CN105503823A - Dibenzo selenophene derivative and preparation method thereof - Google Patents

Dibenzo selenophene derivative and preparation method thereof Download PDF

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CN105503823A
CN105503823A CN201510969285.4A CN201510969285A CN105503823A CN 105503823 A CN105503823 A CN 105503823A CN 201510969285 A CN201510969285 A CN 201510969285A CN 105503823 A CN105503823 A CN 105503823A
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compound
preparation
dibenzo
selenium
amphyl
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马杰
胡益民
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Anhui Normal University
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Anhui Normal University
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D345/00—Heterocyclic compounds containing rings having selenium or tellurium atoms as the only ring hetero atoms

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Abstract

The invention provides a dibenzo selenophene derivative and a preparation method thereof. The preparation method comprises the following steps that sodium hydride is used as a catalyst, malonic ester and propargyl bromide are added into an acetonitrile solvent, and a reaction is performed in an ice-water bath for 8-14 h to obtain a compound a; on the oxygen-free and water-free conditions, the compound a and a substituted complex of phenyl acetylene bromide are subjected to a reaction in an acetonitrile solvent under the effect of a catalyst and alkali at the temperature of 20-30 DEG C for 8-14 h to obtain a compound b; the compound b and diphenyl diselenide are subjected to a reaction at the temperature of 95-105 DEG C, and after separation and purification, the dibenzo selenophene derivative can be obtained. Compared with the prior art, the novel polysubstitution dibenzo selenophene synthesis method is provided, a series of novel selenophene derivatives are generated, multi-loops exist in the obtained dibenzo selenophene derivative compared with a common selenophene derivative, the structure is more complex and diversified, and wider application prospect is represented in chemical production and clinic medicine.

