CN103275052A - Method for synthesizing isoflavone by nickel-catalyzed Negishi cross coupling reaction at room temperature - Google Patents

Abstract

The invention belongs to the technical field of heterocyclic compounds, and particularly relates to a heterocyclic non-hydrogenated heterocyclic compound containing a six-membered ring and taking an oxygen atom as the only heteroatom and condensed with other rings. The invention provides a new method for synthesizing isoflavone by a nickel-catalyzed Negishi cross coupling reaction at room temperature, which comprises the following steps of: adding reactants (substituted) 3-iodine chromone or (substituted) 3-bromine chromone and an aryl zinc reagent into a solvent, and performing a nickel-catalyzed reaction at room temperature; and after the reaction, performing column chromatographic separation and purification to obtain a pure product of the compound isoflavone. The method provided by the invention is used for preparing medical isoflavones such as ipriflavone, formononetin, isoflavoues aglycone, genistein, puerarin and the like, provides a new technical way to the industrial production of the medicines, and is also used for preparing a series of new isoflavone compounds with potential physiological activity.

Description

The Negishi cross-coupling reaction of room temperture nickel catalysis synthesizes isoflavones

Technical field

The invention belongs to the heterogeneous ring compound technical field, be specifically related to the six-membered ring that contains of not hydrogenation of heterocycle, a Sauerstoffatom is arranged as ring hetero atom is only arranged, with other ring condensed heterocycle compound.

Background technology

Isoflavones is in the plant phenylalanine metabolic process, and cyclisation forms the phenolic compound based on the benzochromone ring after being prolonged by cinnyl coenzyme A side chain, and its 3-phenyl derivatives is isoflavones, the platymiscium secondary metabolite.Modern pharmacological research shows, isoflavonoid is at cardiovascular systems, endocrine system, central nervous system, immunity system and antitumor, anti-oxidant and remove aspects such as free radical effect, the effect of female hormone sample, anti-inflammatory anti-allergic effects, antibiotic and antivirus action and have tangible pharmacological action.For example can prevent and treat the onocol of mammary cancer, prostate cancer and colorectal carcinoma and can bring out programmed cell death, improve anticancer drug effect, suppress the genistein of vasculogenesis (referring to J.Med.Chem, 2006,49,3973-3981) be used for fields such as healthcare products, food, medicine with the osteoporotic ipriflavone for the treatment of and many isoflavones such as daidzein of slowing down the Woman climacteric illness.

Well-known soybean is human isoflavones---the effective source of daidzein and genistein that obtains.Under the strong situation of oestrogenic hormon physiologically active, soybean isoflavones can play estrogenic antagonist, and reduction is subjected to the cancer of oestrogenic hormon activation such as the risk of mammary cancer, and when the reduction of postmenopausal women estrogen level in period, soybean isoflavones can play substitution effect, avoids menelipsis phase symptom generations such as hectic fever.Its anticancer property is very outstanding simultaneously, can hinder growth and the diffusion of cancer cells, and only cancer cells be had effect, to the normal cell did not influence.Soybean isoflavones not only self has antioxygenation, also can induce increasing of activities of antioxidant enzymes, improves the oxidation-resistance of serum LDL with the formation of prevention of arterial vessel wall atheromatous plaque, anti-hemostatic tube congee sample sclerosis; Increase arterial vascular conformability simultaneously, vasodilation.Soybean isoflavones also suppresses Atherosclerosis by influencing Tyrosylprotein kinase, comprises that foam cell, fat-like line, hyperplasia, fibrous plaque soak into, break and ulcer, have kept the unblocked of heart arter blood vessel, the generation of preventing cardiovascular disease.Come from the plumule part of leguminous plants garbanzo seed and the Biochanin A of red clover herb and have estrogen-like effects, can suppress the rising of cholesterol, also have antimycotic and antitumor action and the hormonal readiness in the human body is had two-ways regulation and anticancer spasmolysis reducing blood lipid.In addition, ipriflavone produces anti-bone resorption indirectly by the secretion of estrogen-like effects increase thyrocalcitonin; Promote the formation of bone in the clinical osteoporosis that is used for the treatment of.Now successfully be developed as the medicine ipriflavone sheet that reduces for the bone amount due to the clinical improvements osteoporosis.The onocol physiologically active is also comparatively outstanding in numerous medicinal isoflavones, antitumous effect is not only arranged, can prevent and treat mammary cancer, prostate cancer and colorectal carcinoma and have estrogen effect simultaneously, and the male albinism rat hyperlipidemia that TritonWR-1339 causes is had reducing blood lipid.The clinical diuretic(s) that has been used as is (referring to WO93/23069; JP62-10601616A2; WO99/43335; WO00/644438).The puerarin scope of application is the widest and formulation is very abundant in the clinical medicinal isoflavones.Wherein preparations such as puerarin infusion solutions, puerarin injection, puerarin capsule, puerarin eye drop have been used for the treatment of illnesss such as alcoholism, retina arteriovenous obstruction, sudden deafness, myocardial infarction, coronary heart disease, hypertension, hyperlipidemia.

Yet existing isoflavonoid only depends on and extracts from natural phant is can not satisfy necessary for human far away, is subjected to plant-growth cycle, the restriction of natural causes such as growing environment on the one hand; It is lower and to the environment friendly and relatively poor restriction of this more solvability of class natural flavone action site inadequately to be subjected to the limited productive rate of extracting method on the other hand, therefore produces flavonoid compound and its structure is modified to satisfy necessary for human accordingly by the method for chemosynthesis.

The synthetic isoflavones main method of early stage bibliographical information is the phenylpropiophenone approach, claims the deoxybenzoin approach again.This method comprises two big step reactions: the one, and preparation intermediate deoxybenzoin, another step is the ring-closure reaction of deoxybenzoin.According to the difference of raw materials used, reagent and reaction process, the common method that 4 kinds of synthetic deoxybenzoins are arranged, they are respectively benzene second eyeball method, toluylic acid method, phenyllacetyl chloride method and Fries rearrangement method.The carburetting ring closure reaction method research of deoxybenzoin is more, can with deoxybenzoin respectively with alkyl formate, alkoxalyl halogen, prussic acid or prussic acid inorganic salt, organic acid anhydride, N, N-dialkyl amide/trichlorine phosphine oxide, 1,3,5-triazine, DMF/ Methanesulfonyl chloride, DMF/ five phosphonium chlorides, N, dinethylformamide contracting dialkyl group alcohol, alkyl orthoformate, the reaction of N-formylimidazoles constitute the isoflavones ring.Most ring closure reaction condition harshnesses, agents useful for same price height, toxicity are bigger, are the bottlenecks of synthetic isoflavones.The phenylpropiophenone approach synthesizes isoflavones, and agents useful for same costliness, reaction conditions are violent, reagent toxicity is big, long reaction time, product purification more complicated, yield are lower.

LeoA.Paquette and Heinz Stucki have studied the condensation reaction of salicylaldhyde and enamine, use to replace salicylaldhyde and the synthetic isoflavone compounds of N-styryl beautiful jade reaction.The yield of the synthetic isoflavones of this method and 8-methoxyl group isoflavones is 46.2% and 42.8%, and reaction requires anhydrous solvent and nitrogen protection, and cost is higher.Ib Thomsen etc. has also reported with salicylaldoxime and the synthetic isoflavones of enamine (N-styryl agate beautiful jade) reaction; need to obtain isoflavone compounds through acetylize, reduction, ring-closure reaction; yield is 37%; the reaction process complexity; yield is low and need carry out separation and purification with tlc, so industrial application value is lower.

The seventies in 20th century, the synthetic isoflavones of cinnamophenone approach has appearred, mainly be to be raw material with substituted acetophenone and substituted benzaldehyde, generate corresponding cinnamophenone through the Claisen-Schemidt condensation, cinnamophenone utilizes rearrangement reaction to synthesize isoflavones under the effect of heavy metal thallium salt, uses poisonous thallium salt in a large number in the lower and production technique of this method yield; And then improved cinnamophenone resets the method prepare isoflavones through oxidation, and productive rate is also lower.It also is one of method for preparing isoflavones that flavanone oxidation rearrangement prepares isoflavones, how to do the catalyst reaction with thallium salt and periodide and take place, but catalyzer and solvent is bigger to the influence of the productive rate of reaction.

Linked reaction is synthesized isoflavones reaction conditions gentleness, the atom utilization height, and productive rate can reach 80%～90%.Utilize Suzuki linked reaction, Stille organotin linked reaction, the coupling of Stille organo-bismuth and the Negishi organic zinc linked reaction reported are at present synthesized isoflavones, catalyzer all is expensive palladium catalyst, palladium catalyst easily produces palladium black in reaction, reduce catalytic efficiency, and the palladium black that forms is difficult for removing, and influences product purity and quality.Than the linked reaction of palladium catalysis, the present invention adopts cheap nickel catalyzing N egishi linked reaction to synthesize isoflavones, the catalytic efficiency height, and product is easy to separation and purification; Zincon preparation simple, active high, toxicity is little, low price, plurality of advantages such as applied widely, and the Negishi linked reaction has good tolerance to various functional groups, can tolerate the existence of thiazolinyl, ester group, cyano group etc.

For this reason, the present invention is by having realized that economical and efficient synthesizes isoflavonoid under the condition of Negishi linked reaction with (replacement) 3-iodine chromone or (replacement) 3-bromine chromone and the nickel catalysis in the tetrahydrofuran (THF) equal solvent of aryl zincon, and save energy is at room temperature carried out in reaction.

Summary of the invention

The object of the present invention is to provide the novel method of the synthetic isoflavones of a kind of nickel catalyzing N egishi linked reaction, and use the efficiently synthetic medicinal isoflavonoid with physiologically active of this method.

The raw material that relates among the present invention (replacement) 3-iodine chromone, (replacement) 3-bromine chromone and aryl zincon compounds all are synthetic with reference to pertinent literature, and synthetic route is as follows:

The synthetic route of (replacement) 3-iodine chromone and (replacement) 3-bromine chromone (referring to J.Med.Chem., 2006,49,3973-3981 and Russ.Chem.Rev., 2003,72,489-516):

Formula (1) X=I, formula (2) X=Br

R ₁～R ₄Any one or a few substituting group in=alkyl, alkoxyl group, nitro, hydrogen, hydroxyl, glycosyl, alkoxyl group alkoxyl group, fluorine, the chlorine.

The synthetic route of aryl zincon (referring to Tetrahedron Letters, 2003,44,6417-6420):

Formula (3)

R ₅Any one substituting group in=alkyl, alkoxyl group, alkoxyl group alkoxyl group, nitro, hydrogen, ester group, trifluoromethyl, cyano group, fluorine, the chlorine.

