CN106905126A - The synthetic method of one inter-species dibenzoyl substituted benzene compound - Google Patents

The synthetic method of one inter-species dibenzoyl substituted benzene compound Download PDF

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CN106905126A
CN106905126A CN201710108111.8A CN201710108111A CN106905126A CN 106905126 A CN106905126 A CN 106905126A CN 201710108111 A CN201710108111 A CN 201710108111A CN 106905126 A CN106905126 A CN 106905126A
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dibenzoyl
substituted benzene
benzene compound
synthetic method
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CN106905126B (en
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石先莹
孙曼
赵雪
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Shaanxi Normal University
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention discloses the synthetic method of an inter-species dibenzoyl substituted benzene compound; the method is using transition metal palladium as catalyst; occur to be based on dibenzoyl substituted benzene compound between the double acylations of carboxyl ortho position C-H, decarboxylation coupling reaction, one-step synthesis by aromatic acid and benzoyl formic acid class compound.In building-up process, carboxyl is used as removable guiding base, after carboxyl ortho position introduces two benzoyls, carboxyl removing.The present invention is efficiently synthesized and is difficult to dibenzoyl substituted benzene compound between synthesis from contraposition substituted benzoyl acids compound simple and easy to get, has the advantages that raw material is simple and easy to get, operation is simple, efficient.

Description

The synthetic method of one inter-species dibenzoyl substituted benzene compound
Technical field
The present invention relates to the synthetic method of an inter-species dibenzoyl substituted benzene compound, and in particular to one kind is with trifluoro Acid chloride (Pd (TFA)2) for catalyst, silver carbonate be oxidant, dipotassium hydrogen phosphate be additive, by aromatic acid and benzoyl Formic acid compound occurs to be based on dibenzoyl between the double acylations of carboxyl ortho position C-H, decarboxylation coupling reaction, one-step synthesis method The method of substituted benzene compound.
Background technology
Aryl ketones are the important skeletons of natural products, medicine correlation molecule and functional material.Diketone as synthetic intermediate, Had a wide range of applications in functional material, with important biomolecule bioactive molecule, the synthesis of drug molecule (J.Nat.Prod.2007,70,2049；J.Med.Chem.2006,49,72；Adv.Functo.Mater.2012,22,378； Zhao,W.L.；Carreira,E.M.Org.Lett.2006,8,99).Wherein 1,3- diacyls benzene as important intermediate, Can by it is derivative for schiff bases so that synthesize with important use metal complex (Coordin.Chem.Rev.2007,251, 1311–1492,Polyhedron 2002,21,1787-1793；Chem.Rev.2010,110:1642-1662).
Traditionally, the preparation method of diacyl benzene and monoacyl substituted benzene seemingly, by the Fu Lide-Kerafyrm on aromatic ring Thatch reaction is realized.It is such to react the anhydrous AlCl for needing equivalent3Catalyst, post processing produces a large amount of acid waste waters containing aluminium, environment Seriously polluted (J.Chem.Crystallogr.2012,42,960-967；Synth.Commun.2003,33,3097-3102).
With the development of transition metal-catalyzed coupling reaction, document reports transition metal-catalyzed diacyl benzene in succession Synthetic method.If diiodo-benzene and phenyl boric acid are under nanometer palladium chtalyst, Suzuki carbonylation can occur, so as to obtain two acyls Base benzene (J.Org.Chem.2014,79,1454-1460).But the reaction needs poisonous CO gas and function dough Halogenated benzene compound, while produce that there is corrosive acid iodate hydrogen.With imines, nitrogen heterocyclic ring as base is oriented to, in vinegar Under sour palladium chtalyst, respectively with aromatic aldehyde, benzoyl formic acid reaction also can synthesis of diacyl benzene-like compounds, but reaction raw materials need it is pre- First synthesize (Org.Biomol.Chem., 2013,11,7869-7876；Adv.Synth.Catal.2016,358,283-295).
