CN110734377B - 1, 5-dicarbonyl derivative and synthetic method thereof - Google Patents

1, 5-dicarbonyl derivative and synthetic method thereof Download PDF

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CN110734377B
CN110734377B CN201911037867.3A CN201911037867A CN110734377B CN 110734377 B CN110734377 B CN 110734377B CN 201911037867 A CN201911037867 A CN 201911037867A CN 110734377 B CN110734377 B CN 110734377B
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付金萍
汪煦
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Guangxi University of Science and Technology
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Abstract

The invention discloses a series of 1, 5-dicarbonyl derivatives and a synthesis method thereof. The synthesis method of the 1, 5-dicarbonyl derivative mainly comprises the following steps: in the presence of alkaline substances and oxygen, reacting phenolic compounds, 2-bromoacetophenone and ketene compounds in an organic solvent under heating or non-heating conditions to prepare a crude product of the target compound. The method adopts three components to carry out series reaction synthesis under the condition of no metal catalysis, and has the advantages of easily obtained raw materials, simple and easily controlled operation and high reaction yield. The 1, 5-dicarbonyl derivative and the raw material phenolic compound, 2-bromoacetophenone and ketene compound used in the synthesis method are respectively shown as the following formulas (I), (II), (III) and (IV):

Description

1, 5-dicarbonyl derivative and synthetic method thereof
Technical Field
The invention relates to a 1, 5-dicarbonyl derivative and a synthesis method thereof, belonging to the technical field of medicines.
Background
1, 5-dicarbonyl compounds have important application value in the fields of medicine and materials, for example, Cuevas reports that 1, 5-dicarbonyl derivative myristone is synthesized, and researches show that the myristone shows good biological activity in the aspect of anti-tumor (Angew. chem., int. Ed.,2004,43, 1724-. Pan reports that two 1, 5-dicarbonyl pigments Monascin and Ankaflavan extracted from red yeast rice show good efficacy in reducing blood lipid and increasing high density lipoprotein cholesterol (J.Agric.food.chem.,2010,58, 8211-8216). Najdenski reports that 3- (3-hydroxyphenyl) -1, 5-dicarbonyl-1, 5-diphenylpentane compounds exhibit good biological activity in antibacterial aspects, and particularly have a significant effect against staphylococcus aureus and escherichia coli (eur.j.med.chem.,2009,44,2211-2218) and the like. Meanwhile, the 1, 5-dicarbonyl compound is also a very useful organic synthon, and is often used for preparing heterocyclic compounds and aromatic compounds, and is especially used for synthesizing prochiral molecules of various chiral compounds, so that the synthetic method of the 1, 5-dicarbonyl compound is of great concern.
At present, the synthesis of 1, 5-dicarbonyl compounds is mainly realized by the 1, 4-addition reaction of various nucleophiles such as metal enolate, amide, monoketone and the like serving as acyl donors and alpha, beta-unsaturated carbonyl compounds. However, the use of toxic reagents and the harsh reaction conditions limit the practical applications of these methods. On the other hand, most of the conventional methods for synthesizing 1, 5-dicarbonyl compounds have the defects of poor atom economy and step economy, low yield, relatively harsh reaction conditions, more byproducts, high post-treatment difficulty and the like, so that the development of a new green synthesis method for efficiently synthesizing the compounds is urgently needed.
Disclosure of Invention
The invention aims to solve the technical problems in the prior art and provides a series of 1, 5-dicarbonyl derivatives with novel structures and a synthesis method thereof.
The 1, 5-dicarbonyl derivative is a compound shown as the following formula (I) or a pharmaceutically acceptable salt thereof:
Figure BDA0002252040450000011
wherein:
R1represents a phenyl group, a halogen atom-substituted phenyl group, an ethoxy group-substituted phenyl group or a naphthyl group;
R2represents a hydrogen atom, a methyl group or a methoxy group;
R3represents a hydrogen atom or an alkyl group;
R4represents an ether group.
In the above compounds, R1Further preferred is a phenyl group, an iodine atom-substituted phenyl group, an ethoxy group-substituted phenyl group or a naphthyl group.
The invention also provides a synthesis method of the compound shown in the formula (I), which mainly comprises the following steps: in the presence of alkaline substances and oxygen, reacting a compound shown as a formula (II), a compound shown as a formula (III) and a compound shown as a formula (IV) in an organic solvent under the heating condition to obtain a crude product of a target compound;
Figure BDA0002252040450000021
wherein:
R1represents a phenyl group, a halogen atom-substituted phenyl group, an ethoxy group-substituted phenyl group or a naphthyl group;
R2represents a hydrogen atom, a methyl group or a methoxy group;
R3represents a hydrogen atom or an alkyl group;
R4represents an ether group.
