CN107880065A - The fluorine boron pyrrolizine ketone and its synthetic method of a kind of stabilization - Google Patents
The fluorine boron pyrrolizine ketone and its synthetic method of a kind of stabilization Download PDFInfo
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- CN107880065A CN107880065A CN201711139015.6A CN201711139015A CN107880065A CN 107880065 A CN107880065 A CN 107880065A CN 201711139015 A CN201711139015 A CN 201711139015A CN 107880065 A CN107880065 A CN 107880065A
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- Prior art keywords
- compound
- pyrrolizine
- fluorine boron
- post
- sodium hydride
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- -1 fluorine boron pyrrolizine ketone Chemical class 0.000 title claims description 6
- 230000006641 stabilisation Effects 0.000 title abstract description 7
- 238000011105 stabilization Methods 0.000 title abstract description 7
- 238000010189 synthetic method Methods 0.000 title description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 48
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- 239000002994 raw material Substances 0.000 claims abstract description 17
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910000104 sodium hydride Inorganic materials 0.000 claims abstract description 14
- 239000012312 sodium hydride Substances 0.000 claims abstract description 14
- WCAYRKIOKGJMHZ-UHFFFAOYSA-N C1C=CN2C=CC=C12.[B].[F] Chemical compound C1C=CN2C=CC=C12.[B].[F] WCAYRKIOKGJMHZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000007787 solid Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 9
- 239000003513 alkali Substances 0.000 claims description 7
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000741 silica gel Substances 0.000 claims description 4
- 229910002027 silica gel Inorganic materials 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 5
- 239000003814 drug Substances 0.000 abstract description 4
- 239000007850 fluorescent dye Substances 0.000 abstract description 2
- 238000001215 fluorescent labelling Methods 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000001308 synthesis method Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 239000004411 aluminium Substances 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- LIQLLTGUOSHGKY-UHFFFAOYSA-N [B].[F] Chemical compound [B].[F] LIQLLTGUOSHGKY-UHFFFAOYSA-N 0.000 description 4
- 239000000975 dye Substances 0.000 description 3
- 206010011224 Cough Diseases 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229960001866 silicon dioxide Drugs 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- FBXGQDUVJBKEAJ-UHFFFAOYSA-N 4h-oxazin-3-one Chemical class O=C1CC=CON1 FBXGQDUVJBKEAJ-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 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
- 206010061218 Inflammation Diseases 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 230000000146 antalgic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/022—Boron compounds without C-boron linkages
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The present invention relates to a kind of fluorine boron pyrrolizine assimilation compound, the compound structure below figure：Compound I adds sodium hydride in THF solvents, methanol, normal-temperature reaction, a kind of new fluorine boron pyrrolizine assimilation compound of stabilization is obtained after purifying recrystallization using fluorine boron pyrrolizine as raw material.The structure of the present invention is novel, and stability is good, good water solubility, and such compound synthesis method is simple, reaction condition is easily controllable, due to good structural stability, water solubility, photochemical properties, can be good at being applied in the fields such as biological medicine and biological fluorescent labelling.
Description
Technical field
The present invention relates to a kind of fine Organic chemical products, the fluorine boron pyrrolizine assimilation compound of particularly a kind of stabilization,
Such compound can be widely used in the fields such as biological medicine, analysis, fluorescent material science.
Background technology
The pyrylium dyes of fluorine boron two (BODIPY) are the more a kind of novel fluorescence dyestuffs of Recent study, and it is by two pyrroles
Cough up the complex that methylene is formed with boron trifluoride.Some 3H-1,2- dihydro -1- Aminopyrrolizineton compounds are reported at present
Synthesis, pharmacological evaluation shows that the derivative of the class formation has stronger antipyretic-antalgic and antiinflammatory action.As can be seen here, pyrrole
It is a kind of compound for having very much medicinal study future to cough up inner oxazinone derivative, to the structure of modification of this kind of compound, modification and excellent
Change, foundation will be provided to find new non-deep and remote body anti-inflammation analgesia medicine.
Fluorine boron Aminopyrrolizineton compound is rarely reported in the literature, and its chemical stability is high, good water solubility, in biology
Medicine, analysis, fluorescent material science etc. are widely used.
The content of the invention
It is a primary object of the present invention to provide new fluorine boron pyrrolizine assimilation compound and its synthesis side of a kind of stabilization
Method.
Technical scheme is as follows：
A kind of new fluorine boron pyrrolizine assimilation compound of stabilization, the chemical structural formula of the compound are：
A kind of synthetic method of the new fluorine boron pyrrolizine assimilation compound of the described stabilization of synthesis, methods described include with
Lower synthesis path：
It the described method comprises the following steps：
(1) raw material is added into reaction bulb at room temperature, THF, until completely dissolved, adds sodium hydride,
Absolute methanol, return stirring reaction 2-30h, reaction are directly spin-dried for after terminating, and obtain solid chemical compound；
The raw material is fluorine boron pyrrolizine compound；
(2) solid chemical compound in the step (1) is isolated and purified, purifying, which is characterized by, first uses alkali
Property aluminum oxide crosses post, then crosses post, isolated red solid compound I with 200-300 mesh silica gel；Institute
It is a kind of azole compounds of fluorine boron two to state compound 1.
