CN109912456A - A kind of preparation method of gamma-carboxylation alkyl nitrile compounds - Google Patents
A kind of preparation method of gamma-carboxylation alkyl nitrile compounds Download PDFInfo
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Abstract
The invention discloses a kind of preparation methods of gamma-carboxylation alkyl nitrile compounds, this method carries out the Bifunctionalized reaction of alkene under the conditions of Raney nickel, silver-colored oxidant with the alkyl nitrile compounds of the alkenes compounds of Formula II, the carboxylic acid compound of formula III, formula IV, prepares a series of gamma-carboxylation alkyl nitrile compounds of various different structures.The synthetic route of gamma-carboxylation alkyl nitrile compounds of the invention is easy to get with raw material sources, and catalyst system is cheap, reaction substrate wide adaptation range, the high advantage of target product yield.
Description
Technical field
The application belongs to technical field of organic synthesis, and in particular to a kind of preparation side of gamma-carboxylation alkyl nitrile compounds
Method.
Background technique
By the chemicals (especially deriving from the raw material of petroleum industry, such as alkene, alkane and aromatic hydrocarbons) being easily obtained, lead to
Mild, economic and practical selective catalysis approach is crossed, rapidly increases the complexity of molecule, is academia and industry
One of main target.In this field, realize that the functionalization of molecule is one by alkene and/or being converted for c h bond
Attractive and challenging target, causes the great interest of vast researcher.Typically strategy includes
Two carbon of alkene are functionalized, by the functional group at two ortho positions of introducing to extend carbochain, to obtain complicated chemical combination
Object.However, most two carbon functionizing methods of alkene are often confined to classical cross-coupling reaction, and such reaction
Often require to use expensive nucleophilic and/or electrophilic reagent (such as organo-metallic compound and organohalogen compounds) and catalytic body
System.Inventor report before this kind of alkenes compounds intermolecular 1,2- dialkylation reaction method (CN108640839A,
20181012), this method realizes the dialkylation of alkene under photoredox/iron (II) concerted catalysis.
Gamma-carboxylation alkyl nitrile compounds are a kind of important organic compounds, widely apply to pharmaceutical synthesis and
In organic synthesis (Org.Biomol.Chem., 2014,12,5407-5426；Journal of Organometallic
Chemistry 177(1979)211-220；US3932159,19760113；US401121,19770308；Zeitschrift
Fuer Naturforschung, Teil B:Anorganische Chemie, Organische Chemie (1982), 37B
(7), 923-9.).However, the prior art synthesize this kind of compound method is less and inefficiency, need by multistep reaction
And/or need to be pre-designed the reaction substrate of composite structure complexity.Such as Wenying Ai etc. reports a kind of γ or δ-carboxylation
The synthetic method of alkyl nitrile compounds, this method is using cyclobutanone or cyclopentanone oxime ester as reaction raw materials, the open loop under copper catalysis
And obtain γ or 6- carboxylation alkyl nitrile compounds (referring to formula one).
Inventor is by concentrating on studies, in the present invention, propose it is a kind of by be easily obtained reaction raw materials (simple olefins,
Carboxylic acid and alkyl nitrile compounds) directly prepare the new methods of gamma-carboxylation alkyl nitrile compounds.
Summary of the invention
It is an object of the invention to overcome the deficiencies in the prior art, propose a kind of (simple by the reaction raw materials being easily obtained
Alkene, carboxylic acid and alkyl nitrile compounds) directly prepare the new methods of gamma-carboxylation alkyl nitrile compounds.This method has original
Material source is easy to get, and catalyst system is cheap, reaction substrate wide adaptation range, the high advantage of target product yield.
A kind of preparation method of gamma-carboxylation alkyl nitrile compounds provided by the invention, includes the following steps:
Carboxylic acid compound shown in alkenes compounds, formula III shown in Formula II is sequentially added into reactor, nickel is urged
Agent, alkyl nitrile compounds shown in silver-colored oxidant and formula IV are anti-at 100~140 DEG C under the conditions of inert atmosphere protection
Answer 12~36h.After fully reacting, reaction solution is concentrated in vacuo, then the γ-by residue through the isolated Formulas I of silica gel column chromatography
Carboxylation alkyl nitrile compounds.
