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CAS No. : | 3029-32-1 | MDL No. : | MFCD00003709 |
Formula : | C22H12O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UFCVADNIXDUEFZ-UHFFFAOYSA-N |
M.W : | 308.33 | Pubchem ID : | 76415 |
Synonyms : |
|
Num. heavy atoms : | 24 |
Num. arom. heavy atoms : | 20 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 94.76 |
TPSA : | 34.14 Ų |
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) : | -4.37 cm/s |
Log Po/w (iLOGP) : | 2.75 |
Log Po/w (XLOGP3) : | 5.37 |
Log Po/w (WLOGP) : | 4.77 |
Log Po/w (MLOGP) : | 3.39 |
Log Po/w (SILICOS-IT) : | 5.59 |
Consensus Log Po/w : | 4.37 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -5.75 |
Solubility : | 0.000547 mg/ml ; 0.00000177 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -5.84 |
Solubility : | 0.000445 mg/ml ; 0.00000144 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -8.58 |
Solubility : | 0.000000813 mg/ml ; 0.0000000026 mol/l |
Class : | Poorly soluble |
PAINS : | 1.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.49 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With sodium hydroxide; ethanol; water; at 28 - 47℃; for 4h; | Preparatory Example 1; Preparation of pentacene-6,13-dione.; A solution of 62.7 grams (0.559 mmoles, 1.0 equivalents) of cyclohexan-1,4-dione and 150 grams of o-phthalaldehyde (1.12 mmoles, 2.0 equivalents) in 2000 mL of ethanol was heat to 28 C. To this solution was added 220 mL of a 1M aqueous solution of sodium hydroxide. The reaction temperature increased to 47 C. during the addition. The mixture was then heated at 40 C. for 4 hours. The mixture was cooled and a yellow solid precipitate was collected. The solid was stirred in 2000 mL of N,N-dimethylformamide and heated to 50 C. for 2 hours. The mixture was cooled to room temperature (i.e., 20 C. to 25 C.) and the yellow solid was collected and washed with N,N-dimethylformamide, then with acetone and dried to give 108.3 grams (62 mole percent yield) of a bright yellow solid. |
With potassium hydroxide; In ethanol; at 0 - 60℃; for 2h; | A mixture of 1,4- cyclohexanedione (33.0 mmol) and potassium hydroxide (132 mmol) were dissolved in ethanol and solution was cooled to 0 C. Then o-phthalaldehyde (66.0 mmol) was added to the solution. The reaction mixture was stirred for 1 h at 0 C, and for an additional 1 h refluxed at 60 C. The product was filtered and washed thoroughly with water and ethanol [34] (Fig. 3). H |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | In tetrahydrofuran; for 1h;Inert atmosphere; Reflux; | To a suspension of <strong>[3029-32-1]6,13-pentacenedione</strong> (0.62 g,2.0 mmol) in 40 mL of anhydrous THF was added 6.0 mLof a solution of thiophen-2-yl-magnesium bromide(1.0 M in THF, 6.0 mmol) under a nitrogen atmosphere atroom temperature. After the suspension was dissolved,the resulting solution was refluxed with stirring for 1 h.The solution was then cooled to room temperature andpoured into saturated NH4Cl aqueous solution. The organiclayer was separated and the aqueous layer was furtherextracted with diethyl ether. The organic layers were combined,dried with anhydrous MgSO4, and concentratedunder reduced pressure. The product was purified bycolumn chromatography on silica gel with an eluent ofCH2Cl2:hexane (3:2) to afford 1a (Yield: 57%). 1H NMR(CDCl3, ppm): d 3.50 (s, 2H), 5.77 (dd, J1 = 3.8 Hz,J2 = 1.0 Hz, 2H), 6,25 (dd, J1 = 5.0 Hz, J2 = 3.8 Hz, 2H), 6.84(dd, J1 = 5.0 Hz, J2 = 1.0 Hz, 2H), 7.60 (dd, J1 = 6.3 Hz,J2 = 3.4 Hz, 4H), 7.90 (dd, J1 = 6.3 Hz, J2 = 3.4 Hz, 4H), 8.38(s, 4H). 