Post is crossed with alkali alumina, can just obtain red solid, the compound otherwise obtained is extremely unstable, simultaneously
It ensure that compound I stability.
The rate of charge of raw material and sodium hydride is 1 in the step 1)：1-20.According to patent (Patent No.：
ZL201610288887.8), self-control obtains raw material, and its purity should be more than 95%, otherwise causes purification difficult, and yield declines.
The rate of charge of the step 1) raw material and absolute methanol is 1：50-100.Commercial methanol should carry out water removal operation, from
Absolute methanol is made, water content should be in below 100ppm.
The order that the step 1) feeds intake is raw material, THF, sodium hydride, absolute methanol, if changing its charging sequence can make
Reaction system reaction gets muddled, and the yield for being not easy to reactant improves.
Step 1) the reaction condition is stirring at normal temperature, reacts 2-30 hours.Reaction can produce reaction without heating, heating
Rate reduces.
The present invention has the beneficial effect that：
1) present invention has successfully synthesized a kind of new fluorine boron pyrrolizine ketone.
2) synthetic reaction condition of the invention is simple, and reaction raw materials agent treatment is simple, and product purification mode is more special, needs
Post first is rushed with alkali alumina, then is purified with common silicagel column.Post is crossed with alkali alumina, can just obtain red solid, otherwise
Obtained compound is extremely unstable, while ensure that compound I stability.
3) compared with existing fluorine boron fluorescent dye, a kind of of a relatively high dyestuff of stability, and the dyestuff have been obtained
It is water-soluble preferable.
Brief description of the drawings
Fig. 1 is I hydrogen spectrum.
Fig. 2 is I carbon spectrum.
Embodiment
The present invention is further illustrated with reference to embodiment, but the scope of protection of present invention is not limited to implement
The scope of example statement.
Embodiment 1
Raw material (361.20mg, 1.00mmol) is taken, measures THF solution 10mL, takes sodium hydride (150mg), absolute methanol
(4ml), normal-temperature reaction 16h, post is rushed through peroxidating aluminium after being then spin-dried for, (petroleum ether is than dichloromethane=1 by chromatographic column:1)
Separation, obtains red solid I 40mg, yield 10.9%.
Embodiment 2
Raw material (361.20mg, 1.00mmol) is taken, measures THF solution 10mL, takes sodium hydride (350mg), absolute methanol
(4ml), normal-temperature reaction 16h, post is rushed through peroxidating aluminium after being then spin-dried for, (petroleum ether is than dichloromethane=1 by chromatographic column:1)
Separation, obtains red solid I 20mg, yield 5.05%.
Embodiment 3
Raw material (361.20mg, 1.00mmol) is taken, measures THF solution 10mL, takes sodium hydride (500mg), absolute methanol
(4ml), normal-temperature reaction 16h, post is rushed through peroxidating aluminium after being then spin-dried for, (petroleum ether is than dichloromethane=1 by chromatographic column:1)
Separation, obtains red solid I 10mg, yield 2.5%.
Embodiment 4
Raw material (361.20mg, 1.00mmol) is taken, measures THF solution 10mL, takes sodium hydride (150mg), absolute methanol
(10ml), normal-temperature reaction 16h, post is rushed through peroxidating aluminium after being then spin-dried for, (petroleum ether is than dichloromethane=1 by chromatographic column:1)
Separation, obtains red solid I 62mg, yield 15.2%.
Embodiment 5
Raw material (361.20mg, 1.00mmol) is taken, measures THF solution 10mL, takes sodium hydride (150mg), absolute methanol
(4ml), normal-temperature reaction 20h, post is rushed through peroxidating aluminium after being then spin-dried for, (petroleum ether is than dichloromethane=1 by chromatographic column:1)
Separation, obtains red solid I 65mg, yield 15.5%.
Embodiment 6
Raw material (361.20mg, 1.00mmol) is taken, measures THF solution 10mL, takes sodium hydride (250mg), absolute methanol
(10ml), normal-temperature reaction 16h, post is rushed through peroxidating aluminium after being then spin-dried for, (petroleum ether is than dichloromethane=1 by chromatographic column:1)
Separation, obtains red solid I 23mg, yield 15%.
Embodiment 7
Raw material (361.20mg, 1.00mmol) is taken, measures THF solution 10mL, takes sodium hydride (50mg), absolute methanol
(4ml), normal-temperature reaction 16h, post is rushed through peroxidating aluminium after being then spin-dried for, (petroleum ether is than dichloromethane=1 by chromatographic column:1)
Separation, obtains red solid I 43mg, yield 10.2%.
