methylene vinyl compounds (shown in formula VII compound) is prepared by (2-acetylphenyl) benzophenone (shown in formula VI compound) replaced; With
(5) step of target compound (shown in formula I compound) is prepared by two isoindole methylene vinyl compounds (shown in formula VII compound).
Its synthetic route is as follows:
Embodiment
In the present invention's preferred technical scheme, R 1for halogen (F, Cl, Br or I) or fluoro C 1~ C 3alkyl;
Further optimal technical scheme is: R 1for halogen (F, Cl, Br or I) or fluoromethyl;
Further optimal technical scheme is: R 1for halogen (F, Cl, Br or I) or trifluoromethyl.
In another preferred technical scheme of the present invention, R 2and R 3independently be selected from: a kind of in hydrogen (H) or methoxyl group.
Shown in preparation formula I provided by the present invention, the method for compound, specifically comprises the steps:
(1) synthesis of 4-substituted-phenyl phenylhydrazine (shown in formula III compound)
Hydrazine hydrate (the N of 20 ~ 25mmol4-substituted ethyl benzoate (shown in formula II compound), 50 ~ 60mmol is added in reaction flask 2h 4h 2o) add 50 ~ 60mL dehydrated alcohol as solvent, simultaneously, stir, after 75 ~ 80 DEG C of reflux 6 ~ 7h, except desolventizing, have Precipitation, filter, dry, obtain 4-substituted-phenyl phenylhydrazine (shown in formula III compound);
(2) synthesis of N-[1-(aryl) ethylidene] fragrant formyl hydrazine (shown in formula V compound)
4-substituted benzoyl hydrazides, 18 ~ 20mmol4 that 15 ~ 20mmol is obtained by step (1) is added in reaction flask, 5-position replaces 2-hydroxy acetophenone (shown in formula IV compound), add the dehydrated alcohol of 50 ~ 60mL simultaneously, stir, after 75 ~ 80 DEG C of reflux 48 ~ 50h, except desolventizing, solid is had to separate out, filter, dry, obtain N-[1-(aryl) ethylidene] fragrant formyl hydrazine (shown in formula V compound);
(3) synthesis of (2-benzoyl) benzophenone (shown in formula VI compound) replaced
The tetrahydrofuran (THF) of 70 ~ 80mL is added successively in reaction flask, the lead tetra-acetate of 10 ~ 12mmol, 5 ~ 8mmol N-[1-(aryl) ethylidene] fragrant formyl hydrazine (shown in formula V compound), after stirring at room temperature 8 ~ 9h, filter, the tetrahydrofuran (THF) adding 5 ~ 10mL washs three times, merge organic phase, steam tetrahydrofuran (THF), remaining liq is successively through washing (to neutral) and extraction, collect organic phase, dry, (2-benzoyl) benzophenone (shown in formula VI compound) that column chromatography for separation must replace;
The synthesis of (4) two isoindole methylene vinyl compounds (shown in formula VII compound)
(2-acetylphenyl) benzophenone (shown in formula VI compound), the methyl alcohol of 30 ~ 40mL, 20 ~ 25mmol acetic acid, 10 ~ 15mmol ammoniacal liquor that 2 ~ 3mmol replaces is added successively in reaction flask, after stirring at room temperature 42-ethanoyl benzophenone ~ 5h, steam except methyl alcohol, washing is to neutral, isolate organic phase, gained organic phase drying and column chromatography obtain two isoindole methylene vinyl compounds (shown in formula VII compound);
(5) synthesis of target compound (shown in formula I compound)
0.5 ~ 0.7mmol bis-isoindole methylene vinyl compound (shown in formula VII compound), the methylene dichloride of 20 ~ 30mL, 1.5 ~ 1.8mmol boron trifluoride ether solution and 1 ~ 1.2mmol N is added in reaction flask, N-diisopropyl ethyl amine, after stirring at room temperature 7 ~ 8h, steaming desolventizes, extraction, gained organic phase drying and column chromatography, obtain target compound (shown in formula I compound).
Wherein, 4-substituted ethyl benzoate (shown in formula II compound) and 4,5-position replace 2-hydroxy acetophenone (shown in formula IV compound) and are known substance, and it can obtain by prior art or obtain by buying.
Below in conjunction with specific embodiment, set forth the present invention further.Should be understood that these embodiments are only not used in for illustration of the present invention to limit the scope of the invention.In addition should be understood that those skilled in the art can make various changes or modifications the present invention, and these equivalent form of values fall within the application's appended claims limited range equally after the content of having read the present invention's instruction.