Be in the method for the synthetic isoflavones formula (4) of raw material with (replacement) 3-iodine chromogen keto-acid (1), the used solvent of chemical reaction is acetonitrile or tetrahydrofuran (THF), the temperature of chemical reaction is room temperature, the time of chemical reaction is 1～3 hour, said nickel catalyzator is anhydrous chlorides of rase nickel or two (triphenylphosphine) nickelous chloride or 1,3-two (diphenylphosphine) propane nickelous chloride or 1,2-two (diphenylphosphine) ethane chlorination nickel; Said part is triphenylphosphine or three (4-aminomethyl phenyl) phosphine or three (4-p-methoxy-phenyl) phosphine or three (2-furyl) phosphine; The solvent that adds (replacement) 3-iodine chromogen keto-acid (1) and (1) 10～30 times of weight of formula in the reactor, the nickel catalyzator of (1) 0.001～0.05 times of molar weight of formula, the part of (1) 0.002～0.1 times of molar weight of formula, the Lithium chloride (anhydrous) of (1) 1.5 times of molar weight of formula, the aryl zincon formula (3) that adds (1) 1.1～1.5 times of molar weight of formula after stirring again, at room temperature react stopped reaction after 1～3 hour, the aqueous hydrochloric acid cancellation reaction of the 1mol/L of (1) 3 times of weight of adding formula, add (1) 30 times of weight distilled water of formula again, with with distilled water equal volume of ethyl acetate three times, merge organic phase, extremely neutral with distillation washing organic phase, anhydrous magnesium sulfate drying, collect ethyl acetate layer, decompression and solvent recovery, and through silica gel column chromatography (sherwood oil is 20: 1 with the ethyl acetate volume ratio) separate the pure product of formula (4) isoflavones.

Formula (1) formula (3) formula (4)

Be in the method for the synthetic isoflavones formula (4) of raw material with (replacement) 3-bromine chromogen keto-acid (2), the used solvent of chemical reaction is acetonitrile or tetrahydrofuran (THF), the temperature of chemical reaction is room temperature, the time of chemical reaction is 1～3 hour, said catalyzer is anhydrous chlorides of rase nickel or two (triphenylphosphine) nickelous chloride or 1,3-two (diphenylphosphine) propane nickelous chloride or diacetyl acetone nickel; Said part is triphenylphosphine or three (2-furyl) phosphine; The solvent that adds (replacement) 3-bromine chromogen keto-acid (2) and (2) 10～30 times of weight of formula in the reactor, the nickel catalyzator of (2) 0.001～0.05 times of molar weights of formula, the part of (2) 0.002～0.1 times of molar weights of formula, the Lithium chloride (anhydrous) of (2) 1.5 times of molar weights of formula, the aryl zincon formula (3) that adds (2) 1.1～1.5 times of molar weights of formula after stirring again, at room temperature react stopped reaction after 1～3 hour, the aqueous hydrochloric acid cancellation reaction of the 1mol/L of (2) 3 times of weight of adding formula, add (2) 30 times of weight distilled water of formula again, with with distilled water equal volume of ethyl acetate three times, merge organic phase, extremely neutral with distillation washing organic phase, anhydrous magnesium sulfate drying, collect ethyl acetate layer, decompression and solvent recovery, and through silica gel column chromatography (sherwood oil is 20: 1 with the ethyl acetate volume ratio) separate the pure product of formula (4) isoflavones.

Formula (2) formula (3) formula (4)

In the formula (4), said substituent R ₁～R ₄Be C ₁～C ₆Alkyl, C ₁～C ₆Alkoxyl group, C ₁～C ₆Alkoxyl group alkoxyl group, nitro, hydrogen, hydroxyl, glycosyl, fluorine, chlorine in any one or a few; Said R ₅Be C ₁～C ₆Alkyl, C ₁～C ₆Alkoxyl group, C ₁～C ₆Alkoxyl group alkoxyl group, nitro, ester group, cyano group, trifluoromethyl, hydrogen, fluorine, chlorine in any one.

Among the preparation method of formula of the present invention (4), when being raw material with (replacement) 3-iodine chromogen keto-acid (1), the top condition of reaction is: the solvents tetrahydrofurane of (1) 15 times of weight of formula, the catalyzer anhydrous chlorides of rase nickel of (1) 0.03 times of molar weight of formula, the part triphenylphosphine of (1) 0.06 times of molar weight of formula, the Lithium chloride (anhydrous) of (1) 1.5 times of molar weight of formula, the aryl zincon of (1) 1.1 times of molar weight of formula, room temperature reaction 1 hour; When being raw material with (replacement) 3-bromine chromogen keto-acid (2), the top condition of reaction is: the solvents tetrahydrofurane of (2) 15 times of weight of formula, catalyzer two (triphenylphosphine) nickelous chloride of (2) 0.05 times of molar weights of formula, the Lithium chloride (anhydrous) of (2) 1.5 times of molar weights of formula, the aryl zincon of (2) 1.1 times of molar weights of formula, room temperature reaction 1 hour.

Because isoflavones comprises that to multiple disease tumour, cardiovascular disorder, osteoporosis and nerve degenerative diseases etc. have prophylactic effect.Therefore the preparation method by formula of the present invention (4) isoflavone compounds synthesizes 14 kinds of new isoflavonoids: 2 '-the cyano group isoflavones, 3 '-the cyano group isoflavones, 4 '-the cyano group isoflavones, 4 '-the trifluoromethyl isoflavones, 2 '-cyano group-6-fluorine isoflavones, 4 '-trifluoromethyl-5-fluorine isoflavones, 2 '-cyano group-7-methoxyl group isoflavones, 4 '-cyano group-7-methoxyl group isoflavones, 4 '-trifluoromethyl-7-methoxyl group isoflavones, 4 '-methyl-7-isopropoxy isoflavones, 2 '-cyano group-7-isopropoxy isoflavones, 4 '-cyano group-7-isopropoxy isoflavones, 4 '-trifluoromethyl-7-isopropoxy isoflavones and 4 '-methyl-formiate base-7-isopropoxy isoflavones.Many studies show that introduced hydroxyl isoreactivity group and can effectively be improved biological activity in 4 of isoflavones ' position in recent years.Shao Guoxian etc. find when soybean isoflavones is carried out structural modification, substituting groups different on 4 ' position can produce different influences to its biological activity, after introducing electron-donating groups such as hydroxyl, methoxyl group, kharophen, compound can obviously prolong the hypoxia endurance time of animal.It is primer with the 7-hydroxyisoflavone that Liu builds medium, introduces methoxyl group in its 4 ' position, has prepared a series of isoflavone derivatives.The rat pharmacological evaluation shows that its hypoxia tolerance effect is obvious.This is because the isoflavonoid physiologically active is wide, but does not absorb very less or fully because it absorbs in enteron aisle, causes activity lower.In molecular structure, introduce hydroxyl and methoxyl group, not only can improve the solvability of isoflavonoid, and strengthen the antitumour activity of compound probably.Substituted radical often has great influence to biological activity, and the introducing of different substituents group in the molecule can make compound change aspect electrical, three-dimensional, hydrophobicity, thereby can have influence on the physiological action of compound.If in molecule, introduce the substituting group that can become the new binding site that mutually combines with acceptor, pharmacophore is changed, produce the physiological action of other types.For example introducing fluorine atom or fluoro-containing group in organic molecule usually can make the physico-chemical property of organic molecule and biological activity produce significant the variation.After a hydrogen atom in the molecule is replaced by fluorine atom, little to the spatial volume influence of molecule, be difficult for being identified by the enzyme in the organism, can make non-hydrogen parent enter bio-metabolic process without difficulty, show the pseudo-effect of intending.Fluorine atom also has the function of hydrogen bond receptor, simultaneously the form that fluorine atom can fluorion is left away, and be a good medium leavings group, the nucleophilic reagent that it can be attached to active part in (or close) enzyme replaces, so the organism that produces part can be connected with the form of covalent linkage enzyme above.Fluorinated organic compound is difficult to by metabolism, thereby the enzyme that constitutes competition suppresses, fluorochemicals is because pseudo-plan effect participates in metabolism but can not be by normal approach metabolism as a result, metabolic disturbance has just appearred in certain stage, thereby has a significant antimetabolic, namely have very high stability, and produce various effects.The introducing of fluorine atom will increase organic lipotropy significantly, show as fluorochemicals film and tissue etc. is had very strong penetrativity, thereby improve absorption and the transmission speed of fluorochemicals in organism.This shows that above preparation method by formula of the present invention (4) isoflavone compounds synthesizes new isoflavonoid biologically active and pharmaceutical use too.

The inventive method not only can be used for the isoflavones of synthetic other new texture, but also is ipriflavone, daidzein, and genistein, onocol, puerarin provide a kind of brand-new synthetic route.Specific implementation method is as follows:

The ipriflavone synthetic route:

The onocol synthetic route:

The daidzein synthetic route:

The genistein synthetic route:

The puerarin synthetic route:

Preparation method of the present invention uses cheap nickel catalyzator catalyzed reaction, and it is easy to have technology, advantages such as used equipment is simple, feedstock production simple, zincon toxicity is little, reaction conditions is gentle, the yield height of product and save energy.

Embodiment

The present invention is described in more detail below in conjunction with embodiment, but the invention is not restricted to these embodiment.

Used reagent is chemical pure among the embodiment.Compound structure determines that used nuclear magnetic resonance analyser is BrukerAM-300,400 NMR spectrometer with superconducting magnet, and TMS is as interior mark; Mass spectrograph is Bruker high resolution electrospray mass spectrometer; Infrared spectra adopts Nicolet170SX FT-IR determination of infrared spectroscopy; Fusing point adopts WRS-113 numeral melting point detector to measure.

One, formula (4) preparation embodiment

Embodiment 1

In the present embodiment, add 3-iodine chromone and 15 times of weight tetrahydrofuran (THF)s of 3-iodine chromone in the reactor, the anhydrous chlorides of rase nickel of 0.03 times of molar weight of 3-iodine chromone, the triphenylphosphine of 0.06 times of molar weight of 3-iodine chromone, the Lithium chloride (anhydrous) of 1.5 times of molar weights of 3-iodine chromone, the phenyl zinc bromide that adds 1.1 times of molar weights of 3-iodine chromone after stirring again, after at room temperature reacting 1 hour, the aqueous hydrochloric acid cancellation reaction that adds the 1mol/L of 3 times of weight of 3-iodine chromone, add 30 times of weight distilled water of 3-iodine chromone again, with with distilled water equal volume of ethyl acetate three times, merge organic phase, extremely neutral with distillation washing organic phase, anhydrous magnesium sulfate drying is collected ethyl acetate layer, decompression and solvent recovery, be that 20: 1 mixed solvent is made eluent with sherwood oil and ethyl acetate volume ratio, through the gradient elution separation pure product of compound (1) isoflavones that obtain of silica gel column chromatography.

Adopt this examples preparation to get compound (1) isoflavones, its physicochemical property is as follows after tested:

Compound (1) isoflavones is white solid, and fusing point is: 131-132 ℃, and productive rate 85%.

Compound in the present embodiment (1) isoflavones molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：3049，1637，1566，1492，1469，1464，1379，1354，1286，1227，1169，1103，1014，906，884，760，696，615，538.

