Home Cart 0 Sign in  

[ CAS No. 6217-22-7 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 6217-22-7
Chemical Structure| 6217-22-7
Structure of 6217-22-7 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 6217-22-7 ]

Related Doc. of [ 6217-22-7 ]

Alternatived Products of [ 6217-22-7 ]

Product Details of [ 6217-22-7 ]

CAS No. :6217-22-7 MDL No. :MFCD00089611
Formula : C16H8O2 Boiling Point : -
Linear Structure Formula :- InChI Key :JKCATVQPENLMQJ-UHFFFAOYSA-N
M.W : 232.23 Pubchem ID :160814
Synonyms :

Calculated chemistry of [ 6217-22-7 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 73.87
TPSA : 34.14 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.44 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.75
Log Po/w (XLOGP3) : 3.2
Log Po/w (WLOGP) : 2.74
Log Po/w (MLOGP) : 2.5
Log Po/w (SILICOS-IT) : 4.56
Consensus Log Po/w : 2.95

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.95
Solubility : 0.0258 mg/ml ; 0.000111 mol/l
Class : Soluble
Log S (Ali) : -3.59
Solubility : 0.0599 mg/ml ; 0.000258 mol/l
Class : Soluble
Log S (SILICOS-IT) : -6.4
Solubility : 0.0000931 mg/ml ; 0.000000401 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.53

Safety of [ 6217-22-7 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 6217-22-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 6217-22-7 ]

[ 6217-22-7 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 129-00-0 ]
  • [ 6217-22-7 ]
YieldReaction ConditionsOperation in experiment
85% With tert.-butylhydroperoxide; Ru(2,4,13,15-tetraphenyl-1,5,12,16-tetraaza-tricyclo[14.2.2.06,11]eicosa-4,6(11),7,9,12-pentaene)Cl2; In acetonitrile; for 6h;Irradiation; General procedure: To a solution of Zn(II)/Ru(II) complex (1.25μmol), pyrene (0.5mmol) and TBHP (1.0mmol) in 10mL of acetonitrile was added. After the reaction was stirred under visible light for 6h, (monitored the reaction by LC-MS) solvent was evaporated using rotavapor. Purification of the crude compounds by column chromatography with dichloromethane/ethyl acetate (9:1, v/v) as eluent to an afforded pure product.
70% With ruthenium trichloride; sodium periodate; In dichloromethane; water; acetonitrile; at 20℃; for 18h; 5.05 g (0.025 mol) of hydrazine was dissolved in 100 mL of dichloromethane and 100 mL of acetonitrile.A dissolved aqueous solution of NaIO4 (25.50 g of NaIO4 dissolved in 120 mL of water) was then added to the reaction system.Thereafter, 0.50 g of antimony trichloride was added, and the mixture was stirred at room temperature for 18 hours.After completion of the reaction, the organic phase was spun off and the aqueous phase was extracted with 100 mL of dichloromethane.The organic phase was combined and the organic phase was dried over anhydrous sodium sulfate.Using a rotary evaporator, evaporate the solvent to dichloromethane:Petroleum ether = 2:1 is the eluent, which is subjected to silica gel column chromatography.For further purification, recrystallization can be carried out with chloroform and petroleum ether.The first compound (Pyrene-4,5-dione) was obtained to give 4 g of an orange solid.The yield was 70%.
58% With potassium bromate; In dichloromethane; water; acetonitrile; at 20℃; for 1h;Sonication; General procedure: A 20-mL flask was charged with CH2Cl2 (5 mL), H2O (5 mL), CH3CN (5 mL), chrysene (228.3 mg, 1 mmol), and KBrO3 (0.5 g, 2.99 mmol). MCM-41-Ru (75 mg) was added into the flask, and the dark suspension was irradiated at room temperature for 1h. The catalyst was separated from the reaction medium by filtration and washed with water and acetone, and then dried at 150 C overnight. The reaction mixture was poured into 50 mL of water, and the organic phase was separated. The aqueous phase was extracted with CH2Cl2 (3×10 mL). The CH2Cl2 extracts were combined with the organic phase, washed with brine (3×10 mL), and dried over anhydrous sodium sulfate to yield a dark orange solution. The solution was concentrated under reduced pressure, and the mixture was purified by preparative thin-layer chromatography (n-hexane/ethyl acetate =10/3), providing chrysene-5,6-dione as the major product and 2-(2-formylphenyl)-1-naphthaldehyde as the side product. The same procedure was also used for the reactions of other arene substrates.
48.95% With 1-methyl-1H-imidazole; sodium periodate; ruthenium(III) chloride trihydrate; In tetrahydrofuran; dichloromethane; water; at 20℃; for 2h;Inert atmosphere; The intermediate pyrene-4,5-dione was preparedaccording to the literature [44]. Pyrene (5.00 g, 24.72 mmol), NMI (0.10 g, 1.22 mmol) and RuCl3•3H2O (0.65 g, 2.49 mmol) weredissolved in the mixed solvent of DCM (100 mL), THF (100 mL) andH2O (125 mL). Then, NaIO4 (23.80 g, 111.27 mmol) was added in smallportions over 5 min. The reaction mixture was stirred for 2 h under anitrogen atmosphere. The resulting mixture was poured into 200 mL ofwater and extracted with dichloromethane (3×100 mL). The organicphase was washed with water (2×100 mL) and dried over anhydrousNa2SO4. After filtration and evaporation of the solvent in vacuum, thecrude was purified by chromatography on silica gel using dichloromethane/petroleum ether (1:5, v/v) as the eluent to obtainpyrene-4,5-dione (2.81 g, 48.95%). 1H NMR (500 MHz, CDCl3, δ): 8.50(d, J=7.4 Hz,
45% With ruthenium trichloride; sodium periodate; In dichloromethane; water; acetonitrile; at 40℃;Inert atmosphere; 62.0 g (300 mmol) of pyrene (I) are dissolved in 1000 ml of dichloromethane and 1000 ml of acetonitrile. 525 g (2.254 mol) of sodium periodate, 1200 ml of dist. water and 7.6 g (36 mmol) of ruthenium trichloride are added. The dark-brown solution is stirred overnight at 40 C., subsequently added to dist. water (4000 ml), and the precipitate is washed with water. The organic phase of the filtrate is separated off, the aqueous phase is extracted a number of times with dichloromethane. The organic phases and the precipitate dissolved in dichloromethane are combined and washed with sodium sulfite solution (10%). The solvent is removed under reduced pressure. The solid is recrystallised from chlorobenzene. The yield is 32.63 g (139.8 mmol), corresponding to 45% of theory.
45% With sodium periodate; rhodium(III) chloride hydrate; In tetrahydrofuran; dichloromethane; water; at 20℃; for 24h; To a stirred CH2Cl2 (90 mL) and THF (90 mL) solution of pyrene (8, 6.068 g, 30 mmol) were added NaIO4 (21.4 g, 100 mmol), H2O (120 mL), and RuCl3nH2O (0.1 g, 0.4 mmol). The mixture was stirred at room temperature for 24 h and filtered through silica gelusing CH2Cl2 (200 mL). The filtrate was divided into organic and aqueous layers, and the aqueous layer was washed with CH2Cl2(50 mL 3). The combined organic layers were washed with saturated NaCl aqueous solution, dried over Na2SO4, filtered, and concentrated in vacuo, giving a residue that was subjected to silicagel column chromatography (f 5 cm, l 15 cm, eluent: CH2Cl2,Rf 0.3) to give pyrene-4,5-dione (9, reddish orange solid, 2.99 g,45% yield).
36% With sodium periodate; rhodium(III) chloride hydrate; In dichloromethane; water; acetonitrile; at 20℃; for 12h; Dissolve elemental hydrazine (2.80 g, 14.0 mmol) in a mixed organic solvent of 60 mL of dichloromethane and 60 mL of acetonitrile, then add NaIO 4 (12.30 g, 57.3 mmol), 80 mL of deionized water, and finally add the catalyst RuCl 3 .xH 2 O ( 0.35 g, 1.7 mmol). The dark brown reaction system was stirred at 20C for 12 hours. After the reaction was completed, the crude product was extracted with dichloromethane. The organic phase was dried over anhydrous magnesium sulfate for 6 hours and then filtered. The filtrate was then spin-dried by a rotary evaporator under reduced pressure to give a dark orange solid which was purified by column chromatography using petroleum ether:dichloromethane=1 : 1 solvent as eluent. A red powder (1.21 g) was finally obtained with a yield of 36%.
36% With sodium periodate; ruthenium(III) trichloride hydrate; acetic acid; In dichloromethane; water; at 20℃; for 12h; NaIO4 (12.30 g, 57.3 mmol), H2O (80 mL) andTrihydrate ruthenium trichloride (RuCl3·3H2O) (0.35g, 1.7mmol) was addedTo a mixed solution of pyrene (2.80 g, 14.0 mmol) in dichloromethane (60 mL) and acetic acid (60 mL) gave a dark brown suspension. The suspension was stirred overnight at room temperature (12 hours). Extracted with chloroform. Distillation under reduced pressure gave a dark orange solid, using silica gel powder as a stationary phase, methylene chloride as eluent, and 1.21 g of a red product (yield: 36%). The reaction equation is as follows:
With ruthenium trichloride; sodium periodate; In water; acetonitrile; at 30℃; for 12h; (1) take a single pyrene (4.02g),Sodium periodate (20 g) was added to a 500 mL round bottom flask,Add 100 mL of distilled water and 100 mL of acetonitrile solution,The catalyst RuCl3 was added at 30 C for 12 hours.And purified by separation to give 4,5-pyrene diquinone as an orange powder.
With ruthenium trichloride; sodium periodate; In water; acetonitrile; at 30℃; for 12h; (1) Take pyrene (4.02g)Sodium periodate (20 g) was added to a 500 mL round bottom flask,Add 100mL distilled water and100mL acetonitrile solution,Add catalyst RuCl3,The reaction was carried out at 30 C for 12 hours.After separation and purification to give an orange powder 4,5-pyrene diquinone.
With sodium periodate; ruthenium(III) chloride hydrate; In dichloromethane; water; acetonitrile; at 20℃; for 18h; With dichloromethane (100ml),Acetonitrile (100ml) pyrene (5.05g, 25mmol) dissolved in 500ml round bottom flask, the mechanical stirrer,Then sodium periodate (25.5 g, 120 mmol) was added in sequence.Ruthenium trichloride monohydrate (0.5g),Water (120 ml) was reacted at room temperature for 18 h.After evaporating the solvent in a round bottom flask with a rotary evaporator, the product was extracted with dichloromethane.After drying the solvent, use petroleum ether.Dichloromethane (1:1) can be used to obtain a crude product.Then, it is recrystallized from chloroform and petroleum ether, and the crude product can be completely dissolved under reflux of chloroform, and then petroleum ether is added until the solid matter is no longer precipitated to obtain a final product. Traits: orange-red solid.

Reference: [1]Polyhedron,2019,vol. 170,p. 412 - 423
[2]Chemistry - A European Journal,2022,vol. 28
[3]Patent: CN108658993,2018,A .Location in patent: Paragraph 0041; 0043
[4]Chemistry - A European Journal,2020,vol. 26,p. 438 - 453
[5]Journal of Materials Chemistry C,2019,vol. 7,p. 3512 - 3521
[6]Cuihua Xuebao/Chinese Journal of Catalysis,2016,vol. 37,p. 153 - 158
[7]European Journal of Organic Chemistry,2016,vol. 2016,p. 5933 - 5936
[8]European Journal of Organic Chemistry,2021,vol. 2021,p. 2013 - 2017
[9]Dyes and Pigments,2020,vol. 172
[10]Photochemistry and Photobiology,2021,vol. 97,p. 301 - 308
[11]Journal of Organic Chemistry,2005,vol. 70,p. 707 - 708
[12]Organic Letters,2011,vol. 13,p. 2240 - 2243
[13]Patent: US9029425,2015,B2 .Location in patent: Page/Page column 131
[14]Tetrahedron,2019,vol. 75
[15]Organic Letters,2017,vol. 19,p. 1382 - 1385
[16]Organic Letters,2021,vol. 23,p. 2019 - 2023
[17]Organic Letters,2008,vol. 10,p. 3547 - 3550
[18]Journal of Organic Chemistry,2017,vol. 82,p. 6865 - 6873
[19]Journal of Materials Chemistry C,2016,vol. 4,p. 3809 - 3814
[20]Chemical Communications,2016,vol. 52,p. 7986 - 7989
[21]Patent: CN107056710,2017,A .Location in patent: Paragraph 0070; 0071; 0072
[22]Patent: CN108148001,2018,A .Location in patent: Paragraph 0071; 0080; 0081; 0082
[23]Journal of Materials Chemistry C,2019,vol. 7,p. 10273 - 10280
[24]Chemistry - An Asian Journal,2013,vol. 8,p. 2111 - 2124
[25]Organic Letters,2010,vol. 12,p. 4520 - 4523
[26]Angewandte Chemie - International Edition,2018,vol. 57,p. 10559 - 10563
    Angew. Chem.,2018,vol. 130,p. 10719 - 10723,5
[27]Journal of Organic Chemistry,1959,vol. 24,p. 1226,1228
[28]Synthesis,1974,p. 229 - 272
[29]Journal of Organic Chemistry,1983,vol. 48,p. 4198 - 4202
[30]European Journal of Organic Chemistry,2016,vol. 2016,p. 1772 - 1780
[31]Patent: CN107129469,2017,A .Location in patent: Paragraph 0082; 0083; 0103; 0104; 0108; 0109
[32]Patent: CN107011267,2017,A .Location in patent: Paragraph 0019; 0080
[33]Molecules,2018,vol. 23
[34]Inorganic Chemistry Communications,2019,vol. 100,p. 129 - 133
[35]Patent: CN109942585,2019,A .Location in patent: Paragraph 0054-0059
[36]Dyes and Pigments,2013,vol. 96,p. 104 - 115,12
  • 4
  • [ 6217-22-7 ]
  • [ 102-04-5 ]
  • [ 108868-49-1 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; In methanol; at 20℃;Inert atmosphere; Reflux; 32.63 g (139.8 mmol) of compound (II) and 31.08 g (147.4 mmol) of 1,3-diphenylacetone (III) are dissolved in 4500 ml of methanol. The orange suspension is heated under reflux, and a potassium hydroxide solution (7.76 g) in methanol (31 ml) is slowly added dropwise. An immediate black-violet coloration occurs. The mixture is heated under reflux for 60 min and subsequently stirred overnight at room temperature. After filtration, the precipitate is washed with cold methanol, dried under reduced pressure and reacted without further purification. The yield is 41.89 g (103.1 mmol), corresponding to 73% of theory
  • 6
  • [ 6217-22-7 ]
  • [ 111171-77-8 ]
  • 7
  • phenanthrene-4,5-dicarboxylic acid dimethyl ester [ No CAS ]
  • [ 6217-22-7 ]
  • 8
  • [ 78-94-4 ]
  • [ 6217-22-7 ]
  • 2-methylpyreno[4,5-b]furan-3-carboxaldehyde [ No CAS ]
  • 9
  • [ 2177-32-4 ]
  • [ 6217-22-7 ]
  • 2-i-butylylpyreno[4,5-b]furan-3-carboxaldehyde [ No CAS ]
  • 10
  • [ 1629-58-9 ]
  • [ 6217-22-7 ]
  • 2-ethylpyreno[4,5-b]furan-3-carboxaldehyde [ No CAS ]
  • 11
  • [ 159152-14-4 ]
  • [ 6217-22-7 ]
  • C68H48N4O2 [ No CAS ]
  • C68H48N4O2 [ No CAS ]
  • 12
  • [ 4356-69-8 ]
  • [ 6217-22-7 ]
  • 10,10-bis(4-methoxyphenyl)-10,11-dihydro-9,12-dioxabenzo[e]pyrene [ No CAS ]
  • 13
  • [ 6217-22-7 ]
  • 3-bromo-1-(4-{1-[4-(3-bromopropoxy)phenyl]vinyl}phenoxy)propane [ No CAS ]
  • 10,10-bis[4-(3-bromopropoxy)phenyl]-10,11-dihydro-9,12-dioxabenzo[e]pyrene [ No CAS ]
  • 15
  • [ 54523-47-6 ]
  • [ 6217-22-7 ]
  • [ 908352-01-2 ]
  • 16
  • [ 6217-22-7 ]
  • trans-4,5-dihydroxy-1,2,3,3a,4,5,-hexahydropyrene [ No CAS ]
  • 17
  • [ 6217-22-7 ]
  • [ 101226-71-5 ]
  • 18
  • [ 42333-78-8 ]
  • [ 6662-72-2 ]
  • [ 63994-76-3 ]
  • [ 7732-18-5 ]
  • [ 6217-22-7 ]
  • Pd6(C18H12N6)2(C14H16N2)3(N2C2H8)6(12+)*2C16H8O2*12NO3(1-)*27H2O=Pd6C36H24N12(C14H16N2)3(N2H8C2)6(C16H8O2)2(NO3)12*27H2O [ No CAS ]
  • 19
  • [ 42333-78-8 ]
  • [ 63994-76-3 ]
  • [ 7732-18-5 ]
  • [ 6217-22-7 ]
  • 1-pyridyl-4-(4'-pyridylethynyl)benzene [ No CAS ]
  • 6Pd(2+)*2C18H12N6*3C18H12N2*6N2C2H8*4C16H8O2*12NO3(1-)*26H2O=Pd6C36H24N12(C18H12N2)3(N2H8C2)6(C16H8O2)4(NO3)12*26H2O [ No CAS ]
  • 20
  • [ 42333-78-8 ]
  • [ 63994-76-3 ]
  • [ 7732-18-5 ]
  • [ 13362-78-2 ]
  • [ 6217-22-7 ]
  • Pd6(C18H12N6)2(C12H10N2)3(N2C2H8)6(12+)*3C16H8O2*12NO3(1-)*20H2O=Pd6C36H24N12(C12H10N2)3(N2H8C2)6(C16H8O2)3(NO3)12*20H2O [ No CAS ]
  • 21
  • [ 42333-78-8 ]
  • [ 63994-76-3 ]
  • [ 1206837-84-4 ]
  • [ 6217-22-7 ]
  • 6Pd(2+)*2C18H12N6*3C26H24N2O4*6N2C2H8*5C16H8O2*12NO3(1-)=Pd6C36H24N12(C26H24N2O4)3(N2H8C2)6(C16H8O2)5(NO3)12 [ No CAS ]
  • 22
  • [(2,4,6-tri-4-pyridyltriazine)2(pyrazine)3(Pt((CH2NH2)2))6](NO3)12 [ No CAS ]
  • [ 6217-22-7 ]
  • Pt6(C3N3(C5H4N)3)2(C4H4N2)3(NH2C2H4NH2)6(12+)*C16H8O2*12NO3(1-)=Pt6(C3N3(C5H4N)3)2(C4H4N2)3(NH2C2H4NH2)6C16H8O2(NO3)12 [ No CAS ]
  • 23
  • [ 4506-66-5 ]
  • [ 6217-22-7 ]
  • [ 1228192-01-5 ]
  • 24
  • [ 1830-54-2 ]
  • [ 6217-22-7 ]
  • [ 1258508-74-5 ]
  • 25
  • [ 75-77-4 ]
  • [ 6217-22-7 ]
  • [ 1247753-19-0 ]
  • 27
  • [ 6217-22-7 ]
  • [ 1314124-52-1 ]
YieldReaction ConditionsOperation in experiment
With N-Bromosuccinimide; sulfuric acid; at 20℃; for 4h; 2.765 g (0.012 mol) of the first compound obtained above,Add 29 mL of concentrated sulfuric acid,4.25 g of bromosuccinimide (NBS) was added in portions with stirring.Stirring was continued for 4 h at room temperature.The reaction was completed, poured into ice water, suction filtered, washed three times with 100 mL of water, and dried.4.6 g of a yellow solid is obtained as the second compound (4,5-dibromo-9,10-nonanedione) in a yield of 98%.Because the compound is insoluble in most deuterated reagents, for example, deuterated chloroform,Deuterated DMSO and so on. We did not characterize it by NMR.The compound can be directly fed to the next step without purification.
With N-Bromosuccinimide; sulfuric acid; at 20℃; for 4.5h; The powder pyrene 4,5-dione (0.5g, 2.15mmol) was added 100ml of concentrated sulfuric acid was added bis jar (9ml)After magnetic stirring was started, the mixture was stirred uniformly, and N-bromosuccinimide (NBS, 1.21 g, 8.6 mmol) was added in portions to react at room temperature.4.5h. In this embodiment, the method of batch addition ensures that the reactants can be fully reacted after the addition, and the one-time pour-in causes the concentrated sulfuric acid to destroy the activity of the NBS. After the end of the reaction, a large amount of water was added until no more orange-yellow solid precipitated.Filter by suction and dry. This step is not purified.Used directly in the next step of the reaction.
  • 28
  • [ 108-39-4 ]
  • [ 6217-22-7 ]
  • [ 1300655-38-2 ]
  • 29
  • [ 100-52-7 ]
  • [ 62-53-3 ]
  • [ 6217-22-7 ]
  • [ 1403603-83-7 ]
YieldReaction ConditionsOperation in experiment
48.5% With ammonium acetate; acetic acid; for 12h;Inert atmosphere; Reflux; Benzaldehyde (69.0 mg, 0.65 mmol), aniline (74 mg, 0.67 mmol), <strong>[6217-22-7]pyrene-4,5-dione</strong> [39] (150 mg, 0.65 mmol), and ammonium acetate (498 mg, 6.46 mmol) were mixed in glacial acetic acid (10 mL). The mixture was refluxed for 12 h under Ar atmosphere. Water was added to the mixture. The pH was brought to 7 with ammonium hydroxide. The solid was collected by filtration and washed with water. The solid was dissolved in dichloromethane, then concentrated under reduced pressure to give a light brown solid. The crude product was purified by column chromatography (silica gel, CH2Cl2/n-hexane = 50:1, v/v) to give a pale yellow solid [40]. Yield: 123.6 mg, (48.5%). M.p. > 250 C. 1H NMR (400 MHz, CDCl3), δ = 9.13 (d, 1H, J = 7.3 Hz); 8.01-8.20 (m, 5H); 7.57-7.64 (m, 8H); 7.31-7.40 (m, 4H). EI-HRMS: calcd (C29H18N2): m/z = 394.1470, found, m/z = 394.1459.
  • 30
  • [ 6217-22-7 ]
  • 5-amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)cytosine [ No CAS ]
  • [ 1415975-30-2 ]
  • 31
  • [ 168646-54-6 ]
  • [ 6217-22-7 ]
  • C28H16N4 [ No CAS ]
  • 32
  • [ 129-00-0 ]
  • ruthenium chloride (III) trihydrate [ No CAS ]
  • [ 6217-22-7 ]
YieldReaction ConditionsOperation in experiment
23% With sodium periodate; In dichloromethane; water; acetonitrile; Synthesis example 8 Pyrene-4,5-dione (hereinafter referred to as compound 8) represented by the following formula (28) was synthesized by the following method. Pyrene (402 mg, 2.0 mmol), ruthenium chloride (III) trihydrate (41 mg, 0.19 mmol), and sodium periodate (2.0 g, 9.4 mmol) were put in a round bottom flask (50 ml), and methylene chloride (8 ml), acetonitrile (8 ml) and water (10 ml) were added thereto. The reaction liquid was stirred in an argon atmosphere at 35 C. for 21 hours. The reaction liquid was returned to room temperature, and then the reaction liquid was poured into water (100 ml). An organic substance was extracted therefrom by using methylene chloride (20 ml, 3 times). The extracted organic substance was washed with water (20 ml, 2 times), and then a rough product obtained by removing the solvent by an evaporator was subject to silica gel chromatography to isolate pyrene-4,5-dione (105 mg, yield 23%) as an orange solid. An 1H NMR analysis was conducted to find the following results. As a reference, "J. Hu, D. Zhang, F. W. Harris, J. Org. Chem. 2005, 70, 707-708.” can be mentioned. 1H NMR (400 MHz, CDCl3), δ 8.52 (dd, J=1.2, 7.2 Hz, 2H), 8.20 (dd, J=1.3, 8 Hz, 2H), 7.78 (s, 2H), 7.78 (t, J=7.6 Hz)
  • 33
  • [ 87-62-7 ]
  • [ 6217-22-7 ]
  • [ 1443058-46-5 ]
YieldReaction ConditionsOperation in experiment
21.27% With titanium tetrachloride; triethylamine; In toluene; for 0.5h;Reflux; At room temperature, 2,6-dimethylaniline (1.81g,15.00 mmol), triethylamine (45.00 mmol, 4.54g) was added 500ml double neck flask using toluene as a solvent, the system is heated to 90 C, was added dropwise 9. 0M titanium tetrachloride in toluene 1.6ml, after completion of the dropwise addition, the <strong>[6217-22-7]pyrene-4,5-dione</strong> (1.18g, 5mmol) added to the system, and heated to reflux, the reaction is stopped after 30min, column chromatography, petroleum ether: dichloromethane = 5: l (v / v), to give the product 0.47g.Yield: 21.27%
  • 34
  • [ 24544-08-9 ]
  • [ 6217-22-7 ]
  • 4,5-bis(2,6-diethyl-4-methylphenylimino)pyrenylidene [ No CAS ]
  • 36
  • [ 104-87-0 ]
  • [ 6217-22-7 ]
  • 10-para-tolyl-9H-pyreno[4,5-d]imidazole [ No CAS ]
  • 37
  • [ 642-31-9 ]
  • [ 6217-22-7 ]
  • 10-(anthracen-9-yl)-9H-pyreno[4,5-d]imidazole [ No CAS ]
  • 38
  • [ 3029-19-4 ]
  • [ 6217-22-7 ]
  • 10-(pyren-1-yl)-9H-pyreno[4,5-d]imidazole [ No CAS ]
  • 39
  • [ 67707-09-9 ]
  • [ 6217-22-7 ]
  • 10-(9-butyl-9H-carbazol-3-yl)-9H-pyreno[4,5-d]imidazole [ No CAS ]
  • 40
  • [ 138253-30-2 ]
  • [ 6217-22-7 ]
  • [ 1492021-86-9 ]
YieldReaction ConditionsOperation in experiment
70% With ammonium acetate; acetic acid for 2h; Reflux;
  • 42
  • [ 1233939-26-8 ]
  • [ 6217-22-7 ]
  • [ 1612186-46-5 ]
YieldReaction ConditionsOperation in experiment
91% With potassium carbonate; acetic acid;Reflux; Inert atmosphere; General procedure: To a solution of 7-bromo-9,9-dioctyl-9H-fluorene-2,3-diamine(2, 2.4 mmol) or 9,9-dioctyl-9H-fluorene-2,3-diamine (2a,2.4 mmol) in deoxygenated AcOH (20 mL) were added the corresponding dione (2.4 mmol) and potassium carbonate (0.17 g,1.2 mmol). The mixture was heated to reflux under nitrogen for 2-5 h. After cooling down, the mixture was extracted with ethyl acetate(20 mL) and water (50 mL), the organic layerwaswashed withsaturated brine and dried over Na2SO4(S). After removing the solvent,the crude product was purified by column chromatography on silica gel using ethyl acetate-hexane as eluent or recrystallized from dichloromethane (DCM)/MeOH to yield the desired compounds.
  • 43
  • [ 1585966-04-6 ]
  • [ 6217-22-7 ]
  • [ 1612186-49-8 ]
YieldReaction ConditionsOperation in experiment
90% With potassium carbonate; acetic acid;Reflux; Inert atmosphere; General procedure: To a solution of 7-bromo-9,9-dioctyl-9H-fluorene-2,3-diamine(2, 2.4 mmol) or 9,9-dioctyl-9H-fluorene-2,3-diamine (2a,2.4 mmol) in deoxygenated AcOH (20 mL) were added the corresponding dione (2.4 mmol) and potassium carbonate (0.17 g,1.2 mmol). The mixture was heated to reflux under nitrogen for 2-5 h. After cooling down, the mixture was extracted with ethyl acetate(20 mL) and water (50 mL), the organic layerwaswashed withsaturated brine and dried over Na2SO4(S). After removing the solvent,the crude product was purified by column chromatography on silica gel using ethyl acetate-hexane as eluent or recrystallized from dichloromethane (DCM)/MeOH to yield the desired compounds.
  • 44
  • [ 106-95-6 ]
  • [ 6217-22-7 ]
  • [ 1642133-98-9 ]
  • 45
  • [ 51044-13-4 ]
  • [ 6217-22-7 ]
  • 10,11-dihydro-10,11-bis(p-bromophenyl)pyreno[4,5-b]furan [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% To a solution of p-bromophenylmethylphosphonium bromide (1.16 g, 2.26 mmol) in DMSO (10 ml) was added potassium t-butoxide (267 mg, 2.4 mmol), and the mixture was stirred at room temperature for 2 min. A solution of <strong>[6217-22-7]pyrene-4,5-dione</strong> 5 (206 mg, 0.89 mmol) in DMSO (5 ml) was added to the mixture. The reaction mixture was stirred at room temperature for 30 min, quenched with water, and extracted with toluene. The organic layer was washed with brine and dried over Na2SO4. After removing the solvent, the crude product was purified by silica gel column chromatography (toluene:hexane = 1:3) to give a pale yellow solid (299 mg, 0.54 mmol) of 9,10-dihydro-9,10-bis(p-bromophenyl)pyreno[4,5-b]furan in 61% yield. A solution of the dihydrofuran (471 mg, 0.85 mmol) and DDQ (422 mg, 1.9 mmol) in toluene (20 ml) was heated at 70 C for 4 h. After removing the solvent, the crude product was purified by silica gel column chromatography (toluene:hexane = 1:2) to give a pale yellow solid (351 mg, 0.64 mmol) of 4b in 46% yield from 6.
  • 46
  • [ 1100-88-5 ]
  • [ 6217-22-7 ]
  • 10,11-dihydro-10,11-diphenylpyreno[4,5-b]furan [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% To a solution of benzylphosphonium chloride (990 mg, 2.55 mmol) in DMSO (10 ml) was added potassium t-butoxide (286 mg, 2.6 mmol), and the mixture was stirred at room temperature for 2 min. A solution of pyrene-4,5-dione 6 (233 mg, 1.0 mmol) in DMSO (5 ml) was added to the mixture. The reaction mixture was stirred at room temperature for 30 min, quenched with water, and extracted with toluene. The organic layer was washed with brine and dried over Na2SO4. After removing the solvent by evaporator, the crude product was purified by silica gel column chromatography (toluene:hexane = 1:3) to give a pale yellow solid (281 mg, 0.708 mmol) of 9,10-dihydro-9,10-diphenylpyreno[4,5-b]furan in 71% yield. A solution of the dihydrofuran (53.6 mg, 0.135 mmol) and DDQ (49.4 mg, 0.218 mmol) in toluene (20 ml) was heated at 70 C for 4 h. After removing the solvent, the crude product was purified by silica gel column chromatography (toluene:hexane = 1:2) to give a pale yellow solid (45 mg, 0.11 mmol) of 4a in 80% yield from 6.
  • 47
  • [ 623-27-8 ]
  • [ 6217-22-7 ]
  • C40H22N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With ammonium acetate; acetic acid; at 110℃; for 4h; Acetic acid (30 mL)was added to a mixture of the terephthalaldehyde (0.29g, 2.16 mmol), <strong>[6217-22-7]pyrene-4,5-dione</strong> (1.00g, 4.32 mmol), and ammonium acetate (3.33 g, 43.2 mmol). The reaction mixturewas stirred at 110 oC for 4 h, and then ice water was poured in. Theyellow solid of raw product 1 was obtained by filtration. 1 wasrecrystallized from chloroform/ethanol as a yellow solid in a yield of 1.21 g(77 %). Mp: > 300 oC. Main FT-IR absorptions (KBr pellets, cm-1):3417, 3054, 1654, 1557, 1105, 883, 715. 1H NMR (500 MHz, DMSO-d6):δ, 14.39 (s, 2H, imidazol), 8.91 (d, 4H, J= 7.4 Hz, pyrene), 8.65 (s, 4H , benzene), 8.30 (d, 2H, J = 7.2 Hz, pyrene), 8.21(m, 8H, pyrene). 13C NMR (125 MHz, DMSO-d6): δ, 149.3, 132.1, 131.2, 128.2, 127.3, 126.8, 124.9, 122.4, 119.6. EI-TOF-MS (m/z): Calcd for [C40H22N4]+558.2 (100.0 %), found 557.9 (100.0 %). Anal. Calcd. for C40H22N4: C, 86.00; H, 3.97; N, 10.03 %. Found: C,85.82; H, 4.10; N, 9.88 %.
  • 48
  • [ 1383842-42-9 ]
  • [ 6217-22-7 ]
  • 10,13-dibromo-11,12-bis(octyloxy)phenanthro[4,5-abc]phenazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
52.2% In acetic acid; for 12h;Reflux; Inert atmosphere; A mixture of compound (2), <strong>[6217-22-7]pyrene-4,5-dione</strong> (0.40g, 1.73mmol), ethanol (30mL) and acetic acid (HOAc, 60mL) was refluxed for 12h under the protection of nitrogen atmosphere. After cooled to RT, the mixture was extracted with dichloromethane (DCM). The combined organic layer was dried over anhydrous MgSO4 and the solvent was removed off by rotary evaporation. The residue was purified by silica gel column chromatography using petroleum ether (PE)-DCM (V/V, 4/1) as eluent to yield 0.65g (52.2%) of 3 as a yellow solid.
  • 49
  • [ 107-21-1 ]
  • [ 6217-22-7 ]
  • pyrene-4,5-di(ethyleneglycol)ketal [ No CAS ]
  • 50
  • [ 112-71-0 ]
  • [ 6217-22-7 ]
  • C44H66O2 [ No CAS ]
  • 51
  • [ 13362-78-2 ]
  • [ 6217-22-7 ]
  • C28H18N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% In benzene; at 4℃; for 1h;Inert atmosphere; Irradiation; A solution of 0.0895 g (0.77 mmol) of <strong>[6217-22-7]pyrene-4,5-quinone</strong> in 150 mL of benzene and 0.2060 g (1.13 mmol) of trans-1,2-bis(4-pyridyl) ethylene was purged with Ar and placed in a Rayonet Photochemical Reactor. The reaction mixture was irradiated at 419 nm in a water bath with the temperature kept at freezing point of benzene +4 C. After 4 h of irradiation the color of the reaction mixture was yellow. The benzene was evaporated and 150 mL of methanol added. Immediate formation of white powder-like crystals was observed. The solution was left for 24 h in the dark. The crystals were collected by filtration (1st filtration) and washed with a small amount of CHCl3. The collected crystals were partially redissolved in 7 mL of CHCl3 with slight heating. The insoluble material was again collected by filtration (2nd filtration). These collected crystals again were partially dissolved in 3 mL of CHCl3 and the insoluble material collected by filtration (3rd filtration). TLC analysis (ethyl acetate/hexane 1/5) of this third set of crystals indicated that no starting materials were present, and afforded a single striking spot of 2. These crystals were combined with the residue from evaporation of the CHCl3 wash solution to afford 0.082 g of 2. The CHCl3 solutions from the 1st and 2nd filtrations were combined and TLC indicated the presence of pyrene quinone, trans-1,2-bis(4-pyridyl)ethylene and 2. Column chromatography of this material (ethyl acetate/hexane1/5 and then, after the first two bands were collected, CH3OH/CHCl3) afforded 0.059 g of 2 for a combined yield 43% (0.141 g, 0.340 mmol) of a mixture of RR- and SS-isomers. UV 0.01 mg/mL in CHCl3 (calculated ε of 2 at 250 nm is 33,316 M-1cm-1), Fig. S1. 1H NMR (300 MHz, CDCl3) (Fig. S2) δ 8.65 ppm (d, J = 4.70 Hz, 4H), 8.46 (d, J = 7.8 Hz, 2H), 8.19 (d, J = 7.53 Hz, 2H), 8.12 (s, 2H), 8.05 (dd, J = 7.69 Hz, J0 = 7.69 Hz, 2H), 7.21 (d, J = 5.54 Hz, 4H), 5.23 (s, 2H); 1H NMR (500 MHz, DMSO-d6) d 8.58 (d, J = 5.9 Hz, 4H), 8.39 (d,J = 7.8 Hz, 2H), 8.29 (d, J = 7.6 Hz, 2H), 8.18 (s, 2H), 8.09 (dd, J = 7.7 Hz,J0 = 7.7 Hz, 2H), 7.44 (d, J = 5.9 Hz, 4H), 5.94 (s, 2H), Fig. S2; 13C NMR (75 MHz, DMSO-d6) δ 149.1, 143.9, 132.8, 129.7, 126.6, 125.7, 123.6, 123.5, 121.7, 119.3, 117.0, 76.5.C28H19N2O2; HRMS (ESI-Q-TOFMS) calculated for C28H19N2O2 415.1447, found 415.14421. It should be mentioned that this reaction works much better on the smaller scale, since the yield of this reaction was as high as 78% (0.025 g (0.077 mol) of pyrenequinone, 0.412 g (0.226 mmol) of trans-1,2-bis(4-pyridyl) ethylene) with reaction time of 1 h, but that procedure included only onefiltrationwith further recrystallization of the product 2 from CH3OH. Also, the color of that reaction mixture was only slightly yellowish. Still, the NMR quality was acceptable.
  • 52
  • [ 1122-91-4 ]
  • [ 62-53-3 ]
  • [ 6217-22-7 ]
  • 10-(4-bromophenyl)-9-phenyl-9H-pyreno[4,5-d]imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ammonium acetate; at 120℃; for 3h;Inert atmosphere; (2) 4,5-pyrene diquinone (2.32 g, 10 mmol)Aniline (4.65 g, 50 mmol),4-bromobenzaldehyde (5.46 g, 30 mmol) and ammonium acetate (3.85 g, 50 mmol) in a 250 mL round bottom flask,Under nitrogen protection,120 C for 3 hours.And then adding distilled water to the reaction system,Filter to obtain thick crude products,9- (4-bromo) -9-hydrogen-pyrene imidazole was isolated by column chromatography.
With ammonium acetate; at 120℃; for 2h;Inert atmosphere; (2) 4,5-pyrene diquinone (2.32 g) was taken,Aniline (4.65 g),4-Bromobenzaldehyde (5.46 g)And ammonium acetate (3.85 g) in a 250 mL round bottom flask,Under nitrogen protection,Debus-Radziszewski reaction was carried out at 120 C for 2 hours.Then the reaction system was added distilled water, filtered to give a crude product precipitated,9- (4-Bromo) -9-hydro-pyreneimidazole was isolated as a light yellow powder by isolation.
  • 53
  • [ 106-41-2 ]
  • [ 6217-22-7 ]
  • 11-bromopyreno[4,5-b]benzofuran [ No CAS ]
YieldReaction ConditionsOperation in experiment
17% With trifluorormethanesulfonic acid; In 1,2-dichloro-benzene; at 190℃; for 24h;Inert atmosphere; Combine 12g (51.7mmol) of -4-4,5-dione, 7.7g (51.7mmol) of trifluoromethanesulfonic acid (CF3SO3H), 8.9g (51.7mmol) of 4-bromophenol,A mixture of 200 ml of 1,2-dichlorobenzene (ODCB) was degassed and placed under nitrogen, and then heated at 190C for 24 hours.After the completion of the reaction, the solvent was removed, and the residue was purified by silica gel column chromatography to obtain a light green solid product (3.3 g, 17%).
  • 54
  • [ 10111-08-7 ]
  • [ 6217-22-7 ]
  • 10-(1-H-imidazole-2-yl)-9H-pyreno[4,5-d]imidazole [ No CAS ]
  • 55
  • [ 771-97-1 ]
  • [ 6217-22-7 ]
  • benzo[i]phenanthro[4,5-abc]phenazine [ No CAS ]
  • 56
  • [ 3171-45-7 ]
  • [ 6217-22-7 ]
  • 11,12-dimethylphenanthro[4,5-abc]phenazine [ No CAS ]
  • 57
  • [ 619-05-6 ]
  • [ 6217-22-7 ]
  • phenanthro[4,5-abc]phenazine-11-carboxylic acid [ No CAS ]
  • 58
  • [ 6217-22-7 ]
  • [ 49764-63-8 ]
  • 11,12-dibromophenanthro[4,5-abc]phenazine [ No CAS ]
  • 59
  • [ 1109-15-5 ]
  • [ 6217-22-7 ]
  • C28H8BF10O2 [ No CAS ]
  • C<SUB>16</SUB>H<SUB>8</SUB>O<SUB>2</SUB>B(C<SUB>6</SUB>F<SUB>5</SUB>) [ No CAS ]
  • 60
  • [ 7803-58-9 ]
  • [ 6217-22-7 ]
  • [ 51485-74-6 ]
YieldReaction ConditionsOperation in experiment
44.1 mg With nano-sized silica-supported 12-molybdophosphoric acid (MPA); In neat (no solvent); at 150℃; for 15h; General procedure: Condensation reactions were carried out in the temperature range 25-150 C. The used molar ratios of reactants and catalyst were: 2/11.0-14.6; MPA/1 0.008-0.43. The course of the reactions was routinely monitored by TLC. A small sample of the reaction mixture (solventfree reactions: ca. 0.2 mg; reactions in solution: ca. 0.1 mL) was treated with CH2Cl2 (ca. 1 mL), sonicated and the supernatant was analyzedby TLC. Completion of the reaction was judged by the disappearance of the TLC spot of the reagent 1a-h. A few experiments were stopped before the complete disappearance of 1 (Table 1, entries 7and 12). Longer heating did not lead to decomposition of the reaction products 3. Procedure A. A fine powdered mixture (or a paste for liquids 2) of 1, MPA, and 2 placed in a Pyrex glass centrifuge tube (size: 107-109 mm, diameter: 16-17 mm, style type: rimless) was kept at 25-150 C until the reaction was complete. Occasionally the mixture was allowed to cool to r.t. in a desiccator and then was again finely pulverized.
  • 61
  • [ 111-25-1 ]
  • [ 6217-22-7 ]
  • 4,5-dihexoxypyrene [ No CAS ]
  • 62
  • 4,7-bis(5-(2-ethylhexyl)thiophene-2-yl)benzo[c][1,2,5]thiadiazole-5,6-diamine [ No CAS ]
  • [ 6217-22-7 ]
  • 10,14-bis(5-(2-ethylhexyl)thiophen-2-yl)phenanthro[4,5-abc][1,2,5]thiadiazolo[3,4-i]phenazine [ No CAS ]
  • 63
  • 3-phenyl-1-(1H-pyrazol-1-yl)but-3-en-1-one [ No CAS ]
  • [ 6217-22-7 ]
  • (R)-4-phenyl-5′H-spiro[pyran-2,4′-pyrene]-5′,6(3H)-dione [ No CAS ]
  • 64
  • [ 1334680-34-0 ]
  • [ 6217-22-7 ]
  • C52H56N2Si2 [ No CAS ]
  • 65
  • [ 1334680-36-2 ]
  • [ 6217-22-7 ]
  • C50H54N4Si2 [ No CAS ]
  • 66
  • [ 26260-02-6 ]
  • [ 769-92-6 ]
  • [ 6217-22-7 ]
  • 9-(4-(tert-butyl)phenyl)-10-(2-iodophenyl)-9H-pyreno[4,5-d]imidazole [ No CAS ]
  • 67
  • [ 98-03-3 ]
  • [ 6217-22-7 ]
  • 10-(thiophen-2-yl)-9H-pyreno[4,5-d]imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
34.2% Pyrene diketone (4.5 g, 19 mmol), ammonium acetate (18.8 g, 244 mmol) and ethanol (100 mL) were added to a one neck round bottom flask (250 mL) and stirred under reflux at 78 C. Then, 2-thiophenecarboxaldehyde (2.18 g, 19 mmol) was added to the reaction system. After the addition is complete, continue stirring 78 degrees overnight. After the reaction, the ethanol is dried, the solid is washed with water, filtered off with suction, dried and separated and purified on a silica gel column to obtain 2.15g of 10- (thiophen-2-yl) -9H- pyreno [4,5-d](Hereinafter referred to as TPy),Yield 34.2%. 1H NMR (400 MHz, DMSO) δ (ppm): 8.76 (d, J = 7.5 Hz, 1H), 8.70 (d, J = 7.6 Hz, 1H), 8.26-8.08 (m, 7H), 7.98 3.6 Hz, 1H), 7.74 (d, J = 5.0 Hz, 1H), 7.32-7.28 (m, 1H).
  • 68
  • [ 57835-92-4 ]
  • [ 129-00-0 ]
  • [ 31700-39-7 ]
  • [ 17075-03-5 ]
  • [ 6217-22-7 ]
YieldReaction ConditionsOperation in experiment
In isopropyl alcohol for 4h; Inert atmosphere; Irradiation;
  • 69
  • C26H18N6O6Si(2+)*2F6P(1-) [ No CAS ]
  • [ 6217-22-7 ]
  • C42H26N6O2Si(2+)*2F6P(1-) [ No CAS ]
  • 70
  • C30H18N6O6Si(2+)*2F6P(1-) [ No CAS ]
  • [ 6217-22-7 ]
  • C46H26N6O2Si(2+)*2F6P(1-) [ No CAS ]
  • 71
  • [ 18741-85-0 ]
  • [ 6217-22-7 ]
  • (R)-(13Z,21bZ)-dinaphtho[2,1-e:1′,2′-g]pyreno[4,5-b][1,4]diazocine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trifluoroacetic acid; In toluene; at 60℃; for 3h;Inert atmosphere; A mixture of <strong>[6217-22-7]pyrene-4,5-dione</strong> (20.0mg, 0.086mmol) and (R)- or (S)-(+/-)-2,2′-diamino-1,1′-binaphthalene (25.0mg, 0.088mmol) in dried toluene (3.5mL) with CF3COOH (20μL) was heated at 60C under nitrogen for 3h. After being cooled to room temperature, the solvent was then removed in vacuum, and the residue was first subjected to chromatography on a silica gel column using CH2Cl2 as eluent. The crude product was purified by repeated chromatography followed by recrystallization from chloroform and methanol giving the pure target compounds as a green powder (14.7mg, 35.4%). 1H NMR (400MHz, [D6](CD3)2SO): 8.19 (d, 2H, J=8.00Hz), 8.06-8.00 (m, 6H, J=8.00Hz), 7.88 (d, 2H, J=8.00Hz), 7.67 (t, 2H, J=8.00Hz), 7.51 (t, 2H, J=8.00Hz), 7.37-7.32 (m, 4H, J=8.00Hz), 7.01 (d, 2H, J=8.00Hz). UV-Vis (CHCl3): λmax/nm (logε)=294 (4.57), 322 (4.43), 371 (3.97). MALDI-TOF MS: an isotopic cluster peaking at m/z 480.0, Calcd. for C36H20N2, [M]+ 480.2. Anal. Calcd. for C36H20N2·0.25CH2Cl2: C, 86.77; H, 4.12; N, 5.58. found: C, 86.42; H, 4.48; N, 5.62.
  • 72
  • [ 18531-95-8 ]
  • [ 6217-22-7 ]
  • (S)-(13Z,21bZ)-dinaphtho[2,1-e:1′,2′-g]pyreno[4,5-b][1,4]diazocine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trifluoroacetic acid; In toluene; at 60℃; for 3h;Inert atmosphere; A mixture of <strong>[6217-22-7]pyrene-4,5-dione</strong> (20.0mg, 0.086mmol) and (R)- or (S)-(+/-)-2,2′-diamino-1,1′-binaphthalene (25.0mg, 0.088mmol) in dried toluene (3.5mL) with CF3COOH (20μL) was heated at 60C under nitrogen for 3h. After being cooled to room temperature, the solvent was then removed in vacuum, and the residue was first subjected to chromatography on a silica gel column using CH2Cl2 as eluent. The crude product was purified by repeated chromatography followed by recrystallization from chloroform and methanol giving the pure target compounds as a green powder (14.7mg, 35.4%). 1H NMR (400MHz, [D6](CD3)2SO): 8.19 (d, 2H, J=8.00Hz), 8.06-8.00 (m, 6H, J=8.00Hz), 7.88 (d, 2H, J=8.00Hz), 7.67 (t, 2H, J=8.00Hz), 7.51 (t, 2H, J=8.00Hz), 7.37-7.32 (m, 4H, J=8.00Hz), 7.01 (d, 2H, J=8.00Hz). UV-Vis (CHCl3): λmax/nm (logε)=294 (4.57), 322 (4.43), 371 (3.97). MALDI-TOF MS: an isotopic cluster peaking at m/z 480.0, Calcd. for C36H20N2, [M]+ 480.2. Anal. Calcd. for C36H20N2·0.25CH2Cl2: C, 86.77; H, 4.12; N, 5.58. found: C, 86.42; H, 4.48; N, 5.62.
  • 73
  • [ 6217-22-7 ]
  • [ 17075-03-5 ]
  • pyrene‐4,5‐diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; barium carbonate / ethanol / 120 h / Inert atmosphere; Reflux 2: hydrazine hydrate; palladium 10% on activated carbon / water; ethanol / 48 h / Reflux
  • 74
  • [ 100-52-7 ]
  • [ 106-40-1 ]
  • [ 6217-22-7 ]
  • 9-(4-bromophenyl)-10-phenyl-9H-pyreno[4,5-d]imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ammonium acetate; at 120℃; for 3h;Inert atmosphere; (2) 4,5-pyrene diquinone (2.32 g, 10 mmol)4-bromoaniline (8.60 g),Benzaldehyde (3.18 g) and ammonium acetate (3.85 g) in a 250 mL round bottom flask,Under nitrogen protection,120 C for 3 hours.And then adding distilled water to the reaction system,Filter to obtain thick crude products,10- (4-bromo) -9-hydrogen-pyrene imidazole was isolated by column chromatography.
  • 75
  • [ 12126-50-0 ]
  • bis(pentafluorophenyl)zinc toluene monosolvate [ No CAS ]
  • [ 6217-22-7 ]
  • C28H8F10O2Zn(1-)*C20H30Fe(1+) [ No CAS ]
  • 76
  • [ 1122-58-3 ]
  • C28H8F10O2Zn(1-)*C20H30Fe(1+) [ No CAS ]
  • [ 12126-50-0 ]
  • 2C7H10N2*2C6F5(1-)*Zn(2+) [ No CAS ]
  • [ 6217-22-7 ]
  • 77
  • [ 3029-19-4 ]
  • [ 62-53-3 ]
  • [ 6217-22-7 ]
  • 9-phenyl-10-(1-pyrenyl)-9H-pyreno[4,5-d]imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With ammonium acetate; acetic acid; at 20 - 120℃; for 14h;Inert atmosphere; 1-pyrenal(0.58 g, 2.5 mmol), <strong>[6217-22-7]pyrene-4,5-dione</strong>(0.71 g, 3.0 mmol), aniline (1.16 g, 12.5 mmol), ammonium acetate (1.19 g, 10.2mmol), dissolved in 20ml of acetic acid solvent and transferred to a 100ml round bottom flask. After degassing once, nitrogen is used for protection. The gas was shielded, and the mixture was stirred and refluxed at a temperature of 120C for two hours. After the reaction was completed, the mixture was stirred at 20C for 12 hours. Buchner funnel Filter, rinse with a small amount of acetic acid (volume ratio 1:1), filter, and spin down the filtrate through a reduced pressure rotary evaporator. A dark brown solid was obtained, which was purified by column chromatography and washed with a solvent of petroleum ether:methylene chloride = 1:1 by volume. Remove agent. A pale yellow solid (0.56 g) was finally obtained, which was further sublimed and purified using a chemical vapor deposition system. The sublimation temperature was 350. C, 0.40 g of pale yellow target was obtained with a yield of 44%.
  • 78
  • 2,7-di-tert-butyl-9,14-diphenyldibenzo[de,qr]tetracene-11,12-diamine [ No CAS ]
  • [ 6217-22-7 ]
  • 13,18-di-tert-butyl-11,20-diphenylbenzo[8,9]triphenyleno[2,3-i]phenanthro [4,5-abc]phenazine [ No CAS ]
  • 79
  • [ 143-15-7 ]
  • [ 6217-22-7 ]
  • 4,5-bis(dodecyloxy)pyrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% General procedure: The pyrene-4,5,9,10-tetra (10 mmol) obtained in 1A-1 was dissolved in distilled water (10 mmol) with bromotetrabutylammonium (Bu4NBr) (13 mmol) and sodium hydrosulfite (Na2S2O4) (50 ml) and tetrahydrofuran (THF) and refluxed at 65 C for 5 minutes. An aqueous solution prepared by dissolving bromododecyl (60 mmol) and KOH (306 mmol) in distilled water (50 ml) was added to the reaction solution and refluxed at 65 C for 16 hours to obtain 4,5,9,10-tetra Keto (dideoxy) -pyrrole (R = C12H25, compound 11 in Reaction Scheme 5) (yield: 72%).
  • 80
  • 6-bromo-pyrene-1-carbaldehyde [ No CAS ]
  • [ 62-53-3 ]
  • [ 6217-22-7 ]
  • C39H21BrN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With ammonium acetate; acetic acid; for 2h;Reflux; Under a nitrogen atmosphere, to a mixture of 6-bromoindole-1-carbaldehyde (2.6 g, 8.6 mmol), indole-4,5-dione (2.3 g, 9.9 mmol), aniline (3.4 g, 42.9 mmol) Ammonium acetate (2.59 g, 33.6 mmol) and acetic acid (60 mL) were added.Heat to reflux.After 2 hours, the mixture was cooled and filtered.The filter cake is dissolved in chloroform, and then concentrated by column chromatography to obtain intermediate 1(3.8 g, yield 75%).
  • 82
  • 4-(9,9-dihexyl-9H-fluoren-2-yl)benzaldehyde [ No CAS ]
  • [ 62-53-3 ]
  • [ 6217-22-7 ]
  • C54H50N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With ammonium acetate; acetic acid; at 120℃; for 2h;Reflux; Inert atmosphere; At 120 C Under nitrogen protection, 4-(9,9-dihexylfluoren-2-yl)benzaldehyde(0.3 g, 0.683 mmol), <strong>[6217-22-7]pyrene-4,5-dione</strong>(0.16 g, 0.683 mmol), aniline (0.29, 3.07 mmol),Ammonium acetate (0.21 g, 2.73 mmol) and acetic acid (5.46 mL, 5.74 g, 95.58 mmol) were mixed, and the mixture was stirred under reflux for 2 hours. Extract with dichloromethane. Distilled under reduced pressure to give a black solid, using silica gel as a stationary phase, petroleum ether / ethyl acetate as eluent,0.28 g of a white powder (yield 56%) was obtained by column chromatography. The reaction equation is as follows:
  • 83
  • [ 129-00-0 ]
  • [ 4371-27-1 ]
  • 9,10-dioxodihydrophenanthrene-4,5-dialdehyde [ No CAS ]
  • [ 6217-22-7 ]
  • 6,6’-diformylbiphenyl-2,2’dicarboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 27% 2: 15% 3: 19% 4: 35% With ruthenium trichloride; sodium periodate In dichloromethane; water; acetonitrile at 34.84℃; for 4h;
  • 84
  • C42H31NO [ No CAS ]
  • [ 62-53-3 ]
  • [ 6217-22-7 ]
  • C63H47N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With ammonium acetate; acetic acid; for 24h;Inert atmosphere; Reflux; Under nitrogen protection, The reactor was charged with hydrazine (3.48 g, 15 mmol), intermediate 236-3 (5.66 g, 10 mmol), aniline (2.24 g, 12 mmol), Ammonium acetate (0.75g, 100mmol), glacial acetic acid 100mL, reflux reaction for 24h, cooled to room temperature, the reaction was poured into a methanol solution, stirred, separated, filtered, washed, dried to give compound 236 (6.15g, 72%).
  • 85
  • Triallylborane [ No CAS ]
  • [ 6217-22-7 ]
  • 4,5-diallyl-4,5-dihydropyrene-4,5-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
In diethyl ether; at 0 - 22℃; for 0.5h;Inert atmosphere; General procedure: To the stirred solution of 2,4,6-triisopropoxy-1,3,5,2,4,6-trioxatriborinane (1) (383 mg, 1.49 mmol)in anhydrous Et2O (20 mL) under argon at 0 C, a solution of allylmagnesium bromide (1.2 M in Et2O,10 mL, 12 mmol) was added over 5 min. Formation of white precipitate was observed. Next, themixture was warmed up to 22 C. After 15 min this mixture was cooled down to 0 C and quinone 3(3.00 mmol) was added. Next, the reaction mixture was warmed up to 22 C and after 30 min againcooled down to 0 C and saturated solution of NH4Claq (100 mL) was added. The product wasextracted with ethyl acetate (3 × 25 mL) and isolated by column chromatography.
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 6217-22-7 ]

Aryls

Chemical Structure| 3457-41-8

[ 3457-41-8 ]

1,2-Di(naphthalen-1-yl)ethane-1,2-dione

Similarity: 0.97

Chemical Structure| 1334510-66-5

[ 1334510-66-5 ]

Cyclopenta[fg]tetracene-1,2-dione

Similarity: 0.94

Chemical Structure| 6373-11-1

[ 6373-11-1 ]

Aceanthrylene-1,2-dione

Similarity: 0.94

Chemical Structure| 3457-41-8

[ 3457-41-8 ]

1,2-Di(naphthalen-1-yl)ethane-1,2-dione

Similarity: 0.97

Chemical Structure| 6373-11-1

[ 6373-11-1 ]

Aceanthrylene-1,2-dione

Similarity: 0.94

Ketones

Chemical Structure| 3457-41-8

[ 3457-41-8 ]

1,2-Di(naphthalen-1-yl)ethane-1,2-dione

Similarity: 0.97

Chemical Structure| 1334510-66-5

[ 1334510-66-5 ]

Cyclopenta[fg]tetracene-1,2-dione

Similarity: 0.94

Chemical Structure| 6373-11-1

[ 6373-11-1 ]

Aceanthrylene-1,2-dione

Similarity: 0.94

Chemical Structure| 3457-41-8

[ 3457-41-8 ]

1,2-Di(naphthalen-1-yl)ethane-1,2-dione

Similarity: 0.97

Chemical Structure| 6373-11-1

[ 6373-11-1 ]

Aceanthrylene-1,2-dione

Similarity: 0.94