In the synthesis method of the present invention, the molar ratio of the compound represented by the formula (II), the compound represented by the formula (III) and the compound represented by the formula (iv) is a stoichiometric ratio, and in actual operation, the molar ratio of the compound represented by the formula (II), the compound represented by the formula (III) and the compound represented by the formula (iv) is usually 1: 1-1.5: 1.
in the synthesis method, the alkaline substance mainly plays a role in promoting the reaction and plays a role in deprotonation and debromination. The basic substance may be one or a combination of two or more selected from sodium acetate, tripotassium phosphate, sodium hydroxide, potassium hydroxide, calcium hydroxide, cesium carbonate, potassium carbonate, sodium carbonate, potassium tert-butoxide, sodium tert-butoxide, potassium fluoride, cesium fluoride, pyridine, triethylamine and N, N-diisopropylethylamine. The amount of the basic substance added is usually 1 time or more, preferably 2 to 4 times the molar amount of the compound represented by the formula (II).
In the synthesis method of the present invention, the organic solvent is preferably one or a combination of two or more selected from benzene, toluene, dimethyl sulfoxide (DMSO), acetonitrile, N-Dimethylformamide (DMF), N-methylpyrrolidone, ethyl acetate, and petroleum ether, and is preferably benzene, toluene, dimethyl sulfoxide, or N, N-dimethylformamide. The amount of the organic solvent to be used is preferably such that the raw materials to be reacted can be dissolved, and usually, all the raw materials to be reacted are dissolved in an amount of 0.5 to 5mL of the organic solvent based on 0.5mmol of the compound represented by the formula (II).
In the synthesis method of the present invention, the reaction is generally carried out under air conditions, and the reaction is preferably carried out under heating conditions, more preferably at 80 to 100 ℃. The completion of the reaction can be followed by TLC. According to the Applicant's experience, it is advisable to control the reaction time between 2 and 6 hours when the reaction is carried out at a temperature of between 80 and 100 ℃.
The crude compound of formula (I) is obtained by the above process and can be purified by conventional purification methods to increase the purity of the compound of formula (I). The purification is usually carried out by means of silica gel column chromatography, and the eluent used in the chromatography can be ethyl acetate and petroleum ether according to the ratio of 1: 5-100 volume ratio. In the mixed solvent, the volume ratio of ethyl acetate to petroleum ether is preferably 1: 5-50, more preferably 1: 5-20.
Compared with the prior art, the invention provides a series of 1, 5-dicarbonyl derivatives with novel structures and a synthesis method thereof, the method adopts three components to carry out series reaction synthesis under the condition of no metal catalysis, the raw materials are easy to obtain, the operation is simple and easy to control, and the reaction yield is high.
Detailed Description
The present invention will be better understood from the following detailed description of specific examples, which should not be construed as limiting the scope of the present invention.
Example 1
The 1, 5-dicarbonyl derivative (i.e., the compound of formula (I)) of the present invention is synthesized according to the following synthetic route.
Figure BDA0002252040450000031
①：R1Is phenyl, R2Hydrogen atom, R3Hydrogen atom, R4Methoxy;
②：R1a group which is a naphthyl group,R2methoxy radical, R3Hydrogen atom, R4Methoxy;
③：R1ortho iodophenyl radical, R2Hydrogen atom, R3Hydrogen atom, R4Methoxy;
④：R1ortho iodophenyl radical, R2Methoxy radical, R3Hydrogen atom, R4(ii) ethoxy;
⑤：R1ortho iodophenyl radical, R2Methoxy radical, R3Hydrogen atom, R4Methoxy;
⑥：R1ortho iodophenyl radical, R2Methyl, R3Hydrogen atom, R4Methoxy;
⑦：R1ortho iodophenyl radical, R2Methyl, R3Hydrogen atom, R4(ii) ethoxy;
⑧：R14-ethoxyphenyl, R2Methoxy radical, R3Hydrogen atom, R4Methoxy;
⑨：R1ortho iodophenyl radical, R2Methoxy radical, R3Methyl, R4Is methoxy.