Compound in the present embodiment (1) isoflavones molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，DMSO-d ₆/TMS，δ(ppm)]：8.56(s，1H)，8.16(d，J＝7.4Hz，1H)，7.83(d，J＝7.2Hz，1H)，7.55(ddd，J＝30.2，24.3，14.1Hz，7H).

Compound in the present embodiment (1) isoflavones molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，DMSO-d ₆/TMS，δ(ppm)]：175.6，156.1，155.0，143.2，134.6，132.4，132.0，131.0，129.4，129.0，128.6，128.4，126.0，124.4，118.8.

Compound in the present embodiment (1) isoflavones molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI ⁺)：m/z(rel?intensity)：(M+Na)，Cal：245.0578；found：245.0565.

Embodiment 2

In the present embodiment, the acetonitrile that adds 3-iodine chromone and 20 times of weight of 3-iodine chromone in the reactor, the anhydrous chlorides of rase nickel of 0.05 times of molar weight of 3-iodine chromone, three (2-furyl) phosphine of 0.1 times of molar weight of 3-iodine chromone mole, the Lithium chloride (anhydrous) of 1.5 times of molar weights of 3-iodine chromone, the phenyl zinc bromide that adds 1.2 times of molar weights of 3-iodine chromone after stirring again respectively, 4-aminomethyl phenyl zinc bromide, 2-p-methoxy-phenyl zinc bromide, 3-p-methoxy-phenyl zinc bromide, 4-p-methoxy-phenyl zinc bromide, 2-cyano-phenyl zinc bromide, 3-cyano-phenyl zinc bromide, 4-cyano-phenyl zinc bromide, 4-trifluoromethyl zinc bromide, 4-chloro phenyl zinc bromide and 4 benzoic acid methoxycarbonyl zinc bromide, at room temperature react stopped reaction after 2 hours, the separating technology of product is identical with the preparation of isoflavone compounds among the embodiment 1 with method, obtain respectively compound (2) 4 '-the methyl isoflavones, compound (3) 2 '-the methoxyl group isoflavones, compound (4) 3 '-the methoxyl group isoflavones, compound (5) 4 '-the methoxyl group isoflavones, compound (6) 2 '-the cyano group isoflavones, compound (7) 3 '-the cyano group isoflavones, compound (8) 4 '-the cyano group isoflavones, compound (9) 4 '-the trifluoromethyl isoflavones, compound (10) 4 '-chlorine isoflavones and compound (11) 4 '-methyl benzoate base isoflavones.

Compound in the present embodiment (2) is white solid, and fusing point is 154-155 ℃, productive rate 96%.

Compound in the present embodiment (2) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：3074，3028，2919，1637，1614，1572，1511，1464，1376，1357，1285，1144，1047，913，884，851，820，757，694，541，524.

Compound in the present embodiment (2) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，DMSO-d ₆/TMS，δ(ppm)]：8.52(s，1H)，8.15(d，J＝7.5Hz，1H)，7.83(t，J＝7.2Hz，1H)，7.69(d，J＝8.2Hz，1H)，7.50(d，J＝7.6Hz，3H)，7.26(d，J＝7.4Hz，2H).

Compound in the present embodiment (2) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，DMSO-d ₆/TMS，δ(ppm)]：176.3，156.2，152.7，138.1，133.5，129.2，128.9，128.8，126.4，125.4，125.2，124.6，118.0，21.3.

Compound in the present embodiment (2) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI ⁺)：m/z(relintensity)：(M+Na)，Cal：259.0735；found：259.0725.

Compound in the present embodiment (3) is white solid, and fusing point is 167-169 ℃, productive rate 53%.

Compound in the present embodiment (3) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：3058，2924，2847，1637，1607，1495，1462，1379，1356，1289，1245，1162，1020，954，859，770，704，619.

Compound in the present embodiment (3) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，DMSO-d ₆/TMS，δ(ppm)]：8.35(s，1H)，8.11(d，J＝7.8Hz，1H)，7.83(d，J＝7.7Hz，1H)，7.69(d，J＝8.4Hz，1H)，7.51(d，J＝7.5Hz，1H)，7.39(d，J＝7.6Hz，1H)，7.25(s，1H)，7.10(d，J＝8.2Hz，1H)，7.01(t，J＝7.4Hz，1H)，3.73(s，3H).

Compound in the present embodiment (3) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，DMSO-d ₆/TMS，δ(ppm)]：174.8，157.4，155.7，154.7，134.1，131.5，129.7，125.4，125.4，123.7，122.3，120.9，120.1，118.4，111.3，55.5.

Compound in the present embodiment (3) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI ⁺)：m/z(relintensity)：(M+Na)，Cal：275.0684；found：275.0682.

Compound in the present embodiment (4) is white solid, and fusing point is 67-69 ℃, productive rate 91%.

Compound in the present embodiment (4) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：2949，1728，1647，1612，1466，1430，1379，1355，1293，1247，1166，1045，991，856，812，765，696，636.

Compound in the present embodiment (4) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，DMSO-d ₆/TMS，δ(ppm)]：8.57(s，1H)，8.17(d，J＝7.5Hz，1H)，8.11-7.63(m，2H)，7.63-7.34(m，2H)，7.19(d，J＝7.2Hz，2H)，6.98(d，J＝7.1Hz，1H)，3.81(s，3H).

Compound in the present embodiment (4) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

13C?NMR[75MHz，DMSO-d6/TMS，δ(ppm)]：175.0，159.1，155.6，154.7，134.1，133.2，129.2，125.5，123.9，123.7，121.1，118.3，114.6，113.4，55.1.

Compound in the present embodiment (4) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI ⁺)：m/z(rel?intensity)：(M+Na)，Cal：275.0684；found：275.0681.

Compound in the present embodiment (5) is white solid, and fusing point is 146-147 ℃, productive rate 86%.

Compound in the present embodiment (5) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：3027，2950，2853，1607，1565，1511，1464，1379，1352，1289，1245，1103，1031，883，824，795，760，600.

Compound in the present embodiment (5) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，DMSO-d ₆/TMS，δ(ppm)]：8.51(s，1H)，8.16(d，J＝7.7Hz，1H)，7.83(t，J＝7.4Hz，1H)，7.68(d，J＝8.3Hz，1H)，7.53(dd，J＝14.4，7.9Hz，3H)，7.02(d，J＝8.4Hz，2H)，3.80(s，3H).

Compound in the present embodiment (5) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，DMSO-d ₆/TMS，δ(ppm)]：175.8，159.6，156.1，154.4，134.5，130.5，128.9，126.0，125.9，124.5，124.3，124.0，118.8，114.1，114.0，55.6.

Compound in the present embodiment (5) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI ⁺)：m/z(rel?intensity)：(M+Na)，Cal：275.0684；found：275.0663.

Compound in the present embodiment (6) is white solid, and fusing point is 198-199 ℃, productive rate 41%.

Compound in the present embodiment (6) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：3055，2924，2223，1638，1570，1489，1465，1363，1293，1228，1166，1110，956，855，767，730，699，623.

Compound in the present embodiment (6) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，DMSO-d ₆/TMS，δ(ppm)]：8.67(s，1H)，8.17(d，J＝7.0Hz，1H)，8.05-7.71(m，4H)，7.70-7.42(m，3H).

Compound in the present embodiment (6) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，DMSO-d ₆/TMS，δ(ppm)]：174.7，156.5，156.3，136.0，135.2，133.6，133.4，132.0，129.5，126.5，126.0，124.0，123.1，119.1，118.4，113.5.

Compound in the present embodiment (6) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI ⁺)：m/z(rel?intensity)：(M+Na)，Cal：270.0531；found：270.0531.

Compound in the present embodiment (7) is white solid, and fusing point is 199-200 ℃, productive rate 40%.

Compound in the present embodiment (7) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：3067，2226，1646，1464，1361，1292，1161，1079，952，858，802，761，689，625.

Compound in the present embodiment (7) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，DMSO-d ₆/TMS，δ(ppm)]：8.71(s，1H)，8.24-7.48(m，8H).

Compound in the present embodiment (7) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，DMSO-d ₆/TMS，δ(ppm)]：175.3，156.1，135.0，134.2，133.7，132.8，132.0，129.9，129.1，126.3，126.0，124.2，122.5，119.2，118.9，111.8.

Compound in the present embodiment (7) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI ⁺)：m/z(rel?intensity)：(M+Na)，Cal：270.0531；found：270.0525.

Compound in the present embodiment (8) is white solid, and fusing point is 200-201 ℃, productive rate 30%.

Compound in the present embodiment (8) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：3064，2924，2854，2230，1930，1639，1570，1504，1466，1372，1290，1231，1148，946，860，836，754，695，640.

Compound in the present embodiment (8) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，DMSO-d ₆/TMS，δ(ppm)]：8.71(s，1H)，8.16(s，1H)，7.84(t，J＝26.2Hz，6H)，7.56(s，1H).

Compound in the present embodiment (8) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，DMSO-d ₆/TMS，δ(ppm)]：175.2，156.4，156.1，137.5，135.0，133.5，132.6，130.2，126.4，126.0，124.3，122.9，119.3，119.0，111.0.

Compound in the present embodiment (8) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI ⁺)：m/z(rel?intensity)：(M+Na)，Cal：270.0531；found：270.0526.

Compound in the present embodiment (9) is the white plates solid, and fusing point is 152-156 ℃, productive rate 77%.

Compound in the present embodiment (9) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：2922，2071，1638，1570，1513，1466，1413，1377，1338，1287，1110，1073，1013，859，834，759，695，626.

Compound in the present embodiment (9) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，DMSO-d ₆/TMS，δ(ppm)]：8.69(s，1H)，8.18(d，J＝7.9Hz，1H)，7.84(d，J＝4.3Hz，5H)，7.74(d，J＝8.3Hz，1H)，7.56(t，J＝7.5Hz，1H).

Compound in the present embodiment (9) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，DMSO-d ₆/TMS，δ(ppm)]：175.3，166.9，157.5，156.1，153.3，135.0，132.0，130.1，129.2，128.6，126.3，126.0，125.5，125.5，125.4，119.0.

Compound in the present embodiment (9) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI ⁺)：m/z(rel?intensity)：(M+Na)，Cal：313.0452；found：313.0447.

Compound in the present embodiment (10) is white solid, and fusing point is 193-195 ℃, productive rate 88%.

Compound in the present embodiment (10) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：3079，1637，1571，1490，1464，1372，1353，1286，1227，1212，1144，1092，1013，918，886，852，817，754，537，516.

Compound in the present embodiment (10) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，DMSO-d ₆/TMS，δ(ppm)]：8.59(s，1H)，8.13(s，1H)，7.84-7.45(m，7H).

Compound in the present embodiment (10) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，DMSO-d ₆/TMS，δ(ppm)]：175.4，156.1，155.4，134.8，133.1，131.1，128.7，126.2，126.0，123.2，118.9.

