CN110550992A - green synthesis method of amino alcohol compound under catalysis of visible light - Google Patents
green synthesis method of amino alcohol compound under catalysis of visible light Download PDFInfo
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- CN110550992A CN110550992A CN201910892375.6A CN201910892375A CN110550992A CN 110550992 A CN110550992 A CN 110550992A CN 201910892375 A CN201910892375 A CN 201910892375A CN 110550992 A CN110550992 A CN 110550992A
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- C07B61/02—Generation of organic free radicals; Organic free radicals per se
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- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
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- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
Abstract
The invention discloses a green synthesis method of amino alcohol compounds under visible light catalysis, which belongs to the technical field of organic synthesis and specifically comprises the following steps of S1, sequentially adding 90.4mg of N-phenylglycine, 1.9mg of photocatalyst, 2ml of water and 20.4ul of benzaldehyde into a dried 10ml Schlenk tube, S2, carrying out gas extraction operation on a reaction bottle for three times to ensure that no water and no oxygen exist in the reaction tube, sealing the reaction tube, S3, stirring the reaction under the irradiation of a Blue LED until TLC detection reaction is finished, S4, respectively extracting for 4 times by using 5ml of ethyl acetate, collecting organic phases, drying by using anhydrous Na 2 SO 4, adding a proper amount of silica gel, concentrating under reduced pressure, and purifying obtained residues by a column chromatography method to obtain the amino alcohol compounds.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a green synthesis method of amino alcohol compounds under the catalysis of visible light.
Background
Amino alcohol compounds of the formula:Among them, the β -aminoalcohol compound, which contains both amino and alcohol groups, exhibits dual chemical reactivity of amine and alcohol, and thus is widely used in various fields of production and life, such as: the product can be used as high molecular material catalyst, pigment dispersant, industrial fluid emulsifier, formaldehyde fixing agent, organic synthetic reagent (especially for synthesizing small molecular drugs), etc. In addition, the structure of amino alcohols is also widely found in many bioactive natural products, such as anti-aids drugs, anti-hypertensive drugs, cordyceps myriocin, marine natural products that resist multidrug resistance, and the like. The synthesis of amino alcohols is therefore of great interest to chemists.
The following documents are available in the prior art for aminoalcohol compounds:
1. tetrahedron Letters; vol.45; nb.44; (2004) (ii) a p.8253-8256; journal of Molecular Catalysis A Chemical; vol.329; nb.1; (2010) (ii) a p.57-63; microporus and mesoporus Materials; vol.123; nb.1; (2009) (ii) a p.338-344; and Organic Letters; vol.2; nb.15; (2000) (ii) a p.2319-2321, all relate to a synthesis method of N-phenyl amino amine, and the specific synthesis reaction formula is as follows:
The method takes toxic epoxyphenylethane As a raw material, and generally needs to add specific catalysts such As [ Co ], [ Rh ], As-14, Tb-MOF and the like, and the catalysts have the defects of difficult preparation, high price and the like. In addition, the process may produce two beta-amino alcohol products due to the chemoselectivity of styrene oxide.
2. RSC Advances; vol.4; nb.105; (2014) (ii) a p.61077-61085; chemical communications-acids; vol.50; nb.58; (2014) (ii) a p.7881-7884, which relate to a synthetic method of amino alcohol compounds, and the specific synthetic reaction formula is as follows:
The method for preparing the amino alcohol compound by reducing the alpha-ketoamide has the defects of more byproducts and low selectivity. In addition, the method requires the additional addition of 3 to 4 equivalents of phenylsilane compound.
3. the Journal of Organic chemistry; vol.80; nb.21; (2015) (ii) a p.11131-11137, relates to a synthesis method of amino alcohol compounds, and the specific synthesis reaction formula is as follows:
KF, 18-crown-6 and trifluoroacetic acid are added as catalysts, an intermediate product is obtained by controlling at 0-30 ℃, and then a target product is obtained by removing a protecting group through a Pd/H2 reduction method on the basis. The method has complex experimental steps and low atom economy.
Disclosure of Invention
In view of the problems in the prior art, the invention aims to provide a green synthesis method of amino alcohol compounds, which has the advantages of high reaction speed, simple synthesis, mild conditions, small environmental pollution and high atom economy.
The green synthesis method of the amino alcohol compound under the catalysis of visible light is characterized by comprising the following steps: the method comprises the following steps:
s1: sequentially adding N-phenylglycine, a photocatalyst, a solvent and a carbonyl compound into a dried Schlenk tube;
S2: performing tertiary air pumping and air exchanging operation on the reaction bottle filled with the materials obtained in the step S1 to ensure that the reaction tube is sealed after no water or oxygen exists;
S3: placing the anhydrous and oxygen-free sealed reaction bottle filled with the materials obtained in the step S2 under the irradiation of a Blue LED, stirring for reaction, and finishing the reaction after TLC detection till the carbonyl compound disappears;
S4: and (4) concentrating the reaction liquid obtained in the step (S3) under reduced pressure, and purifying to obtain the product amino alcohol compound.
the green synthesis method of the amino alcohol compound under the catalysis of visible light is characterized by comprising the following steps: the photocatalyst in the step S1 is Ir (ppy)3、[Ir(ppy)2dtbbpy]PF6、{Ir[dF(CF3)ppy]2bpy}PF6、{Ir[dF(CF3)ppy]2dtbpy}PF6、Ru(bpy)3(PF6)2Or 4-CzIPN, preferably [ Ir (ppy)2dtbbpy]PF6。
the green synthesis method of the amino alcohol compound under the visible light catalyst is characterized by comprising the following steps: the solvent in step S1 is dichloromethane, 1, 2-dichloroethane, tetrahydrofuran, 1, 4-dioxane, acetonitrile or water, the concentration is 0.1M, and the preferred solvent is water, more preferably pure water or tap water.