The content of the invention
The technical problems to be solved by the invention are that a kind of raw material of offer is simple and easy to get, operation is simple, efficient Between dibenzoyl substituted benzene compound synthetic method.
Solving the technical scheme of above-mentioned technical problem use is：
By the aromatic carboxylic acids shown in formula I and the benzoyl formic acid class compound shown in formula II, palladium trifluoroacetate, silver carbonate, ADKP is in molar ratio 1:2~4:0.08~0.15:1.0~4.0:0.5~3.0 adds glycol dimethyl ether In, 110~160 DEG C are reacted 18~36 hours under the airtight condition of inert gas shielding, and reaction is cooled to room temperature after terminating, point From purified product, dibenzoyl substituted benzene compound between obtaining shown in formula III, its reaction equation is as follows：
R, R in formula1Respective independent representative H, C1~C4Alkyl, C1~C4Any one in alkoxy, halogen, preferably R, R1Each any one in independent representative H, methyl, ethyl, methoxyl group, halogen, n=1 or 2.
It is preferred fragrance carboxylic acid, benzoyl formic acid class compound, palladium trifluoroacetate, silver carbonate, anhydrous in above-mentioned synthetic method The mol ratio of dipotassium hydrogen phosphate is 1:3:0.01:3:2.
In above-mentioned synthetic method, 150 DEG C are reacted 24 hours further preferably under the airtight condition of inert gas shielding.
The present invention occurs to be based on carboxylic using transition metal palladium as catalyst by aromatic acid and benzoyl formic acid class compound Dibenzoyl substituted benzene compound between the double acylations of base ortho position C-H, decarboxylation coupling reaction, one-step synthesis.In building-up process In, carboxyl is used as removable guiding base, after carboxyl ortho position introduces two benzoyls, carboxyl removing.The present invention is from simple The contraposition substituted benzoyl acids compound being easy to get sets out, and efficiently synthesizes and is difficult to dibenzoyl substituted benzene chemical combination between synthesis Thing, has the advantages that raw material is simple and easy to get, operation is simple, efficient.
Specific embodiment
With reference to embodiment, the present invention is described in more detail, but protection scope of the present invention is not limited only to these realities Apply example.
Embodiment 1
The following 1,3- dibenzoyl -5- chlorobenzenes of preparation structure formula
0.0156g (0.1mmol) parachlorobenzoic-acid, 0.0450g (0.3mmol) benzene first are added in the pressure-resistant reaction tubes of 10mL Acyl formic acid, 0.0033g (0.01mmol) palladium trifluoroacetate, 0.0826g (0.3mmol) silver carbonate, 0.0348g (0.2mmol) nothing Water dipotassium hydrogen phosphate, 0.6mL glycol dimethyl ethers, under the enclosed system of argon gas protection, 150 DEG C of stirring reactions 24 hours, instead Room temperature is cooled to after should terminating, salt and catalyst are filtered to remove using column chromatography silica gel post, with TLC separation, obtain 1,3- Dibenzoyl -5- chlorobenzenes, its yield is 66%, and structural characterization data are as follows：
1H NMR(400MHz,CDCl3):δ (ppm)=8.03 (s, 1H), 7.98 (s, 2H), 7.81 (d, J=7.7Hz, 4H), 7.63 (t, J=7.3Hz, 2H), 7.51 (t, J=7.5Hz, 4H)；13C NMR(151MHz,CDCl3):δ (ppm)= 194.5,139.4,136.4,135.0,133.3,133.1,130.0,129.0,128.6；HRMS(ESI)m/z:C20H13ClO2[M + H] theoretical value 321.0682, measured value 321.0688.
