CN108863971A - A kind of 2-（2,4,6- trimethylbenzene seleno）- 5 carboxylate compound of -1,3- oxazole and preparation method - Google Patents
A kind of 2-（2,4,6- trimethylbenzene seleno）- 5 carboxylate compound of -1,3- oxazole and preparation method Download PDFInfo
- Publication number
- CN108863971A CN108863971A CN201810445406.9A CN201810445406A CN108863971A CN 108863971 A CN108863971 A CN 108863971A CN 201810445406 A CN201810445406 A CN 201810445406A CN 108863971 A CN108863971 A CN 108863971A
- Authority
- CN
- China
- Prior art keywords
- copper
- oxazole
- preparation
- reaction
- seleno
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
The present invention relates to a kind of 2- (2,4,6- trimethylbenzene seleno) -1, -5 carboxylate compound of 3- oxazole and preparation method, in organic solvent, with 1, -5 carboxylic acid, ethyl ester of 3- oxazole and 2,4,6- trimethyl iodobenzenes are reaction raw materials, using elemental selenium as seleno reagent, copper catalyst and alkali collectively promote effect under, a kind of -2- (2,4 is obtained by tandem reaction, 6- trimethylbenzene seleno) - -5 carboxylate compound of 1,3- oxazole.The method reaction condition is simple, the yield of product and purity is high, has opened up new synthetic route and method for a kind of -2- (2,4,6- trimethylbenzene seleno)--5 carboxylate compound of 1,3- oxazole, has had good application potential and researching value.
Description
Technical field
The invention belongs to organic compound synthesis technical fields, more particularly, to a kind of 2- (2,4,6- trimethylbenzene selenium
Base)--5 carboxylate compound of 1,3- oxazole and preparation method.
Background technique
Selenium has anticancer, anti-oxidant, enhancing human immunity, antagonism harmful heavy metal, the absorption for adjusting vitamin, adjusts people
The synthesis of vivo protein and enhancing reproductive function, at the same be also muscle, in refining peroxidase important composition ingredient,
It is referred to as " king of anticancer " of body trace element by scientist.
So far, people are for example medical in multiple concrete application fields, and chemical development is multiple to contain selenide knot
The drug molecule of structure：Ebselen (ebselen) is that Japanese first pharmacy and the novel of Nattermann company of Germany exploitation resist
Scorching medicine, being currently in the clinical III phase studies；The group thiophosphate compound of Tegafur with anti-tumor activity containing selenium,
The rhizoma et Radix Baphicacanthis Cusiae compound of polysaccharide of the selenizing modification inhibited to various tumor cell strains.Even agriculture field, selenide
Wide spectrum is present in fungicide and herbicide compound structure again, is such as used as the triazolylamide containing selenium of crops herbicide.Largely
Scientific investigations showed that, selenium be constitute glutathione peroxidase active constituent effectively prevent as free radical inhibitors
Beta Cell of islet Oxidative demage promotes sugared part metabolism, reduces blood glucose and glucose in urine, improves the symptom of diabetic, and human body institute
Cysteine, the methionine needed is also selenium-containing compound.
In addition, 1,3- oxazole compounds are a kind of important containing multiple hetero atom aromatic rings, it is the important of organic synthesis
Guide's skeleton and synthon, parent nucleus are widely present in many natural products and the drug molecule of bioactivity, such as：Commodity
The etoxazole (etoxazole) of change, insect growth regulator, IGR (2,5- bis- (2,4- dichlorophenyls) -1,3,4- oxazoles.By drug
The continuous research of scholars, a large amount of 1,3- oxazole analog derivative are synthesized, and they have extensive bioactivity,
The new world has been opened up in development for medicine and chemistry of pesticide, provides new approach to find the newtype drug of high-efficiency low-toxicity,
However, on 5- carboxylate -1,3 oxazole skeleton introduce arylseleno functional group research method do not report so far, there are still after
Continuous necessity studied and explored, this is also the basis that the present invention is accomplished and power place.
Summary of the invention
Here, applicant is intended to illustrate, the technical scheme is that in state natural sciences fund (number：
21602158) it is accomplished under subsidy, expresses thanks herein.
