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CAS No. : | 3274-56-4 | MDL No. : | MFCD00958534 |
Formula : | C16H13N | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FSBPQTRUHOMNPG-UHFFFAOYSA-N |
M.W : | 219.28 | Pubchem ID : | 76761 |
Synonyms : |
|
Num. heavy atoms : | 17 |
Num. arom. heavy atoms : | 17 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 71.66 |
TPSA : | 15.79 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.8 cm/s |
Log Po/w (iLOGP) : | 2.49 |
Log Po/w (XLOGP3) : | 4.0 |
Log Po/w (WLOGP) : | 4.35 |
Log Po/w (MLOGP) : | 3.26 |
Log Po/w (SILICOS-IT) : | 4.68 |
Consensus Log Po/w : | 3.75 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.33 |
Solubility : | 0.0103 mg/ml ; 0.000047 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.03 |
Solubility : | 0.0203 mg/ml ; 0.0000926 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -6.65 |
Solubility : | 0.0000493 mg/ml ; 0.000000225 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 2.3 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H317 | 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 |
---|---|---|
98% | With morpholine; sulfur; ammonium acetate; In neat (no solvent); at 80℃; for 0.5h; | General procedure: A mixture of 4-nitro-1,3-diphenylbutan-1-one (1a, 1 mmol),sulfur (3 mmol), morpholine (3 mmol), and NH4OAc (6 mmol)within a 5 mL round-bottomed flask was magnetically stirred ina silicone oil bath at 80 C for 30 min. Progress of the reaction was followed by TLC monitoring. Then the reaction mixture wascooled to ambient temperature, H2O (2.5 mL) was added, andthe product was extracted into CH2Cl2 (2 × 2.5 mL). The organiclayer was dried over Na2SO4, filtered, the solvent was removed,and the residue was purified by crystallization from EtOAc. 2,4-Diphenyl-1H-pyrrole (3a) Colorless crystals, mp 176-177 C, yield 0.214 g, 98%. IR (KBr):3435 (NH), 1598, 1481, 1451, 1411, 1258, 1185, 1157, 1129,1075, 1030, 903, 807, 746, 688 cm-1. 1H NMR (300.1 MHz,DMSO-d6): d = 6.96 (1 H, s, CH), 7.13 (1 H, t, J = 7.5 Hz, CH), 7.18(1 H, t, J = 7.5 Hz, CH), 7.32 (2 H, t, J = 7.5 Hz, 2 × CH), 7.35 (1 H,s, CH), 7.37 (2 H, t, J = 7.6 Hz, 2 × CH), 7.61 (2 H, d, J = 7.5 Hz, 2 ×CH), 7.69 (2 H, d, J = 7.5 Hz, 2 × CH), 11.45 (1 H, br s, NH). 13CNMR (75.5 MHz, DMSO-d6): d = 103.7 (C3H), 117.1 (C5H), 123.9(2 × CH), 124.9 (2 × CH), 125.2 (C4), 125.5 and 126.2 (2 × CH),129.0 (2 × CH), 129.2 (2 × CH), 132.7 and 133.1 (2 × C) 136.2(C2). MS: m/z (%) = 219 (100) [M+], 191 (37), 165 (15), 115 (38),110 (13), 102 (10), 95 (6), 89 (11), 77 (10), 63 (10), 51 (11). HRMS (ES+): m/z calcd for C16H14N [M + H]+: 220.1126; found:220.1124. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
<strong>[3274-56-4]3,5-diphenylpyrrole</strong>-2-carboxaldehyde was prepared from <strong>[3274-56-4]2,4-diphenylpyrrole</strong> by the Vilsmeyer Haak formylation. 2,4-Diphenylpyrrole was prepared as described in C. F. H. Allen et al., ORG. SYNTH. COLL. Vol. III, p. 33. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With trichlorophosphate; In dichloromethane; for 16h;Inert atmosphere; | To a flame-dried 5mL microwave vial equipped with a magnetic stir bar was added anhydrous CH2Cl2 (1 mL), POCl3 (98 mL,1.05 mmol, 1.05 equiv), and anhydrous DMF (92 mL, 1.2 mmol, 1.2equiv). After stirring for 5 min, a solution of <strong>[3274-56-4]2,4-diphenylpyrrole</strong> (219 mg, 1.0 mmol 1.0 equiv) in CH2Cl2 (3 mL) was transferred by syringe to this flask. After stirring for 16 h, the reaction was concentrated first under a stream of nitrogen and then underreduced pressure. When no solvent remained, the flask was backfilled with nitrogen and then the gas line adapter was quickly replaced with a rubber septum and a balloon of nitrogen. To this flask was added THF (2 mL) and 3M NaOH (aq) (2 mL). This biphasic mixture was stirred vigorously for 30-60 min. To the flask was added H2O (5 mL) and Et2O (5 mL). The organic layer was separated,and the aqueous layer was extracted with Et2O (3 50 mL). The combined organic layers were washed with water (1 100 mL) and brine (1 100 mL). The combined organic layers were then dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure by rotary evaporation. Purification by flash column chromatography on silica gel (hexanes/Et2O 100:0 to 70:30) afforded the title compound (132 mg, 53%) as a pink solid. Rf: 0.39 (hexanes:Et2O 1:1) 1H NMR (600 MHz, CDCl3): d 9.65 (s, 1H), 9.49 (brs, 1H), 7.65 (d, J 8.4 Hz, 2H), 7.55 (d, J 8.2 Hz, 2H), 7.47 (at,J 7.6 Hz, 4H), 7.43e7.35 (m, 2H), 6.74 (dd, J 2.9, 1.2 Hz, 1H). 