CN104496831B - The method of beta-amino carbonyl compound is prepared in graphene oxide catalysis - Google Patents
The method of beta-amino carbonyl compound is prepared in graphene oxide catalysis Download PDFInfo
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Abstract
The invention discloses a kind of graphene oxide and be catalyzed the method preparing β aminocarboxyl compound, the method is with water as solvent, and by aromatic aldehyde, aromatic amine, aliphatic ketone under graphene oxide catalytic action, direct chemical combination obtains β aminocarboxyl compound.Solvent for use environmental protection of the present invention, used catalyst non-toxic inexpensive, stable to water and air, preparation method is easy, reaction condition is gentle, the response time is short, after the productivity of β aminocarboxyl compound is high, and reaction terminates, catalyst graphene oxide can recycle.
Description
Technical field
Present invention relates particularly to a kind of method that beta-amino carbonyl compound is prepared in graphene oxide catalysis.
Background technology
Beta-amino carbonyl compound is utilized Dakin-West to be synthesized as far back as nineteen twenty-eight by Dakin to obtain, it
It is the important compound of a class, there is multiple different biological activity, as beta-amino carbonyl compound can be as TR
(Thyroid Hormone Receptors)-co-activation factor inhibitors.This compounds also be synthesis 1,3-amino alcohol compound, β-
The precursor of the important biomolecule bioactive molecule such as aminoacid, lactams, such as nikkomycins and neopolyoxines etc..
Therefore, this type of synthesis is a popular research field.Utilize Mannich reaction by direct to ketone, aldehyde, amine three component
Link is the classical way preparing beta-amino carbonyl compound.The method is generally completed by two categories below catalyst system and catalyzing:
One class is typical acid catalyst, as sour in Lewis,Acid, Ps-SO3H, sulfamic acid, ion
Liquid acid and heteropoly acid etc., this kind of acid catalyst existence catalysis productivity is low, catalytic reaction time length, catalytic reaction step
The most loaded down with trivial details, pollute environment and to shortcomings such as equipment corrosions；Another kind of is various salt or oxide catalyst, such as mistake
Cross slaine, rare earth metal salt, pyridine trifluoroacetate, Fe (Cp)2PF6、NaBAr4F、Yb(OTf)3、
Re-(PFO)3、Re(OPf)3, nano-TiO2Deng, although this kind of catalyst shows good catalytic performance, but deposit
In separation difficulty, catalyst amount is big, catalysis productivity is low, pollute environment and catalyst is difficult to recycling etc. and asks
Topic.
Summary of the invention
The technical problem to be solved is to overcome existing beta-amino carbonyl compound preparation method to exist
Shortcoming, it is provided that a kind of using water as solvent, reaction condition is gentle, the response time is short, the repeatable utilization of catalyst and
Nontoxic cheap catalyst, enriches beta-amino carbonyl compound synthetic method.
Solve above-mentioned technical problem and be the technical scheme is that with water as solvent, with graphene oxide as catalyst,
Aromatic aldehyde, aromatic amine, aliphatic ketone are reacted 3～6 hours at room temperature to 50 DEG C, obtains beta-amino carbonyl compound
Thing, the addition of wherein said graphene oxide is the 5%～20% of aromatic aldehyde quality, preferential oxidation Graphene
Addition is aromatic aldehyde quality 10%～15%.
Above-mentioned aromatic aldehyde isWherein R1Representing H, Cl, Br, methyl, methoxyl group etc., m represents
R1Replacement number, its value is the integer of 0～2, concrete preferably benzaldehyde, o-methoxybenzaldehyde, adjacent chlorine
Benzaldehyde, 4-chloro-benzaldehyde, m chlorobenzaldehyde etc..
Above-mentioned aromatic amine isWherein R2Representing H, Cl, Br, methyl, methoxyl group etc., n represents
R2Replacement number, its value is the integer of 0～2, concrete preferably aniline, o-toluidine, m-toluidine,
Open-chain crown ether, o-aminoanisole, P-nethoxyaniline, m-chloroaniline, o-chloraniline, parachloroanilinum etc..
The preferred Ketohexamethylene of above-mentioned aliphatic ketone.
Preferred fragrance aldehyde of the present invention, aromatic amine, alkenolic mol ratio are 1:1～1.5:1～1.5.