Compound in the present embodiment (10) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI ⁺)：m/z(rel?intensity)：(M+Na)，Cal：279.0189；found：279.0165.

Compound in the present embodiment (11) is white solid, and fusing point is 44-45 ℃, productive rate 61%.

Compound in the present embodiment (11) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：2925，2854，1713，1638，1565，1467，1365，1277，1156，1071，956，858，769，699，622.

Compound in the present embodiment (11) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，DMSO-d ₆/TMS，δ(ppm)]：8.68(s，1H)，8.17(d，J＝7.9Hz，1H)，8.03(d，J＝8.2Hz，2H)，7.85(d，J＝7.2Hz，1H)，7.79(d，J＝8.2Hz，2H)，7.72(d，J＝8.4Hz，1H)，7.55(t，J＝7.5Hz，1H)，3.89(s，3H).

Compound in the present embodiment (11) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，DMSO-d ₆/TMS，δ(ppm)]：175.3，166.5，156.1，156.0，137.4，134.9，131.0，129.6，129.4，128.7，126.3，126.0，125.9，124.3，123.4，118.9，52.7.

Compound in the present embodiment (11) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI ⁺)：m/z(rel?intensity)：(M+Na)，Cal：303.0633；found：303.0628.

Embodiment 3

In the present embodiment, the acetonitrile that adds 6-fluoro-3-iodine chromone and 30 times of weight of 6-fluoro-3-iodine chromone in the reactor, the anhydrous chlorides of rase nickel of 0.02 times of molar weight of 6-fluoro-3-iodine chromone, three (4-aminomethyl phenyl) phosphine of 0.04 times of molar weight of 6-fluoro-3-iodine chromone, the Lithium chloride (anhydrous) of 1.5 times of molar weights of 6-fluoro-3-iodine chromone, the phenyl zinc bromide that adds 1.5 times of molar weights of 6-fluoro-3-iodine chromone after stirring again respectively, 4-aminomethyl phenyl zinc bromide, 4-p-methoxy-phenyl zinc bromide, 2-cyano-phenyl zinc bromide, 4-trifluoromethyl zinc bromide and 4-chloro-phenyl-zinc bromide, at room temperature react stopped reaction after 3 hours, the separating technology of product is identical with the preparation of isoflavone compounds among the embodiment 1 with method, obtains compound (12) 6-fluorine isoflavones respectively, compound (13) 6-fluoro-4 '-the methyl isoflavones, compound (14) 6-fluoro-4 '-the methoxyl group isoflavones, compound (15) 6-fluoro-2 '-the cyano group isoflavones, compound (16) 6-fluoro-4 '-trifluoromethyl isoflavones and compound (17) 6-fluoro-4 '-the chlorine isoflavones.

Compound in the present embodiment (12) is white solid, and fusing point is 190-191 ℃, productive rate 75%.

Compound in the present embodiment (12) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：3076，1638，1575，1481，1364，1266，1211，1164，1133，1097，942，878，821，735，690，614，549.

Compound in the present embodiment (12) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，DMSO-d ₆/TMS，δ(ppm)]：8.61(s，1H)，7.89-7.68(m，3H)，7.60(d，J＝6.9Hz，2H)，7.45(d，J＝7.7Hz，3H).

Compound in the present embodiment (12) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，DMSO-d ₆/TMS，δ(ppm)]：175.0，161.2，157.9，155.5，152.6，129.4，128.7，128.5，125.5，125.4，123.7，122.7，121.8，121.7，110.6，110.3.

Compound in the present embodiment (12) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI ⁺)：m/z(rel?intensity)：(M+Na)，Cal：263.0484；found：263.0469.

Compound in the present embodiment (13) is white solid, and fusing point is 170-171 ℃, productive rate 88%.

Compound in the present embodiment (13) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：3079，3028，2919，1639，1579，1515，1483，1367，1271，1134，1102，943，887，819，750，726，602.

Compound in the present embodiment (13) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，DMSO-d ₆/TMS，δ(ppm)]：8.56(s，1H)，7.84-7.68(m，3H)，7.50(d，J＝7.5Hz，2H)，7.26(d，J＝7.6Hz，2H)，2.35(s，3H).

Compound in the present embodiment (13) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，DMSO-d ₆/TMS，δ(ppm)]：174.5，160.6，157.4，154.6，152.1，137.3，128.8，128.7，128.6，125.0，124.9，1231，122.5，122.1，121.3，121.2，110.1，109.8，20.8.

Compound in the present embodiment (13) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI ⁺)：m/z(rel?intensity)：(M+Na)，Cal：277.0641；found：277.0627.

Compound in the present embodiment (14) is white solid, and fusing point is 189-190 ℃, productive rate 70%.

Compound in the present embodiment (14) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：3075，3010，2961，2834，1635，1571，1516，1482，1367，1293，1253，1168，1132，1100，1030，943，818，751，726，601，542.

Compound in the present embodiment (14) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，DMSO-d ₆/TMS，δ(ppm)]：8.55(s，1H)，7.87-7.68(m，3H)，7.55(d，J＝8.5Hz，2H)，7.02(d，J＝8.5Hz，2H)，3.80(s，3H).

Compound in the present embodiment (14) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，DMSO-d ₆/TMS，δ(ppm)]：161.1，159.7，154.9，130.6，124.1，123.4，123.0，122.6，121.7，114.2，110.6，110.3，55.7.

Compound in the present embodiment (14) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI ⁺)：m/z(rel?intensity)：(M+Na)，Cal：293.0590；found：293.0571.

Compound in the present embodiment (15) is white solid, and fusing point is 199-200 ℃, productive rate 41%.

Compound in the present embodiment (15) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(em ^-1)：3052，2962，2927，2856，2225，1730，1639，1579，1477，1376，1333，1285，1260，1215，1138，1104，945，879，829，800，770，724，623.

Compound in the present embodiment (15) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，DMSO-d ₆/TMS，δ(ppm)]：8.71(s，1H)，7.98(d，J＝7.6Hz，1H)，7.89(d，J＝4.1Hz，1H)，7.82(t，J＝7.2Hz，3H)，7.64(t，J＝9.3Hz，2H).

Compound in the present embodiment (15) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，DMSO-d ₆/TMS，δ(ppm)]：174.2，161.4，156.8，152.8，135.6，133.7，133.4，132.0，129.6，123.6，122.1，122.0，118.4，113.5，110.7，110.4.

Compound in the present embodiment (15) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI ⁺)：m/z(fel?intensity)：(M+Na)，Cal：288.0437；found：288.0434.

Compound in the present embodiment (16) is white solid, and fusing point is 148-149 ℃, productive rate 75%.

Compound in the present embodiment (16) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：3064，2926，1634，1481，1366，1329，1271，1139，1075，951，849，788，757，728，625.

Compound in the present embodiment (16) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，DMSO-d ₆/TMS，δ(ppm)]：8.50(s，1H)，7.83(dd，J＝20.5，7.2Hz，5H)，7.70(d，J＝7.0Hz，1H)，7.51(d，J＝6.9Hz，1H).

Compound in the present embodiment (16) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，DMSO-d ₆/TMS，δ(ppm)]：174.5，160.8，157.5，154.7，152.4，133.4，129.1，128.7，126.1，124.5，122.8，121.5，121.4，110.0，109.7.

Compound in the present embodiment (16) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI ⁺)：m/z(rel?intensity)：(M+Na)，Cal：331.0358；found：331.0353.

Compound in the present embodiment (17) is white solid, and fusing point is 222-223 ℃, productive rate 87%.

Compound in the present embodiment (17) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：3069，1636，1578，1480，1452，1364，1271，1168，1140，1095，945，884，823，767，722，518.

Compound in the present embodiment (17) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，DMSO-d ₆/TMS，δ(ppm)]：8.64(s，1H)，7.82(s，3H)，7.63(d，J＝7.7Hz，2H)，7.51(d，J＝7.3Hz，2H).

Compound in the present embodiment (17) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，DMSO-d ₆/TMS，δ(ppm)]：174.8，161.2，158.0，155.8，152.6，133.3，131.0，128.7，122.8，122.5，121.8，110.6，110.3.

Compound in the present embodiment (17) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI ⁺)：m/z(rel?intensity)：(M+Na)，Cal：297.0095；found：297.0073.

Embodiment 4

In the present embodiment, the tetrahydrofuran (THF) that adds 7-methoxyl group-3-iodine chromone and 7-methoxyl group-25 times of weight of 3-iodine chromone in the reactor, the anhydrous chlorides of rase nickel of 7-methoxyl group-0.01 times of molar weight of 3-iodine chromone, three (4-p-methoxy-phenyl) phosphine of 7-methoxyl group-0.02 times of molar weight of 3-iodine chromone, the Lithium chloride (anhydrous) of 7-methoxyl group-1.5 times of molar weights of 3-iodine chromone, the phenyl zinc bromide that adds 7-methoxyl group-1.3 times of molar weights of 3-iodine chromone after stirring again respectively, 4-aminomethyl phenyl zinc bromide, 4-p-methoxy-phenyl zinc bromide, 4-cyano-phenyl zinc bromide, 4-trifluoromethyl zinc bromide and 4-chloro-phenyl-zinc bromide, at room temperature react stopped reaction after 3 hours, the separating technology of product is identical with the preparation of isoflavone compounds among the embodiment 1 with method, obtains compound (18) 7-methoxyl group isoflavones respectively, compound (19) 7-methoxyl group-4 '-the methyl isoflavones, compound (20) 7-methoxyl group-4 '-the methoxyl group isoflavones, compound (21) 7-methoxyl group-4 '-the cyano group isoflavones, compound (22) 7-methoxyl group-4 '-trifluoromethyl isoflavones and compound (23) 7-methoxyl group-4 '-the chlorine isoflavones.

Compound in the present embodiment (18) is white solid, and fusing point is 229-231 ℃, productive rate 55%.

Compound in the present embodiment (18) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：3052，2913，2834，1631，1597，1430，1255，1078，1023，828，787，730，696，448，422.

Compound in the present embodiment (18) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，DMSO-d ₆/TMS，δ(ppm)]：8.46(s，1H)，8.05(d，J＝8.9Hz，1H)，7.59(d，J＝6.8Hz，2H)，7.51-7.31(m，3H)，7.16(d，J＝2.1Hz，1H)，7.09(dd，J＝8.9，2.2Hz，1H)，3.91(s，3H).

Compound in the present embodiment (18) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，DMSO-d ₆/TMS，δ(ppm)]：174.4，163.8，157.4，154.1，131.9，128.9，128.1，127.9，127.8，126.9，123.7，117.6，114.8，100.6，56.1.

Compound in the present embodiment (18) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI+)：m/z(rel?intensity)：(M+Na)，Cal：275.0684；found：275.0669.

Compound in the present embodiment (19) is white solid, and fusing point is 143-144 ℃, productive rate 92%.

Compound in the present embodiment (19) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：3062，2970，2929，2834，1638，1622，1436，1357，1269，1067，935，829，765，683.