In Formula II and Formulas I, R is selected from substituted or unsubstituted C6-C20Aryl, substituted or unsubstituted C3-C20Heteroaryl
Base, substituted or unsubstituted C6-C20Aryl vinyl；
R1Selected from hydrogen, C1-C20Alkyl, C6-C20Aryl；
R2Selected from hydrogen, C1-C20Alkyl；
In formula III and Formulas I, R3Selected from substituted or unsubstituted C1-C20Alkyl, substituted or unsubstituted C6-20Aryl,
Substituted or unsubstituted C3-C20Naphthenic base, substituted or unsubstituted C3-C20Heterocycle；
In formula IV and Formulas I, R4Selected from hydrogen, C1-C20Alkyl, C6-C20Aryl ,-COOR5, wherein R5Selected from C1-C6Alkane
Base.
Preferably, in Formula II and Formulas I, R is selected from substituted or unsubstituted C6-C14Aryl, substituted or unsubstituted C3-C12
Heteroaryl, substituted or unsubstituted C6-C14Aryl vinyl；
R1Selected from hydrogen, C1-C12Alkyl, C6-C14Aryl；
R2Selected from hydrogen, C1-C12Alkyl；
In formula III and Formulas I, R3Selected from substituted or unsubstituted C1-C12Alkyl, substituted or unsubstituted C6-C14Virtue
Base, substituted or unsubstituted C3-C12Naphthenic base, substituted or unsubstituted C3-C12Heterocycle；
In formula IV and Formulas I, R4Selected from hydrogen, C1-C12Alkyl, C6-C14Aryl ,-COOR5, wherein R5Selected from C1-C6Alkane
Base.
In the definition of arbitrary portion of the invention for substituent R: the substituted or unsubstituted C6-C20Aryl,
Substituted or unsubstituted C6-C14Aryl in substituent group be selected from halogen, C1-C6Alkyl, C1-C6Alkoxy, C1-C6Alkane
Sulfenyl ,-NO2、C1-C6Alkyl-carbonyl in any one or a few." C therein6-C20Aryl ", " C6-C14Aryl "
It is preferably selected from such as phenyl, naphthalene, anthryl, phenanthryl.
" the substituted or unsubstituted C3-C20Heteroaryl ", " substituted or unsubstituted C3-C12Heteroaryl " in, take
Dai Ji is selected from halogen, C1-C6Alkyl, C1-C6Alkoxy in any one or a few.Heteroatomic type can be selected from
O, S, N etc., specific heteroaryl can be selected from such as thienyl, furyl, pyridyl group, indyl, benzofuranyl, quinoline
Base, benzopyranyl etc..
The substituted or unsubstituted C6-C20Aryl vinyl, substituted or unsubstituted C6-C14Aryl vinyl in
Substituent group be selected from halogen, C1-C6Alkyl, C1-C6Alkoxy in any one or a few." C therein6-C20Virtue
Base vinyl ", " C6-C14Aryl vinyl " such as styryl, naphthalene vinyl can be selected from.
In arbitrary portion of the invention for R1, R2And R4Group definition in, " the C1-C20Alkyl ", " C1-C12's
Alkyl ", " C1-C6Alkyl " concrete instance include but is not limited to methyl, ethyl, propyl, butyl, isopropyl, isobutyl group, uncle
Butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, 3- heptyl, n-octyl, undecyl etc..The C6-C20's
Aryl, " C6-C14Aryl " can be selected from being for example preferably selected from such as phenyl, naphthalene, anthryl, phenanthryl.
In arbitrary portion of the invention for R3Group definition in, " the substituted or unsubstituted C1-C20Alkyl ",
" substituted or unsubstituted C1-C12Alkyl " in, substituent group be selected from halogen, NHBoc, N (Me) (Boc), N (Et) (Boc), benzene
Any one or a few in base, benzyloxy." C therein1-C20Alkyl ", " C1-C12Alkyl " have such as above-mentioned R1, R2With
R4Group definition in identical definition.
" the substituted or unsubstituted C6-20Aryl ", " substituted or unsubstituted C6-C14Aryl " have as herein
Aforementioned R substituent define in " substituted or unsubstituted C6-20Aryl ", " substituted or unsubstituted C6-C14Aryl " it is identical
Definition.