First technical problem to be solved by this invention is 2- (2,4,6- trimethylbenzene seleno)--5 carboxylic acid of 1,3- oxazole
The problem of synthetic route of ethyl ester compound.
Second technical problem to be solved by this invention is 2- (2,4,6- trimethylbenzene seleno)--5 carboxylic acid of 1,3- oxazole
Ethyl ester compound preparation process is suitble to the problem of large-scale industrial production.
In order to solve the above technical problems, the present invention provides following technical proposals：
A kind of 2- (2,4,6- trimethylbenzene seleno)--5 carboxylate compound of 1,3- oxazole and preparation method, organic
In solvent, with 2,4,6- front threes of structure shown in -5 carboxylic acid, ethyl ester of 1,3- oxazole and formula (II) with the structure as shown in formula (I)
Base iodobenzene is reaction raw materials, using elemental selenium as seleno reagent, copper catalyst and alkali collectively promote effect under, pass through formula
(I) the c h bond arylseleno tandem reaction of compound obtains the 2- (2,4,6- trimethylbenzene seleno) -1 of structure shown in formula (III),
- 5 carboxylate compound of 3- oxazole.
Above-mentioned reaction process can be indicated with following reaction equations：
2,4,6- trimethyl iodobenzenes of structure shown in -5 carboxylic acid, ethyl ester of 1,3- oxazole and formula (II) of structure shown in (I)
Molar ratio be 1: 1-1: 5, preferably 1: 3；Mole of 1,3- oxazole -5 carboxylic acid, ethyl ester and elemental selenium of structure shown in (I)
Than being 1: 1-1: 5, preferably 1: 3.
(1) copper catalyst
Copper catalyst in the present invention be stannous chloride, cuprous iodide, cuprous bromide, copper oxide, copper chloride, copper bromide,
At least one of copper fluoride, three fluosulfonic acid copper, acetylacetone copper, copper acetate, copper powder, cuprous sulfocyanide, preferably copper chloride；With
Molar amount, the dosage of copper catalyst are the 1-10% of the formula (I) compound amount, preferably 10%.
(2) alkali
Alkali in the present invention is lithium carbonate, cesium carbonate, potassium carbonate, sodium carbonate, ammonium hydrogen carbonate, sodium acetate, lithium acetate, acetic acid
At least one of potassium, potassium phosphate, sodium phosphate, sodium tert-butoxide, potassium fluoride, sodium fluoride, tert-butyl alcohol lithium or potassium tert-butoxide, preferably phosphorus
Sour potassium；With molar amount, the dosage of the potassium phosphate and the formula (I) amount ratio are 1: 1-1: 5, preferably 1: 3.
(3) organic solvent
Reaction dissolvent in the present invention is organic solvent, and the organic solvent is dimethyl sulfoxide, N, N- dimethyl formyl
Amine, polyethylene glycol, methylene chloride, ethyl acetate, pyridine, n-hexane, six alkane of Isosorbide-5-Nitrae-dioxy, 1,2- dichloroethanes, toluene, tetrahydro
At least one of furans, methanol, ether, carbon tetrachloride, chloroform, n-butanol, preferably n,N-Dimethylformamide.
(4) reaction temperature
In preparation method of the invention, reaction temperature be 80-140 DEG C, may be, for example, in non-limiting manner 80 DEG C, 100 DEG C,
120 DEG C and 140 DEG C, preferably 140 DEG C of reaction temperature.
(5) reaction time
In the preparation process in accordance with the present invention, the reaction time, there is no particular limitation, such as can be detected by liquid chromatograph
The residual percentage of target product or raw material and determine suitable reaction time, it typically is 15-24 hours, it is non-limiting for example
It is 15 hours, 17 hours, 19 hours, 21 hours, 23 hours or 24 hours, the reaction time preferably 24 hours.
(6) it isolates and purifies
Mixture resulting after reaction can be isolated and purified further, purer final products have been obtained.This
The field method well-known to the ordinarily skilled artisan isolated and purified, such as can chromatograph, distill, filter, be centrifuged, wash using extraction, column
It washs, be fractionated and adsorb or the methods of at least two combination is isolated and purified, such as extraction, column chromatography.
