CN107973715B - Preparation method of polysubstituted remote allyl ketone derivative - Google Patents
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Abstract
The invention discloses a preparation method of a polysubstituted far-end allyl ketone derivative, and relates to a preparation method of a polysubstituted far-end allyl ketone derivative. The invention aims to provide a preparation method of a polysubstituted far-end allyl ketone derivative, which is characterized in that a tertiary cyclic alcohol derivative, an unsaturated alkene compound and a photocatalyst are dissolved in an organic solvent under the atmosphere of nitrogen at room temperature, the mixture is uniformly mixed, then the mixture is placed under a blue LED lamp for illumination reaction, and the solvent is removed by rotary evaporation and then the mixture is separated and purified by silica gel column chromatography, so that the obtained product is the polysubstituted far-end allyl ketone derivative. The invention is applied to the field of organic synthesis.
Description
Technical Field
The invention relates to a preparation method of a polysubstituted remote allyl ketone derivative.
Background
The cyclic alcohol widely exists in natural products and drug molecules with biological activity, and is also an important raw material intermediate of a plurality of chemical products and other natural products, and according to literature reports, various important chemical raw material intermediates can be obtained through a series of conversion reactions, such as unsaturated remote diketone compounds 1, remote enol compounds 2 and diols 3.
At present, ring opening of cyclic alcohol is used for synthesizing polysubstituted far-end allyl ketone derivatives, and ring opening fluorination reaction, alkynyl reaction, cyanation reaction and amination reaction of cyclic alcohol are mainly reported, but direct allylation is not reported. And most of the existing synthetic methods adopt a high-temperature heating system, so that the energy consumption is high, the requirements on equipment are high due to harsh conditions, and the yield is low and is 50-60 percent mostly. Therefore, the problem to be solved at present is to find a synthesis method of the polysubstituted remote allyl ketone derivative with mild conditions, simple method, convenient operation and high yield.
Disclosure of Invention
The invention aims to solve the problems that most of the existing methods for synthesizing the polysubstituted far-end allyl ketone derivative by ring opening of cyclic alcohol adopt a high-temperature heating system, the energy consumption is high, the requirements on equipment are high due to harsh conditions, and the yield is low.
The preparation method of the polysubstituted far-end allyl ketone derivative comprises the following steps:
dissolving the tertiary cyclic alcohol derivative, the unsaturated alkene compound, the alkali and the photocatalyst in an organic solvent under the atmosphere of nitrogen at room temperature, uniformly mixing, placing under a blue LED lamp for illumination reaction, removing the solvent by rotary evaporation, and then separating and purifying by silica gel column chromatography to obtain a product, namely the polysubstituted far-end allyl ketone derivative; the molar ratio of the unsaturated alkene compound to the tertiary cyclic alcohol derivative to the base to the photocatalyst is 2:1:2.5: 0.5;
wherein the chemical structural formula of the tertiary cyclic alcohol derivative is as follows:
the unsaturated alkene compound has the chemical structural formula:
the chemical structural formula of the photocatalyst is as follows:
wherein R is1、R2And R3Is alkyl, alkoxy or halogen, and the substituent on Ar is alkoxy, alkyl or polycyclic aryl; n is 0 to 9.
The invention provides a preparation method of a polysubstituted far-end allyl ketone derivative, and the polysubstituted far-end allyl ketone derivative has various conversion ways and can be used as intermediates of a plurality of chemical raw materials, so that the compound provided by the invention has higher research value and can be used for research and development of drug development, synthesis of chemical raw material intermediates and the like. The present invention can also be used as a starting material for the synthesis of other isoxazolidine-containing derivatives. The method can be used for reaction at normal temperature and normal pressure, has mild reaction conditions, has the yield of 80 percent, and has the advantages of simple operation, no pollution, safety, environmental protection and low cost.
Detailed Description
The first embodiment is as follows: the preparation method of the polysubstituted distal allyl ketone derivative in the embodiment comprises the following steps:
dissolving the tertiary cyclic alcohol derivative, the unsaturated alkene compound, the alkali and the photocatalyst in an organic solvent under the atmosphere of nitrogen at room temperature, uniformly mixing, placing under a blue LED lamp for illumination reaction, removing the solvent by rotary evaporation, and then separating and purifying by silica gel column chromatography to obtain a product, namely the polysubstituted far-end allyl ketone derivative; the molar ratio of the unsaturated alkene compound to the tertiary cyclic alcohol derivative to the base to the photocatalyst is 2:1:2.5: 0.5;
wherein the chemical structural formula of the tertiary cyclic alcohol derivative is as follows:
the unsaturated alkene compound has the chemical structural formula:
the chemical structural formula of the photocatalyst is as follows:
wherein R is1、R2And R3Is alkyl, alkoxy or halogen, and the substituent on Ar is alkoxy, alkyl or polycyclic aryl; n is 0 to 9.