" the substituted or unsubstituted C3-C20Naphthenic base ", " substituted or unsubstituted C3-C12Naphthenic base " in, take
Dai Ji is selected from halogen, C1-C6Alkyl, C1-C6Alkoxy in any one or a few." C therein3-C20Cycloalkanes
Base ", " C3-C12Naphthenic base " be preferably selected from monocycle such as cyclopropyl, cyclobutyl, cyclopenta, cyclohexyl；It is bicyclic for example
Two rings [2.2.2] octyl, two rings [2,2,1] heptane base, decahydronaphthalene naphthalene；It is polycyclic such as adamantyl.
" the substituted or unsubstituted C3-C20Heterocycle ", " substituted or unsubstituted C3-C12Heterocycle " in, take
Dai Ji is selected from halogen, C1-C6Alkyl, C1-C6Alkoxy, any one or a few in-Boc.Heteroatomic type can be with
Selected from O, S, N etc., " C therein3-C20Heterocycle ", " C3-C12Heterocycle " such as furyl, thienyl, pyrrole can be selected from
Piperidinyl, tetrahydro-thienyl, tetrahydrofuran base, nafoxidine base, piperidyl, piperazinyl, THP trtrahydropyranyl, dioxane,
Quinoline base etc.；It is preferably selected from furyl, nafoxidine base, THP trtrahydropyranyl, piperidyl.
Most preferably, Formula II compound is selected from the compound having the following structure:
Formula III compound is selected from the compound having the following structure:
Formula IV compound is selected from the compound having the following structure:
A kind of preparation method of gamma-carboxylation alkyl nitrile compounds above-mentioned according to the present invention, wherein the nickel catalysis
Agent is selected from NiI2、Ni(acac)2、NiBr2、Ni(OAc)2With Ni (PPh3)4In any one.Preferably, the Raney nickel
Selected from NiI2。
A kind of preparation method of gamma-carboxylation alkyl nitrile compounds above-mentioned according to the present invention, wherein the silver oxidation
Agent is selected from Ag2CO3、Ag2O, any one in AgOAc, AgF, it is preferable that the silver-colored oxidant is selected from Ag2CO3。
A kind of preparation method of gamma-carboxylation alkyl nitrile compounds above-mentioned according to the present invention, wherein the indifferent gas
Atmosphere is the atmosphere inert to reaction, and is not mechanically considered inert gas.It to those skilled in the art, can be with
Understand, the inert atmosphere for being usually used in organic reaction can be selected from argon atmosphere or nitrogen atmosphere.It is preferred that argon atmosphere.
A kind of preparation method of gamma-carboxylation alkyl nitrile compounds above-mentioned according to the present invention, wherein the reaction temperature
Preferably 120 DEG C of degree, the reaction time is preferably 24 hours.
A kind of preparation method of gamma-carboxylation alkyl nitrile compounds above-mentioned according to the present invention, wherein the alkene of the Formula II
Hydrocarbon compound, the carboxylic acid compound of formula III, Raney nickel, silver-colored oxidant molar ratio example be 1: (1~3):
(0.05~0.2): (1~3)；Preferably 1: 2: O.01: 2.While the alkyl nitrile compounds of formula IV are as reactant, also fill
When reaction medium (solvent), additional amount can be determined by those skilled in the art's conventional selection, so that material is uniform
Disperse and is easy to stirring.
Beneficial effects of the present invention are as follows:
1, the present invention report for the first time with the alkenes compounds of Formula II, the carboxylic acid compound of formula III, formula IV alkyl
Nitrile compounds carry out the Bifunctionalized reaction of alkene under the conditions of Raney nickel, silver-colored oxidant, prepare a series of various different knots
The synthetic route of the gamma-carboxylation alkyl nitrile compounds of structure, understands according to inventor, and the alkene under the catalyst system is Bifunctionalized anti-
It should have no that the prior art is reported.
2, the synthetic route of gamma-carboxylation alkyl nitrile compounds of the invention is easy to get with raw material sources, catalyst system valence
Lattice are cheap, reaction substrate wide adaptation range, the high advantage of target product yield.
Specific embodiment
Below in conjunction with specific embodiment, further detailed description is carried out to the present invention.