Certainly it directly reacts if necessary to which the reaction mixture of acquisition can also be introduced directly into other processes to produce
Other products.Optionally, before being introduced into other processes, reaction mixture can be pre-processed, for example, concentration, extraction
It one of takes and is evaporated under reduced pressure or kinds of experiments operation, to obtain crude product or pure product, be then introduced into other processes.
In a preferred embodiment, post-processing step after reaction can be following method：After reaction,
Ethyl acetate filtering will be added after reaction solution cooling, be concentrated under reduced pressure, (wherein silica gel is 300- by pillar layer separation by concentrate
400 mesh silica gel), using petroleum ether and ether body mixed liquor as eluant, eluent, eluent is collected, obtains target product after concentration.
The preparation method of 2- (2,4,6- trimethylbenzene seleno)--5 carboxylate compound of 1,3- oxazole provided by the invention
It has the advantages that：
A) reaction efficiently, high income, post-processing it is simple, easy to operate；
B) alkali, copper catalyst are cheap and easy to get；
C) using elemental selenium as seleno reagent；
D) reaction efficiency is higher after reaction amplification.
The present invention is to be easy structure shown in -5 carboxylic acid, ethyl ester of 1,3- oxazole and formula (II) of the structure as shown in (I) of preparation
2,4,6- trimethyl iodobenzenes are reaction raw materials, using elemental selenium as seleno reagent, under nitrogen reaction atmosphere, in transition metal copper
Catalyst and alkali collectively promote under effect, and reaction obtains the 2- (2,4,6- trimethylbenzene seleno) -1 of structure shown in formula (III),
- 5 carboxylate compound of 3- oxazole.Reaction condition, post-processing operation are simple, are suitble to large-scale industrial production.
Specific embodiment
Below by specific embodiment, the present invention is described in detail, but the purposes of these exemplary embodiments and
Purpose is only used to enumerate the present invention, not constitutes any type of any restriction to real protection scope of the invention, more non-to incite somebody to action
Protection scope of the present invention is confined to this.
The data and purity of noval chemical compound given by following embodiment are identified by nuclear magnetic resonance.
Embodiment 1
2- (2,4,6- trimethylbenzene seleno)--5 carboxylate compound of 1,3- oxazole synthesis
At room temperature, by 2,4,6- trimethyl iodobenzenes (1.2mmol, 3equiv), elemental selenium (1.2mmol, 3equiv), 1,
- 5 carboxylic acid, ethyl ester of 3- oxazole (0.4mmol, 1equiv), copper chloride (0.04mmol), potassium phosphate (1.2mmol, 3equiv) are added
Into reaction tube, it is then charged with nitrogen, and replace three times, under nitrogen reaction environment, 2mLN, N- dimethyl methyl is then added
Amide reaction dissolvent stirs for 24 hours under 140 DEG C of reaction temperatures.After reaction by thin-layer chromatography monitoring, by reaction mixture
It is cooling, ethyl acetate is then added and is diluted, the solution after dilution is transferred in separatory funnel, is extracted with saturated salt solution
It takes, isolates water phase and organic phase, then be extracted with ethyl acetate water phase 3 times, merge organic phase, 5g anhydrous sodium sulfate is added, it is quiet
Only 30min is washed filter cake 3 times with 5mL ethyl acetate every time, then spin off solvent totally, obtains product (elution through column chromatography for separation
Agent: petroleum ether: ether=98: 2), product is yellow solid, and fusing point is 68-69 DEG C, yield 68%, products weight 92mg.
The data of the nuclear magnetic resonance spectroscopy of products therefrom are as follows：
1H NMR (500MHz, CDCl3)：δ 7.62 (s1H), 7.01 (s, 2H), 4.34 (q, J=7.1Hz, 2H), 2.48 (s,
6H), 2.30 (s, 3H), 1.35 (t, J=7.1Hz, 3H).
The data of the carbon-13 nmr spectra of products therefrom are as follows：
13C NMR (125MHz, CDCl3)：δ 159.3,157.4,145.2,143.3,140.6,135.5,129.3,
129.0,123.2,61.3,24.3,21.1,14.2.
