CN109422631A - A kind of synthetic method of indanone compounds - Google Patents

A kind of synthetic method of indanone compounds Download PDF

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CN109422631A
CN109422631A CN201710740921.5A CN201710740921A CN109422631A CN 109422631 A CN109422631 A CN 109422631A CN 201710740921 A CN201710740921 A CN 201710740921A CN 109422631 A CN109422631 A CN 109422631A
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CN109422631B (en
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刘运奎
杨欢
郑立孟
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Zhejiang University of Technology ZJUT
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    • C—CHEMISTRY; METALLURGY
    • 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
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
    • C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic

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

Abstract

The present invention provides a kind of preparation methods of indanone compounds.The synthetic method is using dialkyne shown in formula (I) as raw material, and in the presence of water, using iodic anhydride as oxidant, acetonitrile and water are mixed solvent, reacts 12 hours under the conditions of 50 DEG C, corresponding target product is made.The features such as synthetic method of the invention has small to environmental hazard, and reaction condition is relatively mild, saves energy consumption, and selectivity of product is high, easy to operate.

Description

A kind of synthetic method of indanone compounds
Technical field
The present invention relates to a kind of synthetic method of organic compound, the system with a kind of indanone compounds is related in particular to Preparation Method.
Background technique
Indone is the important feature in natural products, universally present in molecular structure of compounds such as dyestuff, medicine, pesticides In the middle.In addition, indanone compounds are a kind of organic compounds containing multiple biological activities.It has now been found that including indone structure Natural products has more than 100 kinds to have pharmaceutical activity, and most representational natural products is to isolate and purify from the seaweed blueness bacterium of ocean Obtained Pterosin B, Pterosin C, it is living that the drug molecule containing indone structure or dependency structure can show its biology Property.Such as smooth muscle relaxation activity, Cycloxygenase inhibitory activity etc..It is to prepare indone class that Friedel-Crafts, which is cyclized method, at present The main path of compound.But traditional Friedel-Crafts is cyclized method to the preparation of aromatic ketone by the substitution on aromatic ring Base is affected, and when there is strong electron-withdrawing group group (such as nitro, carbonyl) on aromatic ring, the reaction does not occur.So that reaction Raw material is limited, and substrate universality is poor.A large amount of spent acid and the acid containing organic matter are generated when industrially prepared indanone compounds simultaneously Property waste water and lead to environmental pollution, increase control expense, in addition the poor selectivity of this method, cause the waste of raw material, and There are a variety of side reactions, cause overall production rate not high.
At present many improved Friedel-Crafts cyclisation methods of document report prepare indanone compounds and Nazarov is cyclized method, polyphosphoric acids (PPA) cyclisation method, Pinacol rearrangement method etc..But gold is required in these method systems Belong to and participate in reaction, and post-processing is relatively cumbersome, generates more spent acid, has greater environmental impacts, yield is not also high.Cause Therefore this in view of important application of the indanone compounds in terms of pharmaceutical chemistry and organic fine Chemical Manufacture, explores a kind of letter Just, efficiently the synthetic method of indanone compounds is of great significance.
Summary of the invention
In view of the deficienciess of the prior art, the present invention is intended to provide a kind of method for preparing indanone compounds, overcomes Indanone compounds are prepared under conditions of no metal participates in the shortcomings that prior art at a lower temperature.
In order to achieve the above object of the invention, the technical solution adopted by the present invention is that:
A kind of method of indanone compounds shown in preparation formula (II), the method are as follows: with diine shown in formula (I) Compound is starting material, under conditions of no metal participates in, in the in the mixed solvent that organic solvent and water mix, in oxygen It under agent effect, is reacted 5-48 hours under conditions of 25-100 DEG C, reaction solution is isolated and purified shown in the formula of being prepared (II) Indanone compounds；The oxidant is iodic anhydride, iodobenzene diacetate or potassium peroxydisulfate；
In formula (I) or formula (II), one of R H, methyl, bromine, propyl.
Reaction equation is as follows:
Dialkyne shown in the starting materials of formulae (I) that the present invention uses, those skilled in the art can be according to existing literature Disclosed method is voluntarily prepared.