The test of embodiment 1-17 reaction condition optimization
To be original to BOC-N- ethyl glycine shown in methoxy styrene, formula III -1 and acetonitrile shown in Formula II -1
Material, has inquired into influence of the differential responses condition for process optimization result, has selected wherein representative embodiment 1-17,
As a result as shown in Table 1:
Wherein the model experiment operation of embodiment 1 is as follows:
4- methoxy styrene shown in Formula II -1 is sequentially added into dry, closed Schlenk reactor
BOC-N- ethyl glycine (2equiv), NiI shown in (0.2mmol), formula III -12(10mol%), Ag2CO3(2equiv) and
CH3CN (1mL) reacts for 24 hours at 120 DEG C using argon gas as protection gas.After fully reacting, reaction solution is concentrated in vacuo, then will
Residue separates (n-hexane/ethyl acetate=10: 1, volume ratio) through silica gel column chromatography and obtains the target product of Formulas I -1
(67.7mg, 90%).Yellow oily liquid；1H NMR (500 MHz, CDCl3) δ: 7.28-7.24 (m, 2H), 6.90-6.88 (m,
2H), 5.85-5.82 (m, 1H), 4.00-3.89 (m, 2H), 3.80 (s, 3H), 3.36-3.25 (m, 2H), 2.39-2.25 (m,
3H), 2.17-2.10 (m, 1H), 1.47 (s, 5H), 1.32 (s, 4H), 1.11-1.07 (m, 3H)；13C NMR (125MHz,
CDCl3) δ: 169.4,159.9,159.7,155.6,154.8,130.2,130.0,127.9,127.7,118.9,118.7,
114.2,114.1,80.1,77.3,77.2,77.0,76.8,74.5,74.4,55.3,48.9,48.8,43.5,42.9,32.0,
31.6,28.3,28.1,13.8,13.6,13.6,13.2.；HRMS m/z(ESI)calcd for C20H29N2O5([M+H]+)
377.2071 found 377.2080..
Table one:
Wherein, the concrete operations of embodiment 2-17 and parameter except variable listed by above-mentioned table one and embodiment 1 it is not identical it
Outside, remaining operation and parameter are same as Example 1.
Optimum process condition of the present invention is the technique of embodiment 1 it can be seen from the representative embodiment 1-17 in table one
Condition.On the basis of obtaining optimum process condition, inventor further selects Formula II, formula III and the formula IV of different substituents
Reaction raw materials, reacted under optimum process condition (embodiment 1) to prepare the target compounds of various Formulas I.As a result such as table two
It is shown, wherein raw material compound II-1~II-11 involved in table two, III-1~III-30, IV-1~IV-4 and herein
Identical structure defined in aforementioned no longer draws the structure of these raw material compounds to save space herein.
Table two:
Embodiment described above is merely a preferred embodiment of the present invention, and the simultaneously exhaustion of the feasible implementation of non-present invention.For
It is any apparent to made by it under the premise of without departing substantially from the principle of the invention and spirit for those skilled in the art
Change, should all be contemplated as falling within claims of the invention.
Claims (10)
1. the preparation method of gamma-carboxylation alkyl nitrile compounds, includes the following steps: shown in a kind of Formulas I
Carboxylic acid compound shown in alkenes compounds, formula III shown in Formula II, nickel catalysis are sequentially added into reactor
Agent, alkyl nitrile compounds shown in silver-colored oxidant and formula IV react at 100~140 DEG C under the conditions of inert atmosphere protection
After fully reacting, reaction solution is concentrated in vacuo by 12~36h, then by residue through shown in the isolated Formulas I of silica gel column chromatography
Gamma-carboxylation alkyl nitrile compounds；
In Formula II and Formulas I, R is selected from substituted or unsubstituted C6-C20Aryl, substituted or unsubstituted C3-C20Heteroaryl, take
Generation or unsubstituted C6-C20Aryl vinyl；
R1Selected from hydrogen, C1-C20Alkyl, C6-C20Aryl；
R2Selected from hydrogen, C1-C20Alkyl；
In formula III and Formulas I, R3Selected from substituted or unsubstituted C1-C20Alkyl, substituted or unsubstituted C6-20Aryl, replace
Or unsubstituted C3-C20Naphthenic base, substituted or unsubstituted C3-C20Heterocycle；
In formula IV and Formulas I, R4Selected from hydrogen, C1-C20Alkyl, C6-C20Aryl ,-COOR5, wherein R5Selected from C1-C6Alkyl；
Wherein, the Raney nickel is selected from NiI2、Ni(acac)2、NiBr2、Ni(OAc)2With Ni (PPh3)4In it is any one
Kind；
The silver-colored oxidant is selected from Ag2CO3、Ag2O, any one in AgOAc, AgF.