The green synthesis method of the amino alcohol compound under the visible light catalyst is characterized by comprising the following steps: the carbonyl compound in the step S1 is benzaldehyde, p-methoxybenzaldehyde, p-methylbenzaldehyde, o-fluorobenzaldehyde, trifluoromethylbenzaldehyde, 2-naphthaldehyde, p-phenylbenzaldehyde, furfural, 2-thiophenecarboxaldehyde, isovaleraldehyde, or acetophenone.
The green synthesis method of the amino alcohol compound under the catalysis of visible light is characterized by comprising the following steps: the carbonyl compound in step S1: n-phenylglycine: the mass ratio of the photocatalyst is 1:3: 0.01.
The green synthesis method of the amino alcohol compound under the visible light catalyst is characterized by comprising the following steps: in the step S3, 455nm Blue LED lamp is used for irradiation, and the distance between the Schlenk tube and the Blue LED lamp is 3 cm.
the green synthesis method of the amino alcohol compound under the visible light catalyst is characterized by comprising the following steps: the stirring time in the step S3 is 1-6 h.
The green synthesis method of the amino alcohol compound under the visible light catalyst is characterized by comprising the following steps: the stirring temperature in step S3 is room temperature.
The green synthesis method of the amino alcohol compound under the visible light catalyst is characterized by comprising the following steps: the ratio of the developing solvent used for detecting the degree of reaction progress in the TLC plate in step S3 is PE: EA ═ 5:1 to 3: 1.
The green synthesis method of the amino alcohol compound under the visible light catalyst is characterized by comprising the following steps: in the step S4, ethyl acetate is used for extraction, an organic phase is collected and is extracted by anhydrous Na2SO4Drying, adding an appropriate amount of silica gel, concentrating under reduced pressure, and purifying the resulting residue by column chromatography to obtain the aminoalcohol compound.
The invention has the beneficial effects that:
The method for synthesizing the amino alcohol compound by the free radical mechanism under the catalysis of visible light is different from the complexity of other chemical synthesis methods, and has the characteristics of simple synthesis route, simple and convenient operation, mild reaction conditions, good controllability of the reaction conditions and the like.
Compared with many synthesis methods, the method for synthesizing the amino alcohol compound has the advantages of low cost ratio, no need of expensive catalysts and reaction reagents, convenient obtainment of raw materials and light sources and high yield.
The method takes water as a solvent to prepare the amino alcohol compound, is safe, has little pollution, is nontoxic to human, and accords with the green chemical concept.
The substrate of the method has wide application range, and the corresponding amino alcohol compound can be prepared by the method no matter the benzaldehyde derivative with the electron withdrawing group or the electron donating group. In addition, when the raw material is aliphatic aldehyde, the reaction can still be well performed.
Drawings
FIG. 1: the nuclear magnetic hydrogen spectrogram of the N-phenyl phenylethanolamine synthesized by the method is shown;
FIG. 2: the nuclear magnetic carbon spectrogram of the N-phenyl phenylethanolamine synthesized by the method is shown;
FIG. 3: the mass spectrum of the high-resolution liquid chromatography-mass spectrometry of the N-phenyl phenylethanolamine synthesized by the method is shown.
FIG. 4: is a nuclear magnetic hydrogen spectrum diagram of 1- (4-methoxyphenyl) -2- (phenylamino) ethan-1-ol synthesized by the invention;
FIG. 5: is the nuclear magnetic carbon spectrum of the 1- (4-methoxyphenyl) -2- (phenylamino) ethan-1-ol synthesized by the invention;
FIG. 6: the mass spectrogram of the high-resolution liquid chromatography-mass spectrometry of the 1- (4-methoxyphenyl) -2- (phenylamino) ethan-1-ol synthesized by the invention;
FIG. 7: is a nuclear magnetic hydrogen spectrum diagram of 1- (p-methylphenyl) -2- (phenylamino) -ethan-1-ol synthesized by the invention;
FIG. 8: is the nuclear magnetic carbon spectrum of the 1- (p-methylphenyl) -2- (phenylamino) -ethane-1-alcohol synthesized by the invention;
FIG. 9: the mass spectrum of the high resolution liquid chromatography-mass spectrometry of the 1- (p-methylphenyl) -2- (phenylamino) -ethan-1-ol synthesized by the invention;
FIG. 10: is a nuclear magnetic hydrogen spectrum diagram of 1- (p-fluorophenyl) -2- (phenylamino) ethane-1-alcohol synthesized by the invention;
FIG. 11: the nuclear magnetic carbon spectrum of the 1- (p-fluorophenyl) -2- (phenylamino) ethane-1-alcohol synthesized by the invention;
FIG. 12: the mass spectrum of the high resolution liquid chromatography-mass spectrometry of the 1- (p-fluorophenyl) -2- (phenylamino) ethane-1-alcohol synthesized by the invention;
FIG. 13: is a nuclear magnetic hydrogen spectrum diagram of 1- (p-trifluoromethyl phenyl) -2- (phenylamino) ethan-1-ol synthesized by the invention;