The structural formula of the polysubstituted distal allyl ketone derivative of the embodiment is as follows:
Preferably, the substituted aryl is p-methoxyphenyl.
The embodiment provides a preparation method of the polysubstituted far-end allyl ketone derivative, and the polysubstituted far-end allyl ketone derivative has various conversion ways and can be used as intermediates of a plurality of chemical raw materials, so that the compound provided by the embodiment has high research value and can be used for research and development of drug development, synthesis of chemical raw material intermediates and the like. This embodiment can also be used as a starting material for the synthesis of other isoxazolidine-containing derivatives. The method can be used for reaction at normal temperature and normal pressure, has mild reaction conditions, can achieve a yield of 80 percent, and has the advantages of simple operation, no pollution, safety, environmental protection and low cost.
The second embodiment is as follows: the first difference between the present embodiment and the specific embodiment is: the unsaturated olefin compound is methyl-substituted alpha, beta unsaturated ester, ethyl-substituted alpha, beta unsaturated ester, nitro-substituted alpha, beta unsaturated ester or cyano-substituted alpha, beta unsaturated ester. The rest is the same as the first embodiment.
The third concrete implementation mode: the difference between the first embodiment and the second embodiment is as follows: the tertiary cyclic alcohol derivative is ternary cyclic alcohol, quaternary cyclic alcohol, quinary cyclic alcohol, deca-dihydric cyclic alcohol, ortho-position polyalkyl-substituted cyclic alcohol or ortho-position aryl-substituted cyclic alcohol. The others are the same as in the first or second embodiment.
The fourth concrete implementation mode: the difference between this embodiment mode and one of the first to third embodiment modes is: the organic solvent is dichloromethane, dichloroethane, acetonitrile or N, N-dicarboximide. The others differ from one of the first to third embodiments.
The fifth concrete implementation mode: the difference between this embodiment and one of the first to fourth embodiments is: the molar volume ratio of the tertiary cyclic alcohol derivative to the organic solvent is 1mmol (10-20) mL. The others differ from one of the first to fourth embodiments.
The sixth specific implementation mode: the difference between this embodiment and one of the first to fifth embodiments is: the reaction time of illumination under a blue LED lamp is 12-48 h. The others differ from one of the first to fifth embodiments.
The seventh embodiment: the difference between this embodiment and one of the first to sixth embodiments is: the solvent used for silica gel column chromatography separation and purification is a mixed solvent of petroleum ether and ethyl acetate. The rest is the same as one of the first to sixth embodiments.
The specific implementation mode is eight: the present embodiment differs from one of the first to seventh embodiments in that: the volume ratio of the petroleum ether to the ethyl acetate in the mixed solvent is (20-50): 1. The others differ from one of the first to seventh embodiments.
The specific implementation method nine: the present embodiment differs from the first to eighth embodiments in that: the photocatalyst is Ir [ dF (CF)3)ppy]2(dtbpy)PF6. The others differ from the first to eighth embodiments.
The detailed implementation mode is ten: the present embodiment differs from one of the first to ninth embodiments in that: the base is 2.4.6-trimethylpyridine. The others differ from one of the first to ninth embodiments.