It is as follows to the theoretical calculation and experimental result of product progress high resolution mass spectrum：
HRMS(ESI)：calcd for C15H17NO3Se[M+H]+340.0447 found 340.0463.
Embodiment 2
A kind of amplification synthesis of 2- (2,4,6- trimethylbenzene seleno)--5 carboxylate compound of 1,3- oxazole
At room temperature, by 2,4,6- trimethyl iodobenzenes (12mmol, 3equiv), elemental selenium (12mmol, 3equiv), 1,3-
- 5 carboxylic acid, ethyl ester of oxazole (4mmol, 1equiv), copper chloride (0.4mmol), potassium phosphate (12mmol, 3equiv) are added to reaction
Guan Zhong is then charged with nitrogen, and replaces three times, and under nitrogen reaction environment, 20mL n,N-Dimethylformamide is then added
Reaction dissolvent stirs for 24 hours under 140 DEG C of reaction temperatures.After reaction by thin-layer chromatography monitoring, reaction mixture is cold
But, ethyl acetate is then added to be diluted, the solution after dilution is transferred in separatory funnel, is extracted with saturated salt solution,
Water phase and organic phase are isolated, then is extracted with ethyl acetate water phase 3 times, organic phase is merged, 25g anhydrous sodium sulfate is added, it is static
30min is washed filter cake 3 times with 50mL ethyl acetate every time, then spin off solvent totally, obtains product (elution through column chromatography for separation
Agent: petroleum ether: ether=98: 2), yield 77%, products weight 1.044g.
It can be seen that by above-described embodiment 1-2, when using the method described in the present invention, can be obtained with high yield, high-purity
To 2- (2,4,6- trimethylbenzene seleno)--5 carboxylate compound of 1,3- oxazole.
Embodiment 3-14
In addition to catalyst copper chloride therein is replaced with following copper catalyst respectively, with with highest products collection efficiency
The identical mode of embodiment 1 and implement embodiment 3-14 respectively, the yield of used copper compound and corresponding product is as follows
Shown in table 1.
Table 1
| Number | Copper catalyst | Reaction yield (%) |
| Embodiment 4 | It does not react | |
| Embodiment 5 | Stannous chloride | 29 |
| Embodiment 6 | Copper acetate | 24 |
| Embodiment 7 | Cuprous bromide | 44 |
| Embodiment 8 | Copper oxide | 26 |
| Embodiment 9 | Cuprous iodide | 33 |
| Embodiment 10 | Copper bromide | 14 |
| Embodiment 11 | Copper fluoride | 55 |
| Embodiment 12 | Three fluosulfonic acid copper | 31 |
| Embodiment 13 | Acetylacetone copper | 25 |
| Embodiment 14 | Copper powder | It does not react |
| Embodiment 15 | Cuprous sulfocyanide | 19 |
It can be seen that by upper table 1, when using other copper compounds, products collection efficiency is greatly lowered.Thus this is demonstrated
Catalyst copper chloride used in inventing has efficient catalytic performance for the reaction.
Embodiment 15-28
In addition to alkali potassium phosphate therein is replaced with following inorganic base respectively, with the implementation with highest products collection efficiency
The identical mode of example 1 and implement embodiment 15-28 respectively, the yield of used alkali cpd and corresponding product such as the following table 2 institute
Show.
Table 2
| Number | Alkali | Reaction yield (%) |
| Embodiment 15 | Ammonium hydrogen carbonate | It does not react |
| Embodiment 16 | Lithium carbonate | It does not react |
| Embodiment 17 | Sodium carbonate | It does not react |
| Embodiment 18 | Cesium carbonate | It does not react |
| Embodiment 19 | Potassium carbonate | It does not react |
| Embodiment 20 | Sodium phosphate | It does not react |
| Embodiment 21 | Tert-butyl alcohol lithium | It does not react |
| Embodiment 22 | Sodium tert-butoxide | It does not react |
| Embodiment 23 | Potassium tert-butoxide | It does not react |
| Embodiment 24 | Sodium acetate | It does not react |
| Embodiment 25 | Lithium acetate | It does not react |
| Embodiment 26 | Potassium acetate | It does not react |
| Embodiment 27 | Potassium fluoride | It does not react |
| Embodiment 28 | Sodium fluoride | It does not react |
It can be seen that by upper table 2, when using other alkali, almost do not react, thus demonstrating potassium phosphate is the reaction
Successful key factor, and it is maximally efficient to the reaction system.