Compound in the present embodiment (19) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，DMSO-d ₆/TMS，δ(ppm)]：8.41(s，1H)，8.03(d，J＝8.9Hz，1H)，7.47(d，J＝7.8Hz，2H)，7.23(d，J＝7.8Hz，2H)，7.14(s，1H)，7.08(d，J＝8.9Hz，1H)，3.90(s，3H)，2.34(s，3H).

Compound in the present embodiment (19) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，DMSO-d ₆/TMS，δ(ppm)]：174.5，163.7，157.4，153.7，137.1，128.9，128.7，128.7，126.9，123.6，117.6，114.7，100.5，56.1，20.8.

Compound in the present embodiment (19) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI ⁺)：m/z(rel?intensity)：(M+Na)，Cal：289.0841；found：289.0825.

Compound in the present embodiment (20) is white solid, and fusing point is 157-158 ℃, productive rate 76%.

Compound in the present embodiment (20) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：3077，2933，2915，2836，1631，1599，1513，1440，1332，1290，1250，1176，1094，1023，939，882，825，779，615，544.

Compound in the present embodiment (20) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，DMSO-d ₆/TMS，δ(ppm)]：8.42(s，1H)，8.04(d，J＝8.9Hz，1H)，7.53(d，J＝8.7Hz，2H)，7.21-6.95(m，4H)，3.91(s，3H)，3.80(s，3H).

Compound in the present embodiment (20) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，DMSO-d ₆/TMS，δ(ppm)]：174.2，163.2，158.5，157.0，153.0，129.6，126.5，123.6，122.9，117.1，114.3，113.1，100.1，55.6，54.7.

Compound in the present embodiment (20) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI ⁺)：m/z(rel?intensity)：(M+Na)，Cal：305.0790；found：305.0775.

Compound in the present embodiment (21) is white solid, and fusing point is 206-207 ℃, productive rate 38%.

Compound in the present embodiment (21) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：3062，2924，2227，1638，1602，1570，1505，1441，1375，1264，1155，947，859，834，620.

Compound in the present embodiment (21) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，DMSO-d ₆/TMS，δ(ppm)]：8.62(s，1H)，8.04(d，J＝8.7Hz，1H)，7.87(dd，J＝23.8，6.0Hz，4H)，7.20(s，1H)，7.11(d，J＝8.7Hz，1H)，3.92(s，3H).

Compound in the present embodiment (21) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，DMSO-d ₆/TMS，δ(ppm)]：174.0，164.7，158.2，155.9，136.1，133.5，133.4，132.0，129.4，127.4，123.0，118.4，117.8，115.7，113.6，101.5，56.7.

Compound in the present embodiment (21) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI ⁺)：m/z(rel?intensity)：(M+Na)，Cal：300.0637；found：300.0632.

Compound in the present embodiment (22) is white solid, and fusing point is 182-184 ℃, productive rate 56%.

Compound in the present embodiment (22) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：3067，2926，2853，1631，1568，1502，1442，1373，1328，1259，1165，1118，1074，1020，945，839，691，621.

Compound in the present embodiment (22) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，DMSO-d ₆/TMS，δ(ppm)]：8.61(s，1H)，8.06(d，J＝8.8Hz，1H)，7.82(d，J＝4.3Hz，5H)，7.21(s，1H)，7.12(d，J＝7.3Hz，1H)，3.92(s，3H).

Compound in the present embodiment (22) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，DMSO-d ₆/TMS，δ(ppm)]：174.5，164.5，159.1，157.9，155.9，149.2，137.6，132.5，130.1，127.5，122.7，119.3，118.0，115.6，110.9，101.3，56.7.

Compound in the present embodiment (22) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI ⁺)：m/z(rel?intensity)：(M+Na)，Cal：343.0558；found：343.0551.

Compound in the present embodiment (23) is white solid, and fusing point is 226-227 ℃, productive rate 89%.

Compound in the present embodiment (23) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：3062，2931，2836，1638，1605，1442，1259，1143，1090，1048，821.

Compound in the present embodiment (23) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，DMSO-d6/TMS，δ(ppm)]：8.51(s，1H)，8.04(s，1H)，7.62(s，2H)，7.49(s，2H)，7.14(d，J＝21.8Hz，2H)，3.90(s，3H).

Compound in the present embodiment (23) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，DMSO-d ₆/TMS，δ(ppm)]：174.6，164.5，158.0，155.6，136.8，130.1，129.4，129.2，129.0，127.5，125.4，125.4，123.0，118.0，115.5，101.2，56.7.

Compound in the present embodiment (23) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI ⁺)：m/z(rel?intensity)(M+Na)，Cal：309.0294；found：309.0275.

Embodiment 5

In the present embodiment, the tetrahydrofuran (THF) that adds 7-isopropoxy-3-iodine chromone and 7-isopropoxy-15 times of weight of 3-iodine chromone in the reactor, the anhydrous chlorides of rase nickel of 7-isopropoxy-0.03 times of molar weight of 3-iodine chromone, three (2-furyl) phosphine of 7-isopropoxy-0.06 times of molar weight of 3-iodine chromone, the Lithium chloride (anhydrous) of 7-isopropoxy-1.5 times of molar weights of 3-iodine chromone, the phenyl zinc bromide that adds 7-isopropoxy-1.1 times of molar weights of 3-iodine chromone after stirring again respectively, 4-aminomethyl phenyl zinc bromide, 4-p-methoxy-phenyl zinc bromide, 4-cyano-phenyl zinc bromide, 4-trifluoromethyl zinc bromide, 4-chloro-phenyl-zinc bromide and 4-methyl-formiate base phenyl zinc bromide, at room temperature react stopped reaction after 1 hour, the separating technology of product is identical with the preparation of isoflavone compounds among the embodiment 1 with method, obtains compound (24) 7-isopropoxy isoflavones (ipriflavone) respectively, compound (25) 7-isopropoxy-4 '-the methyl isoflavones, compound (26) 7-isopropoxy-4 '-the methoxyl group isoflavones, compound (27) 7-isopropoxy-4 '-the cyano group isoflavones, compound (28) 7-isopropoxy-4 '-the trifluoromethyl isoflavones, compound (29) 7-isopropoxy-4 '-chlorine isoflavones and compound (30) 4 '-methyl-formiate base-7-isopropoxy isoflavones.

Compound in the present embodiment (24) is white solid, and fusing point is 120-121 ℃, productive rate 88%.

Compound in the present embodiment (24) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：3050，2985，2972，2938，1637，1597，1561，1496，1439，1371，1325，1261，1022，907，883，820，780，748，694.

Compound in the present embodiment (24) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，DMSO-d ₆/TMS，δ(ppm)]：8.46(s，1H)，8.03(d，J＝8.3Hz，1H)，7.58(s，2H)，7.43(d，J＝7.4Hz，3H)，7.16(s，1H)，7.06(d，J＝7.9Hz，1H)，4.98-4.76(m，1H)，1.34(d，J＝4.1Hz，6H).

Compound in the present embodiment (24) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，DMSO-d ₆/TMS，δ(ppm)]：174.9，162.5，158.0，154.5，137.2，132.5，129.4，128.6，128.2，127.5，124.2，117.9，116.1，102.4，71.0，22.0.

Compound in the present embodiment (24) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI ⁺)：m/z(rel?intensity)：(M+Na)，Cal：303.0997；found：303.0969.

Compound in the present embodiment (25) is white solid, and fusing point is 156-157 ℃, productive rate 95%.

Compound in the present embodiment (25) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：3098，2980，2921，1809，1645，1621，1441，1374，1260，1159，955，859.

Compound in the present embodiment (25) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，DMSO-d ₆/TMS，δ(ppm)]：8.42(s，1H)，8.02(d，J＝8.9Hz，1H)，7.48(d，J＝7.4Hz，2H)，7.24(d，J＝7.3Hz，2H)，7.15(s，1H)，7.05(d，J＝8.8Hz，1H)，4.97-4.75(m，1H)，2.34(s，3H)，1.33(d，J＝5.4Hz，6H).

Compound in the present embodiment (25) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，DMSO-d ₆/TMS，δ(ppm)]：162.5，158.3，158.0，154.2，137.6，129.5，129.2，127.6，124.1，121.7，117.9，116.1，103.5，102.3，100.8，90.7，71.0，22.1，21.3.

Compound in the present embodiment (25) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI ⁺)：m/z(rel?intensity)：(M+Na)，Cal：295.1334；found：295.1332.

Compound in the present embodiment (26) is white solid, and fusing point is 151-152 ℃, productive rate 93%.

Compound in the present embodiment (26) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：2981，2913，1808，1634，1513，1441，1375，1254，1158，970，858，696.

Compound in the present embodiment (26) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，DMSO-d ₆/TMS，δ(ppm)]：8.40(s，1H)，8.02(d，J＝8.8Hz，1H)，7.53(d，J＝8.0Hz，2H)，7.14(s，1H)，7.02(t，J＝11.6Hz，3H)，4.97-4.75(m，1H)，3.80(s，3H)，1.33(d，J＝5.5Hz，6H).

Compound in the present embodiment (26) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，DMSO-d ₆/TMS，δ(ppm)]：175.1，162.4，159.5，157.9，153.8，130.5，127.5，124.6，123.8，117.8，116.0，114.1，102.3，70.9，55.6，22.0.

Compound in the present embodiment (26) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI ⁺)：m/z(rel?intensity)：(M+Na)，Cal：333.1103；found：300.1100.

Compound in the present embodiment (27) is white solid, and fusing point is 196-199 ℃, productive rate 34%.

Compound in the present embodiment (27) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：3077，2981，2930，2234，1635，1566，1504，1445，1375，1261，1107，976，859，624.

Compound in the present embodiment (27) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，DMSO-d ₆/TMS，δ(ppm)]：8.11(d，J＝8.9Hz，1H)，7.92(s，1H)，7.64(s，5H)，6.91(d，J＝8.9Hz，1H)，6.79(s，1H)，4.98-4.75(m，1H)，1.34(d，J＝5.8Hz，6H).

Compound in the present embodiment (27) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，DMSO-d ₆/TMS，δ(ppm)]：173.9，162.9，158.2，156.8，155.8，136.1，133.5，133.3，132.0，129.4，127.5，123.0，118.4，116.5，113.6，102.7，71.1，22.3，22.0.

Compound in the present embodiment (27) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI ⁺)：m/z(rel?intensity)：(M+Na)，Cal：328.0950；found：328.0949.

Compound in the present embodiment (28) is white solid, and fusing point is 145-147 ℃, productive rate 83%.

Compound in the present embodiment (28) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：3076，2983，2932，1636，1567，1498，1445，1378，1323，1262，1202，1167，1138，1070，1016，972，841，788，690，625.

Compound in the present embodiment (28) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，DMSO-d ₆/TMS，δ(ppm)]：38.11(d，J＝8.8Hz，1H)，7.89(s，1H)，7.61(s，4H)，6.89(d，J＝8.4Hz，1H)，6.77(s，1H)，4.75-4.52(m，1H)，1.34(d，J＝5.1Hz，6H).

