CN107973715A - A kind of preparation method of polysubstituted distal end allyl ketone derivative - Google Patents
A kind of preparation method of polysubstituted distal end allyl ketone derivative Download PDFInfo
- Publication number
- CN107973715A CN107973715A CN201711351437.XA CN201711351437A CN107973715A CN 107973715 A CN107973715 A CN 107973715A CN 201711351437 A CN201711351437 A CN 201711351437A CN 107973715 A CN107973715 A CN 107973715A
- Authority
- CN
- China
- Prior art keywords
- polysubstituted
- distal end
- ketone derivative
- preparation
- allyl ketone
- 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
- PUDYTOCWJLPKOW-UHFFFAOYSA-N OCC(CCCCC(c1ccccc1)=O)O Chemical compound OCC(CCCCC(c1ccccc1)=O)O PUDYTOCWJLPKOW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
Abstract
A kind of preparation method of polysubstituted distal end allyl ketone derivative, the present invention relates to a kind of preparation method of polysubstituted distal end allyl ketone derivative.The purpose of the invention is to provide a kind of preparation method of polysubstituted distal end allyl ketone derivative, the present invention is in nitrogen atmosphere, at room temperature by three-level cyclol derivant, ethylenic unsaturation compound and photochemical catalyst dissolving are in organic solvent, it is uniformly mixed, it is placed in again under blue LED lamp and carries out illumination reaction, through silica gel column chromatography separating purification after revolving removal solvent, products therefrom is that polysubstituted distal end allyl ketone derivative the method for the present invention can react at normal temperatures and pressures, reaction condition is gentle, yield is up to 80%, and with easy to operate, it is pollution-free, safety and environmental protection, the advantages of cost is low.The present invention is applied to organic synthesis field.
Description
Technical field
The present invention relates to a kind of preparation method of polysubstituted distal end allyl ketone derivative.
Background technology
Cyclic alcohol is widely existed among biologically active natural products and drug molecule, while still very much
The important raw material midbody of work product and other natural products, according to the literature, passes through a series of conversion reaction, it is possible to
All kinds of important chemical raw material intermediates are obtained, such as undersaturated distal end diketone ketone compounds 1, distal end enols used 2,
Glycolsization 3.
At present, synthesizing polysubstituted distal end allyl ketone derivative report by cyclic alcohol open loop mainly has cyclic alcohol open loop fluorination instead
Should, alkynyl, cyanalation reaction, ammoxidation, but directly allylation is not yet reported that.And existing synthetic method is big
Use high-temperature heating system, energy consumption is high, and requirement of the condition harshness to equipment is big, and low yield more, is mostly 50%-60%.Cause
This, seeks to a kind of mild condition, the conjunction for the polysubstituted distal end allyl ketone derivative that method is simple and easy to operate yield is high
It is current urgent problem to be solved into method.
The content of the invention
The purpose of the present invention is to solve the method that existing cyclic alcohol open loop synthesizes polysubstituted distal end allyl ketone derivative
High-temperature heating system is used mostly, energy consumption is high, and requirement of the condition harshness to equipment is big, and the problem of low yield, there is provided it is a kind of
The preparation method of polysubstituted distal end allyl ketone derivative.
A kind of preparation method of polysubstituted distal end allyl ketone derivative of the present invention includes the following steps：
In nitrogen atmosphere, at room temperature three-level cyclol derivant, ethylenic unsaturation compound, alkali and photochemical catalyst are dissolved in
In solvent, it is uniformly mixed, then is placed under blue LED lamp and carries out illumination reaction, revolving is divided after removing solvent through silica gel column chromatography
From purifying, products therefrom is polysubstituted distal end allyl ketone derivative；Ethylenic unsaturation compound, three-level cyclol derivant, alkali
Molar ratio with photochemical catalyst is 2:1:2.5:0.5；
The chemical structural formula of wherein three-level cyclol derivant is：
The chemical structural formula of ethylenic unsaturation compound is：
The chemical structural formula of photochemical catalyst is：
Wherein, R1、R2And R3For alkyl, alkoxy or halogen, it is alkoxy, alkyl or polyaromatic that the upper substituents of Ar, which are,；
N is 0-9.