The above embodiments are only the preferred technical solution of the present invention, and are not construed as the limitation for the present invention, this Shen
Please in embodiment and embodiment in feature in the case where not conflicting, can mutually be combined.The protection model of the present invention
Enclose the equivalent substitution side of technical characteristic in the technical scheme that should be recorded with claim, including the technical scheme of claim record
Case is protection domain.Equivalent substitution i.e. within this range is improved, also within protection scope of the present invention.
Claims (6)
1. a kind of fluorine boron pyrrolizine assimilation compound, it is characterised in that the chemical structural formula is：
2. synthesize claim 1 described in fluorine boron pyrrolizine assimilation compound method, it is characterised in that methods described include with
Lower synthesis path：
Specifically include following steps：
(1) raw material is added into reaction bulb at room temperature, THF, until completely dissolved, adds sodium hydride, absolute methanol, backflow is stirred
Reaction 2-30h is mixed, reaction is directly spin-dried for after terminating, and obtains solid chemical compound；The raw material is fluorine boron pyrrolizine compound；
(2) solid chemical compound in the step (1) is isolated and purified, purifying is characterized by first with alkali alumina mistake
Post, then cross post, isolated red solid compound I with 200-300 mesh silica gel.
Post is crossed with alkali alumina, can just obtain red solid, the compound otherwise obtained is extremely unstable, while ensure that chemical combination
Thing I stability.
3. method according to claim 2, it is characterised in that：It is step 1) the fluorine boron pyrrolizine compound, sodium hydride, anhydrous
The rate of charge of methanol is 1：1-20：50-100.
4. method according to claim 2, it is characterised in that：The order that the step 1) feeds intake is fluorine boron pyrrolizine chemical combination
Thing, THF, sodium hydride, absolute methanol.
5. method according to claim 2, it is characterised in that：Step 2) the purifying is characterized by first is rushed with alkali alumina
Post, then cross post with common silica gel.
6. method according to claim 2, it is characterised in that：Step 1) the counterflow condition stirs 2-30h.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711139015.6A CN107880065A (en) | 2017-11-16 | 2017-11-16 | The fluorine boron pyrrolizine ketone and its synthetic method of a kind of stabilization |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711139015.6A CN107880065A (en) | 2017-11-16 | 2017-11-16 | The fluorine boron pyrrolizine ketone and its synthetic method of a kind of stabilization |
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| Publication Number | Publication Date |
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| CN107880065A true CN107880065A (en) | 2018-04-06 |
Family
ID=61777493
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| Application Number | Title | Priority Date | Filing Date |
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| CN201711139015.6A Pending CN107880065A (en) | 2017-11-16 | 2017-11-16 | The fluorine boron pyrrolizine ketone and its synthetic method of a kind of stabilization |
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| Country | Link |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109734736A (en) * | 2019-01-18 | 2019-05-10 | 三峡大学 | Seven yuan of fluorine boron fluorescent dyes of one kind and its synthetic method |
| CN111100476A (en) * | 2019-12-05 | 2020-05-05 | 三峡大学 | Synthesis and application of pH fluorescent probe |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105925004A (en) * | 2016-05-04 | 2016-09-07 | 三峡大学 | Fluorine-boron pyrrolizinone fluorochrome and synthesizing method thereof |
| CN106831785A (en) * | 2017-01-19 | 2017-06-13 | 三峡大学 | A kind of Aminopyrrolizineton compound and its synthetic method |
| CN106831786A (en) * | 2017-01-19 | 2017-06-13 | 三峡大学 | A kind of synthetic method of pyrrolizines |
-
2017
- 2017-11-16 CN CN201711139015.6A patent/CN107880065A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105925004A (en) * | 2016-05-04 | 2016-09-07 | 三峡大学 | Fluorine-boron pyrrolizinone fluorochrome and synthesizing method thereof |
| CN106831785A (en) * | 2017-01-19 | 2017-06-13 | 三峡大学 | A kind of Aminopyrrolizineton compound and its synthetic method |
| CN106831786A (en) * | 2017-01-19 | 2017-06-13 | 三峡大学 | A kind of synthetic method of pyrrolizines |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109734736A (en) * | 2019-01-18 | 2019-05-10 | 三峡大学 | Seven yuan of fluorine boron fluorescent dyes of one kind and its synthetic method |
| CN109734736B (en) * | 2019-01-18 | 2021-01-26 | 三峡大学 | Seven-element fluoroboric fluorescent dye and synthetic method thereof |
| CN111100476A (en) * | 2019-12-05 | 2020-05-05 | 三峡大学 | Synthesis and application of pH fluorescent probe |
| CN111100476B (en) * | 2019-12-05 | 2021-03-23 | 三峡大学 | Synthesis and application of pH fluorescent probe |
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