Reaction of the present invention is in the presence of water, its main feature is that cheap and easy to get, low toxicity efficiently, and is not necessarily to additionally match Body assists
The volume ratio of in the mixed solvent organic solvent and water of the present invention is 1~74:1, the water conduct of in the mixed solvent Source of hydroxyl groups provides hydroxyl for the reaction, the amount of substance be the amount of dialkyne substance shown in formula (I) 1%~ 20%, preferably 18%.
Reaction of the present invention, the oxidant are preferably iodic anhydride.
The amount of oxidant species of the present invention be formula (I) shown in dialkyne substance amount 100%~ 200%, preferably 120%.
The organic solvent of in the mixed solvent of the present invention is acetonitrile, tetrahydrofuran, methylene chloride, nitromethane or first Benzene, preferably acetonitrile.
The volume ratio of in the mixed solvent organic solvent and water of the present invention is 1~74:1, preferably 4:1.The mixing Solvent is most preferably that the volume ratio of acetonitrile and water is the mixed solution of 4:1.
Reaction of the present invention preferably carries out under the conditions of 50 DEG C, and the reaction time is preferably 6-12 hours, more preferably 12 hours.
The present invention specifically recommends the synthetic method of the indone and its derivative, it is characterised in that: the synthesis side Method include the following steps: by dialkyne, iodic anhydride, acetonitrile, water be added voltage-resistant reactor in, stirred under the conditions of 50 DEG C Reaction 6-12 hours is mixed, gained reaction solution is through isolating and purifying to obtain target product.
Further, following method can be used in described isolate and purify: column chromatography silica gel being added in reaction solution, and passes through decompression Be distilled off solvent, then by pillar layer separation, using petroleum ether and ethyl acetate volume ratio for 30:1 mixed liquor as eluting Agent elution, collects the eluent containing target product, solvent is evaporated off and obtains 3- carbonyl indanone compounds shown in formula (II).
Further, the column chromatography silica gel is 100~200 mesh.Further, the quality of the column chromatography silica gel is with formula (I) amount of the substance of compound shown in is calculated as 0.5g/mmol.
Further, indanone compounds shown in formula (II) of the present invention are preferably one of following compounds:
The present invention is by dialkyne in I2O5/H2Under the effect of O system, indone class is made by freely cyclization activate Compound, the utility model has the advantages that with it is existing prepare indanone compounds method compared with, without using metal participate in reaction, to environment endanger Evil is small；Reaction condition is relatively mild, saves energy consumption；Selectivity of product is high；In addition, also have substrate universality strong, operation The features such as easy.
Specific embodiment
Invention is further described in detail combined with specific embodiments below, and the scope of protection of the present invention is not limited to this.
Embodiment 1
Bis- (phenylene-ethynylene) benzene of 0.3mmol 1,2-, 0.36mmol iodic anhydride are added to 10mL pressure resistance reaction In device, 4mL acetonitrile, 54uL water as solvent are added.Then, the magnetic agitation 5h under the conditions of 50 DEG C.Then, add in reaction solution Enter two spoon column chromatography silica gels (100-200 mesh), and by vacuum distillation remove solvent, then by pillar layer separation obtain as Pure product 3- benzoyl -2- phenyl -1H- 1-Indanone shown in structural formula (using petrol ether/ethyl acetate=30:1 as Eluant, eluent).The substance is yellow solid, yield 85%.
Characterize data:1H NMR(500MHz,CDCl3):δ7.94(dd,J1=8Hz, J2=1Hz, 2H), 7.35 (d, J= 7Hz,1H),7.54-7.50(m,1H),7.50-7.43(m,2H), 7.40-7.35(m,3H),7.32-7.29(m,1H), 7.25-7.23 (m, 3H), 7.06 (d, J=7Hz, 1H),13C NMR(125MHz,CDCl3):δ195.99,194.56,150.39, 144.06,135.17,134.64, 134.39,134.36,129.68,129.55,129.35,129.33,128.96, 128.80,128.29,123.86, 121
Embodiment 2
Bis- (phenylene-ethynylene) benzene of 0.3mmol 1,2-, 0.36mmol iodic anhydride are added to 10mL voltage-resistant reactor In, add 4mL tetrahydrofuran, 1mL water as solvent.Then, the magnetic agitation 48h under the conditions of 50 DEG C.Then, in reaction solution Two spoon column chromatography silica gels of middle addition (10 0-200 mesh), and solvent is removed by vacuum distillation, then obtain by pillar layer separation To the pure product 3- benzoyl -2- phenyl -1H- 1-Indanone as shown in structural formula (with petrol ether/ethyl acetate=30:1 As eluant, eluent).The substance is yellow solid, yield 76%.