The present invention use graphene oxide as catalyst, by aromatic aldehyde, aromatic amine, alkenolic Mannich
Reaction obtains beta-amino carbonyl compound.The present invention using water as solvent, environmental protection, used catalyst is inexpensive,
Nontoxic, stable to air and water, preparation method is easy, and reaction condition is gentle, the response time is short, Atom economy
Height, after the productivity of product beta-amino carbonyl compound is high, and reaction terminates, catalyst graphene oxide can circulate
Use.
Detailed description of the invention
Below in conjunction with embodiment, the present invention is described in more detail, but protection scope of the present invention is not limited only to these
Embodiment.
Embodiment 1
As a example by preparing following formula: compound 2-[(phenyl) (anilino-) methyl]-Ketohexamethylene, raw materials used and system
Preparation Method is as follows:
16mg graphene oxide is added in 4mL distilled water, the solution of ultrasonic disperse to formation transparent and stable,
Under agitation, in this solution, add 102 μ L (106mg, 1.0mmol) benzaldehydes, stir 15 points
Zhong Hou, is sequentially added into 92 μ L (1.0mmol) aniline, 124 μ L (1.2mmol) Ketohexamethylene, 50 DEG C of reactions 3
Hour, stopped reaction, to filter, filtrate is extracted with ethyl acetate (3 × 10mL), merges organic facies, uses anhydrous sulfur
Acid magnesium is dried, and the column chromatography for separation mixed liquor that volume ratio is 1:5 of ethyl acetate and petroleum ether (developing solvent be) must
To white solid product 2-[(phenyl) (anilino-) methyl]-Ketohexamethylene, its productivity is 87%.Products therefrom is used
Bruker-Avance type superconduction Fourier digitizing nuclear magnetic resonance spectrometer characterizes, and characterizes data as follows:1H NMR
(400MHz, CDCl3) δ ppm:7.18-7.38 (m, 5H), 7.03-7.09 (m, 2H), 6.59-6.66
(m, 1H), 6.51-6.56 (m, 2H), 4.80 (d, J=4.5Hz, 1H), 4.62 (d, J=7.0Hz, 1H),
4.59 (brs, 1H), 2.73-2.81 (m, 1H), 2.25-2.44 (m, 2H), 1.52-2.08 (m, 6H)；13C NMR (101MHz, CDCl3) δ ppm:213.2,211.6,147.7,147.2,141.74,141.71,
129.3,129.2,128.7,128.6,127.7,127.5,127.4,127.2,117.9,114.3,114.0,
58.4,57.6,57.5,56.8,42.6,42.0,31.5,28.9,28.1,27.3,25.1,23.9.
The filter cake that will obtain after filtering, directly as catalyst, repeats above-mentioned reaction, investigates catalyst and recycles secondary
Several impacts on product 2-[(phenyl) (anilino-) methyl]-Ketohexamethylene productivity, the results are shown in Table 1.
The impact on products collection efficiency of the table 1 catalyst cycle-index
| Cycle-index (secondary) | 1 | 2 | 3 | 4 | 5 |
| Productivity (%) | 87 | 85 | 84 | 82 | 80 |
From table 1, the recycling performance of catalyst graphene oxide of the present invention is good, reuses 5 times, 2-[(benzene
Base) (anilino-) methyl] the productivity change of-Ketohexamethylene is little.
Embodiment 2
In embodiment 1, the amount of graphene oxide used reduces to 5.3mg, other steps and embodiment 1 phase
With, obtaining white solid product 2-[(phenyl) (anilino-) methyl]-Ketohexamethylene, its productivity is 65%.
Embodiment 3
In embodiment 1, the amount of graphene oxide used reduces to 21.2mg, other steps and embodiment 1
Identical, obtain white solid product 2-[(phenyl) (anilino-) methyl]-Ketohexamethylene, its productivity is 80%.
Embodiment 4
As a example by preparing following formula: compound 2-[(phenyl) (3-toluidine) methyl]-Ketohexamethylene, raw materials used
And preparation method thereof as follows:
In embodiment 1, aniline used is replaced with equimolar m-toluidine, room temperature reaction 4 hours, its
His step is same as in Example 1, obtains white solid 2-[(phenyl) (3-toluidine) methyl]-Ketohexamethylene,
Its productivity is 90%, characterizes data and is:1H NMR (400MHz, CDCl3) δ ppm:7.36-7.24 (m,
2H), 7.19 (t, J=7.5Hz, 2H), 7.15-7.06 (m, 1H), 6.85 (t, J=7.8Hz, 1H), 6.41-6.20
(m, 3H), 4.57 (s, 1H), 4.53 (m, 1H), 2.65 (dd, J=7.1,5.4Hz, 1H), 2.36-2.15
(m, 2H), 2.09 (s, 3H), 2.04-1.68 (m, 4H), 1.60 (dd, J=10.3,8.5,2.6Hz,
2H)；13C NMR (101MHz, CDCl3) δ ppm:211.70,146.25,140.85,137.69,127.90,
127.40,126.20,126.06,117.44,113.52,109.48,56.85,56.46,40.68,30.19,26.83,
22.58,20.52.