13C NMR (CDCl3, ppm) d 73.0, 125.1, 126.7, 127.1,127.5, 127.9, 128.8, 138.6, 140.9, 155.0 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With sulfur tetrafluoride; hydrogen fluoride; at -78 - 100℃; under 13501.4 Torr; for 6h; | Example 9 Synthesis of 6,6,13,13-tetrafluoro-6,13-dihydropentacene (15) Pentacen-6,13-dione (14) (2 g, 6.49 mmol) was introduced into a 100-mL SUS autoclave; the vessel was cooled to -78 C.; and hydrogen fluoride (32 g) and then sulfur tetrafluoride (5.6 g, 51.7 mmol) were added. Heating was thereafter carried out to 100 C. with the reaction vessel sealed. The pressure in the reaction vessel reached 1.8 MPa (gauge pressure) at this time. After reaction for 6 hours, the reaction vessel was slowly cooled to room temperature and the low-boiling compounds were gradually discarded into a detoxification apparatus. Nitrogen was introduced into the vessel when the internal pressure reached ambient pressure and the residual hydrogen fluoride was completely eliminated. The reaction product was then extracted with 800 mL hot chlorobenzene, and the crude product mixture obtained by concentrating the filtrate was purified by silica gel column chromatography (developing solvent: chlorobenzene) to give 1.0 g (2.89 mmol, 40% yield) 6,6,13,13-tetrafluoro-6,13-dihydropentacene (15). 1H NMR (200 MHz, solvent: CDCl3, reference: Me4Si). delta8.55 (s, 4H) 8.11-8.06 (m, 4H) 7.74-7.68 (m, 4H). 19F NMR (188 MHz, solvent: CDCl3, reference: CFCl3). delta -83.1 (s, 4F). mass analysis (MS m/z): 352 (M+, 100). elemental analysis calculated for C22H12F4: C, 74.86; H, 3.85. found: C, 83.91; H, 3.42. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfur tetrafluoride; hydrogen fluoride; at -78 - 70℃; under 8250.83 Torr; for 6h; | Example 10 Synthesis of 6,6,13,13-tetrafluoro-6,13-dihydropentacene (15) Pentacen-6,13-dione (14) (2 g, 6.49 mmol) was introduced into a 100-mL SUS autoclave; the vessel was cooled to -78 C.; and hydrogen fluoride (32 g) and then sulfur tetrafluoride (7.2 g, 66.5 mmol) were added. Heating was thereafter carried out to 70 C. with the reaction vessel sealed. The pressure in the reaction vessel reached 1.1 MPa (gauge pressure) at this time. After reaction for 6 hours, the reaction vessel was slowly cooled to room temperature and the low-boiling compounds were gradually discarded into a detoxification apparatus. Nitrogen was introduced into the vessel when the internal pressure reached ambient pressure and the residual hydrogen fluoride was completely eliminated, yielding 1.99 g of a mixture of 6,6,13,13-tetrafluoro-6,13-dihydropentacene (15) and 13,13-difluoro-13H-pentacen-6-one (19) ((15):(19)=1:3 (weight ratio)). (19) 1H NMR (200 MHz, solvent: CDCl3, reference: Me4Si). delta 8.98 (s, 2H) 8.6 (s, 2H) 8.18-8.05 (m, 4H) 7.78-7.68 (m, 4H). 19F NMR (188 MHz, solvent: CDCl3, reference: CFCl3). delta -75.2 (s, 2F). mass analysis (MS m/z): 330 (M+, 100). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With methanol; sodium tetrahydroborate; at 0 - 20℃; for 1.5h;Inert atmosphere; | trans-6,13-Dihydroxy-6,13-dihydropentacene To a suspension of <strong>[3029-32-1]6,13-<strong>[3029-32-1]pentacenequinone</strong></strong> (1.0 g, 3.24 mmol) in dry MeOH (40 mL) at 0 C. under an argon atmosphere was slowly added NaBH4 (1.22 g, 32.46 mmol). The reaction mixture was stirred at 0 C. for 0.5 h and at RT for 1 h, and then quenched with H2O at 0 C. The resulting mixture was filtered and washed with H2O. The resulting solid was taken up in CHCl3, then filtered and washed with CHCl3, and dried in vacuo to give product as an off-white solid (0.92 g, 91%): mp 235 C. 1H NMR (500 MHz, DMSO-d6): delta 8.12 (s, 4H), 7.95 (m, 4H), 7.48 (m, 4H), 6.63 (s, 2H), 5.81 (s, 2H). 13C NMR (125.68 MHz, DMSO-d6): delta 138.19, 131.67, 127.47, 125.44, 120.91, 66.98. LDI-MS m/z: 312 [M+], 296 [M+-OH], 280 [M+-2(OH)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | To a solution of triisopropylsilylacetylene (3 mL, 13.6 mmol) in dry THF (50 mL), under argon and cooled to 0 C, was added dropwise butyl lithium (2.5 M in hexanes, 5.45 mL, 13.6 mmol). The solution was allowed to stir for 10 min before being transferred slowly via cannula into a suspension of <strong>[3029-32-1]6,13-<strong>[3029-32-1]pentacenequinone</strong></strong> (7 g, 22.7 mmol) in dry THF (200 mL) at rt. The reaction mixture was stirred overnight. The reaction was quenched with ice water. The suspension was filtered