The following experiments were performed to verify the beneficial effects of the present invention:
the first embodiment is as follows: preparation method of polysubstituted remote allyl ketone derivative
Under nitrogen atmosphere at room temperature, 35.6mg (0.2mmol) of p-methoxycyclobutanol, 100mg (0.4mmol) of unsaturated ester, 1.2mg (0.005mmol) of [ dF (CF)3)ppy]2(dtbpy)PF6And 0.5mmol of 2.4.6-trimethyl pyridine are dissolved in 4mL of dichloromethane, the mixture is uniformly mixed, then the mixture is placed under a blue LED lamp for illumination reaction for 28 hours, and after dichloromethane is removed by concentration of a rotary evaporator, the mixture is further processed by the following steps of: using the mixed solution of ethyl acetate as eluent to carry out silica gel column chromatography purification and separation,the obtained product is the polysubstituted far-end allyl ketone derivative; the reaction formula is as follows:
the product purity was 99% and the yield was 73%. The nuclear magnetic data analysis was:1H NMR(400MHz,CDCl3):H7.98-7.88(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):C198.9,167.4,163.4,140.7,130.4,130.2,124.7,113.8,60.7,55.5,38.1,31.8,28.2,24.1,14.3。
EXAMPLE two preparation method of polysubstituted remote allyl ketone derivative
Under nitrogen atmosphere at room temperature, 38.4mg (0.2mmol) of p-methoxycyclopentanol, 100mg (0.4mmol) of unsaturated ester, 1.2mg (0.005mmol) of [ dF (CF)3)ppy]2(dtbpy)PF6And 0.5mmol of 2.4.6-trimethyl pyridine are dissolved in 4mL of dichloromethane, the mixture is uniformly mixed, then the mixture is placed under a blue LED lamp for illumination reaction for 28 hours, and after dichloromethane is removed by concentration of a rotary evaporator, the mixture is further processed by the following steps of: taking the mixed solution of ethyl acetate as an eluent, and carrying out silica gel column chromatography purification and separation to obtain a product, namely the polysubstituted far-end allyl ketone derivative; the reaction formula is as follows:
the product purity was 99% and the yield was 70%. The nuclear magnetic data analysis is as follows:1H NMR(600MHz,CDCl3):H7.93(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):C199.1,167.4,163.4,141.0,130.4,130.2,124.5,113.8,60.7,55.5,38.2,31.8,29.1,28.4,24.4,14.3。
EXAMPLE III preparation of polysubstituted remote allyl ketone derivative
Under nitrogen atmosphere at room temperature, 58.0mg (0.2mmol) of p-methoxycyclododecanol, 100mg (0.4mmol) of the unsaturated ester, and 1.2mg (0.005mmol) of [ dF (CF)3)ppy]2(dtbpy)PF6And 0.5mmol of 2.4.6-trimethyl pyridine are dissolved in 4mL of dichloromethane, the mixture is uniformly mixed, then the mixture is placed under a blue LED lamp for illumination reaction for 28 hours, and after dichloromethane is removed by concentration of a rotary evaporator, the mixture is further processed by the following steps of: taking the mixed solution of ethyl acetate as an eluent, and carrying out silica gel column chromatography purification and separation to obtain a product, namely the polysubstituted far-end allyl ketone derivative; the reaction formula is as follows:
the product purity was 99% and the yield was 81%. The nuclear magnetic data analysis is as follows:1H NMR(600MHz,CDCl3):H7.93(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):C199.3,167.5,163.4,141.2,130.4,130.3,124.2,113.7,60.6,55.5,38.4,31.9,29.7,29.7,29.7,29.6,29.5,29.5,29.3,28.5,24.7,14.3。
EXAMPLE IV preparation of polysubstituted remote allyl ketone derivative
Under nitrogen atmosphere at room temperature, 44.0mg (0.2mmol) of substituted p-methoxycyclopentanol, 100mg (0.4mmol) of unsaturated ester, 1.2mg (0.005mmol) of [ dF (CF)3)ppy]2(dtbpy)PF6And 0.5mmol of 2.4.6-trimethyl pyridine are dissolved in 4mL of dichloromethane, the mixture is uniformly mixed, then the mixture is placed under a blue LED lamp for illumination reaction for 28 hours, and after dichloromethane is removed by concentration of a rotary evaporator, the mixture is further processed by the following steps of:taking the mixed solution of ethyl acetate as an eluent, and carrying out silica gel column chromatography purification and separation to obtain a product, namely the polysubstituted far-end allyl ketone derivative; the reaction formula is as follows:
the product was 99% pure and 78% yield. The nuclear magnetic data analysis is as follows:1H NMR(400MHz,CDCl3):H7.92(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):C199.1,167.5,163.3,139.9,131.9,130.6,126.4,113.7,60.7,55.5,49.6,48.5,42.3,34.7,28.1,27.9,22.5,14.4。
EXAMPLE V preparation of polysubstituted remote allyl ketone derivative