Adding 0.5mmol of a compound (namely a phenolic compound) shown as a formula (II), 0.6mmol of a compound (namely 2-bromoacetophenone) shown as a formula (III), 0.5mmol of a compound (namely an ketene compound) shown as a formula (IV) into a 15mL reaction tube, 3 equivalents of alkaline substances (wherein the alkaline substance adopted by a target compound (r) -c is potassium carbonate, the alkaline substance adopted by the target compound (r) -c is sodium hydroxide, the alkaline substance adopted by the target compound (r) 0 is pyridine, the alkaline substance adopted by a target compound (r 1) is cesium carbonate, the alkaline substance adopted by a target compound (r 2) is a composition of potassium fluoride and tripotassium phosphate according to a molar ratio of 1: 1), and an organic solvent (wherein the organic solvent adopted by the target compound (r) -c is dimethyl sulfoxide, the organic solvent adopted by the target compound (r) is toluene, and the organic solvent adopted by the target compound (r) is DMF, the organic solvent adopted by the target compound is benzene, the organic solvent adopted by the target compound is ethyl acetate) 2mL,heating to react at 85 deg.C, 100 deg.C and 60 deg.C, cooling to room temperature, filtering, removing solvent from the filtrate under reduced pressure, and purifying by flash silica gel column chromatography (V)Ethyl acetate：VPetroleum ether1: 5-20) to obtain the target compound. The different target compounds and their characterization were as follows:
(5-oxo-4-phenoxy-5-phenylpentanoic acid methyl ester)
Figure BDA0002252040450000041
A yellow liquid; yield: 81 percent;1H NMR(400MHz,CDCl3)δ8.19-8.13(m,2H),7.60(t,J＝7.4Hz,1H),7.50(t,J＝7.6Hz,2H),7.25-7.17(m,2H),6.92(t,J＝7.4Hz,1H),6.84(d,J＝7.9Hz,2H),5.55(dd,J＝9.2,3.8Hz,1H),3.69(s,3H),2.74(ddd,J＝17.0,8.3,6.9Hz,1H),2.62(dt,J＝17.2,6.2Hz,1H),2.41(dddd,J＝10.6,8.4,6.8,3.8Hz,1H),2.31-2.19(m,1H)；13C NMR(101MHz,CDCl3)δ197.9,173.4,157.5,134.2,133.9,129.6,128.9,128.8,121.6,115.2,78.7,51.8,29.5,28.1。
② 5- (4-methoxyphenyl) -4- (naphthalene-1-acyloxy) -5-oxoglutaric acid methyl ester
Figure BDA0002252040450000042
A yellow liquid; yield: 80 percent;1H NMR(400MHz,CDCl3)δ8.38(dd,J＝6.0,3.1Hz,1H),8.20(t,J＝5.8Hz,2H),7.76(dd,J＝6.1,3.2Hz,1H),7.58-7.44(m,2H),7.38(d,J＝8.3Hz,1H),7.22(dd,J＝15.6,7.7Hz,1H),6.92(d,J＝8.9Hz,2H),6.59(d,J＝7.7Hz,1H),5.61(dd,J＝7.2,5.9Hz,1H),3.82(s,3H),3.67(s,3H),2.83-2.64(m,2H),2.58-2.39(m,2H)；13C NMR(101MHz,CDCl3)δ196.4,173.5,164.1,153.2,134.6,131.3,127.5,127.1,126.6,125.7,125.6,125.3,122.1,121.0,114.1,105.6,79.5,55.5,51.8,29.9,28.4。
(3) 4- (2-Iodophenoxy) -5-oxo-5-phenylpentanoic acid methyl ester
Figure BDA0002252040450000043
A yellow liquid; yield: 84%;1H NMR(400MHz,CDCl3)δ8.21-8.14(m,2H),7.75(dd,J＝7.8,1.5Hz,1H),7.63-7.57(m,1H),7.49(dd,J＝10.6,4.7Hz,2H),7.13(td,J＝8.3,1.6Hz,1H),6.66(td,J＝7.6,1.2Hz,1H),6.53(dd,J＝8.3,1.1Hz,1H),5.53(dd,J＝9.1,4.1Hz,1H),3.69(s,3H),2.93-2.80(m,1H),2.71(ddd,J＝17.4,6.8,5.8Hz,1H),2.53-2.28(m,2H)；13C NMR(101MHz,CDCl3)δ197.2,173.3,155.8,139.7,133.9,133.7,129.3,128.9,128.8,123.1,112.4,86.4,80.1,51.7,29.5,28.1。
4- (2-Iodophenoxy) -2- (4-methoxyphenyl) -5-oxopentanecarboxylic acid ethyl ester