FIG. 14: is the nuclear magnetic carbon spectrum of the 1- (p-trifluoromethyl phenyl) -2- (phenylamino) ethane-1-alcohol synthesized by the invention;
FIG. 15: the mass spectrum of the high resolution liquid chromatography-mass spectrometry of the 1- (p-trifluoromethyl phenyl) -2- (phenylamino) ethane-1-alcohol synthesized by the invention;
FIG. 16: is a nuclear magnetic hydrogen spectrum diagram of 1- (2-naphthyl) -2- (phenylamino) ethane-1-alcohol synthesized by the invention;
FIG. 17: the nuclear magnetic carbon spectrum of the 1- (2-naphthyl) -2- (phenylamino) ethane-1-alcohol synthesized by the invention;
FIG. 18: the mass spectrum of the high resolution liquid chromatography-mass spectrometry of the 1- (2-naphthyl) -2- (phenylamino) ethane-1-alcohol synthesized by the invention;
FIG. 19: is a nuclear magnetic hydrogen spectrum diagram of 1- (4-biphenyl) -2- (phenylamino) ethane-1-alcohol synthesized by the invention;
FIG. 20: the nuclear magnetic carbon spectrum of the 1- (4-biphenyl) -2- (phenylamino) ethane-1-alcohol synthesized by the invention;
FIG. 21: the mass spectrum of the high resolution liquid chromatography mass spectrometry of the 1- (4-biphenyl) -2- (phenylamino) ethane-1-alcohol synthesized by the invention;
FIG. 22: is a nuclear magnetic hydrogen spectrum diagram of 1- (2-furyl) -2- (phenylamino) ethane-1-alcohol synthesized by the invention;
FIG. 23: is the nuclear magnetic carbon spectrum of the 1- (2-furyl) -2- (phenylamino) ethane-1-alcohol synthesized by the invention;
FIG. 24: the mass spectrum of the high resolution liquid chromatography-mass spectrometry of the 1- (2-furyl) -2- (phenylamino) ethane-1-alcohol synthesized by the invention;
FIG. 25: is a nuclear magnetic hydrogen spectrum diagram of 1- (2-thienyl) -2- (phenylamino) ethane-1-alcohol synthesized by the invention;
FIG. 26: is the nuclear magnetic carbon spectrum of the 1- (2-thienyl) -2- (phenylamino) ethane-1-alcohol synthesized by the invention;
FIG. 27 is a schematic view showing: the mass spectrum of the high resolution liquid chromatography-mass spectrometry of the 1- (2-thienyl) -2- (phenylamino) ethane-1-alcohol synthesized by the invention;
FIG. 28: is a nuclear magnetic hydrogen spectrum diagram of 1- (isoamyl) -2- (phenylamino) ethane-1-alcohol synthesized by the invention;
FIG. 29: the nuclear magnetic carbon spectrum of the 1- (isoamyl) -2- (phenylamino) ethane-1-alcohol synthesized by the invention;
FIG. 30: the mass spectrum of the high resolution liquid chromatography-mass spectrometry of the 1- (isoamyl) -2- (phenylamino) ethane-1-alcohol synthesized by the invention;
FIG. 31: is a nuclear magnetic hydrogen spectrum diagram of the 2-phenyl-1- (phenylamino) propan-2-ol synthesized by the invention;
FIG. 32: is a nuclear magnetic carbon spectrum of the 2-phenyl-1- (phenylamino) propan-2-ol synthesized by the invention;
FIG. 33: the high resolution liquid chromatography-mass spectrometry spectrum of the 2-phenyl-1- (phenylamino) propan-2-ol synthesized by the invention;
FIG. 34: is a nuclear magnetic hydrogen spectrum diagram of the 1-phenyl-2- (phenylamino) propan-1-ol synthesized by the invention;
FIG. 35: is the nuclear magnetic carbon spectrum of the 1-phenyl-2- (phenylamino) propan-1-ol synthesized by the invention;
FIG. 36: the mass spectrum of the high resolution liquid chromatography-mass spectrometry of the 1-phenyl-2- (phenylamino) propan-1-ol synthesized by the invention;
FIG. 37: is a nuclear magnetic hydrogen spectrum diagram of the phenyl (1-phenyl pyrrolidine-2-yl) methanol synthesized by the invention;
FIG. 38: is a nuclear magnetic carbon spectrum of the phenyl (1-phenyl pyrrolidine-2-yl) methanol synthesized by the invention;
FIG. 39: is a high-resolution liquid chromatography mass spectrum of the phenyl (1-phenylpyrrolidine-2-yl) methanol synthesized by the invention.
Detailed Description
The invention will be further described with reference to the drawings and the embodiments, but the scope of protection of the invention is not limited to the scope.
Example 1
To a dry 10ml Schlenk tube were added 90.4mg of N-phenylglycine, 1.9mg of photocatalyst [ Ir (ppy)2dtbbpy]PF62ml of water, 20.4. mu.l of benzaldehyde, benzaldehyde: n-phenylglycine: the mass ratio of the photocatalyst is 1:3: 0.01. And (3) carrying out air pumping and exchanging operation for three times on the reaction bottle to ensure that the reaction tube is water-free and oxygen-free, sealing, and stirring the reaction for 4 hours under the irradiation of 455nm Blue light (Blue LED lamp), wherein the distance between the Blue LED lamp and the Schlenk tube is 3 cm. After the TLC detection reaction is finished, the reaction solution is respectively subjected toextracting with 5ml ethyl acetate for 4 times, collecting organic phase, and extracting with anhydrous Na2SO4Drying, addition of an appropriate amount of silica gel, concentration under reduced pressure and purification of the resulting residue by column chromatography (PE/EA ═ 5:1) as shown in fig. 1-3, the product synthesized was indeed N-phenylphenylethanolamine by qualitative and quantitative analysis to give the product N-phenylphenylethanolamine 41.0mg, yield 96.2%.