Characterize data:1H NMR(500MHz,CDCl3):δ7.94(dd,J1=8Hz, J2=1Hz, 2H), 7.35 (d, J= 7Hz,1H),7.54-7.50(m,1H),7.50-7.43(m,2H), 7.40-7.35(m,3H),7.32-7.29(m,1H), 7.25-7.23 (m, 3H), 7.06 (d, J=7Hz, 1H),13C NMR(125MHz,CDCl3):δ195.99,194.56,150.39, 144.06,135.17,134.64, 134.39,134.36,129.68,129.55,129.35,129.33,128.96, 128.80,128.29,123.86, 121
Embodiment 3
Bis- (phenylene-ethynylene) benzene of 0.3mmol 1,2-, 0.36mmol iodobenzene diacetate are added to 10mL pressure resistance reaction In device, 1mL acetonitrile, 1mL water as solvent are added.Then, the magnetic agitation 12h under the conditions of 80 DEG C.Then, add in reaction solution Enter two spoon column chromatography silica gels (100-200 mesh), and by vacuum distillation remove solvent, then by pillar layer separation obtain as Pure product 3- benzoyl -2- phenyl -1H- 1-Indanone shown in structural formula (using petrol ether/ethyl acetate=30:1 as Eluant, eluent).The substance is yellow solid, yield 74%.
Characterize data:1H NMR(500MHz,CDCl3):δ7.94(dd,J1=8Hz, J2=1Hz, 2H), 7.35 (d, J= 7Hz,1H),7.54-7.50(m,1H),7.50-7.43(m,2H), 7.40-7.35(m,3H),7.32-7.29(m,1H), (7.25-7.23 m, 3H), 7.06 (d, J=7Hz, 1H),13C NMR(125MHz,CDCl3):δ195.99,194.56,150.39, 144.06,135.17,134.64, 134.39,134.36,129.68,129.55,129.35,129.33,128.96, 128.80,128.29,123.86, 121
Embodiment 4
Bis- (phenylene-ethynylene) benzene of 0.3mmol 1,2-, 0.36mmol potassium peroxydisulfate are added to 1 0mL voltage-resistant reactor In, add 4mL acetonitrile, 0.2mL water as solvent.Then, the magnetic agitation 12h under the conditions of 60 DEG C.Then, add in reaction solution Enter two spoon column chromatography silica gels (100-200 mesh), and by vacuum distillation remove solvent, then by pillar layer separation obtain as Pure product 3- benzoyl -2- phenyl -1H- 1-Indanone shown in structural formula (using petrol ether/ethyl acetate=30:1 as Eluant, eluent).The substance is yellow solid, yield 70%.
Characterize data:1H NMR(500MHz,CDCl3):δ7.94(dd,J1=8Hz, J2=1Hz, 2H), 7.35 (d, J= 7Hz,1H),7.54-7.50(m,1H),7.50-7.43(m,2H), 7.40-7.35(m,3H),7.32-7.29(m,1H), 7.25-7.23 (m, 3H), 7.06 (d, J=7Hz, 1H),13C NMR(125MHz,CDCl3):δ195.99,194.56,150.39, 144.06,135.17,134.64, 134.39,134.36,129.68,129.55,129.35,129.33,128.96, 128.80,128.29,123.86, 121
Embodiment 5
Bis- (p- tolylethynyl) benzene of 0.3mmol 1,2-, 0.36mmol iodic anhydride are added to 10mL pressure resistance In reactor, 5mL acetonitrile, 1.08mL water as solvent are added.Then, the magnetic agitation 12h under the conditions of 100 DEG C.Then, exist It is added in reaction solution two spoon column chromatography silica gels (100-200 mesh), and solvent is removed by vacuum distillation, then pass through column chromatography The isolated pure product 3- as shown in structural formula (4- methyl benzoyl) -2- (p-methylphenyl) -1H- 1-Indanone is (with stone Oily ether/ethyl acetate=30:1 is as eluant, eluent).The substance is yellow solid, yield 88%.