Compound in the present embodiment (28) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，DMSO-d ₆/TMS，δ(ppm)]：174.8，162.9，158.0，153.2，137.0，132.2，129.5，127.8，123.7，118.7，117.9，116.0，111.8，101.8，71.0，21.8.

Compound in the present embodiment (28) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI ⁺)：m/z(rel?intensity)：(M+Na)，Cal：371.0871；found：371.0864.

Compound in the present embodiment (29) is white solid, and fusing point is 161-162 ℃, productive rate 91%.

Compound in the present embodiment (29) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：2981，2912，1808，1633，1512，1441，1375，1253，1158，970，857，695.

Compound in the present embodiment (29) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，DMSO-d ₆/TMS，δ(ppm)]：8.51(s，1H)，8.02(d，J＝8.9Hz，1H)，7.63(d，J＝8.3Hz，2H)，7.50(d，J＝8.2Hz，2H)，7.07(d，J＝8.9Hz，1H)，4.61-4.58(m，1H)，1.34(d，J＝5.8Hz，6H).

Compound in the present embodiment (29) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，DMSO-d ₆/TMS，δ(ppm)]：174.6，164.5，158.0，155.6，136.8，130.1，129.4，129.2，129.0，128.9，128.5，127.5，125.4，125.4，123.0，118.0，115.5，101.2，56.7.

Compound in the present embodiment (29) molecular structure is as follows through high resolution flight mass spectrometer test result:

HRMS(ESI ⁺)：m/z(rel?intensity)：(M+Na)，Cal：337.0607；found：337.0606.

Compound in the present embodiment (30) is white solid, and fusing point is 182-184 ℃, productive rate 65%.

Compound in the present embodiment (30) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：3066，2981，2928，1718，1635，1563，1498，1440，1370，1259，1156，1113，971，861，786，762，703，620.

Compound in the present embodiment (30) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，DMSO-d ₆/TMS，δ(ppm)]：8.11(d，J＝8.8Hz，1H)，8.01(d，J＝7.9Hz，2H)，7.90(s，1H)，7.58(d，J＝7.9Hz，2H)，6.89(d，J＝8.7Hz，1H)，6.76(s，1H)，4.66-4.51(m，1H)，3.85(s，3H)，1.33(d，J＝5.9Hz，6H).

Compound in the present embodiment (30) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，DMSO-d ₆/TMS，δ(ppm)]：174.7，162.6，158.0，154.8，133.0，131.4，131.1，128.6，127.5，123.0，117.7，116.2，102.4，71.0，22.0.

Compound in the present embodiment (30) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI ⁺)：m/z(rel?intensity)：(M+Na)，Cal：339.1232；found：339.1227.

Embodiment 6

In the present embodiment, the acetonitrile that adds 3-iodine chromone and 30 times of weight of 3-iodine chromone in the reactor, 1 of 0.001 times of molar weight of 3-iodine chromone, 3-two (diphenylphosphine) propane nickelous chloride, the Lithium chloride (anhydrous) of 1.5 times of molar weights of 3-iodine chromone mole, the phenyl zinc bromide that adds 1.3 times of molar weights of 3-iodine chromone after stirring again, react stopped reaction after 2 hours under the room temperature, the separating technology of product is identical with the preparation of isoflavone compounds among the embodiment 1 with method, obtains the pure product of compound (1) isoflavones (productive rate 16%).

Embodiment 7

In the present embodiment, the tetrahydrofuran (THF) that adds 7-isopropoxy-3-iodine chromone and 7-isopropoxy-10 times of weight of 3-iodine chromone in the reactor, 1 of 7-isopropoxy-0.005 times of molar weight of 3-iodine chromone, 3-two (diphenylphosphine) ethane chlorination nickel, the Lithium chloride (anhydrous) of 7-isopropoxy-1.5 times of molar weights of 3-iodine chromone, the 4-cyano-phenyl zinc bromide that adds 7-isopropoxy-1.1 times of molar weights of 3-iodine chromone after stirring again, at room temperature react stopped reaction after 3 hours, the separating technology of product is identical with the preparation of isoflavone compounds among the embodiment 1 with method, obtain compound (27) 7-isopropoxy-4 '-the pure product of cyano group isoflavones (productive rate 17%).

Embodiment 8

In the present embodiment, the tetrahydrofuran (THF) that adds 6-fluoro-3-iodine chromone and 25 times of weight of 6-fluoro-3-iodine chromone in the reactor, two (triphenylphosphine) nickelous chloride of 0.006 times of molar weight of 6-fluoro-3-iodine chromone, the Lithium chloride (anhydrous) of 1.5 times of molar weights of 6-fluoro-3-iodine chromone, the 4-trifluoromethyl zinc bromide that adds 1.4 times of molar weights of 6-fluoro-3-iodine chromone after stirring again, at room temperature react stopped reaction after 2 hours, the separating technology of product is identical with the preparation of isoflavone compounds among the embodiment 1 with method, obtain compound (16) 6-fluoro-4 '-the pure product of trifluoromethyl isoflavones (productive rate 75%).

Embodiment 9

In the present embodiment, the tetrahydrofuran (THF) that adds 7-methoxy methyl ether-3-iodine chromone and 7-methoxy methyl ether-10 times of weight of 3-iodine chromone in the reactor, two (triphenylphosphine) nickelous chloride of 7-methoxy methyl ether-0.008 times of molar weight of 3-iodine chromone, the Lithium chloride (anhydrous) of 7-methoxy methyl ether-1.5 times of molar weights of 3-iodine chromone, the 4-p-methoxy-phenyl zinc bromide and the 4-methoxy methyl ether phenyl-bromide zinc that add 7-methoxy methyl ether-1.2 times of molar weights of 3-iodine chromone after stirring again respectively, at room temperature react stopped reaction after 1 hour, behind the reclaim under reduced pressure reaction solvent, the hydrochloric acid that adds the 3mol/L of 7-methoxy methyl ether-20 times of weight of 3-iodine chromone, the methyl alcohol of 7-methoxy methyl ether-30 times of weight of 3-iodine chromone, 68 ℃ of 0.5 hour stopped reaction that refluxes, with the chloroform extraction of 7-methoxy methyl ether-60 times of weight of 3-iodine chromone three times, merge organic phase, extremely neutral with distillation washing organic phase, the anhydrous magnesium sulfate drying organic phase, collect chloroform layer, decompression and solvent recovery, and separate through silica gel column chromatography (sherwood oil is 20: 1 with the ethyl acetate volume ratio), obtain the pure product of compound (31) onocol (7-hydroxyl-4 '-methoxyl group isoflavones) and compound (32) daidzein (7,4 '-dihydroxy isoflavone) respectively.

Compound in the present embodiment (31) is white solid, and fusing point is 273-274 ℃, productive rate 90%.

Compound in the present embodiment (31) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：3697，3078，2985，2835，1638，1600，1513，1453，1386，1316，1273，1249，1177，1100，1025，887，840，813，780.

Compound in the present embodiment (31) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，DMSO-d ₆/TMS，δ(ppm)]：10.74(s，1H)，8.24(s，1H)，7.90(d，J＝8.7Hz，1H)，7.43(d，J＝8.5Hz，2H)，6.86(m，4H)，3.71(s，3H).

Compound in the present embodiment (31) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，DMSO-d ₆/TMS，δ(ppm)]：174.6，162.5，158.9，157.4，153.0，130.0，127.3，124.2，123.1，116.6，115.1，113.6，102.1，55.1.

Compound in the present embodiment (31) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI ⁺)：m/z(rel?intensity)：(M+Na)，Cal：291.0633；found：291.0649.

Compound in the present embodiment (32) is white solid, and fusing point is 304-306 ℃, productive rate 81%.

Compound in the present embodiment (32) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：3509，1941，1816，1710，1616，1536，1499，1417，1323，1296，1267，1207，1112，1059，1029，971，913，862，805，762，704，564，536，515.

Compound in the present embodiment (32) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[400MHz，CDCl ₃/TMS，δ(ppm)]：10.70(s，1H)，9.45(s，1H)，8.19(m，1H)，7.89(d，J＝8.8Hz，1H)，7.39-7.24(m，2H)，6.85(dd，J＝8.8，2.2Hz，1H)，6.78(d，J＝2.0Hz，1H)，6.74(d，J＝8.6Hz，2H).

Compound in the present embodiment (32) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[100MHz，CDCl ₃/TMS，δ(ppm)]：179.9，167.7，162.6，162.4，158.0，157.9，135.3，132.5，128.7，127.8，121.9，120.3，120.2，107.3.

Compound in the present embodiment (32) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI+)：m/z(rel?intensity)：(M+Na)，Cal：277.0477；found：277.0499.

Embodiment 10

In the present embodiment, add 5 in the reactor, 7-dimethoxy methyl ether base-3-iodine chromone and 5, the tetrahydrofuran (THF) of 7-dimethoxy methyl ether base-25 times of weight of 3-iodine chromone, 5, the anhydrous chlorides of rase nickel of 7-dimethoxy methyl ether base-0.03 times of molar weight of 3-iodine chromone, 5, the triphenylphosphine of 7-dimethoxy methyl ether base-0.06 times of molar weight of 3-iodine chromone, 5, the Lithium chloride (anhydrous) of 7-dimethoxy methyl ether base-1.5 times of molar weights of 3-iodine chromone, add 5 again after stirring, the 4-methoxy methyl ether phenyl-bromide zinc of 7-dimethoxy methyl ether base-1.4 times of molar weights of 3-iodine chromone, at room temperature react stopped reaction after 1 hour, behind the reclaim under reduced pressure reaction solvent, the concentrated hydrochloric acid that adds 5-dimethoxy methyl ether base-40 times of weight of 3-iodine chromone, 5, the methyl alcohol of 7-dimethoxy methyl ether base-30 times of weight of 3-iodine chromone, 68 ℃ of 0.5 hour stopped reaction that refluxes, the separating technology of product is identical with the preparation of isoflavone compounds among the embodiment 9 with method, separate the pure product of compound (33) genistein (7,5,4 '-trihydroxy-isoflavone) that obtain.

Compound in the present embodiment (33) is white solid, and fusing point is 309-311 ℃, productive rate 49%.

Compound in the present embodiment (33) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：3410，3105，1816，1652，1614，1568，1503，1427，1394，1360，1312，1256，1204，1176，1143，1063，1042，912，883，843，816，788，744，641，613，568，532，488，439.

Compound in the present embodiment (33) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，CDCl ₃/TMS，δ(ppm)]：12.86(s，1H)，10.79(s，1H)，9.51(s，1H)，8.20(s，1H)，7.28(d，J＝8.4Hz，2H)，6.73(d，J＝8.4Hz，2H)，6.20(m，2H).

Compound in the present embodiment (33) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，CDCl ₃/TMS，δ(ppm)]：180.2，164.2，162.0，157.5，157.4，153.8，130.1，122.3，121.2，115.0，104.4，98.9，93.6.