Embodiment 2
Preparation structure formula following 1,3- bis- (4- methyl benzoyls) -5- chlorobenzenes
In embodiment 1, benzoyl formic acid used with it is equimolar to toluyl formic acid replace, other steps with Embodiment 1 is identical, obtains 1,3- bis- (4- methyl benzoyls) -5- chlorobenzenes, and its yield is 68%, and structural characterization data are as follows：
1HNMR(400MHz,CDCl3):δ (ppm)=7.98 (s, J=0.6Hz, 1H), 7.94 (s, 2H), 7.72 (d, J= 7.9Hz, 4H), 7.30 (d, J=7.9Hz, 4H)；13C NMR(101MHz,CDCl3):δ (ppm)=194.1,144.3,139.6, 134.8,133.7,132.8,130.3,129.3,128.9,21.7；HRMS(ESI)m/z:C22H17ClO2[M+H]+Theoretical value 349.0995；Measured value 349.1085.
Embodiment 3
Preparation structure formula following 1,3- bis- (4- chlorobenzene formacyls) -5- chlorobenzenes
In embodiment 1, benzoyl formic acid used is replaced with equimolar to chlorobenzoyl formic acid, other steps and reality Apply example 1 identical, obtain 1,3- bis- (4- chlorobenzene formacyls) -5- chlorobenzenes, its yield is 52%, and structural characterization data are as follows：
1H NMR(600MHz,CDCl3):δ (ppm)=7.98 (s, 1H), 7.95 (s, 2H), 7.76 (d, J=8.5Hz, 4H), 7.50 (d, J=8.5Hz, 4H)；13C NMR(101MHz,CDCl3):δ (ppm)=193.1,140.0,139.2,135.3, 134.6,133.2,131.4,129.1,128.7；HRMS(ESI)m/z:C20H11Cl3O2[M+Na],[M+Na+2]+Theoretical value 410.9722,412.9693；Measured value 410.9717,412.9688.
Embodiment 4
Preparation structure formula following 1,3- bis- (2- methyl benzoyls) -5- chlorobenzenes
In embodiment 1, benzoyl formic acid used is replaced with equimolar o-methyl-benzene GA, other steps with Embodiment 1 is identical, obtains 1,3- bis- (2- methyl benzoyls) -5- chlorobenzenes, and its yield is 63%, and structural characterization data are as follows：
1H NMR(400MHz,CDCl3):δ (ppm)=8.06 (s, 1H), 7.94 (s, 2H), 7.42 (t, J=7.4Hz, 2H),7.32-7.24(m,6H),2.37(s,6H)；13C NMR(101MHz,CDCl3):δ (ppm)=196.1,139.8, 137.5,136.9,135.3,133.8),131.5,131.2,129.3,128.9,125.4,20.2；HRMS(ESI)m/z: C22H17ClO2[M+H]+Theoretical value 349.0995；Measured value 349.1000.
Embodiment 5
The following 1,3- bis- of preparation structure formula (4- methoxybenzoyls base) -5- chlorobenzenes
In embodiment 1, benzoyl formic acid used is replaced with equimolar to methoxybenzoyl formic acid, other steps It is same as Example 1,1,3- bis- (4- methoxybenzoyls base) -5- chlorobenzenes are obtained, its yield is 62%, and structural characterization data are such as Under：
1H NMR(400MHz,CDCl3):δ (ppm)=7.93 (s, 1H), 7.91 (s, 2H), 7.82 (d, J=8.8Hz, 4H), 6.98 (d, J=8.8Hz, 4H), 3.89 (s, 6H)；13C NMR(100MHz,CDCl3):δ (ppm)=193.2,163.8, 140.0,134.8,132.6,132.3,129.0,128.5,113.9,55.6；HRMS(ESI)m/z:C22H17ClO4[M+H]+Reason By value 381.0894；Measured value 381.0892.