13CNMR (151 MHz, CDCl3): d 179.3, 138.7, 138.1, 133.4, 130.4, 129.2,129.2, 129.1, 128.8, 128.8, 123.0, 125.2, 109.0. IR (cm1): 3282, 1640,1467, 1449, 1260, 1078, 1008, 813, 758, 699, 685, 667, 486. ESI-MS(m/z): [MH] calc'd for C17H14NO: 248.1; found: 248.1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | Procedure B:Pyrrole derivative (0.1 mmol) was dissolved in acetic acid (1 ml) by heating, the mixture was quickly cooled down in a water bath (about 10 C), NaNO2 (0.1 mmol) was added with stirring, stirred for 10 minutes, warmed to room temperature, followed by addition of acetic anhydride (0.4 ml). The second pyrrole moiety (0.1 mmol) was added in one portion, stirred for 30 minutes at ambient temperature followed by heating at 80 0C for 10 minutes. The reaction mixture was cooled down, quenched with crushed ice, neutralized with aqueous sodium carbonate, and extracted with dichloromethane. The organic solution was filtered through a pad of silica gel, washed with dichloromethane. After removal of solvent, the resulted solid was used for the next step without further purification. EPO <DP n="17"/>.Procedure D:The solid of crude azadipyrromethene was added 1,2-dichloromethane (3 ml) dried over molecular sieves (3 A) and Hunig's amine (~5 eq). Boron trifluoride diethyl ether (~4.5 eq) was added dropwise with stirring at room temperature. The mixture was stirred for 5 minutes, followed by heating at 80 0C for 10 minutes. The complex formation reaction was monitored by UV spectroscopy. More Hnig's amine and Boron trifluoride diethyl ether may be required until UV spectra indicated complete conversion. The mixture was cooled down, quenched with water. Organic laser was separated, aqueous layer was extracted with dichloromethane. The combined organic solution was filtrated through a pad of alumina (activity III). Solvent was removed, the residue was digested with dichloromethane/hexane mixture, and recrystalized from dichloromethane/hexane. The mother liquid was purified by chromatography on alumina (activity III) and recrystalized from dichloromethane/hexane.Compound 4; The general procedures B and D were followed, starting from 7 -methoxy-3 -phenyl - 4,5-dihydro-lH-Benz[g]indole, then with 2,4-diphenyl-lH-pyrrole, 28.2 mg coppery crystal was obtained (52%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | General procedure: Under N2, to a stirred solution of 6a (66.5 mg, 0.44 mmol) and 2,4-dimethylpyrrole (45.0 muL, 0.44 mmol) in CH2Cl2 (5 mL) was added POCl3 (40.0 muL, 0.44 mmol) at 0 C. When TLC analysis showed the reaction was over, Et3N (0.61 mL, 4.4 mmol) was added at 0 C and stirred for 10 min. BF3·OEt2 (0.56 mL, 4.4 mmol) was added to the mixture. The reaction mixture was stirred for 12 h at room temperature, quenched with saturated aqueous NaHCO3, extracted with CH2Cl2, washed with brine, dried over Na2SO4, and purified by chromatography column (CH2Cl2/n-hexane=1:1) to afford BODIPY 8a as coppery solid (69.9 mg, 58%). 1H NMR (400 MHz, CDCl3) delta 7.51 (d, J=5.2 Hz, 1H), 7.20 (s, 1H), 7.14 (d, J=5.2 Hz, 1H), 6.97 (s, 1H), 6.18 (s, 1H), 2.62 (s, 3H), 2.27 (s, 3H); 13C NMR (100 MHz, CDCl3) delta 162.3, 155.7, 145.4, 137.7, 136.9, 124.6, 121.7, 116.7, 113.4, 46.8, 15.3, 11.4, 8.6; HRMS-MALDI (m/z): [M]+ calcd for C13H11BF2N2S: 276.0710; found: 276.0709. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22% | General procedure: Under N2, to a stirred solution of 6a (66.5 mg, 0.44 mmol) and 2,4-dimethylpyrrole (45.0 muL, 0.44 mmol) in CH2Cl2 (5 mL) was added POCl3 (40.0 muL, 0.44 mmol) at 0 C. When TLC analysis showed the reaction was over, Et3N (0.61 mL, 4.4 mmol) was added at 0 C and stirred for 10 min. BF3·OEt2 (0.56 mL, 4.4 mmol) was added to the mixture. The reaction mixture was stirred for 12 h at room temperature, quenched with saturated aqueous NaHCO3, extracted with CH2Cl2, washed with brine, dried over Na2SO4, and purified by chromatography column (CH2Cl2/n-hexane=1:1) to afford BODIPY 8a as coppery solid (69.9 mg, 58%). 1H NMR (400 MHz, CDCl3) delta 7.51 (d, J=5.2 Hz, 1H), 7.20 (s, 1H), 7.14 (d, J=5.2 Hz, 1H), 6.97 (s, 1H), 6.18 (s, 1H), 2.62 (s, 3H), 2.27 (s, 3H); 13C NMR (100 MHz, CDCl3) delta 162.3, 155.7, 145.4, 137.7, 136.9, 124.6, 121.7, 116.7, 113.4, 46.8, 15.3, 11.4, 8.6; HRMS-MALDI (m/z): [M]+ calcd for C13H11BF2N2S: 276.0710; found: 276.0709. |
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