Compound in the present embodiment (33) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI ⁺)：m/z(rel?intensity)：(M+Na)，Cal：293.0426；found：291.0450.

Embodiment 11

In the present embodiment; the acetonitrile that adds 7-methoxy methyl ether-3-iodine chromone and 7-methoxy methyl ether-30 times of weight of 3-iodine chromone in the reactor; the anhydrous chlorides of rase nickel of 7-methoxy methyl ether-0.04 times of molar weight of 3-iodine chromone; three (4-p-methoxy-phenyl) phosphine of 7-methoxy methyl ether-0.08 times of molar weight of 3-iodine chromone; the Lithium chloride (anhydrous) of 7-methoxy methyl ether-1.5 times of molar weights of 3-iodine chromone; the 4-p-methoxy-phenyl zinc bromide and the 4-methoxy methyl ether phenyl-bromide zinc that add 7-methoxy methyl ether-1.5 times of molar weights of 3-iodine chromone after stirring again respectively; at room temperature react stopped reaction after 1 hour; method and the purifying process flow process of sloughing blocking group are identical with embodiment 9; obtain respectively compound (31) onocol (7-hydroxyl-4 '-the methoxyl group isoflavones; productive rate 83%) and compound (32) daidzein (7; 4 '-dihydroxy isoflavone, productive rate 72%) pure product.

Embodiment 12

In the present embodiment; add 5 in the reactor; 7-dimethoxy methyl ether base-3-iodine chromone and 5; the acetonitrile of 7-dimethoxy methyl ether base-15 times of weight of 3-iodine chromone; 5; the anhydrous chlorides of rase nickel of 7-dimethoxy methyl ether base-0.007 times of molar weight of 3-iodine chromone; 5; three (2-furyl) phosphine of 7-dimethoxy methyl ether base-0.014 times of molar weight of 3-iodine chromone, the Lithium chloride (anhydrous) of 5,7-dimethoxy methyl ether base-1.5 times of molar weights of 3-iodine chromone; add 5 again after stirring; the 4-methoxy methyl ether phenyl-bromide zinc of 7-dimethoxy methyl ether base-1.3 times of molar weights of 3-iodine chromone at room temperature reacts stopped reaction after 1 hour, and method and the purifying process flow process of sloughing blocking group are identical with embodiment 10; separate and obtain compound (33) genistein (7; 5,4 '-trihydroxy-isoflavone, productive rate 32%) pure product.

Embodiment 13

In the present embodiment, the tetrahydrofuran (THF) that adds 3-bromine chromone and 20 times of weight of 3-bromine chromone in the reactor, two (triphenylphosphine) nickelous chloride of 0.05 times of molar weight of 3-bromine chromone, the Lithium chloride (anhydrous) of 1.5 times of molar weights of 3-bromine chromone, the phenyl zinc bromide that adds 1.2 times of molar weights of 3-bromine chromone after stirring again respectively, 4-aminomethyl phenyl zinc bromide, 4-p-methoxy-phenyl zinc bromide and 4-trifluoromethyl zinc bromide, at room temperature react stopped reaction after 2 hours, the separating technology of product is identical with the preparation of isoflavone compounds among the embodiment 1 with method, obtains the pure product of compound (1) isoflavones (productive rate 85%) respectively, compound (2) 4 '-methyl isoflavones (productive rate 92%), compound (5) 4 '-methoxyl group isoflavones (productive rate 90%) and compound (9) 4 '-trifluoromethyl isoflavones (productive rate 79%).

Embodiment 14

In the present embodiment, the acetonitrile that adds 6-fluoro-3-bromine chromone and 25 times of weight of 6-fluoro-3-bromine chromone in the reactor, 1 of 0.03 times of molar weight of 6-fluoro-3-bromine chromone, 3-two (diphenylphosphine) propane nickelous chloride, the Lithium chloride (anhydrous) of 1.5 times of molar weights of 6-fluoro-3-bromine chromone, the phenyl zinc bromide that adds 1.2 times of molar weights of 6-fluoro-3-bromine chromone after stirring again respectively, 4-aminomethyl phenyl zinc bromide, 4-p-methoxy-phenyl zinc bromide and 4-trifluoromethyl zinc bromide, at room temperature react stopped reaction after 2 hours, the separating technology of product is identical with the preparation of isoflavone compounds among the embodiment 1 with method, obtains compound (12) 6-fluorine isoflavones (productive rate is 80%) respectively, compound (13) 6-fluoro-4 '-methyl isoflavones (productive rate 89%), compound (14) 6-fluoro-4 '-methoxyl group isoflavones (productive rate 84%) and compound (16) 6-fluoro-4 '-trifluoromethyl isoflavones (productive rate 73%).

Embodiment 15

In the present embodiment, the tetrahydrofuran (THF) that adds 7-methoxyl group-3-bromine chromone and 7-methoxyl group-10 times of weight of 3-bromine chromone in the reactor, the diacetyl acetone nickel of 7-methoxyl group-0.04 times of molar weight of 3-bromine chromone, the Lithium chloride (anhydrous) of 7-methoxyl group-1.5 times of molar weights of 3-bromine chromone, the phenyl zinc bromide that adds 7-methoxyl group-1.5 times of molar weights of 3-bromine chromone after stirring again respectively, 4-aminomethyl phenyl zinc bromide, 4-p-methoxy-phenyl zinc bromide and 4-trifluoromethyl zinc bromide, at room temperature react stopped reaction after 1 hour, the separating technology of product is identical with the preparation of isoflavone compounds among the embodiment 1 with method, obtains compound (18) 7-methoxyl group isoflavones (productive rate 80%) respectively, compound (19) 7-methoxyl group-4 '-methyl isoflavones (productive rate 85%), compound (20) 7-methoxyl group-4 '-methoxyl group isoflavones (productive rate 82%) and compound (22) 7-methoxyl group-4 '-trifluoromethyl isoflavones (productive rate 76%).

Embodiment 16

In the present embodiment, the tetrahydrofuran (THF) that adds 7-isopropoxy-3-bromine chromone and 7-isopropoxy-30 times of weight of 3-bromine chromone in the reactor, the anhydrous chlorides of rase nickel of 7-isopropoxy-0.02 times of molar weight of 3-bromine chromone, the triphenylphosphine of 7-isopropoxy-0.04 times of molar weight of 3-bromine chromone, the Lithium chloride (anhydrous) of 7-isopropoxy-1.5 times of molar weights of 3-bromine chromone, the phenyl zinc bromide that adds 7-isopropoxy-1.2 times of molar weights of 3-bromine chromone after stirring again respectively, 4-aminomethyl phenyl zinc bromide, 4-p-methoxy-phenyl zinc bromide and 4-trifluoromethyl zinc bromide, at room temperature react stopped reaction after 3 hours, the separating technology of product is identical with the preparation of isoflavone compounds among the embodiment 1 with method, obtains compound (24) 7-isopropoxy isoflavones (productive rate 76%) respectively, compound (25) 7-isopropoxy-4 '-methyl isoflavones (productive rate 83%), compound (26) 7-isopropoxy-4 '-methoxyl group isoflavones (productive rate 81%) and compound (28) 7-isopropoxy-4 '-trifluoromethyl isoflavones (productive rate 72%).

Embodiment 17

In the present embodiment, the acetonitrile that adds 3-bromine chromone and 15 times of weight of 3-bromine chromone in the reactor, the anhydrous chlorides of rase nickel of 0.05 times of molar weight of 3-bromine chromone, three (2-furyl) phosphine of 0.10 times of molar weight of 3-bromine chromone, the Lithium chloride (anhydrous) of 1.5 times of molar weights of 3-bromine chromone, the 4-fluorophenyl zinc bromide that adds 1.2 times of molar weights of 3-bromine chromone after stirring again, at room temperature react stopped reaction after 2 hours, the separating technology of product is identical with the preparation of isoflavone compounds among the embodiment 1 with method, separate obtain compound (34) 4 '-the pure product of fluorine isoflavones.

Compound in the present embodiment (34) is white solid, and fusing point is 197-198 ℃, productive rate 76%.

Compound in the present embodiment (34) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：2925，2854，1713，1638，1565，1467，1365，1277，1156，1071，956，858，769，699，622.

Compound in the present embodiment (34) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，CDCl ₃/TMS，δ(ppm)]：8.68(s，1H)，8.17(d，J＝7.9Hz，1H)，8.03(d，J＝8.2Hz，2H)，7.85(d，J＝7.2Hz，1H)，7.79(d，J＝8.2Hz，2H)，7.72(d，J＝8.4Hz，1H)，7.55(t，J＝7.5Hz，1H)，3.89(s，3H).

Compound in the present embodiment (34) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，CDCl ₃/TMS，δ(ppm)]：176.2，156.2，152.9，133.7，130.7，130.6，127.8，127.8，126.4，125.4，124.5，124.5，118.1，115.6，115.4

Compound in the present embodiment (34) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI ⁺)：m/z(rel?intensity)：(M+Na)，Cal：303.0634，found：303.0628.

Embodiment 18

In the present embodiment, the tetrahydrofuran (THF) that adds 6-fluoro-3-bromine chromone and 10 times of weight of 6-fluoro-3-bromine chromone in the reactor, two (triphenylphosphine) nickelous chloride of 0.001 times of molar weight of 6-fluoro-3-bromine chromone, the Lithium chloride (anhydrous) of 1.5 times of molar weights of 6-fluoro-3-bromine chromone, the 4-fluorophenyl zinc bromide that adds 1.5 times of molar weights of 6-fluoro-3-bromine chromone after stirring again, at room temperature react stopped reaction after 3 hours, the separating technology of product is identical with the preparation of isoflavone compounds among the embodiment 1 with method, separate obtaining compound (32) 6,4 '-the pure product of difluoro isoflavones.

Compound in the present embodiment (35) is white solid, and fusing point is 223-224 ℃, productive rate 62%.

Compound in the present embodiment (35) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：3080，1640，1606，1574，1517，1483，1366，1272，1245，1167，1133，944，830，753，726，522.

Compound in the present embodiment (35) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[400MHz，CDCl ₃/TMS，δ(ppm)]：8.03(d，J＝3.2Hz，1H)，7.99-7.90(m，1H)，7.57-7.40(m，4H)，7.13(d，J＝8.5Hz，2H).

Compound in the present embodiment (35) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[100MHz，CDCl ₃/TMS，δ(ppm)]：175.4，164.1，161.6，160.9，158.5，153.0，152.5，130.7，130.64，127.4，123.9，122.2，121.9，120.2，120.2，115.7，115.5，111.3，111.1.

Compound in the present embodiment (35) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI ⁺)：m/z(rel?intensity)：(M+Na)，Cal：281.0390，found：281.0373.