Embodiment 6
Preparation structure formula following 1,3- bis- (4- fluoro benzoyls) -5- chlorobenzenes
In embodiment 1, benzoyl formic acid used is replaced with equimolar to fluorobenzoyl formic acid, other steps and reality Apply example 1 identical, obtain 1,3- bis- (4- fluoro benzoyls) -5- chlorobenzenes, its yield is 76%, and structural characterization data are as follows：
1H NMR(400MHz,CDCl3):δ (ppm)=7.97 (s, 1H), 7.94 (s, 2H), 7.85 (dd, J=7.6, 5.9Hz, 4H), 7.19 (t, J=8.3Hz, 4H)；13C NMR(101MHz,CDCl3):δ (ppm)=192.8,165.8 (d, J= 254.5Hz),139.3,135.2,133.0,132.7(d,JC-F=9.3Hz), 132.6 (d, JC-F=3.0Hz), 128.7, 116.0(d,JC-F=22.0Hz)；HRMS(ESI)m/z:C20H11ClF2O2[M+H]+Theoretical value 357.0494；Measured value 357.0500。
Embodiment 7
Preparation structure formula following 1,3- bis- (2,4- dimethylbenzoyls) -5- chlorobenzenes
In embodiment 1, benzoyl formic acid used is replaced with equimolar 2,4- dimethyl phenacyls formic acid, other steps It is rapid same as Example 1,1,3- bis- (2,4- dimethylbenzoyl) -5- chlorobenzenes are obtained, its yield is 70%, structural characterization number According to as follows：
1H NMR(400MHz,CDCl3):δ (ppm)=8.03 (s, 1H), 7.91 (s, 2H), 7.23 (d, J=7.8Hz, 2H), 7.13 (s, 2H), 7.06 (d, J=7.8Hz, 2H), 2.39 (s, 6H), 2.37 (s, 6H)；13C NMR(100MHz, CDCl3):δ (ppm)=196.1,141.8,140.3,138.1,135.0,134.0,133.5,132.4,129.7,12 9.2, 126.1,21.4,20.3；HRMS(ESI)m/z:C24H21ClO2[M+H]+Theoretical value 377.1308；Measured value 377.1304.
Embodiment 8
Preparation structure formula following 3,5- bis- (4- methyl benzoyls) toluene
In example 2, parachlorobenzoic-acid used is replaced with equimolar p-methylbenzoic acid, other steps with implement Example 2 is identical, obtains 3,5- bis- (4- methyl benzoyls) toluene, and its yield is 75%, and structural characterization data are as follows：
1H NMR(400MHz,CDCl3):δ (ppm)=7.89 (s, 1H), 7.80 (s, 2H), 7.72 (d, J=8.0Hz, 4H), 7.28 (d, J=7.9Hz, 4H), 2.49 (s, 3H), 2.43 (s, 6H)；13C NMR(100MHz,CDCl3):δ (ppm)= 195.9,143.6,138.6,138.04,134.5,133.7,130.3,129.1,128.3,21.6,21.3；HRMS(ESI)m/ z:C23H20O2[M+H]+Theoretical value 329.1542；Measured value 329.1543.
Embodiment 9
Preparation structure formula following 3,5- bis- (4- methyl benzoyls) ethylbenzene
In example 2, parachlorobenzoic-acid used is replaced with equimolar p-ethylbenzoic acid, other steps with implement Example 2 is identical, obtains 3,5- bis- (4- methyl benzoyls) ethylbenzene, and its yield is 61%, and structural characterization data are as follows：
1H NMR(400MHz,CDCl3):δ (ppm)=7.90 (s, 1H), 7.83 (s, 2H), 7.73 (d, J=8.0Hz, 4H), 7.28 (d, J=7.9Hz, 4H), 2.79 (q, J=7.6Hz, 2H), 2.44 (s, 6H), 1.29 (d, J=7.6Hz, 3H)；13C NMR(100MHz,CDCl3):δ (ppm)=195.9,144.9,143.6,138.1,134.5,132.6,130.3,129.1, 128.6,28.7,21.7,15.4；HRMS(ESI)m/z:C24H22O2[M+H]+Theoretical value 343.1698；Measured value 343.1706.