The present invention provides a kind of preparation method of polysubstituted distal end allyl ketone derivative, polysubstituted distal end allyl ketone
Derivative has various path for transformation, can be as the intermediate of many industrial chemicals, so compound provided by the invention
With higher researching value, it may be used as the research and development such as drug development and the synthesis of industrial chemicals intermediate and use.The present invention is also
It can be used as other raw materials for containing isoxazole alkane derivatives are synthesized.The method of the present invention at normal temperatures and pressures can be anti-
Should, reaction condition is gentle, and yield has the advantages that easy to operate, pollution-free, safety and environmental protection, cost are low up to 80%.
Embodiment
Embodiment one：A kind of preparation method of polysubstituted distal end allyl ketone derivative of present embodiment is included such as
Lower step：
In nitrogen atmosphere, at room temperature three-level cyclol derivant, ethylenic unsaturation compound, alkali and photochemical catalyst are dissolved in
In solvent, it is uniformly mixed, then is placed under blue LED lamp and carries out illumination reaction, revolving is divided after removing solvent through silica gel column chromatography
From purifying, products therefrom is polysubstituted distal end allyl ketone derivative；Ethylenic unsaturation compound, three-level cyclol derivant, alkali
Molar ratio with photochemical catalyst is 2:1:2.5:0.5；
The chemical structural formula of wherein three-level cyclol derivant is：
The chemical structural formula of ethylenic unsaturation compound is：
The chemical structural formula of photochemical catalyst is：
Wherein, R1、R2And R3For alkyl, alkoxy or halogen, it is alkoxy, alkyl or polyaromatic that the upper substituents of Ar, which are,；
N is 0-9.
The structural formula of the polysubstituted distal end allyl ketone derivative of present embodiment is：
Wherein R1、R2For substituted aromatic base or alkyl, R3For alkyl, the substituent on Ar is
Aryl；The substituted aromatic base is substituted-phenyl or polyaromatic, n 0-9.
Preferably, the substituted aromatic base is p-methoxyphenyl.
Present embodiments provide for a kind of preparation method of polysubstituted distal end allyl ketone derivative, polysubstituted distal end allyl
Base ketone derivatives have various path for transformation, can be as the intermediate of many industrial chemicals, so present embodiment provides
Compound there is higher researching value, may be used as drug development and industrial chemicals intermediate synthesis etc. research and development use.
Present embodiment can also be used as other raw materials for containing isoxazole alkane derivatives are synthesized.Present embodiment method is normal
Can be reacted under normal temperature and pressure, reaction condition is gentle, yield up to 80%, and with easy to operate, pollution-free, safety and environmental protection, into
The advantages of this is low.
Embodiment two：The present embodiment is different from the first embodiment in that：Ethylenic unsaturation compound is first
The α of base substitution, β beta-unsaturated esters, the α of ethyl substitution, β beta-unsaturated esters, nitro substitution α, β beta-unsaturated esters or cyano group substitution α, β is not
Saturated ester.Other are identical with embodiment one.
Embodiment three：This embodiment party is unlike embodiment one or two：Three-level cyclol derivant is
Ternary cyclic alcohol, quaternary cyclic alcohol, five-membered ring alcohol, twelve-ring alcohol, the more alkyl substitution cyclic alcohol in ortho position or ortho position aryl substitution cyclic alcohol.Its
He is the same as one or two specific embodiments.
Embodiment four：Unlike one of present embodiment and embodiment one to three：Organic solvent is
Dichloromethane, dichloroethanes, acetonitrile or N, N- dicarboximide.Other are different from one of embodiment one to three.
Embodiment five：Unlike one of present embodiment and embodiment one to four：Three-level cyclic alcohol spreads out
The molal volume ratio of biology and organic solvent is 1mmol:(10-20)mL.Other are different from one of embodiment one to four.