Embodiment 19

In the present embodiment, the tetrahydrofuran (THF) that adds 7-methoxyl group-3-bromine chromone and 7-methoxyl group-25 times of weight of 3-bromine chromone in the reactor, the anhydrous chlorides of rase nickel of 7-methoxyl group-0.005 times of molar weight of 3-bromine chromone, the triphenylphosphine of 7-methoxyl group-0.01 times of molar weight of 3-bromine chromone, the Lithium chloride (anhydrous) of 7-methoxyl group-1.5 times of molar weights of 3-bromine chromone, the 4-fluorophenyl zinc bromide that adds 7-methoxyl group-1.1 times of molar weights of 3-bromine chromone after stirring again, at room temperature react stopped reaction after 3 hours, the separating technology of product is identical with the preparation of isoflavone compounds among the embodiment 1 with method, separate obtain compound (33) 7-methoxyl group-4 '-the pure product of fluorine isoflavones.

Compound in the present embodiment (36) is white solid, and fusing point is 186-187 ℃, productive rate 73%.

Compound in the present embodiment (36) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：3068，2928，2840，1637，1608，1509，1443，1260，1141，825，541.

Compound in the present embodiment (36) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，CDCl ₃/TMS，δ(ppm)]：8.19(d，J＝8.9Hz，1H)，7.92(s，1H)，7.53(dd，J＝8.6，2.9Hz，2H)，7.11(t，J＝8.7Hz，2H)，6.99(dd，J＝8.9，2.3Hz，1H)，6.85(d，J＝2.2Hz，1H)，3.91(s，3H).

Compound in the present embodiment (36) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，CDCl ₃/TMS，δ(ppm)]：175.5，164.4，164.1，157.9，152.4，151.6，130.7，130.6，127.9，127.8，124.4，118.3，115.6，115.3，114.7，100.1，55.8.

Compound in the present embodiment (36) molecular structure is as follows through the high-resolution mass spectrometer test result:

HRMS(ESI ⁺)：m/z(rel?intensity)：(M+Na)，Cal：293.0590，found：293.0568.

Embodiment 20

In the present embodiment, the acetonitrile that adds 7-isopropoxy-3-bromine chromone and 7-isopropoxy-20 times of weight of 3-bromine chromone in the reactor, the diacetyl acetone nickel of 7-isopropoxy-0.01 times of molar weight of 3-bromine chromone, the Lithium chloride (anhydrous) of 7-isopropoxy-1.5 times of molar weights of 3-bromine chromone, the 4-fluorophenyl zinc bromide that adds 7-isopropoxy-1.3 times of molar weights of 3-bromine chromone after stirring again, at room temperature react stopped reaction after 2 hours, the separating technology of product is identical with the preparation of isoflavone compounds among the embodiment 1 with method, separate obtain compound (34) 7-isopropoxy-4 '-the pure product of fluorine isoflavones.

Compound in the present embodiment (37) is white solid, and fusing point is 149-150 ℃, productive rate 64%.

Compound in the present embodiment (37) molecular structure is as follows through the infrared spectrometer test result:

IR(KBr)，ν(cm ^-1)：3080，2987，2940，1636，1603，1565，1512，1444，1370，1257，1231，1198，1137，1102，1043，886，829，779.

Compound in the present embodiment (37) molecular structure is as follows through nuclear magnetic resonance analyser test H-NMR result:

¹H?NMR[300MHz，CDCl3/TMS，δ(ppm)]：8.18(d，J＝8.9Hz，1H)，7.91(s，1H)，7.53(dd，J＝8.6，2.9Hz，2H)，7.11(t，J＝8.7Hz，2H)，6.96(dd，J＝8.9，2.2Hz，1H)，6.83(d，J＝2.1Hz，1H)，4.67(dt，J＝12.0，6.0Hz，1H)，1.41(d，J＝6.0Hz，6H).

Compound in the present embodiment (37) molecular structure is as follows through nuclear magnetic resonance analyser test C-NMR result:

¹³C?NMR[75MHz，CDCl ₃/TMS，δ(ppm)]：175.6，164.0，157.9，152.6，131.9，128.9，128.5，128.1，127.8，125.3，118.5，114.6，100.1，55.8，25.2.

Compound in the present embodiment (37) molecular structure is as follows through the high-resolution mass spectrometer test result:

ESIMS：m/z(rel?intensity)：(M+Na)，Cal：321.0903，found：321.0920.

Embodiment 21

In the present embodiment; the tetrahydrofuran (THF) that adds 7-methoxy methyl ether-3-bromine chromone and 7-methoxy methyl ether-10 times of weight of 3-bromine chromone in the reactor; the anhydrous chlorides of rase nickel of 7-methoxy methyl ether-0.04 times of molar weight of 3-bromine chromone; the triphenylphosphine of 7-methoxy methyl ether-0.08 times of molar weight of 3-bromine chromone; the Lithium chloride (anhydrous) of 7-methoxy methyl ether-1.5 times of molar weights of 3-bromine chromone; the 4-p-methoxy-phenyl zinc bromide and the 4-methoxy methyl ether phenyl-bromide zinc that add 7-methoxy methyl ether-1.1 times of molar weights of 3-bromine chromone after stirring again respectively; at room temperature react stopped reaction after 2 hours; method and the purifying process flow process of sloughing blocking group are identical with embodiment 9; obtain respectively compound (31) onocol (7-hydroxyl-4 '-the methoxyl group isoflavones; productive rate 87%) and compound (32) daidzein (7; 4 '-dihydroxy isoflavone, productive rate 79%) pure product.

Embodiment 22

In the present embodiment; add 5 in the reactor; 7-dimethoxy methyl ether base-3-bromine chromone and 5; the acetonitrile of 7-dimethoxy methyl ether base-25 times of weight of 3-bromine chromone; 5; two (triphenylphosphine) nickelous chloride of 7-dimethoxy methyl ether base-0.05 times of molar weight of 3-bromine chromone; 5; the Lithium chloride (anhydrous) of 7-dimethoxy methyl ether base-1.5 times of molar weights of 3-bromine chromone; add 5 again after stirring; the 4-methoxy methyl ether phenyl-bromide zinc of 7-dimethoxy methyl ether base-1.5 times of molar weights of 3-bromine chromone at room temperature reacts stopped reaction after 3 hours, and method and the purifying process flow process of sloughing blocking group are identical with embodiment 10; separate and obtain compound (33) genistein (7; 5,4 '-trihydroxy-isoflavone, productive rate 53%) pure product.

Claims (5)

1. the preparation method of an isoflavone compounds formula (4), this method may further comprise the steps:

Formula (1) formula (3) formula (4)

In the formula (1), said substituent R ₁～R ₄Be C ₁～C ₆Alkyl, C ₁～C ₆Alkoxyl group, C ₁～C ₆Alkoxyl group alkoxyl group, nitro, hydrogen, hydroxyl, glycosyl, fluorine, chlorine in any one or a few; Said R in the formula (3) ₅Be C ₁～C ₆Alkyl, C ₁～C ₆Alkoxyl group, C ₁～C ₆Alkoxyl group alkoxyl group, nitro, ester group, cyano group, trifluoromethyl, hydrogen, fluorine, chlorine in any one; Said solvent is acetonitrile or tetrahydrofuran (THF); Said nickel catalyzator is anhydrous chlorides of rase nickel or two (triphenylphosphine) nickelous chloride or 1,3-two (diphenylphosphine) propane nickelous chloride or 1,2-two (diphenylphosphine) ethane chlorination nickel; Said part is triphenylphosphine or three (4-aminomethyl phenyl) phosphine or three (4-p-methoxy-phenyl) phosphine or three (2-furyl) phosphine; The solvent that adds (replacement) 3-iodine chromogen keto-acid (1) and (1) 10～30 times of weight of formula in the reactor, the nickel catalyzator of (1) 0.001～0.05 times of molar weight of formula, the part of (1) 0.002～0.1 times of molar weight of formula, the Lithium chloride (anhydrous) of (1) 1.5 times of molar weight of formula, the aryl zincon formula (3) that adds (1) 1.1～1.5 times of molar weight of formula after stirring again, at room temperature react stopped reaction after 1～3 hour, the aqueous hydrochloric acid cancellation reaction that adds the 1mol/L of (1) 3 times of weight of formula again, (1) 30 times of weight distilled water of adding formula, with with distilled water equal volume of ethyl acetate three times, merge organic phase, to neutral, anhydrous magnesium sulfate drying is collected ethyl acetate layer with distillation washing organic phase, decompression and solvent recovery, and get the pure product of isoflavones through silica gel column chromatography separating purification.

2. the preparation method of an isoflavone compounds formula (4), this method may further comprise the steps:

Formula (2) formula (3) formula (4)

In the formula, said substituent R ₁～R ₅Identical with claim 1; Said solvent is identical with claim 1; Said catalyzer is anhydrous chlorides of rase nickel or two (triphenylphosphine) nickelous chloride or 1,3-two (diphenylphosphine) propane nickelous chloride or diacetyl acetone nickel; Said part is triphenylphosphine or three (2-furyl) phosphine; The solvent that adds (replacement) 3-bromine chromogen keto-acid (2) and (2) 10～30 times of weight of formula in the reactor, the nickel catalyzator of (2) 0.001～0.05 times of molar weights of formula, the part of (2) 0.002～0.1 times of molar weights of formula, the Lithium chloride (anhydrous) of (2) 1.5 times of molar weights of formula, the aryl zincon formula (3) that adds (2) 1.1～1.5 times of molar weights of formula after stirring again, at room temperature react stopped reaction after 1～3 hour, the aqueous hydrochloric acid cancellation reaction that adds the 1mol/L of (2) 3 times of weight of formula again, (2) 30 times of weight distilled water of adding formula, with with distilled water equal volume of ethyl acetate three times, merge organic phase, to neutral, anhydrous magnesium sulfate drying is collected ethyl acetate layer with distillation washing organic phase, decompression and solvent recovery, and get the pure product of isoflavones through silica gel column chromatography separating purification.

3. the preparation method according to claim 1 or the described formula of claim 2 (4) isoflavone compounds synthesizes 14 kinds of new isoflavonoids: 2 '-the cyano group isoflavones, 3 '-the cyano group isoflavones, 4 '-the cyano group isoflavones, 4 '-the trifluoromethyl isoflavones, 2 '-cyano group-6-fluorine isoflavones, 4 '-trifluoromethyl-5-fluorine isoflavones, 2 '-cyano group-7-methoxyl group isoflavones, 4 '-cyano group-7-methoxyl group isoflavones, 4 '-trifluoromethyl-7-methoxyl group isoflavones, 4 '-methyl-7-isopropoxy isoflavones, 2 '-cyano group-7-isopropoxy isoflavones, 4 '-cyano group-7-isopropoxy isoflavones, 4 '-trifluoromethyl-7-isopropoxy isoflavones, 4 '-methyl-formiate base-7-isopropoxy isoflavones.

According to the preparation method of the described formula of claim 1 (4) isoflavone compounds at synthetic drug isoflavones---ipriflavone, daidzein, genistein, the application in onocol and the puerarin.

According to the preparation method of the described formula of claim 2 (4) isoflavone compounds at synthetic drug isoflavones---ipriflavone, daidzein, genistein, the application in onocol and the puerarin.