CN106117254A - A kind of synthesis technique of Carboxybenzeneboronic acid - Google Patents
A kind of synthesis technique of Carboxybenzeneboronic acid Download PDFInfo
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- CN106117254A CN106117254A CN201610436979.6A CN201610436979A CN106117254A CN 106117254 A CN106117254 A CN 106117254A CN 201610436979 A CN201610436979 A CN 201610436979A CN 106117254 A CN106117254 A CN 106117254A
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- phenylboric acid
- acid
- glucose
- phenylboric
- synthesis technique
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- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 16
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title claims abstract description 14
- KWNPRVWFJOSGMZ-UHFFFAOYSA-N 2-boronobenzoic acid Chemical compound OB(O)C1=CC=CC=C1C(O)=O KWNPRVWFJOSGMZ-UHFFFAOYSA-N 0.000 title claims abstract description 12
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 claims abstract description 41
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims abstract description 23
- 239000008103 glucose Substances 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 8
- 125000001424 substituent group Chemical group 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- -1 alkyl lithium Chemical compound 0.000 claims abstract description 6
- 229920005862 polyol Polymers 0.000 claims abstract description 6
- 150000003077 polyols Chemical class 0.000 claims abstract description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 4
- KYOIPUDHYRWSFO-UHFFFAOYSA-N [Br].[Li] Chemical group [Br].[Li] KYOIPUDHYRWSFO-UHFFFAOYSA-N 0.000 claims abstract description 4
- ULKGULQGPBMIJU-UHFFFAOYSA-N benzene;hydron;bromide Chemical compound Br.C1=CC=CC=C1 ULKGULQGPBMIJU-UHFFFAOYSA-N 0.000 claims abstract description 4
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 23
- 230000008859 change Effects 0.000 claims description 12
- 102000004877 Insulin Human genes 0.000 claims description 11
- 108090001061 Insulin Proteins 0.000 claims description 11
- 229940125396 insulin Drugs 0.000 claims description 11
- 238000001514 detection method Methods 0.000 claims description 8
- 150000004676 glycans Chemical class 0.000 claims description 7
- 229920001282 polysaccharide Polymers 0.000 claims description 7
- 239000005017 polysaccharide Substances 0.000 claims description 7
- 239000010409 thin film Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 5
- 150000001720 carbohydrates Chemical class 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 230000002860 competitive effect Effects 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 239000003792 electrolyte Substances 0.000 claims description 3
- 230000013595 glycosylation Effects 0.000 claims description 3
- 238000006206 glycosylation reaction Methods 0.000 claims description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 3
- 239000010931 gold Substances 0.000 claims description 3
- 229910052737 gold Inorganic materials 0.000 claims description 3
- 239000011806 microball Substances 0.000 claims description 3
- 239000000178 monomer Substances 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- LXDRHVXMGDKBEK-UHFFFAOYSA-N [B].C1=CC=CC=C1 Chemical compound [B].C1=CC=CC=C1 LXDRHVXMGDKBEK-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 108700004813 glycosylated insulin Proteins 0.000 claims 1
- 238000013461 design Methods 0.000 abstract description 7
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000000463 material Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002596 correlated effect Effects 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- 238000002795 fluorescence method Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 230000000452 restraining effect Effects 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000003886 Glycoproteins Human genes 0.000 description 1
- 108090000288 Glycoproteins Proteins 0.000 description 1
- 102000004856 Lectins Human genes 0.000 description 1
- 108090001090 Lectins Proteins 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- 238000005700 Stille cross coupling reaction Methods 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 125000003147 glycosyl group Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000002523 lectin Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- MLSKXPOBNQFGHW-UHFFFAOYSA-N methoxy(dioxido)borane Chemical compound COB([O-])[O-] MLSKXPOBNQFGHW-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood 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
- C07F5/025—Boronic and borinic acid compounds
-
- G—PHYSICS
- G01—MEASURING; TESTING
- 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
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
- G01N27/26—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating electrochemical variables; by using electrolysis or electrophoresis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Immunology (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pathology (AREA)
- Organic Chemistry (AREA)
- Optics & Photonics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Electrochemistry (AREA)
- Saccharide Compounds (AREA)
Abstract
The invention discloses the synthesis technique of a kind of Carboxybenzeneboronic acid, belong to technical field of chemical synthesis；It comprises the steps of (1), bromide benzene elder generation and lithium alkylide generation lithium bromine exchange reaction；(2), alkyl lithium reagents is directly added drop-wise to obtain in the mixed liquor of substituent group bromobenzene and trialkylborates the dialkyl of phenylboric acid；(3), add glucose and form coordination compound；(4), add polyol to coordinate；(5) react with trialkylborates, hydrolyze to obtain corresponding substituent group phenylboric acid.Its technological design is reasonable, simple to operate, low cost, and success rate is high, is suitable for commercial production, it is to avoid drawback present in prior art, substantially increases the utilization rate of phenylboric acid, applied widely.