Characterize data:1H NMR(500MHz,CDCl3): δ 7.87 (d, J=3.5Hz, 2H), 7.65 (d, J=7Hz, 1H), 7.60-7.34 (m, 3H), 7.29-7.26 (m, 1H), 7.19 (d, J=8Hz, 2H), 7.07 (d, J=8Hz, 2H), 6.99 (d, J =7Hz), 2.37 (s, 3H), 2.28 (s, 3H)13C NMR(125MHz,CDCl3) δ:196.05,194.18,149.58, 149.71,143.86,143.56,134.47,134.17,133.26, 129.99,128.58,128.34,128.21, 127.85,127.60,127.49,127.13,125.65,122.68, 38.51,37.89
Embodiment 6
It is anti-that bis- (p- tolylethynyl) benzene of 0.3mmol 1,2-, 0.3mmol iodic anhydride are added to 10mL pressure resistance It answers in device, adds 4mL methylene chloride, 1mL water as solvent.Then, the magnetic agitation 12h under the conditions of 50 DEG C.Then, it is reacting It is added in liquid two spoon column chromatography silica gels (100-200 mesh), and solvent is removed by vacuum distillation, then pass through pillar layer separation The pure product 3- as shown in structural formula (4- methyl benzoyl) -2- (p-methylphenyl) -1H- 1-Indanone is obtained (with petroleum Ether/ethyl acetate=30:1 is as eluant, eluent).The substance is yellow solid, yield 76%.
Characterize data:1H NMR(500MHz,CDCl3): δ 7.87 (d, J=3.5Hz, 2H), 7.65 (d, J=7Hz, 1H), 7.60-7.34 (m, 3H), 7.29-7.26 (m, 1H), 7.19 (d, J=8Hz, 2H), 7.07 (d, J=8Hz, 2H), 6.99 (d, J =7Hz), 2.37 (s, 3H), 2.28 (s, 3H)13C NMR(125MHz,CDCl3) δ:196.05,194.18,149.58, 149.71,143.86,143.56,134.47,134.17,133.26, 129.99,128.58,128.34,128.21, 127.85,127.60,127.49,127.13,125.65,122.68, 38.51,37.89
Embodiment 7
It is anti-that bis- (p- tolylethynyl) benzene of 0.3mmol 1,2-, 0.6mmol iodic anhydride are added to 10mL pressure resistance It answers in device, adds 4mL nitromethane, 1mL water as solvent.Then, the magnetic agitation 12h under the conditions of 50 DEG C.Then, it is reacting It is added in liquid two spoon column chromatography silica gels (100-200 mesh), and solvent is removed by vacuum distillation, then pass through pillar layer separation The pure product 3- as shown in structural formula (4- methyl benzoyl) -2- (p-methylphenyl) -1H- 1-Indanone is obtained (with petroleum Ether/ethyl acetate=30:1 is as eluant, eluent).The substance is yellow solid, yield 70%.
Characterize data:1H NMR(500MHz,CDCl3): δ 7.87 (d, J=3.5Hz, 2H), 7.65 (d, J=7Hz, 1H), 7.60-7.34 (m, 3H), 7.29-7.26 (m, 1H), 7.19 (d, J=8Hz, 2H), 7.07 (d, J=8Hz, 2H), 6.99 (d, J =7Hz), 2.37 (s, 3H), 2.28 (s, 3H)13C NMR(125MHz,CDCl3) δ:196.05,194.18,149.58, 149.71,143.86,143.56,134.47,134.17,133.26, 129.99,128.58,128.34,128.21, 127.85,127.60,127.49,127.13,125.65,122.68, 38.51,37.89
Embodiment 8
Bis- ((4- bromophenyl) acetenyl) benzene of 0.3mmol 1,2-, 0.36mmol iodic anhydride are added to 10mL pressure resistance In reactor, 4mL nitromethane, 1mL water as solvent are added.Then, the magnetic agitation 12h under the conditions of 50 DEG C.Then, anti- It answers and is added in liquid two spoon column chromatography silica gels (100-200 mesh), and solvent is removed by vacuum distillation, then pass through column chromatography point From obtaining the pure product 3- as shown in structural formula (4- benzoyl bromide) -2- (4- bromophenyl) -1H- 1-Indanone (with petroleum Ether/ethyl acetate=30:1 is as eluant, eluent).The substance is brown-red solid, yield 70%.
