Oxime ether containing active group and synthetic method thereof
阅读说明：本技术 一种含活性基团的肟醚及其合成方法 (Oxime ether containing active group and synthetic method thereof ) 是由 徐书群 叶利民 祝俊 王艳霞 叶黎霞 于 2019-09-17 设计创作，主要内容包括：本发明涉及有机物合成技术领域,尤其是一种含活性基团的肟醚及其合成方法,其具体如下通式(I)所示结构,<Image he="233" wi="501" file="DDA0002204038760000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>式中,R<Sub>1</Sub>包括为氢、甲基、乙基；R<Sub>2</Sub>为氢、C<Sub>1</Sub>-C<Sub>10</Sub>的烷基、环烷基或芳香基；R<Sub>3</Sub>为烯丙基或甲基烯丙基或环氧丙烷基,本发明引进活性基团可以大大扩展产品应用。(The invention relates to the technical field of organic matter synthesis, in particular to oxime ether containing active groups and a synthesis method thereof, which have a structure shown in a general formula (I), in the formula, R 1 Comprises hydrogen, methyl and ethyl; r 2 Is hydrogen, C 1 ‑C 10 Alkyl, cycloalkyl or aryl of (a); r 3 The invention introduces active groups to greatly expand the application of products.)
1. An oxime ether containing an active group, characterized in that: the structure is shown in the following general formula (I),
in the formula, R1Comprises hydrogen, methyl and ethyl;
R2is hydrogen, C1-C10Alkyl, cycloalkyl or aryl of (a);
R3is allyl or methallyl or propylene oxide.
2. The oxime ether containing an active group as claimed in claim 1 wherein: in the general formula (I), R3The structural formula of (A) is: -C ═ C or
3. A synthetic method of oxime ether containing active groups is characterized in that: the method comprises the following steps:
(1) adding ketoxime, a solvent and alkali into a reaction kettle;
(2) adding an alkylating reagent to carry out alkylation reaction;
(3) carrying out solid-liquid separation after the alkylation reaction is finished;
(4) and detecting the content of oxime ether in the organic phase.
4. The method of claim 3, wherein the oxime ether contains an active group, and the method comprises the following steps: the alkali is sodium hydroxide, potassium methoxide, sodium methoxide, potassium ethoxide, sodium ethoxide, potassium tert-butoxide, and sodium tert-butoxide.
5. The method of claim 3, wherein the oxime ether contains an active group, and the method comprises the following steps: according to the steps (1) and (2), the reaction temperature in the reaction process is 20-60 ℃.
6. The method of synthesizing oxime ethers containing active groups according to claim 5 wherein: and after the reaction is finished, dropwise adding a compound reagent, wherein the compound reagent is chloropropene, bromopropylene, methallyl chloride or epoxy chloropropane.
7. The method of claim 3, wherein the oxime ether contains an active group, and the method comprises the following steps: the molar ratio of ketoxime to alkylation is 1: 0.9-1.2.
8. The method of claim 3, wherein the oxime ether contains an active group, and the method comprises the following steps: the molar ratio of the ketoxime to the alkali is 1: 0.9-1.5.
9. The method of claim 3, wherein the oxime ether contains an active group, and the method comprises the following steps: the molar ratio of the ketoxime to the solvent is 1: 0.9-3.
10. The method of claim 3, wherein the oxime ether contains an active group, and the method comprises the following steps: according to the step (2), the alkylation time is 1-6 hours.
Technical Field
The invention relates to the technical field of organic matter synthesis, in particular to oxime ether containing active groups and a synthesis method thereof.
Background
The oxime ether is an important chemical product, and is applied to synthesis of high polymer materials, medicines, pesticides and low-toxicity bactericides.
Disclosure of Invention
The invention aims to provide oxime ether containing active groups and a synthesis method thereof.
In order to achieve the purpose, the invention provides the following technical scheme: an oxime ether containing active groups, which has a structure shown in a general formula (I),
in the formula, R1Comprises hydrogen, methyl and ethyl;
R2is hydrogen, C1-C10Alkyl, cycloalkyl or aryl of (a);
R3is allyl or methallyl or propylene oxide.
Preferably, in the formula (I), R3The structural formula of (A) is:
-C ═ C or
In order to achieve the above purpose, the invention also provides the following technical scheme: a synthetic method of oxime ether containing active groups comprises the following steps:
(1) adding ketoxime, a solvent and alkali into a reaction kettle;
(2) adding an alkylating reagent to carry out alkylation reaction;
(3) carrying out solid-liquid separation after the alkylation reaction is finished;
(4) and detecting the content of oxime ether in the organic phase.
Preferably, the base is sodium hydroxide, potassium methoxide, sodium methoxide, potassium ethoxide, sodium ethoxide, potassium tert-butoxide, sodium tert-butoxide.
Preferably, according to the steps (1) and (2), the reaction temperature in the reaction process is 20-60 ℃.
Preferably, a compound reagent is dropwise added after the reaction is completed, wherein the compound reagent is chloropropene, bromopropylene, methallyl chloride or epichlorohydrin.
Preferably, the molar ratio of ketoxime to alkylation is 1: 0.9-1.2.
Preferably, the molar ratio of the ketoxime to the alkali is 1: 0.9-1.5.
Preferably, the molar ratio of the ketoxime to the solvent is 1: 0.9-3.
Preferably, according to step (2), the alkylation time is 1 to 6 hours.
Compared with the prior art, the invention has the beneficial effects that: the oxime ether containing active groups is introduced, the application of products can be greatly expanded, and the oxime ether containing active groups can be applied to the synthesis of high polymer materials, medicines, pesticides and low-toxicity bactericides.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The invention provides a technical scheme that: an oxime ether containing active groups, which has a structure shown in a general formula (I),
in the formula, R1Comprises hydrogen, methyl and ethyl;
R2is hydrogen, C1-C10Alkyl, cycloalkyl or aryl of (a);
R3is allyl or methallyl or propylene oxide.
In the general formula (I), R3The structural formula of (A) is:
-C ═ C or
A synthetic method of oxime ether containing active groups comprises the following steps:
(1) adding ketoxime, a solvent and alkali into a reaction kettle;
(2) adding an alkylating reagent to carry out alkylation reaction;
(3) carrying out solid-liquid separation after the alkylation reaction is finished;
(4) and detecting the content of oxime ether in the organic phase.
The alkali is sodium hydroxide, potassium methoxide, sodium methoxide, potassium ethoxide, sodium ethoxide, potassium tert-butoxide, and sodium tert-butoxide.
According to the steps (1) and (2), the reaction temperature in the reaction process is 20-60 ℃.
And after the reaction is finished, dropwise adding a compound reagent, wherein the compound reagent is chloropropene, bromopropylene, methallyl chloride or epoxy chloropropane.
The molar ratio of ketoxime to alkylation is 1: 0.9-1.2.
The molar ratio of the ketoxime to the alkali is 1: 0.9-1.5.
The molar ratio of the ketoxime to the solvent is 1: 0.9-3.
According to the step (2), the alkylation time is 1-6 hours.
According to the steps, solid-liquid separation is carried out after the alkylation reaction is finished;
extracting the organic phase in the solid by an extracting agent; combining the extract phases; the ketoxime ether is isolated.
According to the process, the extracting agent is n-hexane, DMSO, ethyl acetate.
The ketoxime is acetone oxime, butanone oxime, diamyl ketoxime, methyl isobutyl ketoxime, benzaldehyde oxime, cyclohexanone oxime, n-butyraldehyde oxime or isobutyraldehyde oxime.
The present invention will be described in further detail with reference to examples, but the present invention is not limited to the examples.