and the solid was washed with 1:1 THF/water (50 mL), then THF (50 mL). This allowed for the recovery of the excess <strong>[3029-32-1]6,13-<strong>[3029-32-1]pentacenequinone</strong></strong>, which could be used in subsequent reactions after drying under high vacuum). The filtrate was collected into a round bottom flask and acidified with 2M HCl, and this mixture was extracted with DCM (2 x 100 mL), the organic phase was washed with sat. aq. NaCl (50 mL), dried (MgSO4), and the solvent removed in vacuo to obtain an orange solid residue. This solid was redissolved in boiling DCM (100 mL) and precipitated by adding hexanes and cooling. The beige coloured solid was collected by vacuum filtration and washed with hexanes. The solid was redissolved in acetone (50 mL) and filtered to remove traces of insoluble impurities. The solvent of the filtrate was removed in vacuo to afford 6'-(triisopropylsilylethynyl)-6-hydroxy-13-<strong>[3029-32-1]pentacenequinone</strong> (5.65 g, 85%) as a beige solid. 1H NMR (400 MHz, CDCl3) delta 8.85 (s, 2H), 8.77 (s, 2H), 8.06 (d, J = 7.8, 2H), 7.97 (d, J = 8.1, 2H), 7.67 (t, J = 7.0, 2H), 7.61 (t, J = 6.9, 2H), 3.10 (s, 1H), 1.21 (m, 21H). 13C NMR (101 MHz, CDCl3) delta 185.43, 138.68, 135.65, 132.87, 129.86, 129.76, 128.99, 128.59, 128.30, 127.44, 127.35, 108.16, 90.26, 68.76, 18.73, 11.31. MS (ESI): m/z 588.8513. M.P. = 215 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With sodium iodide; In N,N-dimethyl-formamide; at 120℃; | 6,13-Pentacenequinone To a clear solution of alpha,alpha,alpha',alpha'-tetrabromo-o-xylene (30.5 g, 0.073 mol) in DMF (100 mL) was added benzoquinone (3.125 g, 0.03 mol) and sodium iodide (27.25 g, 0.18 mol). The resulting brown suspension was heated and stirred at 120 C. overnight. After cooling to RT, the yellow solids were filtered via vacuum filtration. The yellow solids were washed with water, saturated sodium bisulfite solution and dried to yield the product (8.1 g, 91%). 1H NMR (500 MHz, CDCl3): delta 8.96 (s, 4H), 8.14 (m, 4H), 7.72 (m, 4H). 13C NMR (125.68 MHz, CDCl3): delta 183.2, 135.47, 130.80, 130.30, 129.98, 129.66. m/z: 308 [M+]. |
91% | With sodium iodide; In N,N-dimethyl-formamide; at 120℃;Inert atmosphere; | To a clear solution of alpha,alpha,alpha?,alpha?-tetrabromo-o-xylene (30.5 g, 0.073 mol) in DMF (100 mL) was added benzoquinone (3.125 g, 0.03 mol) and sodium iodide (27.25 g, 0.18 mol). The resulting brown suspension was heated and stirred at 120 C. overnight. After cooling to RT, the yellow solids were filtered via vacuum filtration. The yellow solids were washed with water, saturated sodium bisulfite solution and dried to yield the product (8.1 g, 91%). 1H NMR (500 MHz, CDCl3): delta 8.96 (s, 4H), 8.14 (m, 4H), 7.72 (m, 4H). 13C NMR (125.68 MHz, CDCl3): delta 183.2, 135.47, 130.80, 130.30, 129.98, 129.66. m/z: 308 [W]. |
28% | A 500 ml three-necked round-bottom flask (previously cleaned)equipped with stirring bar and argon atmosphere was used todissolve 0.52 g (4.81 mmol) of p-benzoquinone in 150 ml anhydrousDMF. The reaction mixture was stirred at 200 rpm until ahomogeneous solution was achieved. After setting heating bath to70 C in a hotplate, 2.88 g of NaI (19.24 mmol) was added to thereaction flask and the mixture was stirred for 2 h. Next, 4.057 g(9.62 mmol) of TBOX were added and the reaction was continuedfor 18 h. The reaction mixturewas cooled to room temperature and50 ml of ice cold water were added to the reaction. The content wasslowly transferred to a Coors Buchner funnel equipped with aWhatman filter paper 1 and rinsed with 0.5 M sodium sulfite andDMF. A bright yellow solid is obtained and dried in an oven at40 kPa and 25 C for 24 h. The obtained yield was 28%, 1H-RMN(300 MHz, TDF delta = ppm): 8.99 (s, 2H), 8.14 (m, 4H), 7.75 (m, 4H),7.28 (s, 4H). |
Tags: 3029-32-1 synthesis path| 3029-32-1 SDS| 3029-32-1 COA| 3029-32-1 purity| 3029-32-1 application| 3029-32-1 NMR| 3029-32-1 COA| 3029-32-1 structure
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