Characterize data:1H NMR(500MHz,CDCl3): δ 7.98 (d, J=8.5Hz, 2H), 7.62 (d, J=7Hz, 1H), 7.53 (d, J=8.5Hz, 2H), 7.40-7.37 (m, 3H), 7.33-7.28 (m, 3H), 7.02 (d, J=7Hz, 1H)13C NMR (125MHz,CDCl3):δ195.35,193.15,150.06,143.58, 134.57,133.67,133.44,132.37, 131.72,130.75,130.66,130.20,129.69,129.32, 128.37,124.12,123.78,121.83
Embodiment 9
It is anti-that bis- ((4- bromophenyl) acetenyl) benzene of 0.3mmol 1,2-, 0.36mmol potassium peroxydisulfate are added to 10mL pressure resistance It answers in device, adds 4mL acetonitrile, 1.5mL water as solvent.Then, the magnetic agitation 12h under the conditions of 50 DEG C.Then, in reaction solution Two spoon column chromatography silica gels of middle addition (100-200 mesh), and solvent is removed by vacuum distillation, then obtain by pillar layer separation To the pure product 3- as shown in structural formula (4- benzoyl bromide) -2- (4- bromophenyl) -1H- 1-Indanone (with petroleum ether/second Acetoacetic ester=30:1 is as eluant, eluent).The substance is brown-red solid, yield 56%.
Characterize data:1H NMR(500MHz,CDCl3): δ 7.98 (d, J=8.5Hz, 2H), 7.62 (d, J=7Hz, 1H), 7.53 (d, J=8.5Hz, 2H), 7.40-7.37 (m, 3H), 7.33-7.28 (m, 3H), 7.02 (d, J=7Hz, 1H)13C NMR (125MHz,CDCl3):δ195.35,193.15,150.06,143.58, 134.57,133.67,133.44,132.37, 131.72,130.75,130.66,130.20,129.69,129.32, 128.37,124.12,123.78,121.83
Embodiment 10
Bis- ((4- bromophenyl) acetenyl) benzene of 0.3mmol 1,2-, 0.36mmol iodic anhydride are added to 10mL pressure resistance In reactor, 4mL acetonitrile, 1mL water as solvent are added.Then, the magnetic agitation 20h under the conditions of 80 DEG C.Then, in reaction solution Two spoon column chromatography silica gels of middle addition (100-200 mesh), and solvent is removed by vacuum distillation, then obtain by pillar layer separation To the pure product 3- as shown in structural formula (4- benzoyl bromide) -2- (4- bromophenyl) -1H- 1-Indanone (with petroleum ether/second Acetoacetic ester=30:1 is as eluant, eluent).The substance is brown-red solid, yield 82%.
Characterize data:1H NMR(500MHz,CDCl3): δ 7.98 (d, J=8.5Hz, 2H), 7.62 (d, J=7Hz, 1H), 7.53 (d, J=8.5Hz, 2H), 7.40-7.37 (m, 3H), 7.33-7.28 (m, 3H), 7.02 (d, J=7Hz, 1H)13C NMR (125MHz,CDCl3):δ195.35,193.15,150.06,143.58, 134.57,133.67,133.44,132.37, 131.72,130.75,130.66,130.20,129.69,129.32, 128.37,124.12,123.78,121.83
Embodiment 11
By bis- ((the 4- propyl phenyl) acetenyl) benzene of 0.3mmol 1,2-, that 0.36mmol iodic anhydride is added to 10mL is resistance to It presses in reactor, adds 4mL acetonitrile, 1mL water as solvent.Then, the magnetic agitation 12h under the conditions of 50 DEG C.Then, anti- It answers and is added in liquid two spoon column chromatography silica gels (100-200 mesh), and solvent is removed by vacuum distillation, then pass through column chromatography point From obtaining the pure product 3- as shown in structural formula (4- benzoyl bromide) -2- (4- propyl phenyl) -1H- 1-Indanone (with petroleum Ether/ethyl acetate=30:1 is as eluant, eluent).The substance is brown-red solid, yield 84%.