in example 1, a photocatalyst [ Ir (ppy) ]was obtained under excitation with visible light2dtbbpy]PF6and (2) transitioning from a ground state to an excited state, oxidizing the N-phenylglycine to generate an N free radical intermediate (1), enabling the intermediate (1) to be unstable and rapidly decarboxylated, transferring the free radical to a methylene carbon to generate an intermediate (2), and further reacting the intermediate with benzaldehyde to finally obtain the amino alcohol compound. Since N-phenylglycine is easily oxidized by the excited photocatalyst, the reaction speed is high, the reaction is complete within 1h, and the specific reaction formula is as follows:
Benzaldehyde in example 1: n-phenylglycine: photocatalyst [ Ir (ppy)2dtbbpy]PF6The amount of substance (b) was 1:3:0.01, and a specific reaction amount was used. The amount of N-phenylglycine is reduced, the reaction is not completely carried out, and the yield is reduced; if the amount of N-phenylglycine is further increased, the reaction yield is hardly changed. The reaction did not proceed without adding a photocatalyst. The reaction proceeds more completely with the increase of the photocatalyst. When the amount of the photocatalyst is 1 mol%, the reaction can be completed. When the reaction is not illuminated with a Blue LED lamp, the reaction does not proceed because the photocatalyst cannot gain energy to transition from the ground state to the excited state.
photocatalyst in this example [ Ir (ppy)2dtbbpy]PF6By substitution into Ir (ppy)3、{Ir[dF(CF3)ppy]2bpy}PF6、{Ir[dF(CF3)ppy]2dtbpy}PF6、Ru(bpy)3(PF6)2Or 4-CzIPN can also achieve the similar effect of the embodiment 1And (5) fruit.
Example 2
to a dry 10ml Schlenk tube were added 90.4mg of N-phenylglycine, 1.9mg of photocatalyst [ Ir (ppy)2dtbbpy]PF62ml of water, 24.0. mu.l of p-methoxybenzaldehyde, p-methoxybenzaldehyde: n-phenylglycine: the mass ratio of the photocatalyst is 1:3: 0.01. And (3) carrying out air pumping and exchanging operation for three times on the reaction bottle to ensure that the reaction tube is water-free and oxygen-free, sealing, and stirring the reaction for 5 hours under the irradiation of 455nm Blue light (Blue LED lamp), wherein the distance between the Blue LED lamp and the Schlenk tube is 3 cm. After TLC detection reaction, the mixture was extracted 4 times with 5ml of ethyl acetate, and the organic phase was collected and washed with anhydrous Na2SO4dried, added with an appropriate amount of silica gel and concentrated under reduced pressure, and the resulting residue was purified by column chromatography (PE/EA ═ 4:1), as shown in fig. 4-6, by qualitative and quantitative analysis the synthesized product was indeed 1- (4-methoxyphenyl) -2- (phenylamino) ethan-1-ol to give 44.9mg of the product 1- (4-methoxyphenyl) -2- (phenylamino) ethan-1-ol, yield 92.3%.
Example 3
To a dry 10ml Schlenk tube were added 90.4mg of N-phenylglycine, 1.9mg of photocatalyst [ Ir (ppy)2dtbbpy]PF62ml of water, 22.8. mu.l of p-tolualdehyde, p-tolualdehyde: n-phenylglycine: the mass ratio of the photocatalyst is 1:3: 0.01. And (3) sealing the reaction bottle after three times of air pumping and exchanging operations are carried out on the reaction bottle to ensure that the reaction tube has no water and oxygen, and stirring the reaction bottle for 2 hours under the irradiation of 455nm Blue light (Blue LED lamp). After TLC detection reaction, the mixture was extracted 4 times with 5ml of ethyl acetate, and the organic phase was collected and washed with anhydrous Na2SO4Drying, addition of an appropriate amount of silica gel, concentration under reduced pressure and purification of the resulting residue by column chromatography (PE/EA ═ 4:1) as shown in fig. 7-9, the product synthesized was indeed 1- (p-methylphenyl) -2- (phenylamino) -ethan-1-ol by qualitative and quantitative analysis to give the product 1- (p-methylphenyl) -2- (phenylamino) -ethan-1-ol 40.9mg, yield 90.0%.
example 4
To a dry 10ml Schlenk tube were added in sequence 90.4mg of N-phenylglycineacid, 1.9mg photocatalyst [ Ir (ppy)2dtbbpy]PF62ml of water, 21.1ul of o-fluorobenzaldehyde, o-fluorobenzaldehyde: n-phenylglycine: the mass ratio of the photocatalyst is 1:3: 0.01. And (3) carrying out air pumping and exchanging operation for three times on the reaction bottle to ensure that the reaction tube is water-free and oxygen-free, sealing, and stirring the reaction for 2 hours under the irradiation of 455nm Blue light (Blue LED lamp), wherein the distance between the Blue LED lamp and the Schlenk tube is 3 cm. After TLC detection reaction, the mixture was extracted 4 times with 5ml of ethyl acetate, and the organic phase was collected and washed with anhydrous Na2SO4Drying, addition of an appropriate amount of silica gel, concentration under reduced pressure and purification of the resulting residue by column chromatography (PE/EA ═ 3:1) gave 43.8mg of the product 1- (p-fluorophenyl) -2- (phenylamino) eth-1-ol by qualitative and quantitative analysis, as shown in fig. 10-12, of 1- (p-fluorophenyl) -2- (phenylamino) eth-1-ol, yield 94.7%.