Embodiment six：Unlike one of present embodiment and embodiment one to five：In blue LED lamp
The lower progress illumination reaction time will be 12-48h.Other are different from one of embodiment one to five.
Embodiment seven：Unlike one of present embodiment and embodiment one to six：Silica gel column chromatography
Solvent for use is isolated and purified as petroleum ether and the mixed solvent of ethyl acetate.Other phases one of with embodiment one to six
Together.
Embodiment eight：Unlike one of present embodiment and embodiment one to seven：In the mixed solvent
The volume ratio of petroleum ether and ethyl acetate is (20-50):1.Other are different from one of embodiment one to seven.
Embodiment nine：Unlike one of present embodiment and embodiment one to eight：Photochemical catalyst is
Ir[dF(CF3)ppy]2(dtbpy)PF6.Other are different from one of embodiment one to eight.
Embodiment ten：Unlike one of present embodiment and embodiment one to nine：Alkali is 2.4.6-
Trimethylpyridine.Other are different from one of embodiment one to nine.
Following experiment has been carried out for verification beneficial effects of the present invention：
Embodiment one：A kind of preparation method of polysubstituted distal end allyl ketone derivative
In nitrogen atmosphere, at room temperature by 35.6mg (0.2mmol) to methoxyl group cyclobutanol, 100mg (0.4mmol) unsaturations
Ester, 1.2mg (0.005mmol) [dF (CF3)ppy]2(dtbpy)PF64mL is dissolved in 0.5mmol 2.4.6- trimethylpyridines
In dichloromethane, it is uniformly mixed, then is placed in progress illumination reaction 28h under blue LED lamp, Rotary Evaporators concentration removes dichloromethane
After alkane, then using volume ratio as 50:1 petroleum ether：The mixed solution of ethyl acetate carries out silica gel column chromatography purifying as eluant, eluent
Separation, products therefrom is polysubstituted distal end allyl ketone derivative；Its reaction equation is：
Product purity is 99%, yield 73%.Nuclear magnetic data is analyzed：1H NMR(400MHz,CDCl3):δH7.98-
7.88 (m, 2H), 6.97-6.88 (m, 2H), 6.13 (d, J=1.3Hz, 1H), 5.53 (d, J=1.3Hz, 1H), 4.27-4.13
(t, 2H), 3.86 (s, 3H), 2.93 (t, J=7.4Hz, 2H), 2.34 (t, J=7.5Hz, 2H), 1.82-1.68 (m, 2H),
1.62-1.49 (m, 2H), 1.28 (t, J=7.1Hz, 3H).
13C NMR(100MHz,CDCl3):δC 198.9,167.4,163.4,140.7,130.4,130.2,124.7,
113.8,60.7,55.5,38.1,31.8,28.2,24.1,14.3。
Embodiment two, a kind of preparation method of polysubstituted distal end allyl ketone derivative
In nitrogen atmosphere, at room temperature by 38.4mg (0.2mmol) to methoxyl group cyclopentanol, 100mg (0.4mmol) unsaturations
Ester, 1.2mg (0.005mmol) [dF (CF3)ppy]2(dtbpy)PF64mL is dissolved in 0.5mmol 2.4.6- trimethylpyridines
In dichloromethane, it is uniformly mixed, then is placed in progress illumination reaction 28h under blue LED lamp, Rotary Evaporators concentration removes dichloromethane
After alkane, then using volume ratio as 50:1 petroleum ether：The mixed solution of ethyl acetate carries out silica gel column chromatography purifying as eluant, eluent
Separation, products therefrom is polysubstituted distal end allyl ketone derivative；Its reaction equation is：
Product purity is 99%, yield 70%.Its nuclear magnetic data is analyzed：1H NMR(600MHz,CDCl3):δH
7.93 (d, J=8.4Hz, 1H), 6.92 (d, J=8.4Hz, 1H), 6.12 (s, 1H), 5.50 (s, 1H), 4.19 (q, J=
7.1Hz, 1H), 3.85 (s, 2H), 2.90 (t, J=7.4Hz, 1H), 2.30 (t, J=7.6Hz, 1H), 1.80-1.69 (m, 1H),
1.78-1.70 (m, 1H), 1.51 (dt, J=15.2,7.6Hz, 1H), 1.40 (dt, J=15.0,7.7Hz, 1H), 1.28 (t, J
=7.1Hz, 1H).