2. preparation method according to claim 1, it is characterised in that: in Formula II and Formulas I, R is selected from substituted or unsubstituted
C6-C14Aryl, substituted or unsubstituted C3-C12Heteroaryl, substituted or unsubstituted C6-C14Aryl vinyl；
R1Selected from hydrogen, C1-C12Alkyl, C6-C14Aryl；
R2Selected from hydrogen, C1-C12Alkyl；
In formula III and Formulas I, R3Selected from substituted or unsubstituted C1-C12Alkyl, substituted or unsubstituted C6-C14Aryl, take
Generation or unsubstituted C3-C12Naphthenic base, substituted or unsubstituted C3-C12Heterocycle；
In formula IV and Formulas I, R4Selected from hydrogen, C1-C12Alkyl, C6-C14Aryl ,-COOR5, wherein R5Selected from C1-C6Alkyl.
3. preparation method according to claim 1 or 2, it is characterised in that: Formula II compound is selected from and has the following structure
Compound:
Formula III compound is selected from the compound having the following structure:
Formula IV compound is selected from the compound having the following structure:
4. preparation method according to claim 1 to 3, it is characterised in that: the Raney nickel is selected from NiI2。
5. preparation method according to claim 1 to 3, it is characterised in that: the silver-colored oxidant is selected from
Ag2CO3。
6. preparation method according to claim 1 to 3, it is characterised in that: the inert atmosphere is selected from argon gas
Atmosphere or nitrogen atmosphere, preferably argon atmosphere.
7. preparation method according to claim 1 to 3, it is characterised in that: reaction temperature is preferably 120 DEG C, instead
Preferably 24 hours between seasonable.
8. preparation method according to claim 1 to 3, it is characterised in that: olefines chemical combination shown in Formula II
Carboxylic acid compound shown in object, formula III, Raney nickel, silver-colored oxidant molar ratio example be 1: (1~3): (0.05~
0.2): (1~3).
9. preparation method according to claim 8, it is characterised in that: shown in alkenes compounds, formula III shown in Formula II
Carboxylic acid compound, Raney nickel, silver-colored oxidant molar ratio example be 1: 2: 0.01: 2.
10. preparation method according to claim 1 to 3, it is characterised in that: the silica gel column chromatography separation
Eluting solvent is the mixed solvent of n-hexane and ethyl acetate.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108640839A (en) * | 2018-06-21 | 2018-10-12 | 南昌航空大学 | The intermolecular 1,2- dialkylations reaction method of alkenes compounds under a kind of photoredox/iron (II) catalyst system and catalyzing |
| CN108707081A (en) * | 2018-07-09 | 2018-10-26 | 南昌航空大学 | A kind of alkene 1,2- difunctionalities dough reaction method |
| CN108912036A (en) * | 2018-08-24 | 2018-11-30 | 南昌航空大学 | A kind of method that the dough reaction of alkene 1,4- difunctionality prepares allyl Benzazole compounds |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108640839A (en) * | 2018-06-21 | 2018-10-12 | 南昌航空大学 | The intermolecular 1,2- dialkylations reaction method of alkenes compounds under a kind of photoredox/iron (II) catalyst system and catalyzing |
| CN108707081A (en) * | 2018-07-09 | 2018-10-26 | 南昌航空大学 | A kind of alkene 1,2- difunctionalities dough reaction method |
| CN108912036A (en) * | 2018-08-24 | 2018-11-30 | 南昌航空大学 | A kind of method that the dough reaction of alkene 1,4- difunctionality prepares allyl Benzazole compounds |
Non-Patent Citations (3)
| Title |
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| YAN-YUN LIU等: "Oxidative 1,2-carboamination of alkenes with alkyl nitriles and amines toward γ-amino alkyl nitriles", 《NATURE COMMUNICATIONS》 * |
| YING-XIA DONG等: "Copper-Catalyzed Three-Components Intermolecular Alkylesterification of Styrenes with Toluenes and Peroxyesters or Acids", 《ORG. LETT.》 * |
| 姜帅帅等: "过渡金属催化烯烃的双官能团化反应", 《道客巴巴网络》 * |
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