example 5
To a dry 10ml Schlenk tube were added 90.4mg of N-phenylglycine, 1.9mg of photocatalyst [ Ir (ppy)2dtbbpy]PF62ml of water, 27.3. mu.l of p-trifluoromethylbenzaldehyde, p-trifluoromethylbenzaldehyde: n-phenylglycine: the mass ratio of the photocatalyst is 1:3: 0.01. And (3) carrying out air pumping and exchanging operation for three times on the reaction bottle to ensure that the reaction tube is water-free and oxygen-free, sealing, and stirring the reaction for 4 hours under the irradiation of 455nm Blue light (Blue LED lamp), wherein the distance between the Blue LED lamp and the Schlenk tube is 3 cm. After TLC detection reaction, the mixture was extracted 4 times with 5ml of ethyl acetate, and the organic phase was collected and washed with anhydrous Na2SO4drying, addition of an appropriate amount of silica gel, concentration under reduced pressure and purification of the resulting residue by column chromatography (PE/EA ═ 3:1) gave, as shown in fig. 13-15, 42.3mg of the product 1- (p-trifluoromethylphenyl) -2- (phenylamino) ethan-1-ol by qualitative and quantitative analysis, 75.2% yield of 1- (p-trifluoromethylphenyl) -2- (phenylamino) ethan-1-ol.
Example 6
To a dry 10ml Schlenk tube were added 90.4mg of N-phenylglycine, 1.9mg of photocatalyst [ Ir (ppy)2dtbbpy]PF62ml of water, 31.2mg of 2-naphthaldehyde, 2-naphthaldehydeAldehyde: n-phenylglycine: the mass ratio of the photocatalyst is 1:3: 0.01. And (3) carrying out air pumping and exchanging operation for three times on the reaction bottle to ensure that the reaction tube is water-free and oxygen-free, sealing, and stirring the reaction for 6 hours under the irradiation of 455nm Blue light (Blue LED lamp), wherein the distance between the Blue LED lamp and the Schlenk tube is 3 cm. After TLC detection reaction, the mixture was extracted 4 times with 5ml of ethyl acetate, and the organic phase was collected and washed with anhydrous Na2SO4Dried, added with an appropriate amount of silica gel and concentrated under reduced pressure, and the resulting residue was purified by column chromatography (PE/EA ═ 3:1), as shown in fig. 16 to 18, by qualitative and quantitative analysis that the synthesized product was indeed 1- (2-naphthyl) -2- (phenylamino) ethane-1-ol, the product 1- (2-naphthyl) -2- (phenylamino) ethane-1-ol was obtained in 36.3mg, yield 69%.
Example 7
to a dry 10ml Schlenk tube were added 90.4mg of N-phenylglycine, 1.9mg of photocatalyst [ Ir (ppy)2dtbbpy]PF62ml of water, 36.5mg of p-benzaldehyde, p-benzaldehyde: n-phenylglycine: the mass ratio of the photocatalyst is 1:3: 0.01. And (3) carrying out air pumping and changing operation for three times on the reaction bottle to ensure that the reaction tube is anhydrous and anaerobic, sealing, and stirring the reaction for 4 hours under the irradiation of 455nm Blue light (Blue LED lamp), wherein the distance between the LED lamp and the Schlenk tube is 3 cm. After TLC detection reaction, the mixture was extracted 4 times with 5ml of ethyl acetate, and the organic phase was collected and washed with anhydrous Na2SO4Dried, added with an appropriate amount of silica gel and concentrated under reduced pressure, and the resulting residue was purified by column chromatography (PE/EA ═ 4:1), as shown in fig. 19 to 21, by qualitative and quantitative analysis, the synthesized product was indeed 1- (4-biphenyl) -2- (phenylamino) ethane-1-ol, giving 50.4mg of the product 1- (4-biphenyl) -2- (phenylamino) ethane-1-ol, yield 87.1%.
example 8
To a dry 10ml Schlenk tube were added 90.4mg of N-phenylglycine, 1.9mg of photocatalyst [ Ir (ppy)2dtbbpy]PF62ml of water, 16.6 μ l of furfural, furfural: n-phenylglycine: the mass ratio of the photocatalyst is 1:3: 0.01. Performing gas pumping and exchanging operation for three times on the reaction bottle to ensure that the reaction tube is sealed after no water and no oxygen exist, andThe reaction was stirred for 4h under 455nm Blue light (Blue LED lamp) at a distance of 3cm from the Schlenk tube. After TLC detection reaction, the mixture was extracted 4 times with 5ml of ethyl acetate, and the organic phase was collected and washed with anhydrous Na2SO4Drying, addition of an appropriate amount of silica gel was concentrated under reduced pressure and the resulting residue was purified by column chromatography (PE/EA ═ 4:1) as shown in fig. 22-24, and the product synthesized was indeed 1- (2-furyl) -2- (phenylamino) ethane-1-ol by qualitative and quantitative analysis to give 37.8mg of the product 1- (2-furyl) -2- (phenylamino) ethane-1-ol in 93.0% yield.