Figure BDA0002252040450000051
A yellow liquid; yield: 88 percent;1H NMR(400MHz,CDCl3)δ8.16(t,J＝5.8Hz,2H),7.71(dd,J＝7.8,1.5Hz,1H),7.15-7.03(m,1H),6.92(d,J＝8.9Hz,2H),6.65-6.56(m,1H),6.55-6.48(m,1H),5.44(dd,J＝9.0,4.2Hz,1H),4.12(qd,J＝7.1,1.8Hz,2H),3.81(s,3H),2.81(dt,J＝17.0,7.7Hz,1H),2.67(dt,J＝17.2,6.3Hz,1H),2.43-2.30(m,2H),1.21(t,J＝7.2Hz,3H)；13C NMR(101MHz,CDCl3)δ195.8,173.0,164.2,156.0,139.7,131.4,129.4,126.8,123.1,114.1,112.6,86.4,80.4,60.7,55.6,29.9,28.5,14.3。
4- (2-iodophenoxy) -5- (4-methoxyphenyl) -5-oxopentanecarboxylic acid methyl ester
Figure BDA0002252040450000052
A yellow liquid; yield: 85 percent;1H NMR(400MHz,CDCl3)δ8.18(d,J＝8.9Hz,2H),7.73(dd,J＝7.8,1.3Hz,1H),7.16–7.05(m,1H),6.95(d,J＝8.9Hz,2H),6.64(t,J＝7.4Hz,1H),6.53(d,J＝8.4Hz,1H),5.42(dd,J＝8.8,4.3Hz,1H),3.85(s,3H),3.68(s,3H),2.88-2.77(m,1H),2.70(dt,J＝17.3,6.3Hz,1H),2.42-2.33(m,2H)；13C NMR(101MHz,CDCl3)δ195.8,173.5,164.2,156.0,139.7,131.5,129.4,126.8,123.1,114.1,112.5,86.4,80.4,55.6,51.8,29.7,28.5。
sixthly, 4- (2-iodophenoxy) -5-oxo-5- (p-tolyl) pentanoic acid methyl ester
Figure BDA0002252040450000053
A yellow liquid; yield: 83 percent;1H NMR(400MHz,CDCl3)δ8.08(d,J＝8.2Hz,2H),7.72(dd,J＝7.8,1.3Hz,1H),7.27(d,J＝8.1Hz,2H),7.13-7.05(m,1H),6.63(t,J＝7.6Hz,1H),6.52(d,J＝8.2Hz,1H),5.50(dd,J＝8.9,4.1Hz,1H),3.67(s,3H),2.89-2.78(m,1H),2.69(dt,J＝17.3,6.3Hz,1H),2.47-2.31(m,5H)；13C NMR(101MHz,CDCl3)δ196.9,173.4,156.0,145.1,139.7,131.4,129.7,129.5,129.1,123.1,112.6,86.5,80.2,51.8,29.7,28.4,21.8。
4- (2-iodophenoxy) -5-oxo-5- (p-tolyl) pentanoic acid ethyl ester
Figure BDA0002252040450000061
A yellow liquid; yield: 88 percent;1H NMR(400MHz,CDCl3)δ8.08(d,J＝8.3Hz,2H),7.75(dd,J＝7.8,1.6Hz,1H),7.29(d,J＝8.1Hz,2H),7.12(td,J＝8.3,1.6Hz,1H),6.65(td,J＝7.6,1.2Hz,1H),6.53(dd,J＝8.3,1.1Hz,1H),5.49(dd,J＝9.0,4.2Hz,1H),4.23-4.04(m,2H),2.83(dt,J＝17.2,7.7Hz,1H),2.68(ddd,J＝17.2,6.9,5.8Hz,1H),2.48-2.33(m,5H),1.24(t,J＝7.1Hz,3H)；13C NMR(101MHz,CDCl3)δ196.9,173.0,156.0,1451,139.7,131.4,129.6,129.4,129.1,123.1,112.5,86.5,80.3,60.7,29.9,28.4,21.8,14.2。
(4-Ethoxyphenoxy) -5- (4-methoxyphenyl) -5-oxoglutaric acid methyl ester [)
Figure BDA0002252040450000062
A yellow liquid; yield: 82%;1H NMR(400MHz,CDCl3)δ8.20-8.07(m,2H),6.98-6.90(m,2H),6.78-6.71(m,4H),5.34(dd,J＝9.2,3.9Hz,1H),3.91(q,J＝7.0Hz,2H),3.86(s,3H),3.69(s,3H),2.76-2.54(m,2H),2.41-2.15(m,2H),1.37-1.26(m,3H)；13C NMR(101MHz,CDCl3)δ196.9,173.6,164.1,153.7,151.8,131.3,127.2,116.3,115.4,114.1,79.8,63.9,55.5,51.8,29.6,28.4,14.9。
ninthly 4- (2-iodophenoxy) -5- (4-methoxyphenyl) -3-methyl-5-oxopentanoic acid methyl ester
Figure BDA0002252040450000063
A yellow liquid; yield: 63%;1H NMR(400MHz,CDCl3)δ8.22(d,J＝8.9Hz,2H),7.75(dd,J＝8.0,1.3Hz,1H),7.14-7.10(m,1H),6.99(d,J＝8.9Hz,2H),6.65(dd,J＝7.6,1.0Hz,1H),6.40(dd,J＝8.2,0.8Hz,1H),5.66(d,J＝3.0Hz,1H),3.87(s,3H),3.68(s,3H),2.91-2.75(m,3H),1.16(d,J＝7.0Hz,3H)；13C NMR(101MHz,CDCl3)δ194.8,173.4,164.2,156.1,139.6,131.3,129.3,127.4,122.8,114.2,112.2,86.5,81.8,55.6,51.7,37.5,33.5,14.7。

Claims (6)