Description

A kind of dibenzo selenium amphyl and preparation method thereof
Technical field
The present invention relates to organic compound field, be specifically related to a kind of dibenzo selenium amphyl and preparation method thereof.
Background technology
19th-century Sweden in early years chemist Bezreilus, when studying the composition of vitriol chamber mud, first isolates a kind of new element, next year called after selenium (Seslenuim) from chalcopyrite.Selenium is one of useful trace element required in organism, has multiple special function to HUMAN HEALTH.Large quantifier elimination shows, selenium has biological action widely, particularly to cancer (as lung cancer, intestinal cancer, prostate cancer and liver cancer etc.).Clinical trial shows; selenium has powerful provide protection; there is good prophylactic treatment effect to more than 40 kind of human diseasess such as heart trouble, geriatric disease, liver and pancreatic disease, Infertility, hypertension, diabetes, cataract, Keshan disease and anaemias, be described as " kindling material of life " " anticancer king ".
Therefore, Selenium pharaiacology, physiology and biochemistry character cause the great interest of people, and the exploitation containing selenium medicine has now become a study hotspot.Current Xi Yi united state health organization confirms as the trace element of needed by human, and China obtains major progress by the method for mending selenium Prevention Keshan disease, Kaschin-Beck disease and liver cancer.But inorganic Selenium supplement agent toxicity is comparatively large, lethal quantity is relatively little, and application is restricted.And organoselenium is compared with inorganic selenium, there is the features such as bioavailability is high, biological activity is strong, toxicity is low, environmental pollution is little.
American scientist KARAM etc. study discovery, and the organoselenium compound of synthesis has stronger anti-tumor activity and lower toxicity than inorganic selenium compound and natural selenide.If the biomacromolecule compound of the selenium such as selenium chitosan, Selenonic protein, selenium polysaccharide, selenizing methionine(Met), selenocarrageenan, selenizing tea-polyphenol is in antitumor, cardiovascular disorder, anti-ageing and improve in the biological activity such as immunity of organisms apparently higher than the corresponding compound without selenizing.
But, the research of organoselenium chemistry does not cause the interest of chemist always, until early seventies, because modern synthetic method and identification of means make rapid progress, constantly find that organic selenium compounds has a lot of front special performance of not knowing, just make it to enter fast-developing stage, synthesized containing the carbohydrate of selenium, amino acid, polypeptide and some have the selenium organism of important biomolecule activity; Particularly nearly ten years, the development of organoselenium reagent and the discovery of organoselenium antitumor drug have greatly enriched the investigation and application content of organoselenium chemistry.
It is prepared approach and relates to many aspects, mainly comprises: (1) is isostere due to O, S, Se, utilizes principle of isotone, will change the analogue of Se into containing O, S effective antitumor medicine, and synthesis has the organic selenium compounds of antitumour activity; (2) in antitumour activity drug molecule, introduce selenium atom group, thus produce synergistic effect, reach the object improving curative effect; (3) build the organic selenium compounds with antitumour activity of novel texture, organic selenium compounds comprises selenium cyanogen, selenide and containing classifications such as selenium heterocycles, and wherein the research of selenium heterocyclic the most extensively, and have multiple compound for clinical study.
A few days ago, the high and organic selenium compounds that toxicity is low of synthesis of biologically active is still a focus of current drug research.
Summary of the invention
For the deficiencies in the prior art, the invention provides a kind of dibenzo selenium amphyl and preparation method thereof, the method is simple to operate, polysubstituted dibenzo selenium amphyl can be synthesized through three-step reaction.
Technical scheme provided by the invention is:
A kind of dibenzo selenium amphyl, its chemical structural formula is as follows:
Wherein, R is the one of straight chained alkyl, branched-chain alkyl, unsaturated hydro carbons group, arene group; R 1for the one in hydrogen, straight chained alkyl, branched-chain alkyl, halogen, alkoxyl group, amino; R 1can be in its connect the optional position of phenyl ring.
Be preferably, R is that branched-chain alkyl within the straight chained alkyl within 8 C, 10 C, 10 C are with the one of internal unsaturate class group, arene group; R 1it is the one within branched-chain alkyl within straight chained alkyl within 8 C, 10 C, 3 C in alkoxyl group;
Be more preferably, R is methyl or ethyl; R 1for chlorine or methyl.
Present invention also offers above-mentioned dibenzo selenium amphyl preparation method, described preparation method comprises the following steps:
A, be catalyzer with sodium hydride, join in acetonitrile solvent by malonic ester and propargyl bromide, ice-water bath reaction 8 ~ 14 hours, after separation and purification, obtains compound a;
The chemical structural formula of described malonic ester is: r is the one of straight chained alkyl, branched-chain alkyl, unsaturated hydro carbons group, arene group; Be preferably, R is methyl or ethyl; R 1for chlorine or methyl.
B, under anhydrous and oxygen-free condition, the substituent of compound a and phenyl-bromide acetylene is under the effect of catalyzer and alkali, and in acetonitrile solvent, 20 ~ 30 DEG C of reactions 8 ~ 14 hours, after separation and purification, obtain compound b;
The chemical structural formula of the substituent of described phenyl-bromide acetylene is: r 1the optional position of phenyl ring can be positioned at; R 1for the one in hydrogen, straight chained alkyl, branched-chain alkyl, halogen, alkoxyl group; Be preferably, R is methyl or ethyl; R 1for chlorine or methyl.
C, compound b and diphenyl disenenide ether in toluene 95-105 DEG C react, after separation and purification, compound according to claim 1 can be obtained.
In described steps A:
The ratio of the amount of substance of malonic ester, propargyl bromide and sodium hydride three is 1:(2.2 ~ 3.2): (3.5 ~ 5).The concentration of described malonic ester in acetonitrile is 0.4-0.8mol/L.
The method of described separation and purification is: by the product after having reacted through extraction, concentrated after, through column chromatographic isolation and purification; Column chromatography eluent used is ethyl acetate and sherwood oil, and the volume ratio of the two is 1:30 ~ 100.
In described step B:
Catalyzer is by Pd (PPh 3) 2cl 2with CuI composition, the ratio of both amount of substances is 3:1; Described alkali is triethylamine.
The substituent of compound a, phenyl-bromide acetylene, Pd (PPh 3) 2cl 2with the ratio of amount of substance between triethylamine is 1:(2.2 ~ 3.2): (0.01 ~ 0.05): (4 ~ 5).
The concentration of compound a in acetonitrile is 0.30 ~ 0.60mol/L.
The method of described separation and purification is: by the product after having reacted through extraction, concentrated after, through column chromatographic isolation and purification; Column chromatography eluent used is ethyl acetate and sherwood oil, and the volume ratio of the two is 1:30 ~ 100.
In described step C:
Compound b is 1:(1.1 ~ 1.5 with the ratio of the amount of substance of diphenyl disenenide ether); The concentration of compound b in toluene is 0.2-0.5mol/L;
The time of reaction is 10 ~ 16 hours.
The method of described separation and purification is: by the product after having reacted through extraction, concentrated after, through column chromatographic isolation and purification; Column chromatography eluent used is ethyl acetate and sherwood oil, and the volume ratio of the two is 1:20 ~ 50.
The reaction principle of step C disclosed by the invention is: diphenyl disenenide ether homolytic reaction occurs under heating condition and generates free radical, four alkynes substrate b experience HDDA course formation benzyne intermediate c simultaneously, intermediate c and selenium combined with radical form intermediate d, the hydrogen at phenyl ring ortho position that intermediate d is connected with selenium moves, and carbon-to-carbon coupling in molecule occurs and obtains product.The hydroperoxyl radical left forms selenium phenol with selenium free radical again.Its schematic diagram is shown in accompanying drawing 8.
The invention provides a kind of synthetic method of polysubstituted dibenzo selenium phenol completely newly, generate a series of new dibenzo selenium amphyl.Relative to other selenium amphyl, dibenzo selenium amphyl prepared by the present invention has the existence of more rings, and its structure is more complicated various, in Chemical Manufacture, clinical medicine, also will show more wide purposes prospect.
Accompanying drawing explanation
Fig. 1 be dibenzo selenium amphyl synthesis step;
Fig. 2 is the synthesis step of dibenzo selenium amphyl S-1;
Fig. 3 is the synthesis step of dibenzo selenium amphyl S-2;
Fig. 4 is the hydrogen spectrum nuclear-magnetism figure of dibenzo selenium amphyl S-1;
Fig. 5 is the carbon spectrum nuclear-magnetism figure of dibenzo selenium amphyl S-1;
Fig. 6 is the hydrogen spectrum nuclear-magnetism figure of dibenzo selenium amphyl S-2;
Fig. 7 is the carbon spectrum nuclear-magnetism figure of dibenzo selenium amphyl S-2;
Fig. 8 is the reaction principle figure of step C.
Embodiment
Embodiment 1
A kind of dibenzo selenium amphyl, described dibenzo selenium amphyl structural formula be:
Above-mentioned dibenzo selenium amphyl preparation method, comprise the following steps:
A, with sodium hydride (820mmol, 19.7g) be catalyzer, by dimethyl malonate (200mmol, 26.6g) and propargyl bromide (450mmol, 53.5g) join in 250mL anhydrous acetonitrile, stirring reaction 8 hours in ice-water bath, crude product with water and extraction into ethyl acetate, after concentrating under reduced pressure, through silica gel column chromatography separating-purifying, eluent is ethyl acetate: sherwood oil=1:100, obtains white solid product, i.e. compound 1;
B, compound 1 (80mmol, 16.7g) and phenyl-bromide acetylene substituent (176mmol, 37.9g) to be mixed, at 1.3gPd (PPh 3) 2cl 2in/CuI anhydrous and oxygen-free catalyst system, Pd (PPh 3) 2cl 2compare for 3:1 with the amount of substance of CuI, with triethylamine (340mmol, 47.3mL) as alkali, with 200ml anhydrous acetonitrile for solvent, 20 DEG C of stirring reactions 8 hours, crude product with water and extraction into ethyl acetate, after concentrating under reduced pressure, through silica gel column chromatography separating-purifying, eluent is ethyl acetate: sherwood oil=1:100, obtain white solid product, i.e. compound 2.
The chemical structural formula of described phenyl-bromide acetylene substituent is:
C, by compound 2 (1.0mmol, 0.48g) with diphenyl disenenide ether (1.2mmol, 0.38) g adds in 3mL toluene solvant, and 100 DEG C are reacted 10 hours, crude product with water and extraction into ethyl acetate, after concentrating under reduced pressure, through silica gel column chromatography separating-purifying, eluent is ethyl acetate: sherwood oil=1:40, obtains white solid product, i.e. dibenzo selenium amphyl S-1, column chromatography productive rate is 41.2%.
The structural formula of dibenzo selenium amphyl S-1 passes through 1hNMR, 13cNMR measures, and its data characterization is as follows:
1HNMR(300MHz，CDCl 3)：δ7.86(d，J＝7.9Hz，1H)，7.55(d，J＝8.3Hz，2H)，7.36(d，J＝8.3Hz，2H)，7.27(dd，J＝17.6，8.3Hz，4H)，7.13–7.01(m，3H)，6.89(d，J＝8.2Hz，1H)，3.94(s，2H)，3.82(s，2H)，3.82(s，6H)。
13CNMR(125MHz，CDCl 3)：δ172.20，140.53，140.03，139.82，138.93，138.44，136.82，136.35，135.66，134.62，134.30，132.87，131.63，129.48，129.05，126.92，126.86，126.53，125.07，121.99，117.96，96.45，88.13，59.98，53.71，42.34，41.91ppm.
Embodiment 2
A kind of dibenzo selenium amphyl, described dibenzo selenium amphyl structural formula be:
Above-mentioned dibenzo selenium amphyl preparation method, comprise the following steps:
A, with sodium hydride (700mmol, 16.8g) be catalyzer, by dimethyl malonate (200mmol, 26.6g) and propargyl bromide (440mmol, 52.3g) join in 330mL anhydrous acetonitrile, stirring reaction 10 hours in ice-water bath, crude product with water and extraction into ethyl acetate, after concentrating under reduced pressure, through silica gel column chromatography separating-purifying, eluent is ethyl acetate: sherwood oil=1:60, obtains white solid product, i.e. compound 1;
B, compound 1 (80mmol, 16.7g) and phenyl-bromide acetylene substituent (176mmol, 37.9g) to be mixed, at 3.0gPd (PPh 3) 2cl 2in/CuI anhydrous and oxygen-free catalyst system, Pd (PPh 3) 2cl 2compare for 3:1 with the amount of substance of CuI, with triethylamine (320mmol, 44.5mL) as alkali, with 160ml anhydrous acetonitrile for solvent, stirring reaction 12 hours at 25 DEG C, crude product with water and extraction into ethyl acetate, after concentrating under reduced pressure, through silica gel column chromatography separating-purifying, eluent is ethyl acetate: sherwood oil=1:60, obtain white solid product, i.e. compound 2.
The chemical structural formula of described phenyl-bromide acetylene substituent is:
C, by compound 2 (1.0mmol, 0.48g) with diphenyl disenenide ether (1.35mmol, 0.42) g adds in 5mL toluene solvant, and 95 DEG C are reacted 12 hours, crude product with water and extraction into ethyl acetate, after concentrating under reduced pressure, through silica gel column chromatography separating-purifying, eluent is ethyl acetate: sherwood oil=1:30, obtains white solid product, i.e. dibenzo selenium amphyl S-1, column chromatography productive rate is 45%.
Embodiment 3
A kind of dibenzo selenium amphyl, described dibenzo selenium amphyl structural formula is:
Above-mentioned dibenzo selenium amphyl preparation method, comprise the following steps:
A, with sodium hydride (810mmol, 19.4g) be catalyzer, by (200mmol, 37.6g) Diisopropyl malonate and propargyl bromide (500mmol, 59.5g) join in 250ml anhydrous acetonitrile, stirring reaction 10 hours in ice-water bath, crude product with water and extraction into ethyl acetate, after concentrating under reduced pressure, through silica gel column chromatography separating-purifying, eluent is ethyl acetate: sherwood oil=1:100, obtains white solid product, i.e. compound 3;
B, by compound 3 (80mmol, 21.1g) and phenyl-bromide acetylene substituent (200mmol, 39.0g), be blended in 2.17gPd (PPh 3) 2cl 2in the anhydrous and oxygen-free catalyst system of/CuI, Pd (PPh 3) 2cl 2pd (PPh in/CuI 3) 2cl 2compare for 3:1 with the amount of substance of CuI, with triethylamine (350mmol, 48.6mL) make alkali, with 250ml anhydrous acetonitrile for solvent, 28 DEG C of stirring reactions, 10 hours crude product with water and extraction into ethyl acetate, after concentrating under reduced pressure, through silica gel column chromatography separating-purifying, eluent is ethyl acetate: sherwood oil=1:100, i.e. compound 4.
The chemical structural formula of described phenyl-bromide acetylene substituent is:
C, by compound 4 (1.0mmol, 0.51g) with diphenyl disenenide ether (1.1mmol, 0.34g) add in 5mL toluene, 100 DEG C are reacted 12 hours, crude product with water and extraction into ethyl acetate, after concentrating under reduced pressure, through silica gel column chromatography separating-purifying, eluent is ethyl acetate: sherwood oil=1:40, obtains white solid product, i.e. dibenzo selenium amphyl S-2, column chromatography productive rate is about 38.3%.
The structural formula of dibenzo selenium amphyl S-2 passes through 1hNMR, 13cNMR measures, and its data characterization is as follows:
1HNMR(300MHz，CDCl 3)：δ7.84(d，J＝7.8Hz，1H)，7.45(t，J＝7.4Hz，1H)，7.34(d，J＝7.4Hz，1H)，7.23(dd，J＝12.0，6.1Hz，3H)，7.18–7.09(m，1H)，7.09–6.98(m，2H)，6.91(dd，J＝13.4，7.6Hz，3H)，5.11(dt，J＝12.5，6.2Hz，2H)，3.92(s，2H)，3.77(s，2H)，2.44(s，3H)，2.29(s，3H)，1.30(d，J＝6.2Hz，12H)。
13CNMR(125MHz，CDCl 3)：δ171.42，142.22，140.42，139.97，138.94，138.68，138.16，136.25，135.93，135.60，132.42，130.62，129.22，129.05，128.77，128.43，127.24，127.08，126.40，124.83，123.73，118.30，97.39，87.38，69.92，60.16，42.24，41.78，22.00，21.61。
Embodiment 4
A kind of dibenzo selenium amphyl, described dibenzo selenium amphyl structural formula is:
Above-mentioned dibenzo selenium amphyl preparation method, comprise the following steps:
A, with sodium hydride (1100mmol, 26.4g) be catalyzer, by (200mmol, 37.6g) Diisopropyl malonate and propargyl bromide (640mmol, 76.1g) join in 500ml anhydrous acetonitrile, stirring reaction 14 hours in ice-water bath, crude product with water and extraction into ethyl acetate, after concentrating under reduced pressure, through silica gel column chromatography separating-purifying, eluent is ethyl acetate: sherwood oil=1:80, obtains white solid product, i.e. compound 3;
B, by compound 3 (80mmol, 21.1g) and phenyl-bromide acetylene substituent (200mmol, 39.0g), be blended in 1.0gPd (PPh 3) 2cl 2in the anhydrous and oxygen-free catalyst system of/CuI, Pd (PPh 3) 2cl 2pd (PPh in/CuI 3) 2cl 2compare for 3:1 with the amount of substance of CuI, with triethylamine (350mmol, 48.6mL) make alkali, with 130ml anhydrous acetonitrile for solvent, 30 DEG C of stirring reactions, 14 hours crude product with water and extraction into ethyl acetate, after concentrating under reduced pressure, through silica gel column chromatography separating-purifying, eluent is ethyl acetate: sherwood oil=1:80, i.e. compound 4.
The chemical structural formula of described phenyl-bromide acetylene substituent is:
C, by compound 4 (1.0mmol, 0.51g) with diphenyl disenenide ether (1.5mmol, 0.33g) add in 2mL toluene, 100 DEG C are reacted 16 hours, crude product with water and extraction into ethyl acetate, after concentrating under reduced pressure, through silica gel column chromatography separating-purifying, eluent is ethyl acetate: sherwood oil=1:50, obtains white solid product, i.e. dibenzo selenium amphyl S-2, column chromatography productive rate is about 45%.
Above-mentioned detailed description of dibenzo selenium amphyl and preparation method thereof being carried out with reference to embodiment; illustrative instead of determinate; several embodiments can be listed according to institute's limited range; therefore in the change do not departed under general plotting of the present invention and amendment, should belong within protection scope of the present invention.

Claims (10)

1. a dibenzo selenium amphyl, is characterized in that, described dibenzo selenium amphyl chemical structural formula as follows:
Wherein, R is the one of straight chained alkyl, branched-chain alkyl, unsaturated hydro carbons group, arene group;
R 1for the one in hydrogen, straight chained alkyl, branched-chain alkyl, halogen, alkoxyl group, amino;
R 1can be in its connect the optional position of phenyl ring.
2. dibenzo selenium amphyl according to claim 1, is characterized in that, R is methyl or ethyl; R 1for chlorine or methyl.
3. according to claim 1 dibenzo selenium amphyl preparation method, it is characterized in that, described preparation method comprises the following steps:
A, be catalyzer with sodium hydride, join in acetonitrile solvent by malonic ester and propargyl bromide, ice-water bath reaction 8 ~ 14 hours, after separation and purification, obtains compound a;
The chemical structural formula of described malonic ester is: r is the one of straight chained alkyl, branched-chain alkyl, unsaturated hydro carbons group, arene group;
B, under anhydrous and oxygen-free condition, the substituent of compound a and phenyl-bromide acetylene is under the effect of catalyzer and alkali, and in acetonitrile solvent, 20 ~ 30 DEG C of reactions 8 ~ 14 hours, after separation and purification, obtain compound b;
The chemical structural formula of the substituent of described phenyl-bromide acetylene is: r 1the optional position of phenyl ring can be positioned at; R 1for the one in hydrogen, straight chained alkyl, branched-chain alkyl, halogen, alkoxyl group;
C, compound b and diphenyl disenenide ether in toluene 95-105 DEG C react, after separation and purification, compound according to claim 1 can be obtained.
4. preparation method according to claim 3, is characterized in that: in described steps A, and the ratio of the amount of substance of malonic ester, propargyl bromide and sodium hydride three is 1:(2.2 ~ 3.2): (3.5 ~ 5).
5. the preparation method according to claim 3 or 4, is characterized in that: in described steps A, and the concentration of malonic ester in acetonitrile is 0.4-0.8mol/L.
6. preparation method according to claim 3, is characterized in that: in described step B, and catalyzer is by Pd (PPh 3) 2cl 2with CuI composition, the ratio of both amount of substances is 3:1; Described alkali is triethylamine.
7. preparation method according to claim 6, is characterized in that: in described step B, the substituent of compound a, phenyl-bromide acetylene, Pd (PPh 3) 2cl 2with the ratio of amount of substance between triethylamine is 1:(2.2 ~ 3.2): (0.01 ~ 0.05): (4 ~ 5).
8. the preparation method according to claim 3 or 6 or 7, is characterized in that: in described step B, the concentration of compound a in acetonitrile is 0.30 ~ 0.60mol/L.
9. very according to preparation method according to claim 3, it is characterized in that: in described step C, compound b is 1:(1.1 ~ 1.5 with the ratio of the amount of substance of diphenyl disenenide ether); The concentration of compound b in toluene is 0.2-0.5mol/L.
10. very according to the preparation method described in claim 3 or 9, it is characterized in that: in described step C, the time of reaction is 10 ~ 16 hours.
CN201510969285.4A 2015-12-19 2015-12-19 Dibenzo selenophene derivative and preparation method thereof Pending CN105503823A (en)

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CN106866480A (en) * 2017-04-06 2017-06-20 盐城工学院 Many cyclophane selenide analog derivatives and preparation method thereof
CN106966937A (en) * 2017-04-06 2017-07-21 盐城工学院 Diaryl selenide analog derivative and preparation method thereof
CN107043341A (en) * 2017-04-06 2017-08-15 盐城工学院 Diaryl sulfide analog derivative and preparation method thereof
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CN107501234A (en) * 2017-09-23 2017-12-22 安徽师范大学 A kind of oil-source rock correlation and preparation method thereof
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CN104447337A (en) * 2014-12-04 2015-03-25 安徽师范大学 Cinnamic acid ester derivatives and preparation method thereof
CN104926785A (en) * 2015-07-06 2015-09-23 盐城工学院 Selenium aromatic heterocycte derivative and preparation method thereof

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CN104402696A (en) * 2014-12-04 2015-03-11 安徽师范大学 Oxidoreduction method of benzoin organic matter
CN104447337A (en) * 2014-12-04 2015-03-25 安徽师范大学 Cinnamic acid ester derivatives and preparation method thereof
CN104926785A (en) * 2015-07-06 2015-09-23 盐城工学院 Selenium aromatic heterocycte derivative and preparation method thereof

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CN105968013B (en) * 2016-05-16 2018-08-17 安徽师范大学 A kind of π-copolymer and preparation method thereof
CN106866480A (en) * 2017-04-06 2017-06-20 盐城工学院 Many cyclophane selenide analog derivatives and preparation method thereof
CN106966937A (en) * 2017-04-06 2017-07-21 盐城工学院 Diaryl selenide analog derivative and preparation method thereof
CN107043341A (en) * 2017-04-06 2017-08-15 盐城工学院 Diaryl sulfide analog derivative and preparation method thereof
CN107043342A (en) * 2017-04-06 2017-08-15 盐城工学院 Arylalkyl thioethers analog derivative and preparation method thereof
CN107501234A (en) * 2017-09-23 2017-12-22 安徽师范大学 A kind of oil-source rock correlation and preparation method thereof
CN107501234B (en) * 2017-09-23 2019-07-19 安徽师范大学 A kind of oil-source rock correlation and preparation method thereof
CN107986969A (en) * 2017-12-07 2018-05-04 安徽师范大学 A kind of ten dihydros are as two indeno phenanthrene derivative of benzo and its synthetic method
CN107986969B (en) * 2017-12-07 2020-06-19 安徽师范大学 Dodecahydron as benzodiindenophenanthrene derivative and synthesis method thereof
CN108774272A (en) * 2018-05-29 2018-11-09 安徽师范大学 A kind of ferrocene derivatives and preparation method thereof
CN108774272B (en) * 2018-05-29 2020-09-08 安徽师范大学 Ferrocene derivative and preparation method thereof

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