Embodiment 1
1,1'-bis-(4,4'-fluorine) phenyl-3,3'-fluorine boron two isoindole methylene alkene (IA)
(1) synthesis of 4-fluorobenzoyl hydrazine
3.36g (20mmol) parafluorobenzoic acid ethyl ester and 5.00g (50mmol) hydrazine hydrate (N2H4H2O) is added in 100mL reaction flask, 50mL dehydrated alcohol, stirs, after 75 ~ 80 DEG C of reflux 6h, steam except ethanol, the needle-like crystal of adularescent is separated out, and filters, washing, dry, obtain 4-fluorobenzoyl hydrazine 2.78g, productive rate: 90.3%, fusing point: 163 DEG C.
(2) synthesis of N-[1-(2-hydroxy phenyl) ethylidene]-4-fluorobenzoyl hydrazine
2.31g (15mmol) 4-fluorobenzoyl hydrazine is added, the 2-hydroxy acetophenone of 2.44g (18mmol), the dehydrated alcohol of 50mL in 100mL reaction flask, stir, 75 ~ 80 DEG C of reflux 48 hours, after question response terminates, have yellow solid to separate out, filter, washing, dry, obtain N-[1-(2-hydroxy phenyl) ethylidene]-4-fluorobenzoyl hydrazine 3.35g, productive rate: 82.2%, fusing point: 162 ~ 163 DEG C.
(3) 2-(4-fluoro benzoyl) synthesis of methyl phenyl ketone
The tetrahydrofuran (THF) of 70mL is added, the lead tetra-acetate of 4.43g (10mmol), N-[1-(2-hydroxy phenyl) ethylidene]-4-fluorobenzoyl hydrazine 1.36g, stirring at room temperature 8h in 250mL reaction flask.Filter; a small amount of tetrahydrofuran (THF) washs three times; merge mother liquor; steam tetrahydrofuran (THF); residue saturated sodium carbonate is neutralized to neutrality, and extraction, after organic phase drying; column chromatography carries out being separated (eluent is sherwood oil: ethyl acetate=6:1(v/v)), obtain (2-acetylphenyl)-4-fluorobenzene ketone 0.73g.Productive rate 60.5%, fusing point: 137 ~ 139 DEG C. 1HNMR(400MHz,CDCl 3),δ:7.91～7.89(m,1H),7.77～7.73(m,2H),7.66～7.59(m,2H),7.39～7.37(m,1H),7.08(t,2H,J=8.8Hz),2.53(s,3H).
The synthesis of (4) 1,1'-bis-couples fluorophenyl-3,3'-bis-isoindole methylene alkene
0.484g (2mmol) (2-acetylphenyl)-4-fluorobenzene ketone is added in 100mL reaction flask; 30mL methyl alcohol; 4.1mL (60mmol) acetic acid; 19.2mL (30mmol) ammoniacal liquor; after stirring at room temperature 4h; steam except methyl alcohol, saturated sodium carbonate solution is washed till neutrality.Dichloromethane extraction three times, isolates organic phase, dry column chromatography for separation (eluent is sherwood oil: ethyl acetate=10:1), obtains 1,1'-, bis-pairs of fluorophenyls-3,3'-bis-isoindole methylene alkene 0.22g, productive rate 52.2%.
1H NMR(400MHz,CDCl3),δ:8.0～7.90(m,6H),7.62(d,2H,J=8.8Hz),7.51～7.48(br s,2H),7.40～7.35(m,3H),7.01～6.98(m,4H).
(5) preparation of compound shown in IA
0.216g (0.5mmol) 1 is added in 100mL reaction flask, 1'-bis-pairs of fluorophenyls-3,3'-dibenzopyrrole methylene alkene, 20mL methylene dichloride, 0.41mL (1.5mmol) boron trifluoride ether solution, the N of 0.18mL (1mmol) l, N-diisopropyl ethyl amine, after stirring at room temperature 7h, steaming desolventizes.After organism washing, dichloromethane extraction, dry, column chromatography for separation (eluent is sherwood oil: ethyl acetate=10:1), obtains the 0.15g of compound shown in IA, productive rate 64.8%.
1H NMR(400MHz,CDCl3),δ:7.92(d,2H,J=8Hz),7.85～7.79(m,5H),7.59(d,2H,J=8Hz),7.61～7.44(m,2H),7.29～7.26(m,2H),7..20(t,4H,J=8.8Hz).HRESI-MS481.1489([M+H]+，calcd for C 29H 17BF 4N 2:481.1499)；UV:λmax=642nm.Fluorescence:λem=670nm.