Under a nitrogen atmosphere at room temperature, 52.0mg (0.2mmol) of substituted camphorol, 100mg (0.4mmol) of unsaturated ester, and 1.2mg (0.005mmol) of [ dF (CF)3)ppy]2(dtbpy)PF6And 0.5mmol of 2.4.6-trimethyl pyridine are dissolved in 4mL of dichloromethane, the mixture is uniformly mixed, then the mixture is placed under a blue LED lamp for illumination reaction for 28 hours, and after dichloromethane is removed by concentration of a rotary evaporator, the mixture is further processed by the following steps of: taking the mixed solution of ethyl acetate as an eluent, and carrying out silica gel column chromatography purification and separation to obtain a product, namely the polysubstituted far-end allyl ketone derivative; the reaction formula is as follows:
the product purity was 99% and the yield was 82%. The nuclear magnetic data analysis is as follows:H7.93(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):C194.8,167.3,143.9,142.5,140.5,139.3,129.0,127.5,126.0,125.1,124.9,123.1,60.7,39.1,31.8,28.2,24.3,14.3。
EXAMPLE VI preparation of a polysubstituted remote allyl ketone derivative
Under a nitrogen atmosphere at room temperature, 32.6mg (0.2mmol) of p-methoxycyclopropanol, 100mg (0.4mmol) of unsaturated ester, 1.2mg (0.005mmol) of [ dF (CF)3)ppy]2(dtbpy)PF6And 0.5mmol of 2.4.6-trimethyl pyridine are dissolved in 4mL of dichloromethane, the mixture is uniformly mixed, then the mixture is placed under a blue LED lamp for illumination reaction for 28 hours, and after dichloromethane is removed by concentration of a rotary evaporator, the mixture is further processed by the following steps of: taking the mixed solution of ethyl acetate as an eluent, and carrying out silica gel column chromatography purification and separation to obtain a product, namely the polysubstituted far-end allyl ketone derivative; the reaction formula is as follows:
the product purity was 99% and the yield was 83%. 1H NMR (600MHz, CDCl3): H7.93 (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):C 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。
In the first to sixth examples, the light reaction was performed after nitrogen gas was introduced for 30 min.
The embodiments show that the preparation method of the polysubstituted far-end allyl ketone derivative provided by the invention can be used for reaction at normal temperature and normal pressure, has mild reaction conditions and high yield, and has the advantages of simple operation, no pollution, safety, environmental protection and low cost.
Claims (8)
1. A preparation method of a polysubstituted remote allyl ketone derivative is characterized by comprising the following steps:
dissolving the tertiary cyclic alcohol derivative, the unsaturated alkene compound, the alkali and the photocatalyst in an organic solvent under the atmosphere of nitrogen at room temperature, uniformly mixing, placing under a blue LED lamp for illumination reaction, removing the solvent by rotary evaporation, and then separating and purifying by silica gel column chromatography to obtain a product, namely the polysubstituted far-end allyl ketone derivative; the molar ratio of the unsaturated alkene compound to the tertiary cyclic alcohol derivative to the base to the photocatalyst is 2:1:2.5: 0.5;
wherein the chemical structural formula of the tertiary cyclic alcohol derivative is as follows:
the unsaturated alkene compound has the chemical structural formula:
the chemical structural formula of the photocatalyst is as follows:
the structural formula of the polysubstituted far-end allyl ketone derivative is shown in the specification
Wherein R is1、R2And R3Are both alkyl or are both hydrogen; when R is1、R2And R3When the substituents are alkyl, Ar is substituted phenyl, the substituent on Ar is alkoxy or alkyl, and n is 0-9; when R is1、R2And R3When both are hydrogen, Ar is p-methoxyphenyl, n is 0, 1, 2 or 9;
the alkali is 2,4, 6-trimethyl pyridine.
2. The method of claim 1, wherein the tertiary cyclic alcohol derivative is a trihydric cyclic alcohol, a tetrahydric cyclic alcohol, a pentabasic cyclic alcohol, a dodecabasic cyclic alcohol, or an ortho-position polyalkyl-substituted cyclic alcohol.
3. The method of claim 1, wherein the organic solvent is selected from the group consisting of dichloromethane, dichloroethane, and acetonitrile.
4. The method of claim 1, wherein the molar volume ratio of the tertiary cyclic alcohol derivative to the organic solvent is 1mmol (10-20) mL.
5. The method of claim 1, wherein the reaction is carried out under a blue LED lamp for 12-48 h.
6. The method for preparing poly-substituted remote allyl ketone derivative as claimed in claim 1, wherein the solvent used for silica gel column chromatography is a mixed solvent of petroleum ether and ethyl acetate.
7. The method of claim 6, wherein the volume ratio of petroleum ether to ethyl acetate in the mixed solvent is (20-50): 1.
8. The method of claim 1, wherein the photocatalyst is Ir [ dF (CF)3)ppy]2(dtbpy)PF6。
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