Embodiment 29-43
In addition to organic solvent n,N-Dimethylformamide therein is replaced with following organic solvent respectively, with have
The identical mode of embodiment 1 of highest products collection efficiency and implement embodiment 29-43 respectively, used organic solvent and corresponding produce
The yield of object is as shown in table 3 below.
Table 3
| Number | Solvent | Reaction yield (%) |
| Embodiment 29 | Dimethyl sulfoxide | 18 |
| Embodiment 30 | Methanol | It does not react |
| Embodiment 31 | Polyethylene glycol | It does not react |
| Embodiment 32 | Methylene chloride | It does not react |
| Embodiment 33 | Ethyl acetate | It does not react |
| Embodiment 34 | Pyridine | It does not react |
| Embodiment 35 | N-hexane | 24 |
| Embodiment 36 | Six alkane of Isosorbide-5-Nitrae-dioxy | It does not react |
| Embodiment 37 | 1,2- dichloroethanes | It does not react |
| Embodiment 38 | Toluene | It does not react |
| Embodiment 39 | Tetrahydrofuran | It does not react |
| Embodiment 40 | Ether | It does not react |
| Embodiment 41 | Carbon tetrachloride | It does not react |
| Embodiment 42 | Chloroform | It does not react |
| Embodiment 43 | N-butanol | It does not react |
It can be seen that by upper table 3, when using other organic solvents, in addition to that can occur instead in intensive polar solvent dimethyl sulfoxide
It answers, but yield still has significant decrease；And there is no spawn under the conditions of nonpolarity or even weak ligand solvent.This demonstrate that organic
Can the suitable selection of solvent carry out significant, even conclusive influence to reaction.
In conclusion can clearly be found out by above-mentioned all embodiments, copper is selected from when using using method of the invention
Object is closed as catalyst (especially copper chloride), alkali (especially potassium phosphate), suitable organic solvent (especially N, N- dimethyl
Formamide) composed by recombination reaction system when, -5 carboxylic acid, ethyl ester of 1,3- oxazole and elemental selenium and 2,4,6- trimethyls can be made
Iodobenzene is occurred tandem reaction and is synthesized to obtain 2- (2,4,6- trimethylbenzene seleno) -1, -5 carboxylic of 3- oxazole with high yield and high-purity
Acetoacetic ester compound provides completely new synthetic route for the efficient quick synthesis of such compound.
Finally it should be noted that：The above embodiments are only used to illustrate the technical solution of the present invention., rather than its limitations；To the greatest extent
Present invention has been described in detail with reference to the aforementioned embodiments for pipe, those skilled in the art should understand that：Its according to
Right scientific research modifies the technical solutions described in the foregoing embodiments, or to some or all of the technical features into
Row equivalent replacement；And these are modified or replaceed, various embodiments of the present invention technology that it does not separate the essence of the corresponding technical solution
The range of scheme.
Claims (9)
1. a kind of 2- (2,4,6- trimethylbenzene seleno)--5 carboxylate compound of 1,3- oxazole and preparation method, feature exist
In, in organic solvent, to have 2 of structure shown in -5 carboxylic acid, ethyl ester of 1,3- oxazole and formula (II) of the structure as shown in formula (I),
4,6- trimethyl iodobenzenes are reaction raw materials, using elemental selenium as seleno reagent, copper catalyst and alkali collectively promote effect under,
2- (2,4,6- trimethylbenzene seleno)--5 carboxylic acid, ethyl ester of 1,3- oxazole of structure shown in formula (III) is obtained by tandem reaction
Close object.