Characterize data:1H NMR(500MHz,CDCl3): δ 7.86 (d, J=5Hz, 2H), 7.61 (d, J=5Hz, 1H), (7.38 d, J=10Hz, 2H), 7.35 (d, J=5Hz, 1H), 7.28-7.25 (m, 1H), 7.16 (d, J=10 Hz, 2H), 7.06-7.02 (m, 3H), 2.58 (t, J=10Hz, 2H), 2.50 (t, J=10Hz, 2H), 1.64-0.85 (m, 6 H)13C NMR (125MHz,CDCl3)δ:196.35,194.28,149.98,149.91,144.36, 143.66,134.37,134.27, 133.06,129.62,129.48,129.24,129.01,128.85,128.60, 128.39,127.13,123.65, 121.58,38.01,37.69,24.11,23.93,13.59(2C).
Embodiment 12
By bis- ((the 4- propyl phenyl) acetenyl) benzene of 0.3mmol 1,2-, that 0.36mmol iodic anhydride is added to 10mL is resistance to It presses in reactor, adds 4mL toluene, 1mL water as solvent.Then, the magnetic agitation 12h under the conditions of 50 DEG C.Then, anti- It answers and is added in liquid two spoon column chromatography silica gels (100-200 mesh), and solvent is removed by vacuum distillation, then pass through column chromatography point From obtaining the pure product 3- as shown in structural formula (4- benzoyl bromide) -2- (4- propyl phenyl) -1H- 1-Indanone (with petroleum Ether/ethyl acetate=30:1 is as eluant, eluent).The substance is brown-red solid, yield 58%.
Characterize data:1H NMR(500MHz,CDCl3): δ 7.86 (d, J=5Hz, 2H), 7.61 (d, J=5Hz, 1H), 7.38 (d, J=10Hz, 2H), 7.35 (d, J=5Hz, 1H), 7.28-7.25 (m, 1H), 7.16 (d, J=10 Hz, 2H), 7.06-7.02 (m, 3H), 2.58 (t, J=10Hz, 2H), 2.50 (t, J=10Hz, 2H), 1.64-0.85 (m, 6 H)13C NMR (125MHz,CDCl3)δ:196.35,194.28,149.98,149.91,144.36, 143.66,134.37,134.27, 133.06,129.62,129.48,129.24,129.01,128.85,128.60, 128.39,127.13,123.65, 121.58,38.01,37.69,24.11,23.93,13.59(2C)。

Claims (10)

1. a kind of method of indanone compounds shown in preparation formula (II), it is characterised in that the method are as follows: shown in formula (I) Dialkyne be starting material, under conditions of no metal participates in, in the mixed solvent that organic solvent and water mix In, under oxidant effect, reacted 5-48 hours under conditions of 25-100 DEG C, reaction solution is through isolating and purifying the formula of being prepared (II) indanone compounds shown in；The oxidant is iodic anhydride, iodobenzene diacetate or potassium peroxydisulfate；
In formula (I) or formula (II), one of R H, methyl, bromine, propyl.
2. the method as described in claim 1, it is characterised in that: the volume ratio of the in the mixed solvent organic solvent and water is 1 ~74:1, the amount of the substance of the water are the 1%~20% of the amount of dialkyne substance shown in formula (I).
3. the method as described in claim 1, it is characterised in that: the amount of the oxidant species is two ethynylations shown in formula (I) Close the 100%~200% of the amount of object substance.
4. method as claimed in claim 3, it is characterised in that: the oxidant is iodic anhydride.
5. the method as described in claim 1, it is characterised in that: the organic solvent be acetonitrile, tetrahydrofuran, methylene chloride, Nitromethane or toluene.
6. the method as described in claim 1, it is characterised in that: the reaction temperature of the reaction is 50 DEG C.
7. the method as described in claim 1, it is characterised in that: the reaction time of the reaction is 6-12 hours.
8. the method according to claim 1, it is characterised in that: described to isolate and purify as column layer is added in reaction solution Silica gel is analysed, and solvent is removed by vacuum distillation, then be 30:1 with petroleum ether and ethyl acetate volume ratio by pillar layer separation Mixed liquor as eluent, collect the eluent containing target product, solvent be evaporated off and obtains 3- carbonyl shown in formula (II) Indanone compounds.
9. method according to claim 8, it is characterised in that: the column chromatography silica gel is 100~200 mesh.
10. method according to claim 8, it is characterised in that: the quality of the column chromatography silica gel is with compound shown in formula (I) The amount of substance be calculated as 0.5g/mmol.
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CN114890883A (en) * 2022-02-10 2022-08-12 上海应用技术大学 Indanone and preparation method thereof

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