Embodiment 10
Preparation structure formula following 1,3- bis- (4- methyl benzoyls) -5- methoxybenzenes
In example 2, parachlorobenzoic-acid used is replaced with equimolar P-methoxybenzoic acid, other steps and reality Apply example 2 identical, obtain 1,3- bis- (4- methyl benzoyls) -5- methoxybenzenes, its yield is 60%, and structural characterization data are such as Under：
1HNMR(400MHz,CDCl3):δ (ppm)=7.76 (d, J=8.0Hz, 4H), 7.68 (s, 1H), 7.55 (s, 2H), 7.30 (d, J=8.0Hz, 4H), 3.93 (s, 3H), 2.45 (s, 6H)；13C NMR(100MHz,CDCl3):δ (ppm)=195.4, 159.6,143.8,139.3,134.3,130.3,129.1,123.6,118.5,55.8,21.7；HRMS(ESI)m/z:C23H20O3 [M+H]+Theoretical value 345.1491；Measured value 345.1499.
Embodiment 11
Preparation structure formula following 1,3- bis- (4- methyl benzoyls) -5- bromo benzene
In example 2, parachlorobenzoic-acid used is replaced with equimolar parabromobenzoic acid, other steps and embodiment 2 is identical, obtains 1,3- bis- (4- methyl benzoyls) -5- bromo benzene, and its yield is 53%, and structural characterization data are as follows：
1H NMR(400MHz,CDCl3):δ (ppm)=8.09 (s, 2H), 8.03 (s, 1H), 7.72 (d, J=7.9Hz, 4H), 7.30 (d, J=7.9Hz, 4H), 2.45 (s, 6H)；13C NMR(100MHz,CDCl3):δ (ppm)=194.0,144.3, 139.8,135.6,133.7,130.3,129.3,129.3,122.7,21.7；HRMS(ESI)m/z:C22H17BrO2[M+H]+Reason By value 393.0490；Measured value 393.0486.

Claims (4)

1. the synthetic method of an inter-species dibenzoyl substituted benzene compound, it is characterised in that：By the aromatic carboxylic acids shown in formula I It is in molar ratio 1 with benzoyl formic acid class compound, palladium trifluoroacetate, silver carbonate, the ADKP shown in formula II:2 ~4:0.08~0.15:1.0~4.0:In 0.5~3.0 addition glycol dimethyl ether, under the airtight condition of inert gas shielding 110~160 DEG C are reacted 18~36 hours, and reaction is cooled to room temperature after terminating, and product is isolated and purified, two between obtaining shown in formula III Benzoyl substituted benzene compound；
R, R in formula1Respective independent representative H, C1~C4Alkyl, C1~C4Any one in alkoxy, halogen, n=1 or 2.
2. the according to claim 1 synthetic method of dibenzoyl substituted benzene compound, it is characterised in that：It is described R, R1Respective any one in independent representative H, methyl, ethyl, methoxyl group, halogen.
3. the according to claim 1 and 2 synthetic method of dibenzoyl substituted benzene compound, it is characterised in that： The aromatic carboxylic acids, benzoyl formic acid class compound, palladium trifluoroacetate, silver carbonate, the mol ratio of ADKP are 1: 3:0.01:3:2。
4. the according to claim 1 and 2 synthetic method of dibenzoyl substituted benzene compound, it is characterised in that： 150 DEG C are reacted 24 hours under the airtight condition of inert gas shielding.
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CN114315542A (en) * 2021-12-21 2022-04-12 扬州市普林斯医药科技有限公司 Preparation method of dibenzoyl methane

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Publication number Priority date Publication date Assignee Title
CN114315542A (en) * 2021-12-21 2022-04-12 扬州市普林斯医药科技有限公司 Preparation method of dibenzoyl methane
CN114315542B (en) * 2021-12-21 2023-11-24 扬州市普林斯医药科技有限公司 Preparation method of dibenzoylmethane

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