13C NMR(151MHz,CDCl3):δC 199.1,167.4,163.4,141.0,130.4,130.2,124.5,
113.8,60.7,55.5,38.2,31.8,29.1,28.4,24.4,14.3。
Embodiment three, a kind of preparation method of polysubstituted distal end allyl ketone derivative
In nitrogen atmosphere, at room temperature by 58.0mg (0.2mmol) to methoxyl group cyclododecanol, 100mg (0.4mmol) insatiable hunger
With ester, 1.2mg (0.005mmol) [dF (CF3)ppy]2(dtbpy)PF6It is dissolved in 0.5mmol 2.4.6- trimethylpyridines
In 4mL dichloromethane, it is uniformly mixed, then is placed in progress illumination reaction 28h under blue LED lamp, Rotary Evaporators concentration removes two
After chloromethanes, then using volume ratio as 50:1 petroleum ether：The mixed solution of ethyl acetate carries out silica gel column chromatography as eluant, eluent
Purifies and separates, products therefrom are polysubstituted distal end allyl ketone derivative；Its reaction equation is：
Product purity is 99%, yield 81%.Its nuclear magnetic data is analyzed：1H NMR(600MHz,CDCl3):δH
7.93 (d, J=8.6Hz, 2H), 6.91 (d, J=8.6Hz, 2H), 6.10 (s, 1H), 5.49 (s, 1H), 4.18 (q, J=
7.1Hz, 2H), 3.85 (s, 3H), 2.89 (t, J=7.4Hz, 2H), 2.27 (t, J=7.6Hz, 2H), 1.74-1.64 (m, 2H),
1.43 (dd, J=14.3,7.0Hz, 2H), 1.38-1.18 (m, 20H).
13C NMR(151MHz,CDCl3):δC 199.3,167.5,163.4,141.2,130.4,130.3,124.2,
113.7,60.6,55.5,38.4,31.9,29.7,29.7,29.7,29.6,29.5,29.5,29.3,28.5,24.7,14.3。
Example IV, a kind of preparation method of polysubstituted distal end allyl ketone derivative
In nitrogen atmosphere, at room temperature by 44.0mg (0.2mmol) substitutions to methoxyl group cyclopentanol, 100mg (0.4mmol) no
Saturated ester, 1.2mg (0.005mmol) [dF (CF3)ppy]2(dtbpy)PF6It is dissolved in 0.5mmol 2.4.6- trimethylpyridines
In 4mL dichloromethane, it is uniformly mixed, then is placed in progress illumination reaction 28h under blue LED lamp, Rotary Evaporators concentration removes two
After chloromethanes, then using volume ratio as 50:1 petroleum ether：The mixed solution of ethyl acetate carries out silica gel column chromatography as eluant, eluent
Purifies and separates, products therefrom are polysubstituted distal end allyl ketone derivative；Its reaction equation is：
Product purity is 99%, yield 78%.Its nuclear magnetic data is analyzed：1H NMR(400MHz,CDCl3):δH7.92
(d, J=8.9Hz, 2H), 6.91 (d, J=8.9Hz, 2H), 6.15 (d, J=1.7Hz, 1H), 5.46 (s, 1H), 4.17 (qd, J
=7.1,0.7Hz, 2H), 3.85 (s, 3H), 2.82 (q, J=14.5Hz, 2H), 2.36 (dd, J=13.3,5.4Hz, 1H),
2.04 (dd, J=13.4,8.5Hz, 1H), 1.85-1.74 (m, 1H), 1.43 (dd, J=14.1,3.9Hz, 1H), 1.34-1.24
(m, 4H), 1.03 (d, J=4.3Hz, 6H), 0.89 (d, J=6.7Hz, 3H).