Example 9
To a dry 10ml Schlenk tube were added 90.4mg of N-phenylglycine, 1.9mg of photocatalyst [ Ir (ppy)2dtbbpy]PF62ml of water, 18.7. mu.l of 2-thiophenecarboxaldehyde, 2-thiophenecarboxaldehyde: n-phenylglycine: the mass ratio of the photocatalyst is 1:3: 0.01. And (3) carrying out air pumping and exchanging operation for three times on the reaction bottle to ensure that the reaction tube is water-free and oxygen-free, sealing, and stirring the reaction for 3 hours under the irradiation of 455nm Blue light (Blue LED lamp), wherein the distance between the Blue LED lamp and the Schlenk tube is 3 cm. After TLC detection reaction, the mixture was extracted 4 times with 5ml of ethyl acetate, and the organic phase was collected and washed with anhydrous Na2SO4drying, addition of an appropriate amount of silica gel was concentrated under reduced pressure and the resulting residue was purified by column chromatography (PE/EA ═ 4:1) as shown in fig. 25-27, and the product synthesized was indeed 1- (2-thienyl) -2- (phenylamino) ethane-1-ol by qualitative and quantitative analysis to give the product 1- (2-thienyl) -2- (phenylamino) ethane-1-ol 40.9mg, yield 93.3%.
Example 10
To a dry 10ml Schlenk tube were added 90.4mg of N-phenylglycine, 1.9mg of photocatalyst [ Ir (ppy)2dtbbpy]PF62ml of water, 21.5ul of isovaleraldehyde, isovaleraldehyde: n-phenylglycine: the mass ratio of the photocatalyst is 1:3: 0.01. And (3) carrying out air pumping and exchanging operation for three times on the reaction bottle to ensure that the reaction tube is water-free and oxygen-free, sealing, and stirring the reaction for 3 hours under the irradiation of 455nm Blue light (Blue LED lamp), wherein the distance between the Blue LED lamp and the Schlenk tube is 3 cm. After the TLC detection reaction, 5ml of ethyl is respectively usedExtracting with ethyl acetate for 4 times, collecting organic phase, and extracting with anhydrous Na2SO4drying, addition of an appropriate amount of silica gel and concentration under reduced pressure and purification of the resulting residue by column chromatography (PE/EA ═ 3:1) gave, as shown in fig. 28-30, 26.5mg of the product 1- (isopentyl) -2- (phenylamino) ethan-1-ol by qualitative and quantitative analysis, with 68.7% yield.
Example 11
To a dry 10ml Schlenk tube were added 90.4mg of N-phenylglycine, 1.9mg of photocatalyst [ Ir (ppy)2dtbbpy]PF62ml of water, 23.4. mu.l of acetophenone, acetophenone: n-phenylglycine: the mass ratio of the photocatalyst is 1:3: 0.01. And (3) carrying out air pumping and exchanging operation for three times on the reaction bottle to ensure that the reaction tube is water-free and oxygen-free, sealing, and stirring the reaction for 5 hours under the irradiation of 455nm Blue light (Blue LED lamp), wherein the distance between the Blue LED lamp and the Schlenk tube is 3 cm. After TLC detection reaction, the mixture was extracted 4 times with 5ml of ethyl acetate, and the organic phase was collected and washed with anhydrous Na2SO4Drying, addition of an appropriate amount of silica gel, concentration under reduced pressure and purification of the resulting residue by column chromatography (PE/EA ═ 4:1) gave 31.5mg of the product 2-phenyl-1- (phenylamino) propan-2-ol by qualitative and quantitative analysis as shown in fig. 31-33, yield 69.3%.
example 12
to a dry 10ml Schlenk tube were added 93.1mg of 2-phenylamino propionic acid, 1.9mg of photocatalyst [ Ir (ppy)2dtbbpy]PF62ml of water, 20.4. mu.l of benzaldehyde, benzaldehyde: 2-phenylamino propionic acid: the mass ratio of the photocatalyst is 1:3: 0.01. And (3) carrying out air pumping and exchanging operation for three times on the reaction bottle to ensure that the reaction tube is water-free and oxygen-free, sealing, and stirring the reaction for 2.5 hours under the irradiation of 455nm Blue light (Blue LED lamp), wherein the distance between the Blue LED lamp and the Schlenk tube is 3 cm. After TLC detection reaction, the mixture was extracted 4 times with 5ml of ethyl acetate, and the organic phase was collected and washed with anhydrous Na2SO4Drying, adding appropriate amount of silica gel, concentrating under reduced pressure, and subjecting the obtained residue to column chromatography (PE)4:1), as shown in fig. 34-36, the product synthesized by qualitative and quantitative analysis was indeed 1-phenyl-2- (phenylamino) propan-1-ol, yielding 58.9mg of the product 1-phenyl-2- (phenylamino) propan-1-ol, 95.0% yield.
Example 13
To a dry 10ml Schlenk tube were added 114.8mg of N-phenylproline, 1.9mg of photocatalyst [ Ir (ppy)2dtbbpy]PF62ml of water, 20.4. mu.l of benzaldehyde, benzaldehyde: n-phenylproline: the mass ratio of the photocatalyst is 1:3: 0.01. And (3) carrying out air pumping and exchanging operation for three times on the reaction bottle to ensure that the reaction tube is water-free and oxygen-free, sealing, and stirring the reaction for 4 hours under the irradiation of 455nm Blue light (Blue LED lamp), wherein the distance between the Blue LED lamp and the Schlenk tube is 3 cm. After TLC detection reaction, the mixture was extracted 4 times with 5ml of ethyl acetate, and the organic phase was collected and washed with anhydrous Na2SO4After drying, an appropriate amount of silica gel was added and concentrated under reduced pressure, and the resulting residue was purified by column chromatography (PE/EA ═ 3:1), as shown in fig. 37-39, the product synthesized was indeed phenyl (1-phenylpyrrolidin-2-yl) methanol by qualitative and quantitative analysis, yielding 39.4mg of phenyl (1-phenylpyrrolidin-2-yl) methanol as a product in 77.8% yield.