After the catalyst that the present embodiment reclaims recycles 5 times, 2-[(phenyl) (3-toluidine) methyl]-
The productivity of Ketohexamethylene is still up to 80%.
Embodiment 5
As a example by preparing following formula: compound 2-[(phenyl) (3-chloroanilino) methyl]-Ketohexamethylene, raw materials used and
Its preparation method is as follows:
In embodiment 1, the m-chloroaniline of aniline 1.2mmol used is replaced, and the response time extends to 5
Hour, other steps are same as in Example 1, obtain yellow solid 2-[(phenyl) (3-chloroanilino) methyl]-
Ketohexamethylene, its productivity is 89%, characterizes data and is:1H NMR (400MHz, CDCl3) δ ppm:7.39-7.27
(m, 4H), 7.25-7.19 (m, 1H), 6.96 (td, J=8.0,3.6Hz, 1H), 6.60 (t, J=7.5Hz,
1H), 6.53 (dt, J=10.1,2.1Hz, 1H), 6.41 (dt, J=3.8,2.2Hz, 1H), 4.66 (dd,
J=82.0,5.5Hz, 2H), 2.85-2.71 (m, 1H), 2.49-2.25 (m, 2H), 2.08-1.57 (m, 6H)；13C NMR (101MHz, CDCl3) δ ppm:211.18,148.52,141.21,134.72,130.00,
128.49,127.35,127.15,117.58,113.82,111.85,57.35,56.33,42.01,28.66,26.88,
23.89。
After the catalyst that the present embodiment reclaims recycles 5 times, 2-[(phenyl) (3-chloroanilino) methyl]-hexamethylene
The productivity of ketone is still up to 78%.
Embodiment 6
As a example by preparing following formula: compound 2-[(phenyl) (2-chloroanilino) methyl]-Ketohexamethylene, raw materials used and
Its preparation method is as follows:
In embodiment 1, the o-chloraniline of aniline 1.2mmol used is replaced, and Ketohexamethylene consumption increases to
1.5mmol, the response time extends to 4 hours, and other steps are same as in Example 1, obtain yellow solid 2-[(benzene
Base) (2-chloroanilino) methyl]-Ketohexamethylene, its productivity is 87%, characterizes data and is:1H NMR (400MHz,
CDCl3) δ ppm:7.39-7.35 (m, 2H), 7.33-7.28 (m, 2H), 7.25-7.18 (m, 2H), 6.97-6.91
(m, 1H), 6.55 (td, J=7.7,1.4Hz, 1H), 6.47 (dd, J=8.2,1.2Hz, 1H), 5.39
(s, 1H), 4.71 (s, 1H), 2.90-2.78 (m, 1H), 2.47-2.31 (m, 2H), 2.02-1.87 (m,
3H), 1.84-1.65 (m, 3H)；13C NMR (101MHz, CDCl3) δ ppm:211.94,143.21,
141.11,129.05,128.50,127.52,127.28,127.23,119.74,117.40,112.31,57.83,
57.41,42.10,31.57,27.88,24.14.
After the catalyst that the present embodiment reclaims recycles 5 times, 2-[(phenyl) (2-chloroanilino) methyl]-hexamethylene
The productivity of ketone is still up to 75%.