13C NMR(151MHz,CDCl3):δC199.1,167.5,163.3,139.9,131.9,130.6,126.4,
113.7,60.7,55.5,49.6,48.5,42.3,34.7,28.1,27.9,22.5,14.4。
Embodiment five, a kind of preparation method of polysubstituted distal end allyl ketone derivative
In nitrogen atmosphere, at room temperature by 52.0mg (0.2mmol) substitute camphyl alcohol, 100mg (0.4mmol) beta-unsaturated esters,
1.2mg(0.005mmol)[dF(CF3)ppy]2(dtbpy)PF64mL dichloros are dissolved in 0.5mmol 2.4.6- trimethylpyridines
In methane, it is uniformly mixed, then is placed in progress illumination reaction 28h under blue LED lamp, Rotary Evaporators concentration removes dichloromethane
Afterwards, then using volume ratio as 50:1 petroleum ether：The mixed solution of ethyl acetate carries out silica gel column chromatography purifying point as eluant, eluent
From products therefrom is polysubstituted distal end allyl ketone derivative；Its reaction equation is：
Product purity is 99%, yield 82%.Its nuclear magnetic data is analyzed：δH7.93 (d, J=8.9Hz, 2H),
6.92 (d, J=8.9Hz, 2H), 6.20 (d, J=1.7Hz, 1H), 5.41 (d, J=0.6Hz, 1H), 4.24-4.09 (m, 1H),
3.86 (s, 3H), 2.98 (dd, J=15.1,3.3Hz, 1H), 2.72 (dd, J=15.1,10.6Hz, 1H), 2.55-2.44 (m,
1H), 2.37 (d, J=13.0Hz, 1H), 2.26 (d, J=12.9Hz, 1H), 1.99-1.86 (m, 1H), 1.57-1.45 (m,
1H), 1.26 (dd, J=15.4,8.3Hz, 5H), 0.92 (s, 3H), 0.78 (d, J=8.0Hz, 6H).
13C NMR(100MHz,CDCl3):δC 194.8,167.3,143.9,142.5,140.5,139.3,129.0,
127.5,126.0,125.1,124.9,123.1,60.7,39.1,31.8,28.2,24.3,14.3。
Embodiment six, a kind of preparation method of polysubstituted distal end allyl ketone derivative
In nitrogen atmosphere, at room temperature by 32.6mg (0.2mmol) to methoxy basic ring propyl alcohol, 100mg (0.4mmol) unsaturations
Ester, 1.2mg (0.005mmol) [dF (CF3)ppy]2(dtbpy)PF64mL is dissolved in 0.5mmol 2.4.6- trimethylpyridines
In dichloromethane, it is uniformly mixed, then is placed in progress illumination reaction 28h under blue LED lamp, Rotary Evaporators concentration removes dichloromethane
After alkane, then using volume ratio as 50:1 petroleum ether：The mixed solution of ethyl acetate carries out silica gel column chromatography purifying as eluant, eluent
Separation, products therefrom is polysubstituted distal end allyl ketone derivative；Its reaction equation is：
Product purity is 99%, yield 83%.1H NMR(600MHz,CDCl3):δ H 7.93 (d, J=8.6Hz,
2H), 6.92 (d, J=8.6Hz, 2H), 6.17 (s, 1H), 5.56 (s, 1H), 4.19 (q, J=7.1Hz, 2H), 3.86 (s, 3H),
2.94 (t, J=7.3Hz, 2H), 2.40 (t, J=7.5Hz, 2H), 2.00-1.88 (m, 2H), 1.29 (t, J=7.1Hz, 3H).
13C NMR(151MHz,CDCl3):δC 198.6,167.3,163.5,140.4,130.4,130.2,125.1,
113.8,60.8,55.6,37.5,31.4,23.1,14.3；GC-MS(EI,QMS,m/z):135.1,150.1,207.0,
231.1,276.1。
Embodiment one~six is to carry out illumination reaction again after leading to nitrogen 30min.