2. preparation method according to claim 1, which is characterized in that the copper catalyst is organic copper or Inorganic Copper chemical combination
Object；With molar amount, the dosage of the copper catalyst is the 10% of the formula (I) compound amount.
3. preparation method according to claim 1, which is characterized in that the copper catalyst be stannous chloride, cuprous iodide,
Cuprous bromide, copper oxide, copper chloride, copper bromide, copper fluoride, three fluosulfonic acid copper, acetylacetone copper, copper acetate, copper powder, thiocyanic acid
It is at least one of cuprous, preferably copper chloride.
4. preparation method as described in claim 1, which is characterized in that the alkali is lithium carbonate, cesium carbonate, potassium carbonate, carbonic acid
Sodium, ammonium hydrogen carbonate, sodium acetate, lithium acetate, potassium acetate, potassium phosphate, sodium phosphate, sodium tert-butoxide, potassium fluoride, sodium fluoride, the tert-butyl alcohol
Lithium or potassium tert-butoxide, preferably potassium phosphate.
5. preparation method according to claim 1, which is characterized in that the reaction dissolvent is organic solvent, described organic
Solvent is dimethyl sulfoxide, n,N-Dimethylformamide, polyethylene glycol, methylene chloride, ethyl acetate, pyridine, n-hexane, Isosorbide-5-Nitrae-
Six alkane of dioxy, 1,2- dichloroethanes, toluene, tetrahydrofuran, methanol, ether, carbon tetrachloride, chloroform, at least one in n-butanol
Kind, preferably n,N-Dimethylformamide.
6. preparation method according to claim 1, it is characterised in that：- 5 carboxylic acid of 1,3- oxazole of structure shown in (I)
The molar ratio of ethyl ester and 2,4,6- trimethyl iodobenzenes of structure shown in formula (II) is 1: 1-1: 5；1,3- of structure shown in (I)
The molar ratio of -5 carboxylic acid, ethyl ester of oxazole and elemental selenium is 1: 1-1: 5；- 5 carboxylic acid, ethyl ester of 1,3- oxazole of structure shown in (I) with
The molar ratio of alkali is 1: 1-1: 5.
7. preparation method according to claim 1, which is characterized in that the temperature of the range is 80-140 DEG C.
8. preparation method according to claim 1, which is characterized in that the time of the reaction is 15-30h.
9. 2- (2,4,6- trimethylbenzene seleno)-- 5 carboxylate compound's of 1,3- oxazole as described in claim 1-a kind of
Preparation method, it is characterised in that：After reaction, will reaction solution it is cooling after extractant extraction is added, isolate water phase and organic
Phase takes the organic phase containing extractant and target product and is dried with anhydrous sodium sulfate, is concentrated under reduced pressure, concentrate is passed through column chromatography
Separation (wherein silica gel is 300-400 mesh silica gel), is 98: 2 mixed liquors as eluant, eluent using petroleum ether and ether volume ratio, collection is washed
De- liquid, obtains the 2- as shown in formula (III) (2,4,6- trimethylbenzene seleno)--5 carboxylic acid, ethyl ester of 1,3- oxazole after rotating solvent
Close object.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810165331 | 2018-02-19 | ||
| CN2018101653319 | 2018-02-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108863971A true CN108863971A (en) | 2018-11-23 |
| CN108863971B CN108863971B (en) | 2021-06-15 |
Family
ID=64333809
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810445406.9A Active CN108863971B (en) | 2018-02-19 | 2018-05-04 | 2- (2, 4, 6-trimethylphenylseleno) -1, 3-oxazole-5 ethyl carboxylate compound and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108863971B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110357805A (en) * | 2019-06-19 | 2019-10-22 | 温州医科大学 | A kind of preparation method of N- methyl -3- phenylseleno maleimide compound |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104387311A (en) * | 2014-12-03 | 2015-03-04 | 温州大学 | Synthetic method of 3-arylselanyl indole compound |