Embodiment 7
As a example by preparing following formula: compound 2-[(2-methoxyphenyl) (anilino-) methyl]-Ketohexamethylene, used former
Material and preparation method thereof is as follows:
In embodiment 1, benzaldehyde used is replaced with equimolar o-methoxybenzaldehyde, and room temperature reaction 6 is little
Time, other steps are same as in Example 1, are prepared as white solid 2-[(2-methoxyphenyl) (anilino-) first
Base]-Ketohexamethylene, its productivity is 81%, characterizes data and is:1H NMR (400MHz, CDCl3) δ ppm:
7.27 (dd, J=7.5,1.4Hz, 1H), 7.09 (td, J=8.0,1.6Hz, 1H), 6.97 (dd, J=8.3,
7.5Hz, 2H), 6.89-6.73 (m, 2H), 6.63-6.41 (m, 3H), 4.92 (d, J=7.1Hz, 1H),
4.81 (s, 1H), 3.83 (s, 3H), 2.77 (dd, J=12.7,7.0Hz, 1H), 2.40-2.29 (m, 1H),
2.21 (td, J=8.3,4.7Hz, 1H), 1.91-1.74 (m, 4H), 1.72-1.57 (m, 2H)；13C NMR
(101MHz, CDCl3) δ ppm:212.65,156.20,146.36,128.45,128.00,127.20,
127.00,119.79,116.19,112.41,109.20,55.00,54.35,51.49,40.81,30.70,27.19,
22.63。
After the catalyst that the present embodiment reclaims recycles 5 times, 2-[(2-methoxyphenyl) (anilino-) methyl]-
The productivity of Ketohexamethylene is still up to 72%.
Embodiment 8
As a example by preparing following formula: compound 2-[(2-chlorphenyl) (anilino-) methyl]-Ketohexamethylene, raw materials used and
Its preparation method is as follows:
In embodiment 1, benzaldehyde used is replaced with equimolar o-chlorobenzaldehyde, and aniline consumption increases to
1.2mmol, Ketohexamethylene consumption increases to 1.5mmol, and the response time extends to 5 hours, other steps and enforcement
Example 1 is identical, obtains yellow solid 2-[(2-chlorphenyl) (anilino-) methyl]-Ketohexamethylene, and its productivity is 78%,
Sign data are:1H NMR (400MHz, CDCl3) δ ppm:7.60 (dd, J=7.7,1.8Hz, 1H),
7.36 (dd, J=7.8,1.4Hz, 1H), 7.14 (m, 4H), 6.66 (t, J=7.3Hz, 1H), 6.56 (d,
J=7.7Hz, 2H), 5.39 (d, J=3.6Hz, 1H), 5.29 (br, 1H), 4.95 (d, J=4.9Hz, 1H),
2.96 (m, 1H), 2.36 (m, 2H), 2.11 (m, 1H), 2.02 (t, J=12.5Hz, 3H), 1.79
(m, 2H)；13C NMR (101MHz, CDCl3) δ ppm:211.99,209.55,146.14,145.93,
138.20,137.66,132.29,131.71,128.79,128.47,128.25,128.13,127.97,127.19,
126.02,125.89,116.96,116.52,113.04,112.33,54.41,54.34,53.08,52.28,41.75,
41.24,31.60,27.06,26.47,26.03,23.85,23.74.
After the catalyst that the present embodiment reclaims recycles 5 times, 2-[(2-chlorphenyl) (anilino-) methyl]-hexamethylene
The productivity of ketone is still up to 71%.
Embodiment 9
As a example by preparing following formula: compound 2-[(phenyl) (4-methoxybenzene amido) methyl]-Ketohexamethylene, used former
Material and preparation method thereof is as follows:
In embodiment 1, aniline used is replaced with equimolar P-nethoxyaniline, and Ketohexamethylene consumption increases to
1.5mmol, the response time extends to 4 hours, and other steps are same as in Example 1, obtain white solid 2-[(benzene
Base) (4-methoxybenzene amido) methyl]-Ketohexamethylene, its productivity is 91%.
Embodiment 10
As a example by preparing following formula: compound 2-[(phenyl) (2-methoxybenzene amido) methyl]-Ketohexamethylene, used former
Material and preparation method thereof is as follows:
In embodiment 1, aniline used is replaced with equimolar o-aminoanisole, and the response time extends to 4
Hour, other steps are same as in Example 1, obtain white solid 2-[(phenyl) (2-methoxybenzene amido) first
Base]-Ketohexamethylene, its productivity is 88%.
Embodiment 11
As a example by preparing following formula: compound 2-[(2-chlorphenyl) (4-toluidine) methyl]-Ketohexamethylene, used former
Material and preparation method thereof is as follows:
In embodiment 1, benzaldehyde used is replaced with equimolar o-chlorobenzaldehyde, and aniline is with equimolar right
Monomethylaniline. replace, Ketohexamethylene consumption increases to 1.3mmol, and the response time extends to 5 hours, other steps with
Embodiment 1 is identical, obtains yellow solid 2-[(2-chlorphenyl) (4-toluidine) methyl]-Ketohexamethylene, and it produces
Rate is 83%.