As seen from the above embodiment, the present invention provides the preparation method of polysubstituted distal end allyl ketone derivative, the party
Method can react at normal temperatures and pressures, and reaction condition is gentle, and yield is high, and with easy to operate, pollution-free, safety and environmental protection, into
The advantages of this is low.
Claims (10)
1. a kind of preparation method of polysubstituted distal end allyl ketone derivative, it is characterised in that this method comprises the following steps：
In nitrogen atmosphere, at room temperature three-level cyclol derivant, ethylenic unsaturation compound, alkali and photochemical catalyst are dissolved in it is organic molten
In agent, it is uniformly mixed, then is placed under blue LED lamp and carries out illumination reaction, is separated after revolving removal solvent through silica gel column chromatography pure
Change, products therefrom is polysubstituted distal end allyl ketone derivative；Ethylenic unsaturation compound, three-level cyclol derivant, alkali and light
The molar ratio of catalyst is 2:1:2.5:0.5；
The chemical structural formula of wherein three-level cyclol derivant is：
The chemical structural formula of ethylenic unsaturation compound is：
The chemical structural formula of photochemical catalyst is：
Wherein, R1、R2And R3For alkyl, alkoxy or halogen, it is alkoxy, alkyl or polyaromatic that the upper substituents of Ar, which are,；N is
0-9。
2. the preparation method of a kind of polysubstituted distal end allyl ketone derivative according to claim 1, it is characterised in that no
Saturation ene compound is methyl substituted α, and β beta-unsaturated esters, the α of ethyl substitution, β beta-unsaturated esters, nitro substitute α, β beta-unsaturated esters
Or cyano group substitution α, β beta-unsaturated esters.
3. the preparation method of a kind of polysubstituted distal end allyl ketone derivative according to claim 1, it is characterised in that three
Level cyclol derivant is ternary cyclic alcohol, quaternary cyclic alcohol, five-membered ring alcohol, twelve-ring alcohol, the more alkyl substitution cyclic alcohol in ortho position or ortho position
Aryl substitutes cyclic alcohol.
4. the preparation method of a kind of polysubstituted distal end allyl ketone derivative according to claim 1, it is characterised in that have
Solvent is selected from dichloromethane, dichloroethanes, acetonitrile or N, N- dicarboximide.
5. the preparation method of a kind of polysubstituted distal end allyl ketone derivative according to claim 1, it is characterised in that three
The molal volume ratio of level cyclol derivant and organic solvent is 1mmol:(10-20)mL.
A kind of 6. preparation method of polysubstituted distal end allyl ketone derivative according to claim 1, it is characterised in that
It is 12-48h that the illumination reaction time is carried out under blue LED lamp.
A kind of 7. preparation method of polysubstituted distal end allyl ketone derivative according to claim 1, it is characterised in that silicon
Plastic column chromatography isolates and purifies solvent for use as petroleum ether and the mixed solvent of ethyl acetate.
8. the preparation method of a kind of polysubstituted distal end allyl ketone derivative according to claim 7, it is characterised in that mixed
The volume ratio of bonding solvent petrochina ether and ethyl acetate is (20-50):1.