Description
Technical field
The present invention relates to technical field of chemical synthesis, be specifically related to the synthesis technique of a kind of Carboxybenzeneboronic acid.
Background technology:
Phenylboric acid be a kind of molecular weight be the chemical products of 121.93；English name: Phenylboronic Acid；Phenylboric acid is used
Make the boric acid component in the research of Suzuki diaryl cross-coupling；For Stille and Suzuki cross-coupling reaction；At present,
Carboxybenzeneboronic acid is intermediate important in pharmaceutical synthesis, and various synthetic reactions are more and more universal；Phenyl boronic acid derivative kind
Various, development is very fast, is widely used in the fields such as electronics, chemistry, medicine, biology in recent years, such as liquid crystal display material,
The inhibitor of chemiluminescence intensifier, wood product preservative and enzyme, it can also selectively promote glucose by fat pair in addition
The transport of layer, is increasingly used as molecular recognition unit at present, particularly, is used to design and synthesis boron lectin
(glycoprotein) and saccharide sensor device；Phenylboric acid (phenylboronic acid) derivant have in aqueous electrically charged with without
Two kinds of forms of electric charge, the most charged form can with have 1, the polyol shape of 2-or 1,3-glycol group
Become reversible five yuan or hexa-atomic cyclic ester；This process is reversible, and has a large amount of such polyol in nature,
The materials such as such as polysaccharide, they many are present in organism, and the vital movement for organism has a major impact；Existing
Synthesis Carboxybenzeneboronic acid technique extract from toluene, before this by some reagent, then with methyl borate low-temp reaction, so
After be oxidized to Carboxybenzeneboronic acid under the high temperature conditions, between this synthesis technique and effectiveness comparison is good, but when oxidation, need tight
The temperature control of lattice, and it is easily generated water so that easy blackening in purge process；In the synthesis technique of prior art, phenylboric acid stablizes
Property poor, can not increase the quantity of phenylboric acid coordination compound under physiological pH condition, cost is high, and success rate is low, is only suitable for little
Experiment, is not suitable for production and processing.
Summary of the invention
For the problems referred to above, the technical problem to be solved in the present invention be to provide a kind of reasonable in design, easy to operate, add work efficiency
The synthesis technique of the Carboxybenzeneboronic acid of rate height and good stability.
The synthesis technique of a kind of Carboxybenzeneboronic acid of the present invention, it comprises the steps of
1, bromide benzene elder generation and lithium alkylide generation lithium-bromine exchange reaction；
2, directly alkyl lithium reagents is added drop-wise to substituent group bromobenzene and obtains the two of phenylboric acid in the mixed liquor of trialkylborates
Arrcostab；
3, add glucose and form coordination compound；
4, add polyol to coordinate；
5 react with trialkylborates, hydrolyze to obtain corresponding substituent group phenylboric acid.