Embodiment 12
As a example by preparing following formula: compound 2-[(3-chlorphenyl) (2-methoxybenzene amido) methyl]-Ketohexamethylene, used
Raw material and preparation method thereof is as follows:
In embodiment 1, benzaldehyde used is replaced with equimolar m chlorobenzaldehyde, and aniline is adjacent with 1.2mmol
Aminoanisole is replaced, and Ketohexamethylene consumption increases to 1.5mmol, and the response time extends to 4 hours, other steps
Same as in Example 1, obtain yellow solid 2-[(3-chlorphenyl) (2-methoxybenzene amido) methyl]-Ketohexamethylene,
Its productivity is 85%.
Embodiment 13
As a example by preparing following formula: compound 2-[(4-chlorphenyl) (3-chloroanilino) methyl]-Ketohexamethylene, raw materials used
And preparation method thereof as follows:
In embodiment 1, benzaldehyde used is replaced with equimolar 4-chloro-benzaldehyde, aniline 1.2mmol
M-chloroaniline replace, Ketohexamethylene consumption increases to 1.5mmol, and the response time extends to 4 hours, other steps with
Embodiment 1 is identical, obtains yellow solid 2-[(4-chlorphenyl) (3-chloroanilino) methyl]-Ketohexamethylene, its productivity
It is 89%.
Embodiment 14
As a example by preparing following formula: compound 2-[(2-chlorphenyl) (2-aminotoluene base) methyl]-Ketohexamethylene, used former
Material and preparation method thereof is as follows:
In embodiment 1, benzaldehyde used is replaced with equimolar o-chlorobenzaldehyde, aniline 1.2mmol
O-toluidine is replaced, and Ketohexamethylene consumption increases to 1.5mmol, and the response time extends to 5 hours, other steps
Same as in Example 1, obtain yellow solid 2-[(2-chlorphenyl) (2-aminotoluene base) methyl]-Ketohexamethylene, its
Productivity is 71%.
Claims (5)
1. the method that beta-amino carbonyl compound is prepared in a graphene oxide catalysis, it is characterised in that: with water be
Solvent, with graphene oxide as catalyst, aromatic aldehyde, aromatic amine, aliphatic ketone are reacted at room temperature to 50 DEG C 3～
6 hours, obtain beta-amino carbonyl compound；
Above-mentioned aromatic aldehyde isAromatic amine isWherein R1、R2The most independent representative H,
Any one in Cl, Br, methyl, methoxyl group, m, n are the integer of 0～2；Described aliphatic ketone is hexamethylene
Ketone.
The method that beta-amino carbonyl compound is prepared in graphene oxide catalysis the most according to claim 1, its
Be characterised by: described aromatic aldehyde be benzaldehyde, o-methoxybenzaldehyde, o-chlorobenzaldehyde, 4-chloro-benzaldehyde,
Any one in m chlorobenzaldehyde；Aromatic amine be aniline, o-toluidine, m-toluidine, open-chain crown ether,
Any one in o-aminoanisole, P-nethoxyaniline, m-chloroaniline, o-chloraniline, parachloroanilinum.
The method that beta-amino carbonyl compound is prepared in graphene oxide catalysis the most according to claim 1, its
It is characterised by: the addition of described graphene oxide is the 5%～20% of aromatic aldehyde quality.
The method that beta-amino carbonyl compound is prepared in graphene oxide catalysis the most according to claim 1, its
It is characterised by: the addition of described graphene oxide is the 10%～15% of aromatic aldehyde quality.
5. prepare beta-amino carbonyl compound according to the graphene oxide catalysis described in Claims 1 to 4 any one
Method, it is characterised in that: described aromatic aldehyde, aromatic amine, alkenolic mol ratio are 1:1～1.5:1～1.5.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103025685A (en) * | 2010-05-28 | 2013-04-03 | 葛非亚公司 | Carbocatalysts for chemical transformations |
| CN103467319A (en) * | 2013-09-16 | 2013-12-25 | 陕西师范大学 | Method for synthesizing beta-amino-carbonyl compound by pure water phase |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103025685A (en) * | 2010-05-28 | 2013-04-03 | 葛非亚公司 | Carbocatalysts for chemical transformations |
| CN103467319A (en) * | 2013-09-16 | 2013-12-25 | 陕西师范大学 | Method for synthesizing beta-amino-carbonyl compound by pure water phase |
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| Highly Selective Synthesis of β-Amino Carbonyl Compounds over ZSM-5-SO3H under Solvent-free Conditions;Ahmad Reza Massah et al.;《Bull. Korean Chem. Soc.》;20111231;第32卷(第5期);1703-1708 * |
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