Embodiment 2
1,1'-bis-(4,4'-chlorine) phenyl-3,3'-fluorine boron two isoindole methylene alkene (IB)
Divided by outside parafluorobenzoic acid ethyl ester in Ethoforme alternative embodiment 1 step (1), other condition is identical with embodiment 1, obtains title compound.
1H NMR(400MHz,CDCl 3),δ:7.84(d,2H,J=8.4Hz),7.77(s,1H),7.79(d,4H,J=8.4Hz),7.52 (d,2H,J=8.0Hz),7.48～7.39(m,6H),7.20～7.20(m,2H).
HRESI-MS535.0726.([M+Na] +，calcd for C 29H 17BF 2N 2Cl 2Na:535.0722).UV:λmax=648nm.Fluorescence:λem=673nm.
Embodiment 3
1,1'-bis-(4,4'-bromine) phenyl-3,3'-fluorine boron two isoindole methylene alkene (IC)
Divided by outside parafluorobenzoic acid ethyl ester in parabromobenzoic acid ethyl ester alternative embodiment 1 step (1), other condition is identical with embodiment 1, obtains title compound.
1H NMR(400MHz,CDCl 3),δ:7.92(d,2H,J=8.4Hz),7.86(s,1H),7.79(d,4H,J=8.4Hz),7.60(m,4H),7.51～7.47(m,4H),7.08～7.05(m,2H).HRESI-MS622.9715([M+Na] +，calcd for C 29H 17BF 2N 2Br 2Na:622.9712).UV:λmax=648nm.Fluorescence:λem=675nm.
Embodiment 4
1,1'-bis-(4,4'-trifluoromethyl) phenyl-3,3'-fluorine boron two isoindole methylene alkene (ID)
Divided by outside parafluorobenzoic acid ethyl ester in trifluoromethylbenzoic acid ethyl ester alternative embodiment 1 step (1), other condition is identical with embodiment 1, obtains title compound.
1H NMR(400MHz,CDCl 3),δ:7.95～7.90(m,5H),7.77(d,4H,J=8.4Hz),7.60(d,2H,J=8.4Hz),7.54～7.50(m,2H),7.32～7.29(m,2H),7.04(d,2H,J=7.6Hz).HRESI-MS581.1448([M+H] +，calcd for C 31H 17BF 8N 2:581.1435).UV:λmax=647nm.Fluorescence:λem=672nm.
Embodiment 5
1,1'-bis-(4,4'-fluorine) phenyl-6,6'-dimethoxy-3,3'-fluorine boron two isoindole methylene alkene (IE)
Divided by outside 2-hydroxy acetophenone in 2-hydroxyl-4 methoxyacetophenone alternative embodiment 1 step (2), other condition is identical with embodiment 1, obtains title compound.
1H NMR(400MHz,CDCl 3),δ:7.84(d,2H,J=7.6Hz),7.71～7.6871(m,5H),7.34(d,2H,J=8.0Hz),7.10～7.08(m,4H),6.90(d,2H,J=8.0Hz),3,75(s,6H).HRESI-MS541.1708([M+H] +，calcd for C 31H 21BF 4N 2O 2:541.1710).UV:λmax=671nm.Fluorescence:λem=702nm.
Embodiment 6
1,1'-bis-(4,4'-chlorine) phenyl-6,6'-dimethoxy-3,3'-fluorine boron two isoindole methylene alkene (IF)
Divided by parafluorobenzoic acid ethyl ester in Ethoforme alternative embodiment 1 step (1), in 2-hydroxyl-4 methoxyacetophenone alternative embodiment 1 step (2) outside 2-hydroxy acetophenone, other condition is identical with embodiment 1, obtains title compound.
1H NMR(400MHz,CDCl 3),δ:7.68～7.63(m,4H),7.54(d,2H,J=8.2Hz),7.14～7.06(m,4H),6.59(d,1H,J=8.2Hz),6.56～6.48(m,4H).3.87(s,6H).HRESI-MS595.3793([M+Na] +，calcd for C 31H 20BF 2N 2Cl 2NaO 2:595.3793).UV:λmax=678nm.Fluorescence:λem=712nm.
Embodiment 7
1,1'-bis-(4,4'-bromine) phenyl-6,6'-dimethoxy-3,3'-fluorine boron two isoindole methylene alkene (IG)
Divided by parafluorobenzoic acid ethyl ester in parabromobenzoic acid ethyl ester alternative embodiment 1 step (1), in 2-hydroxyl-4 methoxyacetophenone alternative embodiment 1 step (2) outside 2-hydroxy acetophenone, other condition is identical with embodiment 1, obtains title compound.