As preferably, the mixed liquor in described step 2 can introduce determining for polyhydroxy substances such as polysaccharide in sensor
Amount detection, phenylboric acid and other monomers form thin film on the surface of gold electrode, combine when the saccharide in phenylboric acid with solution produces
Time, the electrolyte property of thin film changes thus causes the change of electric current, and this change is the concentration with glucide
It is correlated with, thus can be used for the detection by quantitative of polysaccharide；If introducing fluorophor on phenylboric acid, then it the thing such as with glucose
The bonding behavior of matter may result in the change of fluorescence, can design the materials such as the sensitiveest detection glucose based on this character
Fluorescence method.
As preferably, the glucose in described step 3 insulin is carried out glycosylation modified after, be attached to phenylboric acid
Content is on the gel micro-ball of 4% (mol)；In the presence of glucose, due to its competitive substitution effect to phenylboric acid site, sugar
Base insulin splits away off, and the minor variations of concentration of glucose will cause the rapid release of insulin, and can be along with
The pulsed change of concentration of glucose reaches pulsitile drug release.After amino is introduced phenylboric acid gel, can strengthen phenylboric acid from
The stability of son, increases the quantity of phenylboric acid coordination compound under physiological pH condition, improves insulin useful load, rings glucose
The time that should discharge is 120 h.
When the present invention operates, these compounds can be detected, outside Separation & Purification, it is also possible to by it to internal many
The identification function of hydroxylated material is used for restraining oneself formula drug-supplying system or regulating some vital movement.
Beneficial effects of the present invention: its technological design is reasonable, simple to operate, low cost, and success rate is high, is suitable for industry raw
Produce, it is to avoid drawback present in prior art, substantially increase the utilization rate of phenylboric acid, applied widely.
Detailed description of the invention
This detailed description of the invention is by the following technical solutions: following steps:
1, bromide benzene elder generation and lithium alkylide generation lithium-bromine exchange reaction；
2, directly alkyl lithium reagents is added drop-wise to substituent group bromobenzene and obtains the two of phenylboric acid in the mixed liquor of trialkylborates
Arrcostab；
3, add glucose and form coordination compound；
4, add polyol to coordinate；
5 react with trialkylborates, hydrolyze to obtain corresponding substituent group phenylboric acid.
As preferably, the mixed liquor in described step 2 can introduce determining for polyhydroxy substances such as polysaccharide in sensor
Amount detection, phenylboric acid and other monomers form thin film on the surface of gold electrode, combine when the saccharide in phenylboric acid with solution produces
Time, the electrolyte property of thin film changes thus causes the change of electric current, and this change is the concentration with glucide
It is correlated with, thus can be used for the detection by quantitative of polysaccharide.If introducing fluorophor on phenylboric acid, then it the thing such as with glucose
The bonding behavior of matter may result in the change of fluorescence, can design the materials such as the sensitiveest detection glucose based on this character
Fluorescence method.
As preferably, the glucose in described step 3 insulin is carried out glycosylation modified after, be attached to phenylboric acid and contain
Amount is on the gel micro-ball of 4% (mol).In the presence of glucose, due to its competitive substitution effect to phenylboric acid site, glycosyl
Changing insulin to split away off, the minor variations of concentration of glucose will cause the rapid release of insulin, and can be along with Portugal
The pulsed change of grape sugar concentration reaches pulsitile drug release.After amino is introduced phenylboric acid gel, phenylboric acid ion can be strengthened
Stability, under physiological pH condition increase phenylboric acid coordination compound quantity, improve insulin useful load, to glucose ring
The time that should discharge is 120 h.
During the operation of this detailed description of the invention, these compounds can be detected, outside Separation & Purification, it is also possible to by it
It is used for restraining oneself formula drug-supplying system or regulating some vital movement to the identification function of internal polyhydroxy substance.
The technological design of this detailed description of the invention is reasonable, simple to operate, low cost, and success rate is high, is suitable for commercial production, keeps away
Exempt from drawback present in prior art, substantially increase the utilization rate of phenylboric acid, applied widely.