| CN106565629A (en) * | 2016-10-27 | 2017-04-19 | 温州大学 | Synthesis method of 2-phenylselenic benzothiazole compound |
| CN107056727A (en) * | 2017-03-29 | 2017-08-18 | 温州医科大学 | A kind of oxadiazole compound of 5 arylseleno of 2 aryl 1,3,4 and preparation method |
| CN107188841A (en) * | 2017-05-16 | 2017-09-22 | 温州医科大学 | A kind of synthetic method of asymmetric diaryl list selenide compound |
-
2018
- 2018-05-04 CN CN201810445406.9A patent/CN108863971B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104387311A (en) * | 2014-12-03 | 2015-03-04 | 温州大学 | Synthetic method of 3-arylselanyl indole compound |
| CN106565629A (en) * | 2016-10-27 | 2017-04-19 | 温州大学 | Synthesis method of 2-phenylselenic benzothiazole compound |
| CN107056727A (en) * | 2017-03-29 | 2017-08-18 | 温州医科大学 | A kind of oxadiazole compound of 5 arylseleno of 2 aryl 1,3,4 and preparation method |
| CN107188841A (en) * | 2017-05-16 | 2017-09-22 | 温州医科大学 | A kind of synthetic method of asymmetric diaryl list selenide compound |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110357805A (en) * | 2019-06-19 | 2019-10-22 | 温州医科大学 | A kind of preparation method of N- methyl -3- phenylseleno maleimide compound |
| CN110357805B (en) * | 2019-06-19 | 2020-11-17 | 温州医科大学 | Preparation method of N-methyl-3-phenylseleno maleimide compound |
Also Published As
| Publication number | Publication date |
|---|---|
| CN108863971B (en) | 2021-06-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107188841B (en) | A kind of synthetic method of asymmetry diaryl list selenide compound | |
| CN107056727A (en) | A kind of oxadiazole compound of 5 arylseleno of 2 aryl 1,3,4 and preparation method | |
| CN108675948A (en) | A kind of beta-hydroxy selenide compound and preparation method | |
| CN109320496B (en) | Selenocyanization reagent and preparation method and application thereof | |
| CN107188840B (en) | A kind of synthetic method of asymmetry diaryl selenide compound | |
| CN109651225B (en) | Preparation method of 1-methyl-3-morphinyl-4-arylmercapto maleimide compound | |
| CN107188846A (en) | A kind of synthetic method of arylseleno heterocyclic compound | |
| CN109705013A (en) | A kind of 1-(4- methylbenzyl) -3- amino -4- first seleno maleimide compound and preparation method | |
| CN108675961A (en) | A kind of 1- methyl -2-（2,4,6- trimethylbenzene selenos）Benzimidazole compound and preparation method | |
| CN108863971A (en) | A kind of 2-（2,4,6- trimethylbenzene seleno）- 5 carboxylate compound of -1,3- oxazole and preparation method | |
| CN114702475A (en) | Synthesis process of single-configuration nicotine | |
| CN108484518A (en) | A kind of 2-（2,4,6- trimethylbenzene selenos）- 5- methylbenzoxazoles compound and preparation method | |
| CN107033048A (en) | A kind of synthetic method of aryl methyl selenide compound | |
| CN108864097A (en) | A kind of 2- arylseleno theophylline compound and preparation method | |
| CN114315535A (en) | Preparation method of eldecalcitol isomer impurity | |
| CN102942547A (en) | GA4And/or GA7Separation and purification method of | |
| CN108558785A (en) | A kind of 5- aryl -2- arylseleno -1,3- oxazole compounds and preparation method | |
| CN103130708B (en) | A kind of preparation method of N-tertbutyloxycarbonyl-4-nitro piperidines | |
| CN108912026A (en) | A kind of alkynylalkyl selenide compound and preparation method | |
| CN108912045A (en) | A kind of 2- phenylseleno quinoline compound and preparation method | |
| CN109956926A (en) | A kind of radioactive isotope carbon -14 marks the synthetic method of imidacloprid | |
| CN107540575B (en) | Preparation method of sitagliptin intermediate | |
| CN101348411B (en) | Preparation of 2-alkyl anthracene derivative | |
| CN109824667A (en) | A kind of method of synthesis of indole diindyl zionoes compound | |
| CN113135862A (en) | Synthetic method of 6-fluoro-3-hydroxypyrazine-2-carboxylic acid |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |