CN107954961A - A kind of synthetic method of [60] fullerene dihydrofuran derivative - Google Patents
A kind of synthetic method of [60] fullerene dihydrofuran derivative Download PDFInfo
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- RZNSHBXVTAHWPP-UHFFFAOYSA-N N#CCC(c1ccc[o]1)=O Chemical compound N#CCC(c1ccc[o]1)=O RZNSHBXVTAHWPP-UHFFFAOYSA-N 0.000 description 1
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- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
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Abstract
The invention discloses a kind of synthetic method of [60] fullerene dihydrofuran derivative, belong to the synthesis technical field of fullerene derivate.Technical scheme main points are：With fullerene C60With 1,2 diaryl ethyl ketones,αCarbonyl nitrile,βKetone ester orβCyclohexadione compounds are reaction raw materials, in 120 130 DEG C through CuI and Ag2Oxidative dehydrogenation synthesis target product [60] fullerene dihydrofuran analog derivative that O collaborations promote, or with fullerene C60WithβCarbonyl acetamides are reaction raw materials, and target product [60] fullerene dihydrofuran analog derivative is synthesized in the oxidative dehydrogenation that 120 DEG C promote through CuCl.The present invention has the advantages that extensive substrate applicability, good functional group tolerance and higher yield.
Description
Technical field
The invention belongs to the synthesis technical field of fullerene derivate, and in particular to a kind of [60] fullerene dihydrofuran spreads out
The synthetic method of biology.
Background technology
The structure and photoelectric properties of fullerene uniqueness make it have in fields such as nano material, biological medicine, supramolecular chemistries
And be widely applied value.Thus the functionalization of fullerene also develops into the important research direction of fullerene chemistry.Functionalization
Physico-chemical property including solubility, intermolecular force and surface energy can not only adjust, improved parent fullerene etc., and
And can also continue to create the novel fullerene derivate of structure, provide important material base for the new function of exploitation fullerene
Plinth and method are supported.Therefore, the new method of easy, efficient Functional Fullerene is developed, the novel fullerene of composite structure derives
Thing has important researching value.
Furans is of increasing concern in organic photoelectric field, the full carbon system of fragrance of particularly furans fusion.But for
The full carbon fullerene derivative of three-dimensional of furans fusion it is rarely found in the document of correlative study, it may be possible to accordingly may be used because lacking
Fowler ene adducts.Up to the present, the synthetic route of the fullerene dihydrofuran derivative of report is fairly limited：
Including C60The nucleophilic addition promoted with beta-dicarbonyl compound alkali, C60With beta-dicarbonyl compound or acetophenone through Mn (III) or
The Radical Addition that Cu (II) promotes, the c h bond priming reaction and the lactone from the fusion of [60] fullerene of the catalysis of Pd salt
Indirect reformer.But majority of case nevertheless suffers from the narrow and low-producing limitation of substrate spectrum, which prevent them in correlation
The application in field.Therefore, develop a kind of easy, efficient, wide application range of substrates method to synthesize variation two to substitute
[60] fullerene dihydrofuran derivative there is important researching value.
The content of the invention
The technical problem to be solved by the present invention is to provide a kind of resistance to extensive substrate applicability and good functional group
By the synthetic method of [60] fullerene dihydrofuran derivative of property.
The present invention is to solve above-mentioned technical problem to adopt the following technical scheme that, a kind of [60] fullerene dihydrofuran derivative
Synthetic method, it is characterised in that detailed process is：With fullerene C60With 1,2- diaryl ethyl ketone, alpha-carbonyl nitrile, 'beta '-ketoester or
Beta-diketone compounds are reaction raw materials, in 120-130 DEG C through CuI and Ag2The oxidative dehydrogenation synthesis target that O collaborations promote
Product [60] fullerene dihydrofuran analog derivative, the structural formula of wherein ketone compounds are Corresponding target production
The structural formula of thing [60] fullerene dihydrofuran derivative is
Further preferably, the fullerene C60、CuI、Ag2O and 1,2- diaryl ethyl ketone, alpha-carbonyl nitrile, 'beta '-ketoester or β-
The molar ratio of cyclohexadione compounds is 1:0.2-0.5:2:2-4.
Further preferably, the synthetic method of described [60] fullerene dihydrofuran derivative, it is characterised in that specific steps
For；First by fullerene C60It is added in dry reaction tube, then by CuI, Ag2O and 1,2- diaryl ethyl ketone, alpha-carbonyl
Nitrile, 'beta '-ketoester or beta-diketone compounds compound are added in reaction tube, add trifluoroacetic acid and anhydrous o-dichlorohenzene
Mixed solvent and ultrasonic dissolution, then cock beyond the Great Wall, which is placed in 120-130 DEG C of oil bath pan, stirs reaction, and TLC detections have been reacted
Entirely, reaction mixture is filtered by silicagel column to remove insoluble substance, vacuum evaporating solvent, by remaining solid CS2
Dissolving, loading, cross column, first uses CS2Unreacted fullerene C is collected as eluant, eluent60, then use CS2Make with the mixed solution of DCM
Carry out affording target product [60] fullerene dihydrofuran derivative for eluant, eluent.
The synthetic method of [60] fullerene dihydrofuran derivative of the present invention, it is characterised in that detailed process is：
With fullerene C60It is reaction raw materials with β-carbonyl acetamides, is closed in the oxidative dehydrogenation that 120 DEG C promote through CuCl
Into target product [60] fullerene dihydrofuran analog derivative, the structural formula of wherein β-carbonyl acetamides isCorresponding target product [60]
The structural formula of fullerene dihydrofuran derivative is
Further preferably, the fullerene C60, CuCl and β-carbonyl acetamides molar ratio be 1:
0.5:2。
Further preferably, the synthetic method of described [60] fullerene dihydrofuran derivative, it is characterised in that specific steps
For：First by fullerene C60It is added in dry reaction tube, then CuCl and β-carbonyl acetamides is added to
In reaction tube, the mixed solvent and ultrasonic dissolution of trifluoroacetic acid, acetonitrile and anhydrous o-dichlorohenzene are added, then cock is put beyond the Great Wall
Reaction is stirred in 120 DEG C of oil bath pan, TLC detections are anti-, and the reaction was complete, and reaction mixture is filtered to remove by silicagel column
Insoluble substance, vacuum evaporating solvent, by remaining solid CS2Dissolving, loading, cross column, first uses CS2Collected as eluant, eluent
Unreacted fullerene C60, then use CS2Carry out as eluant, eluent affording target product [60] fowler with the mixed solution of DCM
Alkene dihydrofuran derivative.
Compared with prior art, remarkable advantage of the invention is：1st, extensive substrate applicability；2nd, good functional group is resistance to
By property；3rd, there is higher yield.This provides effective approach for synthesis [60] fullerene dihydrofuran derivative, to explore
Its application in organic electronic research is laid a good foundation.
Embodiment
The above of the present invention is described in further details by the following examples, but this should not be interpreted as to this
The scope for inventing above-mentioned theme is only limitted to following embodiment, and all technologies realized based on the above of the present invention belong to this hair
Bright scope.
Embodiment 1
Prepare [60] fullerene dihydrofuran derivative 2a
Reactions steps：
First by fullerene C60(54.0mg, 0.075mmol) is added in dry reaction tube, then by CuI (2.9mg,
0.015mmol)、Ag2O (35.0mg, 0.15mmol) and(0.15mmol or 0.30mmol) is added
Into reaction tube, the mixed solvent and ultrasonic dissolution of trifluoroacetic acid and anhydrous o-dichlorohenzene are added, then cock is placed in beyond the Great Wall
Reaction is stirred in 120 DEG C or 130 DEG C of oil bath pan, the reaction was complete for TLC detections, and reaction mixture is filtered by short silicagel column
To remove any insoluble substance, vacuum evaporating solvent, by remaining solid CS2Dissolving, loading, cross column, first uses CS2As
Eluant, eluent collects unreacted fullerene C60, then use CS2Carry out as eluant, eluent affording target production with the mixed solution of DCM
Thing 2a.
2a:1H NMR(600MHz,CDCl3/CS2) δ 8.29 (d, J=8.4Hz, 2H), 7.87 (d, J=8.4Hz, 2H),
7.74 (d, J=7.2Hz, 2H), 7.45 (t, J=7.2Hz, 1H), 7.41 (t, J=7.2Hz, 2H)；13C NMR(150MHz,
CDCl3/CS2with Cr(acac)3as relaxation reagent,all 2C unless indicated)δ152.65
(1C),148.12(1C),148.03,147.56(1C),147.43(1C),146.36,146.26,146.20,146.05,
146.01,145.59,145.42,145.31,145.16,145.12,144.94,144.91,144.39,144.32,142.93,
142.76,142.74,142.59,142.38,142.32,142.10,141.83,141.62,140.88(1C),140.34,
139.96,137.25,136.21,132.01,130.13(1C),129.07(1C),128.65,128.28,124.37,110.62
(1C),100.74(sp3-C of C60),77.56(sp3-C of C60)；FT-IRν/cm-1(KBr)2920,2850,2359,
2329,1660,1570,1510,1454,1429,1375,1263,1238,1168,1105,1020,961,840,805,746,
658,615,569,526；UV-vis(CHCl3)λmax/nm 252,274,284,317,687,755；MALDI-TOF MS m/z
calcd for C74H9NO3[M]+959.0577,found959.0565。
Embodiment 2
Prepare [60] fullerene dihydrofuran derivative 2b
Reactions steps：
First by fullerene C60(54.0mg, 0.075mmol) is added in dry reaction tube, then by CuI (2.9mg,
0.015mmol)、Ag2O (35.0mg, 0.15mmol) and(0.15mmol or 0.30mmol) is added to instead
Answer in test tube, add the mixed solvent and ultrasonic dissolution of trifluoroacetic acid and anhydrous o-dichlorohenzene, then cock beyond the Great Wall is placed in 120 DEG C
Or reaction is stirred in 130 DEG C of oil bath pan, the reaction was complete for TLC detections, by reaction mixture by short silicagel column filter with except
No longer hold the post why not soluble substance, vacuum evaporating solvent, by remaining solid CS2Dissolving, loading, cross column, first uses CS2As elution
Unreacted fullerene C is collected in agent60, then use CS2Carry out as eluant, eluent affording target product with the mixed solution of DCM
2b。
2b:1H NMR(600MHz,CDCl3/CS2) δ 7.75 (d, J=6.4Hz, 2H), 7.64 (d, J=7.6Hz, 2H),
7.44 (t, J=7.6Hz, 2H), 7.41-7.35 (m, 4H)；13C NMR(150MHz,CDCl3/CS2with Cr(acac)3as
relaxation reagent,all 2C unless indicated)δ150.22(1C),148.56,147.71(1C),
146.98(1C),145.95,145.85,145.78,145.62,145.58,145.52,145.34,145.16,144.95,
144.80,144.77,144.69,144.05,144.02,142.54,142.36,142.34,142.02,141.96,141.77,
141.63,141.25,139.92,139.50,136.96,135.64,133.11(1C),130.84,129.50(1C),
129.02,128.98,128.06,128.01,127.72,112.10(1C),99.57(sp3-C of C60),78.19(sp3-C
of C60)；FT-IRν/cm-1(KBr)2920,2849,2359,2330,2201,1612,1573,1512,1446,1427,
1329,1204,1171,1154,1095,1028,1004,965,949,922,806,768,748,685,636,575,551,
526；UV-vis(CHCl3)λmax/nm 225,258,284,318,684；MALDI-TOF MS m/z calcd for C74H10O
[M]+914.0726,found 914.0701。
Embodiment 3
Prepare [60] fullerene dihydrofuran derivative 2c
Reactions steps：
First by fullerene C60(54.0mg, 0.075mmol) is added in dry reaction tube, then by CuI (2.9mg,
0.015mmol)、Ag2O (35.0mg, 0.15mmol) and(0.15mmol or 0.30mmol) adds
Enter into reaction tube, add the mixed solvent and ultrasonic dissolution of trifluoroacetic acid and anhydrous o-dichlorohenzene, then cock is put beyond the Great Wall
Reaction is stirred in 120 DEG C or 130 DEG C of oil bath pan, the reaction was complete for TLC detections, and reaction mixture is passed through short silicagel column mistake
Filter to remove any insoluble substance, vacuum evaporating solvent, by remaining solid CS2Dissolving, loading, cross column, first uses CS2Make
Unreacted fullerene C is collected for eluant, eluent60, then use CS2Carry out as eluant, eluent affording target with the mixed solution of DCM
Product 2c.
2c:1H NMR(600MHz,CDCl3/CS2) δ 7.67 (d, J=8.8Hz, 2H), 7.63 (d, J=7.2Hz, 2H),
7.43 (t, J=7.4Hz, 2H), 7.37 (t, J=7.4Hz, 1H), 6.86 (d, J=8.8Hz, 2H), 3.84 (s, 3H)；13C NMR
(150MHz,CDCl3/CS2with Cr(acac)3as relaxation reagent,all 2C unless indicated)δ
159.89(1C),150.02(1C),148.79,146.93(1C),145.90,145.77,145.70,145.56,145.52,
145.46,145.31,145.27,144.85,144.77,144.71,144.62,144.00,143.96,142.67(1C),
142.46,142.35,142.26,141.95,141.89,141.71,141.56,141.19,139.84,139.40,136.96,
135.52,133.36(1C),130.93,129.08,128.91,127.88(1C),121.89(1C),113.37,110.29
(1C),99.51(sp3-C of C60),78.15(sp3-C of C60),54.80(1C)；FT-IRν/cm-1(KBr)2921,
2850,2359,2330,1726,1597,1520,1428,1343,1245,1144,1095,1014,932,915,857,799,
749,700,667,562,527；UV-vis(CHCl3)λmax/nm 266,281,303,324,691；MALDI-TOF MS m/z
calcd for C75H12O2[M]+944.0832,found 944.0812。
Embodiment 4
Prepare [60] fullerene dihydrofuran derivative 2d
Reactions steps：
First by fullerene C60(54.0mg, 0.075mmol) is added in dry reaction tube, then by CuCl
(3.7mg, 0.0375mmol) and(0.15mmol) is added in reaction tube, adds trifluoro second
The mixed solvent and ultrasonic dissolution of acid, acetonitrile and anhydrous o-dichlorohenzene, then cock beyond the Great Wall are placed in 120 DEG C of oil bath pan and stir
Reaction, 12 it is small when (TLC detection the reaction was complete), reaction mixture is filtered to remove any insoluble thing by short silicagel column
Matter, vacuum evaporating solvent, by remaining solid CS2Dissolving, loading, cross column, first uses CS2Collected as eluant, eluent unreacted
Fullerene C60, then use CS2Carry out as eluant, eluent affording target product 2d with the mixed solution of DCM.
2d:1H NMR(400MHz,CDCl3/CS2) δ 7.42 (d, J=4.4Hz, 4H), 7.16 (m, 1H), 5.941 (m, J=
9.2,1H), 5.27 (d, J=9.2Hz, 1H), 4.40-4.30 (m, 2H), 2.35 (s, 3H), 1.32 (t, J=7.2Hz, 3H)13C
NMR(150MHz,CS2/CDCl3with Cr(acac)3as relaxation reagent,all 1C unless
indicated)δ172.74(CO),156.62,154.24,152.40,151.38,147.33,147.20,146.26,
146.24,146.18,146.16,146.12(2C),146.07,145.97(2C),145.88,145.84,145.53,
145.47,145.45,145.38(3C),145.27,145.17,145.11(4C),144.81,144.64,144.40,
144.25,143.07,142.94,142.59(2C),142.54,142.52,142.24,142.22,142.10,142.07,
142.04,141.93,141.82,141.67,141.66,141.61,141.58,141.40,140.22(2C),139.52,
139.44,137.21,136.61,136.27,134.93,129.12(2C),123.37,122.93(2C),77.81,76.67
(sp3-C of C60),67.39(sp3-C of C60),64.89,61.55,23.10,14.32.λmax/nm 263,310,429,
699.1H NMR(600MHz,DMSO-d6/CS2) δ 8.12-8.09 (m, 2H), 7.63-7.58 (m, 5H), 7.23 (t, J=7.6,
2H), 7.03 (t, J=7.6,1H)；13C NMR(150MHz,DMSO-d6/CS2with Cr(acac)3as relaxation
reagent,all 2C unless indicated)δ161.54(1C),155.05(1C),149.50(1C),148.21(1C),
147.39(1C),146.87,146.50,146.32,146.19,146.11,146.08,145.85,145.54,145.28,
145.18,145.12,144.97,144.74,144.31,142.97,142.89,142.80,142.75,142.56,142.43,
142.38,141.90,141.89,140.25,139.95,139.39,137.76,135.40(1C),130.80(1C),129.36
(1C),128.93(1C),128.84(4C),128.74(4C),123.97(1C),120.09(1C),101.06(sp3-C of
C60),75.23(sp3-C of C60)；FT-IRν/cm-1(KBr)2918,2847,2328,1657,1636,1593,1528,
1494,1438,1336,1243,1119,1072,1005,952,929,867,798,750,690,562,526；UV-vis
(CHCl3)λmax/nm 207,247,283,317,488,544,684,757；MALDI-TOF MS m/z calcd for
C75H11NO2[M]+957.0784,found 957.0766。
Embodiment 5
Prepare [60] fullerene dihydrofuran derivative 2e
Reactions steps：
First by fullerene C60(54.0mg, 0.075mmol) is added in dry reaction tube, then by CuCl
(3.7mg, 0.0375mmol) and(0.15mmol) is added in reaction tube, adds three
The mixed solvent and ultrasonic dissolution of fluoroacetic acid, acetonitrile and anhydrous o-dichlorohenzene, then cock beyond the Great Wall are placed in 120 DEG C of oil bath pan
Stirring reaction, 12 it is small when (TLC detection the reaction was complete), reaction mixture is filtered by short silicagel column any insoluble to remove
Property material, vacuum evaporating solvent, by remaining solid CS2Dissolving, loading, cross column, first uses CS2Collected as eluant, eluent not anti-
The fullerene C answered60, then use CS2Carry out as eluant, eluent affording target product 2e with the mixed solution of DCM.
2e:1H NMR(600MHz,CDCl3/CS2) δ 8.08 (d, J=6.5Hz, 2H), 7.87 (d, J=8.6Hz, 2H),
7.69-7.66 (m, 3H), 7.50 (s, 1H), 7.30 (d, J=8.6Hz, 2H), 4.29-4.26 (m, 2H), 1.35-1.33 (m,
3H)；13C NMR(150MHz,DMSO-d6/CS2with Cr(acac)3as relaxation reagent,all 2C unless
indicated)δ163.84(1C),160.98(1C),154.68(1C),148.19,147.05(1C),146.23,145.62,
145.34,145.16,145.04,144.95,144.92,144.66,144.38,144.12,143.96(4C),143.68,
143.56,143.14,142.33 (1C), 141.81,141.73,141.64,141.57,141.38,141.26,141.21,
140.74,140.70,139.09,138.80,136.56,134.29(1C),129.89(1C),129.40,128.08(1C),
127.87,127.62,124.30(1C),118.11,108.19(1C),100.13(sp3-C of C60),74.00(sp3-C of
C60),59.45(1C),29.18(1C),13.97(1C)；FT-IRν/cm-1(KBr)2920,2847,2359,2330,1692,
1659,1642,1594,1512,1462,1444,1427,1343,1228,1096,993,933,916,851,801,767,
748,690,650,605,563,526；UV-vis(CHCl3)λmax/nm 274,282,316,454,684；MALDI-TOF MS
m/z calcd for C78H15NO4[M]+1029.0996,found 1029.1012。
Embodiment 6
Prepare [60] fullerene dihydrofuran derivative 2f
Reactions steps：
First by fullerene C60(54.0mg, 0.075mmol) is added in dry reaction tube, then by CuCl
(3.7mg, 0.0375mmol) and(0.15mmol) is added in reaction tube, adds trifluoro second
The mixed solvent and ultrasonic dissolution of acid, acetonitrile and anhydrous o-dichlorohenzene, then cock beyond the Great Wall are placed in 120 DEG C of oil bath pan and stir
Reaction, 12 it is small when (TLC detection the reaction was complete), reaction mixture is filtered to remove any insoluble thing by short silicagel column
Matter, vacuum evaporating solvent, by remaining solid CS2Dissolving, loading, cross column, first uses CS2Collected as eluant, eluent unreacted
Fullerene C60, then use CS2Carry out as eluant, eluent affording target product 2f with the mixed solution of DCM.
2f:1H NMR(600MHz,CDCl3/CS2) δ 8.06-8.04 (m, 2H), 7.63-7.62 (m, 3H), 5.63 (d, J=
7.2Hz, 1H), 3.90-3.89 (m, 1H), 1.91-1.89 (m, 2H), 1.62-1.57 (m, 3H), 1.34-1.33 (m, 2H)；13C
NMR(150MHz,DMSO-d6/CS2with Cr(acac)3as relaxation reagent,all 2C unless
indicated)δ162.28(1C),157.39(1C),148.49,147.85(1C),147.06(1C),146.89,146.20,
146.00,145.90,145.81,145.74,145.45,145.21,144.96,144.82,144.69,144.37,144.23,
143.97,142.58,142.55,142.45,142.32,142.28,142.11,142.04,141.51,141.41,139.73,
139.67,137.34,135.11,131.03,129.13,128.80,128.71(1C),108.49(1C),101.32(sp3-C
of C60),74.21(sp3-C of C60),48.22(1C),32.68,25.70(1C),24.87(1C)；FT-IRν/cm-1
(KBr)2922,2850,2330,1717,1671,1639,1591,1574,1519,1456,1405,1365,1331,1275,
1173,1151,1106,1023,1004,951,928,849,767,693,576,553,527；UV-vis(CHCl3)λmax/nm
250,283,315,452,685；MALDI-TOF MS m/z calcd for C75H17NO2[M]+963.1254,found
963.1268。
Have been shown and described above the basic principle of the present invention, main feature and advantage, do not depart from spirit of the invention and
On the premise of scope, the present invention also has various changes and modifications, these changes and improvements both fall within claimed invention
Scope.
Claims (6)
1. a kind of synthetic method of [60] fullerene dihydrofuran derivative, it is characterised in that detailed process is：With fullerene C60
Be reaction raw materials with 1,2- diaryl ethyl ketone, alpha-carbonyl nitrile, 'beta '-ketoester or beta-diketone compounds, in 120-130 DEG C through CuI and
Ag2Oxidative dehydrogenation synthesis target product [60] fullerene dihydrofuran analog derivative that O collaborations promote, wherein 1,2- bis- virtue
Base ethyl ketone, alpha-carbonyl nitrile, the structural formula of 'beta '-ketoester or beta-diketone compounds are Corresponding target production
The structural formula of thing [60] fullerene dihydrofuran derivative is
2. the synthetic method of [60] fullerene dihydrofuran derivative according to claim 1, it is characterised in that：The richness
Strangle alkene C60、CuI、Ag2O and 1,2- diaryl ethyl ketone, alpha-carbonyl nitrile, the molar ratio of 'beta '-ketoester or beta-diketone compounds are
1:0.2-0.5:2:2-4。
3. the synthetic method of [60] fullerene dihydrofuran derivative according to claim 1 or 2, it is characterised in that specific
Step is；First by fullerene C60It is added in dry reaction tube, then by CuI, Ag2O and ketone compounds are added to instead
Answer in test tube, add the mixed solvent and ultrasonic dissolution of trifluoroacetic acid and anhydrous o-dichlorohenzene, then cock is placed in 120- beyond the Great Wall
Reaction is stirred in 130 DEG C of oil bath pan, the reaction was complete for TLC detections, reaction mixture is filtered by silicagel column insoluble to remove
Property material, vacuum evaporating solvent, by remaining solid CS2Dissolving, loading, cross column, first uses CS2Collected as eluant, eluent not anti-
The fullerene C answered60, then use CS2Carry out as eluant, eluent affording target product [60] fullerene two with the mixed solution of DCM
Hydrogen furan derivatives.
4. a kind of synthetic method of [60] fullerene dihydrofuran derivative, it is characterised in that detailed process is：With fullerene C60
It is reaction raw materials with β-carbonyl acetamides, target product is synthesized in the oxidative dehydrogenation that 120 DEG C promote through CuCl
[60] structural formula of fullerene dihydrofuran analog derivative, wherein β-carbonyl acetamides isCorresponding target product
[60] structural formula of fullerene dihydrofuran derivative is
5. the synthetic method of [60] fullerene dihydrofuran derivative according to claim 4, it is characterised in that：The richness
Strangle alkene C60, CuCl and β-carbonyl acetamides molar ratio be 1:0.5:2.
6. the synthetic method of [60] fullerene dihydrofuran derivative according to claim 4 or 5, it is characterised in that specific
Step is：First by fullerene C60It is added in dry reaction tube, then CuCl and β-carbonyl acetamides is added
Enter into reaction tube, add the mixed solvent and ultrasonic dissolution of trifluoroacetic acid, acetonitrile and anhydrous o-dichlorohenzene, then revolve beyond the Great Wall
Plug and reaction stirred in 120 DEG C of oil bath pan, TLC detections are anti-, and the reaction was complete, by reaction mixture by silicagel column filter with
Remove insoluble substance, vacuum evaporating solvent, by remaining solid CS2Dissolving, loading, cross column, first uses CS2As eluant, eluent
Collect unreacted fullerene C60, then use CS2Carry out as eluant, eluent affording target product [60] with the mixed solution of DCM
Fullerene dihydrofuran derivative.
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| CN112079765A (en) * | 2020-08-24 | 2020-12-15 | 河南师范大学 | Synthesis method of 1- [60] fullerene pyrrolidine derivative |
| CN112939845A (en) * | 2021-02-17 | 2021-06-11 | 河南师范大学 | Synthesis method of diversified [60] fullerene 1, 2-tetrahydrocarbazole derivative |
| CN114539151A (en) * | 2022-02-21 | 2022-05-27 | 湖北大学 | Method for preparing [60] fullerene dihydropyridine-3-one derivative by catalyzing p-methoxybenzoic acid and copper acetate and product |
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| CN110343064A (en) * | 2019-07-31 | 2019-10-18 | 河南师范大学 | The synthetic method of one kind [60] fullerene and tetrahydro cyclopentyl [2,3-b] indole derivatives |
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| CN110922369A (en) * | 2019-11-29 | 2020-03-27 | 南京工业大学 | Trifluoromethyl substituted dihydrofuran amine compound and preparation method and application thereof |
| CN110922369B (en) * | 2019-11-29 | 2022-12-16 | 南京工业大学 | Trifluoromethyl substituted dihydrofuran amine compound and preparation method and application thereof |
| CN112079765A (en) * | 2020-08-24 | 2020-12-15 | 河南师范大学 | Synthesis method of 1- [60] fullerene pyrrolidine derivative |
| CN112939845A (en) * | 2021-02-17 | 2021-06-11 | 河南师范大学 | Synthesis method of diversified [60] fullerene 1, 2-tetrahydrocarbazole derivative |
| CN114539151A (en) * | 2022-02-21 | 2022-05-27 | 湖北大学 | Method for preparing [60] fullerene dihydropyridine-3-one derivative by catalyzing p-methoxybenzoic acid and copper acetate and product |
| CN114539151B (en) * | 2022-02-21 | 2023-07-14 | 湖北大学 | Method for preparing [60] fullerene dihydropyridin-3-one derivative by catalyzing p-methoxybenzoic acid and copper acetate and product thereof |
| CN115260104A (en) * | 2022-07-31 | 2022-11-01 | 合肥学院 | Preparation method of fullerene tetrahydropyridazine compound |
| CN115260104B (en) * | 2022-07-31 | 2023-10-27 | 合肥学院 | Preparation method of fullerene tetrahydropyridazine compound |
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