A kind of 9. preparation method of polysubstituted distal end allyl ketone derivative according to claim 1, it is characterised in that light
Catalyst is Ir [dF (CF3)ppy]2(dtbpy)PF6。
A kind of 10. preparation method of polysubstituted distal end allyl ketone derivative according to claim 1, it is characterised in that alkali
For 2.4.6- trimethylpyridines.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711351437.XA CN107973715B (en) | 2017-12-15 | 2017-12-15 | Preparation method of polysubstituted remote allyl ketone derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711351437.XA CN107973715B (en) | 2017-12-15 | 2017-12-15 | Preparation method of polysubstituted remote allyl ketone derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN107973715A true CN107973715A (en) | 2018-05-01 |
| CN107973715B CN107973715B (en) | 2020-08-14 |
Family
ID=62006442
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201711351437.XA Active CN107973715B (en) | 2017-12-15 | 2017-12-15 | Preparation method of polysubstituted remote allyl ketone derivative |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107973715B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111393396A (en) * | 2020-04-14 | 2020-07-10 | 汕头大学 | Method for preparing allyl ketone compound by concerted catalysis of visible light and cobalt |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105801410A (en) * | 2016-03-31 | 2016-07-27 | 南京工业大学 | Method for synthezing phenylacrylate derivative through visible light catalysis by dual-catalyst system |
-
2017
- 2017-12-15 CN CN201711351437.XA patent/CN107973715B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105801410A (en) * | 2016-03-31 | 2016-07-27 | 南京工业大学 | Method for synthezing phenylacrylate derivative through visible light catalysis by dual-catalyst system |
Non-Patent Citations (2)
| Title |
|---|
| JUNLEI WANG ET AL.: "Visible-Light-Mediated Ring-Opening Strategy for the Regiospecific Allylation/Formylation of Cycloalkanols", 《J. ORG. CHEM.》 * |
| YINGQIAN DUAN ET AL.: "The direct decarboxylative allylation of N-arylglycine derivatives by photoredox catalysis", 《ORG. CHEM. FRONT.》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111393396A (en) * | 2020-04-14 | 2020-07-10 | 汕头大学 | Method for preparing allyl ketone compound by concerted catalysis of visible light and cobalt |
| CN111393396B (en) * | 2020-04-14 | 2022-05-27 | 汕头大学 | Method for preparing allyl ketone compound by concerted catalysis of visible light and cobalt |
Also Published As
| Publication number | Publication date |
|---|---|
| CN107973715B (en) | 2020-08-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110054541B (en) | Preparation method of deuterated aromatic compound | |
| CN116640088A (en) | Preparation method of high-purity Lei Fen narasin | |
| CN109134875B (en) | Preparation of chiral covalent organic framework material with L-menthol as chiral source | |
| CN107973715A (en) | A kind of preparation method of polysubstituted distal end allyl ketone derivative | |
| CN111072605B (en) | Preparation method of fluoroalkyl-substituted benzofuran derivative or indole derivative | |
| CN106892800A (en) | A kind of preparation method and application of unactivated alkene hydrogen trifluoromethylation | |
| CN110066246B (en) | Method for preparing isoquinoline-1-ketone derivative | |
| CN107473941B (en) | Cyclopropyl substituted allyl alcohol and asymmetric synthesis method thereof | |
| CN107235887B (en) | Polysubstituted diindolylmethane derivative and preparation method thereof | |
| CN113354498B (en) | Method for reducing aromatic C-N/O/Cl/Br/I bond into aromatic C-H/D | |
| CN115215814A (en) | Synthetic method of isoxazolidine compounds | |
| CN110317170B (en) | Green synthesis method of 3-phenanthridinyl propyl formate compound | |
| CN109020895B (en) | Synthesis method of metal-catalyzed 1-benzylamino-substituted benzimidazole | |
| CN108191736B (en) | 2, 3-disubstituted indole derivatives and preparation method thereof | |
| CN107382640B (en) | β -aryl phenylpropanone compound synthesis method | |
| CN102351775B (en) | Preparation method of levo-5-hydroxytryptophan | |
| CN109053543A (en) | A kind of preparation method of cis- 3- alkoxy -1- methylene isoindole derivatives | |
| CN112441997B (en) | Method for synthesizing alpha- (2-tetrahydrofuryl) -acetophenone compound | |
| CN110396072A (en) | (s) preparation method of -3- hydroxyl tetrahydrofuran | |
| CN104327025A (en) | Preparation method of 4-aryltetralin lactone derivatives | |
| CN102702196A (en) | Method for synthesizing 3-methyl-7-diazaindene | |
| CN102675204B (en) | Intermediate for synthesizing (I)-huperzine A, synthesis method and usage thereof | |
| CN110981725B (en) | Synthesis method of difluoroolefin | |
| CN103408439A (en) | Chemical synthetic method of norbelladine | |
| CN108101741B (en) | Method for synthesizing chiral alcohol by alkyne hydration/asymmetric hydrogenation tandem |
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 |