1H NMR(400MHz,CDCl 3),δ:7.73～7.73(m,7H),7.48(d,4H,J=8.2Hz),7.11～7.14(m,2H),6.97(m,2H),3.85(s,6H).HRESI-MS661.0142([M+H] +，calcd for C 31H 21BF 2N 2Br 2O 2:661.0143).UV:λmax=677nm.Fluorescence:λem=714nm.
Embodiment 8
1,1'-bis-(4,4'-trifluoromethyl) phenyl-6,6'-dimethoxy-3,3'-fluorine boron two isoindole methylene alkene (IH)
Divided by parafluorobenzoic acid ethyl ester in trifluoromethylbenzoic acid ethyl ester alternative embodiment 1 step (1), in 2-hydroxyl-4 methoxyacetophenone alternative embodiment 1 step (2) outside 2-hydroxy acetophenone, other condition is identical with embodiment 1, obtains title compound.
1H NMR(400MHz,CDCl 3),δ:7.84(d,2H,J=8.0Hz),7.71～7.63(m,4H),7.34(d,2H,J=8.4Hz),7.09～7.07(m,5H),6.90(d,2H,J=8.0Hz),3.75(s,6H).HRESI-MS641.1658([M+H] +，calcd for C 33H 21BF 8N 2O 2:641.1647).UV:λmax=677nm.Fluorescence:λem=713nm.

Claims (7)

1. a fluorine boron two isoindoles compound, it is compound shown in formula I:
In formula I, R 1for halogen or halo C 1~ C 3alkyl; R 2and R 3independently be selected from: hydrogen or C 1~ C 3a kind of in alkoxyl group.
2. fluorine boron two isoindoles compound as claimed in claim 1, is characterized in that, wherein R 1for halogen or fluoro C 1~ C 3alkyl.
3. fluorine boron two isoindoles compound as claimed in claim 2, is characterized in that, wherein R 1for halogen or fluoromethyl.
4. fluorine boron two isoindoles compound as claimed in claim 3, is characterized in that, wherein R 1for halogen or trifluoromethyl.
5. fluorine boron two isoindoles compound as claimed in claim 1, is characterized in that, wherein R 2and R 3independently be selected from: a kind of in hydrogen or methoxyl group.
6. the fluorine boron two isoindoles compound as described in claim 4 or 5, it is characterized in that, described fluorine boron two isoindoles compound is: 1, 1'-bis-(4, 4'-fluorine) phenyl-3, 3'-fluorine boron two isoindole methylene alkene, 1, 1'-bis-(4, 4'-chlorine) phenyl-3, 3'-fluorine boron two isoindole methylene alkene, 1, 1'-bis-(4, 4'-bromine) phenyl-3, 3'-fluorine boron two isoindole methylene alkene, 1, 1'-bis-(4, 4'-trifluoromethyl) phenyl-3, 3'-fluorine boron two isoindole methylene alkene, 1, 1'-bis-(4, 4'-fluorine) phenyl-6, 6'-dimethoxy-3, 3'-fluorine boron two isoindole methylene alkene, 1, 1'-bis-(4, 4'-chlorine) phenyl-6, 6'-dimethoxy-3, 3'-fluorine boron two isoindole methylene alkene, 1, 1'-bis-(4, 4'-bromine) phenyl-6, 6'-dimethoxy-3, 3'-fluorine boron two isoindole methylene alkene or 1, 1'-bis-(4, 4'-trifluoromethyl) phenyl-6, 6'-dimethoxy-3, 3'-fluorine boron two isoindole methylene alkene.
7. prepare the method as fluorine boron two isoindoles compound as described in any one in Claims 1 to 5, it is characterized in that, described method comprises the steps:
(1) by the step of compound shown in preparation of compounds of formula III shown in formula II;
(2) reacted by compound shown in compound and formula IV shown in formula III, the step of compound shown in preparation formula V;
(3) by the step of compound shown in preparation of compounds of formula VI shown in formula V;
(4) by the step of compound shown in preparation of compounds of formula VII shown in formula VI; With
(5) step of target compound is prepared by compound shown in formula VII;
wherein, R 1, R 2and R 3implication identical with described in any one in Claims 1 to 5.
CN201310441927.4A 2013-09-25 2013-09-25 Fluoro-boron diisoindole compounds and preparation method thereof Pending CN104447824A (en)

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KR102210172B1 (en) 2016-12-19 2021-01-29 후지필름 가부시키가이샤 Light-emitting resin composition for wavelength conversion and its manufacturing method, and wavelength conversion member and light-emitting element
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CN109233325A (en) * 2018-09-03 2019-01-18 南京大学 A kind of two pyrroles's fluorescent dye of asymmetry benzo fluorine boron and its preparation method

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