The ultimate principle of the present invention and principal character and advantages of the present invention have more than been shown and described.The skill of the industry
The art personnel simply explanation it should be appreciated that the present invention is not restricted to the described embodiments, described in above-described embodiment and description
The principle of the present invention, without departing from the spirit and scope of the present invention, the present invention also has various changes and modifications, these
Changes and improvements both fall within scope of the claimed invention.Claimed scope by appending claims and
Its equivalent defines.
Claims (3)
1. the synthesis technique of a Carboxybenzeneboronic acid, it is characterised in that it comprises the steps of
(1), bromide benzene elder generation and lithium alkylide generation lithium-bromine exchange reaction；
(2), directly alkyl lithium reagents is added drop-wise to substituent group bromobenzene and obtains phenylboric acid in the mixed liquor of trialkylborates
Dialkyl；
(3), add glucose and form coordination compound；
(4), add polyol to coordinate；
(5) react with trialkylborates, hydrolyze to obtain corresponding substituent group phenylboric acid.
The synthesis technique of a kind of Carboxybenzeneboronic acid the most according to claim 1, it is characterised in that in described step (2)
Mixed liquor can introduce the detection by quantitative in sensor for polyhydroxy substances such as polysaccharide, phenylboric acid and other monomers at gold electrode
Surface forms thin film, and when the saccharide in phenylboric acid with solution produces and combines, the electrolyte property of thin film changes thus draws
Play the change of electric current, and this change is concentration dependent with glucide, thus can be used for the detection by quantitative of polysaccharide.
The synthesis technique of a kind of Carboxybenzeneboronic acid the most according to claim 1, it is characterised in that in described step (3)
Glucose insulin is carried out glycosylation modified after, be attached on the gel micro-ball that phenylboric acid content is 4% (mol)；Work as glucose
In the presence of, due to its competitive substitution effect to phenylboric acid site, glycosylated insulin splits away off, concentration of glucose small
Change will cause the rapid release of insulin, and can release along with the pulsed change of concentration of glucose reaches pulsed
Medicine；After amino is introduced phenylboric acid gel, the stability of phenylboric acid ion can be strengthened, under physiological pH condition, increase benzene boron
The quantity of acid coordination compound, improves insulin useful load, and the time of glucose responding release is 120h.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610436979.6A CN106117254A (en) | 2016-06-20 | 2016-06-20 | A kind of synthesis technique of Carboxybenzeneboronic acid |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201610436979.6A CN106117254A (en) | 2016-06-20 | 2016-06-20 | A kind of synthesis technique of Carboxybenzeneboronic acid |
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|---|---|---|---|
| CN201610436979.6A Pending CN106117254A (en) | 2016-06-20 | 2016-06-20 | A kind of synthesis technique of Carboxybenzeneboronic acid |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107144616A (en) * | 2017-05-11 | 2017-09-08 | 宁夏医科大学 | The preparation method of the layer assembly film acted on based on boric acid glycol specific recognition |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103724366A (en) * | 2014-01-21 | 2014-04-16 | 贵州威顿晶磷电子材料有限公司 | Preparation method of p-carboxyphenylboronic acid |
| CN104262263A (en) * | 2014-08-29 | 2015-01-07 | 西安交通大学 | N,6 diphenylpyrimidine-4-amine Bcr-Abl inhibitors as well as preparation method and application thereof |
-
2016
- 2016-06-20 CN CN201610436979.6A patent/CN106117254A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103724366A (en) * | 2014-01-21 | 2014-04-16 | 贵州威顿晶磷电子材料有限公司 | Preparation method of p-carboxyphenylboronic acid |
| CN104262263A (en) * | 2014-08-29 | 2015-01-07 | 西安交通大学 | N,6 diphenylpyrimidine-4-amine Bcr-Abl inhibitors as well as preparation method and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| WENJIE LI,ET AL.: ""An Improved Protocol for the Preparation of 3-Pyridyl- and Some Arylboronic Acids"", 《J. ORG. CHEM.》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107144616A (en) * | 2017-05-11 | 2017-09-08 | 宁夏医科大学 | The preparation method of the layer assembly film acted on based on boric acid glycol specific recognition |
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Application publication date: 20161116 |