Example 14
to a dry 10ml Schlenk tube were added 90.4mg of N-phenylglycine, 1.9mg of photocatalyst [ Ir (ppy)2dtbbpy]PF62ml dichloromethane, 20.4 μ l benzaldehyde, benzaldehyde: n-phenylglycine: the mass ratio of the photocatalyst is 1:3: 0.01. And (3) carrying out air pumping and exchanging operation for three times on the reaction bottle to ensure that the reaction tube is water-free and oxygen-free, sealing, and stirring the reaction for 5 hours under the irradiation of 455nm Blue light (Blue LED lamp), wherein the distance between the Blue LED lamp and the Schlenk tube is 3 cm. After the TLC detection reaction was completed, the reaction solution was transferred to an eggplant-shaped bottle, an appropriate amount of silica gel was added thereto, and the mixture was concentrated under reduced pressure, and the resulting residue was purified by column chromatography (PE/EA ═ 4:1) to obtain 39.8mg of N-phenylphenylethanolamine, which is a product, in 93.3% yield.
example 15
Into a dry 10ml Schlenk tube were added 90.4mg of N-phenylglycine and 1.9mg of photocatalyst [ 2 ]Ir(ppy)2dtbbpy]PF62ml tetrahydrofuran, 20.4ul benzaldehyde, benzaldehyde: n-phenylglycine: the mass ratio of the photocatalyst is 1:3: 0.01. And (3) carrying out air pumping and exchanging operation for three times on the reaction bottle to ensure that the reaction tube is water-free and oxygen-free, sealing, and stirring the reaction for 2 hours under the irradiation of 455nm Blue light (Blue LED lamp), wherein the distance between the Blue LED lamp and the Schlenk tube is 3 cm. After the TLC detection reaction was completed, the reaction solution was transferred to an eggplant-shaped bottle, an appropriate amount of silica gel was added and concentrated under reduced pressure, and the resulting residue was purified by column chromatography (PE/EA ═ 3:1) to obtain 36.3mg of N-phenylphenylethanolamine as a product, with a yield of 85.1%.
Example 16
to a dry 10ml Schlenk tube were added 90.4mg of N-phenylglycine, 1.9mg of photocatalyst [ Ir (ppy)2dtbbpy]PF62ml acetonitrile, 20.4 μ l benzaldehyde, benzaldehyde: n-phenylglycine: the mass ratio of the photocatalyst is 1:3: 0.01. And (3) carrying out air pumping and exchanging operation for three times on the reaction bottle to ensure that the reaction tube is water-free and oxygen-free, sealing, and stirring the reaction for 3 hours under the irradiation of 455nm Blue light (Blue LED lamp), wherein the distance between the Blue LED lamp and the Schlenk tube is 3 cm. After the TLC detection reaction was completed, the reaction solution was transferred to an eggplant-shaped bottle, an appropriate amount of silica gel was added thereto, and the reaction solution was concentrated under reduced pressure, and the obtained residue was purified by column chromatography (PE/EA ═ 4:1) to obtain 34.8mg of N-phenylphenylethanolamine as a product, with a yield of 81.6%.
Example 17
to a dry 10ml Schlenk tube were added 90.4mg of N-phenylglycine, 1.9mg of photocatalyst [ Ir (ppy)2dtbbpy]PF62ml of toluene, 20.4. mu.l of benzaldehyde, benzaldehyde: n-phenylglycine: the mass ratio of the photocatalyst is 1:3: 0.01. And (3) carrying out air pumping and exchanging operation for three times on the reaction bottle to ensure that the reaction tube is water-free and oxygen-free, sealing, and stirring the reaction for 3.5 hours under the irradiation of 455nm Blue light (Blue LED lamp), wherein the distance between the Blue LED lamp and the Schlenk tube is 3 cm. After the TLC detection reaction was completed, the reaction solution was transferred to an eggplant-shaped bottle, an appropriate amount of silica gel was added thereto, and the mixture was concentrated under reduced pressure, and the resulting residue was purified by column chromatography (PE/EA ═ 5:1) to obtain 21.5mg of N-phenylphenylethanolamine as a product, with a yield of 50.4%.