1. a method for synthesizing a compound represented by formula (I), characterized in that: the method mainly comprises the following steps: in the presence of alkaline substances and oxygen, reacting a compound shown as a formula (II), a compound shown as a formula (III) and a compound shown as a formula (IV) in an organic solvent under the heating condition to obtain a crude product of a target compound;
Figure DEST_PATH_IMAGE001
(I)、
Figure 98614DEST_PATH_IMAGE002
(II)、
Figure DEST_PATH_IMAGE003
(III)、
Figure 343650DEST_PATH_IMAGE004
(Ⅳ)；
wherein:
R1= phenyl, R2= hydrogen atom, R3= hydrogen atom, R4= methoxy group; or is
R1= naphthyl, R2= methoxy, R3= hydrogen atom, R4= methoxy group; or is
R1= o-iodophenyl, R2= hydrogen atom, R3= hydrogen atom, R4= methoxy group; or is
R1= o-iodophenyl, R2= methoxy, R3= hydrogen atom, R4= ethoxy; or is
R1= o-iodophenyl, R2= methoxy, R3= hydrogen atom, R4= methoxy group; or is
R1= o-iodophenyl, R2= methyl, R3= hydrogen atom, R4= methoxy group; or is
R1= o-iodophenyl, R2= methyl, R3= hydrogen atom, R4= ethoxy; or is
R1= 4-ethoxyphenyl, R2= methoxy, R3= hydrogen atom, R4= methoxy group; or is
R1= o-iodophenyl, R2= methoxy, R3= methyl, R4= methoxy group;
the alkaline substance is selected from sodium acetate, tripotassium phosphate, sodium hydroxide, potassium hydroxide, calcium hydroxide, cesium carbonate, potassium carbonate, sodium carbonate, potassium tert-butoxide, sodium tert-butoxide, potassium fluoride, cesium fluoride, pyridine, triethylamine andN, None or two of (E) -diisopropylethylamineA combination of (a) and (b).
2. The method of synthesis according to claim 1, characterized in that: the organic solvent is selected from benzene, toluene, dimethyl sulfoxide, acetonitrile,N，N-dimethylformamide,N-one or a combination of more than two of methyl pyrrolidone, ethyl acetate and petroleum ether.
3. The method of synthesis according to claim 1, characterized in that: the reaction is carried out at 80-100 ℃.
4. A synthesis method according to any one of claims 1-3, characterized in that: also comprises a step of purifying the prepared crude product of the target compound.
5. The method of synthesis according to claim 4, characterized in that: and the purification step is to perform silica gel column chromatography on the prepared crude target compound to obtain the purified target compound.
6. The method of synthesis according to claim 5, characterized in that: in silica gel column chromatography, ethyl acetate and petroleum ether are adopted according to the ratio of 1: 5-100 volume ratio of the mixed solvent for elution.
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Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
"Phase-transfer catalyzed glycolate conjugate addition";Merritt B. Andrus等;《Tetrahedron Letters》;20071119;第49卷;第534-537页 *
"Synthesis, Crystal Structures and Antioxidant Activities of 1,5-Diketone Derivatives";WANG Xu等;《Chinese J.Struct.Chem.》;20200930;第39卷(第9期);第1655-1661页 *
"Visible light induced redox neutral fragmentation of 1,2-diol derivatives";Kang Chen等;《Chem. Commun》;20191007;第55卷;第1314-13147页 *
Merritt B. Andrus等."Phase-transfer catalyzed glycolate conjugate addition".《Tetrahedron Letters》.2007,第49卷第534-537页. *

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