Example 18
to a dry 100ml round bottom flask were added 2.30g N-phenylglycine, followed by 0.05g of photocatalyst [ Ir (ppy)2dtbbpy]PF650ml of water, 0.53g of benzaldehyde, benzaldehyde: n-phenylglycine: the mass ratio of the photocatalyst is 1:3: 0.01. And (3) carrying out air pumping and exchanging operation for three times on the reaction bottle to ensure that the reaction tube is water-free and oxygen-free, sealing, and stirring the reaction for 3 hours under the irradiation of 455nm Blue light (Blue LED lamp), wherein the distance between the Blue LED lamp and the Schlenk tube is 3 cm. After TLC detection, the reaction mixture was extracted 4 times with 50ml of ethyl acetate, and the organic phase was collected and washed with anhydrous Na2SO4drying, addition of the appropriate amount of silica gel, concentration under reduced pressure and purification of the resulting residue by column chromatography (PE/EA ═ 5:1) gave the product N-phenylphenylethanolamine 0.90g, yield 84.4%.
example 19
To a dry 10ml Schlenk tube were added 90.4mg of N-phenylglycine, 1.9mg of photocatalyst [ Ir (ppy)2dtbbpy]PF62ml of water, 20.4. mu.l of benzaldehyde, benzaldehyde: n-phenylglycine: the mass ratio of the photocatalyst is 1:3: 0.01. And (3) performing air pumping and exchanging operation for three times on the reaction bottle to ensure that the reaction tube is anhydrous and anaerobic, sealing, and stirring for 6 hours under the irradiation of sunlight. After TLC detection reaction, the mixture was extracted 4 times with 5ml of ethyl acetate, and the organic phase was collected and washed with anhydrous Na2SO4Drying, addition of the appropriate amount of silica gel, concentration under reduced pressure and purification of the resulting residue by column chromatography (PE/EA ═ 4:1) gave the product N-phenylphenylethanolamine 33.3mg, yield 78.1%.
Claims (10)
1. a green synthesis method of amino alcohol compounds under visible light catalysis is characterized in that: the method comprises the following steps:
s1: sequentially adding N-phenylglycine, a photocatalyst, a solvent and a carbonyl compound into a dried Schlenk tube;
S2: performing tertiary air pumping and air exchanging operation on the reaction bottle filled with the materials obtained in the step S1 to ensure that the reaction tube is sealed after no water or oxygen exists;
S3: placing the anhydrous and oxygen-free sealed reaction bottle filled with the materials obtained in the step S2 under the irradiation of a Blue LED, stirring for reaction, and finishing the reaction after TLC detection till the carbonyl compound disappears;
S4: and (4) concentrating the reaction liquid obtained in the step (S3) under reduced pressure, and purifying to obtain the product amino alcohol compound.
2. The green synthesis method of amino alcohol compounds under visible light catalysis as claimed in claim 1, wherein: the photocatalyst in the step S1 is Ir (ppy)3、[Ir(ppy)2dtbbpy]PF6、{Ir[dF(CF3)ppy]2bpy}PF6、{Ir[dF(CF3)ppy]2dtbpy}PF6、Ru(bpy)3(PF6)2Or 4-CzIPN, preferably [ Ir (ppy)2dtbbpy]PF6。
3. The green synthesis method of amino alcohol compounds under visible light catalyst according to claim 1, characterized in that: the solvent in step S1 is dichloromethane, 1, 2-dichloroethane, tetrahydrofuran, 1, 4-dioxane, acetonitrile or water, the concentration is 0.1M, and the preferred solvent is water, more preferably pure water or tap water.
4. the green synthesis method of amino alcohol compounds under visible light catalyst according to claim 1, characterized in that: the carbonyl compound in the step S1 is benzaldehyde, p-methoxybenzaldehyde, p-methylbenzaldehyde, o-fluorobenzaldehyde, trifluoromethylbenzaldehyde, 2-naphthaldehyde, p-phenylbenzaldehyde, furfural, 2-thiophenecarboxaldehyde, isovaleraldehyde, or acetophenone.
5. the green synthesis method of amino alcohol compounds under visible light catalysis according to any one of claims 1 to 4, characterized in that: the carbonyl compound in step S1: n-phenylglycine: the mass ratio of the photocatalyst is 1:3: 0.01.
6. The green synthesis method of amino alcohol compounds under visible light catalyst according to claim 1, characterized in that: in the step S3, 455nm Blue LED lamp is used for irradiation, and the distance between the Schlenk tube and the Blue LED lamp is 3 cm.
7. The green synthesis method of amino alcohol compounds under visible light catalyst according to claim 1, characterized in that: the stirring time in the step S3 is 1-6 h.
8. The green synthesis method of amino alcohol compounds under visible light catalyst according to claim 1, characterized in that: the stirring temperature in step S3 is room temperature.
9. The green synthesis method of amino alcohol compounds under visible light catalyst according to claim 1, characterized in that: the ratio of the developing solvent used for detecting the degree of reaction progress in the TLC plate in step S3 is PE: EA ═ 5:1 to 3: 1.
10. The green synthesis method of amino alcohol compounds under visible light catalyst according to claim 1, characterized in that: in the step S4, ethyl acetate is used for extraction, an organic phase is collected and is extracted by anhydrous Na2SO4drying, adding an appropriate amount of silica gel, concentrating under reduced pressure, and purifying the resulting residue by column chromatography to obtain the aminoalcohol compound.
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| RU2736511C1 (en) * | 2020-01-24 | 2020-11-17 | Автономная некоммерческая образовательная организация высшего образования "Сколковский институт науки и технологий" | Biphenyl derivatives having biological activity, pharmaceutical compositions and methods of treatment based on said compounds and use thereof |
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| CN111285809B (en) * | 2020-02-28 | 2023-04-25 | 杭州师范大学 | Green synthesis method of imidazoline under visible light catalysis |
| CN111686762A (en) * | 2020-06-10 | 2020-09-22 | 辽宁工程技术大学 | Green synthesis method of amino alcohol compound under catalysis of visible light |
| CN111909232A (en) * | 2020-08-07 | 2020-11-10 | 上海药明康德新药开发有限公司 | Method for preparing On-DNA1, 2-amino alcohol compound through visible light catalysis in construction of DNA coding compound library |
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