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CAS No. : | 38215-38-2 | MDL No. : | MFCD00458964 |
Formula : | C16H10 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MXJJMQSKDPNPSX-UHFFFAOYSA-N |
M.W : | 202.25 | Pubchem ID : | 10013083 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 67.75 |
TPSA : | 0.0 Ų |
GI absorption : | Low |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.09 cm/s |
Log Po/w (iLOGP) : | 3.1 |
Log Po/w (XLOGP3) : | 4.85 |
Log Po/w (WLOGP) : | 3.48 |
Log Po/w (MLOGP) : | 5.67 |
Log Po/w (SILICOS-IT) : | 4.9 |
Consensus Log Po/w : | 4.4 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.64 |
Solubility : | 0.00465 mg/ml ; 0.000023 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.58 |
Solubility : | 0.00527 mg/ml ; 0.0000261 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -5.08 |
Solubility : | 0.00166 mg/ml ; 0.00000822 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 2.14 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
141 mg | With water; potassium hydroxide; In ethanol; at 20℃; for 24h; | To the solution of crude silylated product (347 mg, 1.0 mmol) in ethanol (50 mL), aqueous 1 M-KOH (20 mL) was added and stirred for 24 h at room temperature. After removing ethanol from the mixture by evaporation, water was added and formed precipitate was extracted by chloroform. The solvent of the organic layer was removed under reduced pressure, and residue was purified by silica gel chromatography (ethyl acetate/hexane = 75/25). 4,4’-Diethynylbiphenyl (4c) was obtained in 70% yield (141 mg). 1H-NMR(400MHz, DMSO-d6) d = 4.30 (s, 2H, -CCH), 7.58 (d, J = 8.4 Hz, 4H, o-H-Ar-CCH), 7.73 (d, J = 8.5 Hz, 4H, m-H-Ar-CCH) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetone; | Example 9 Hydrogenation was effected as in Example 1, except that 0.50 g <strong>[38215-38-2]4,4'-diethynylbiphenyl</strong>, 7.5 g acetone and 50 mg of 5 % Pd-CaCO3(Acros Chemicals) were introduced into the three-necked flask. The amount of hydrogen required for semi-hydrogenation was 112 ml. Yield of 4,4'-diethenylbiphenyl; 99 % (MS: m/e = 206 (M+), 178, 165, 152, 128, 103, 89, 76, 51). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | In methanol; dichloromethane; water; | 4,4'-Bis(trimethylsilylethynyl)biphenyl (1.04 g, 2.99 mmol) was dissolved in dichloromethane (15 ml) and methanol (15 ml). Aqueous potassium hydroxide (1M, 3 ml) was added dropwise with stirring. The mixture was stirred at room temperature for 2.5 h. The organic solvent was removed under reduced pressure. Water (25 ml) was added and the mixture was extracted with ether (3x30 ml). The combined ether extracts were dried (MgSO4), decolourised with activated charcoal and the solvent was removed under reduced pressure to yield 4,4'-diethynylbiphenyl (562 mg, 93%) as a white solid which was used immediately without further purification, m.p. 167-169 C. 1H n.m.r. (200 MHz, CDCl3) δ 7.57, s, 8H, 2xC6H4; 3.15, s, 2H, acetylenic H. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In acetonitrile; at 40℃; for 1h;Product distribution / selectivity; | 3-Effect of the Nature of Alkyne:; In order to generalize this methodology the coupling of the supported aryl halide 6b with various functionalized or non-functionalized alkynes was carried out. These different reactions were monitored with proton NMR. FIG. 7 shows the simplicity and the ease of interpretation of such spectra. The results obtained by varying the alkynes are shown in Table 15. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine; In tetrahydrofuran; at 50℃; for 12h;Inert atmosphere; | General procedure: Following the Sonogashira coupling procedure, 4-((5'-iodo-[2,2'-bithiophen]-5-yl)ethynyl)aniline (1) (5.0 g, 12.3 mmol) was dissolved in dry triethylamine (50 mL) and dry THF (30 mL) under an atmosphere of nitrogen. Copper(I) iodide (47.0 mg, 0.25 mmol), triphenylphosphine (64.5 mg, 0.25 mmol) and dichlorobis(triphenylphosphine)palladium(II) (87.8 mg, 0.12 mmol) were added to the stirred solution. Phenylacetylene (1.25 g, 12.3 mmol) was dropped in and the mixture was heated to 50 C for 12 h. After cooling, the formed precipitate of triethylamine hydroiodide was filtered off and washed with diethyl ether. The combined filtrates were evaporated under reduced pressure, and the crude product was purified by silica column chromatography eluting with petroleum ether/ethyl acetate (V:V = 5:1) to afford compound 2TBEA (3.2 g, 68%) as bright yellow crystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In n-heptane; toluene; at 20℃; for 5h;Inert atmosphere; | General procedure: N,N-diethylamide triethyltin Et2NSnEt3 (0.83 g, 2.98 mmol) dissolved in heptane (5 ml) was added to 4-ethynylbiphenyl (0.51 g,2.86 mmol) in toluene (8 ml). The reaction mixture was kept at room temperature for 5 h, filtered, and the solvent was removed under vacuum and the residue was heated at 70 C under vacuum for 2 h. Compound 5 isolated as a viscous liquid 1.04 g (94%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With tetrakis(triphenylphosphine) palladium(0); triethylamine; In tetrahydrofuran; at 75℃; for 23h;Schlenk technique; | <strong>[29682-15-3]methyl 5-bromopicolinate</strong> (216 mg, 1 mmol) and 4,4?-diethynyl-1,1?-biphenyl (101 mg,0.5 mmol) were introduced in a Schlenk flask containing 8 mL of dry degassed THF. Pd(PPh3)4 (38 mg, 0.033 mmol) and NEt3 (0.2 mL, 1.435 mmol) were then added and the reaction mixture was stirred for 23h. The precipitate was filtered and washed with water and methanol to afford 6a as a white solid (184 mg, 78%). Data for 6a: Anal. Calcd for C30H20N2O4·0.45H2O:C, 74.97; H, 4.38; N, 5.83. Found: C, 74.63; H, 3.94; N, 5.84. 1HNMR (CDCl3): delta = 8.89 (d, J=1.36 Hz, 2H), 8.14 (dd, 3J=8.15 Hz, 5J=0.56 Hz, 2H), 7.96 (dd, 3J=8.13 Hz, 4J=2.05 Hz, 2H), 7.64 (s, 8H), 4.03 (s, 6H)ppm. 13C NMR (CDCl3): delta= 166.37, 153.2, 147.16, 141.88, 140.34, 133.52, 128.24, 125.77, 124.84,122.67, 96.48, 87.48, 53.47 ppm. ESI-TOF MS: m/z 473.15 [M + H]+.Selected IR (KBr, cm-1): 3444.7, 1716.7, 1436.2, 1318.5,1308.5, 1237.9, 1137.5, 1114.6, 823.4, 702.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In toluene; at 110℃; for 24h;Inert atmosphere; | Following the Sonogashira coupling procedure, 4,4′-diethynyl-1,1′-biphenyl (0.15g, 0.75mmol) and DPP-Br (0.90g, 1.50mmol) were dissolved in dry triethylamine (50mL) and dry toluene (50mL) under an atmosphere of nitrogen. Copper(I) iodide (0.15g, 0.75mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.03g, 0.04mmol) were added to the stirred solution. Then the mixture was heated to 110C for 24h by stirring under nitrogen atmosphere. After cooling, the formed precipitate of triethylamine hydroiodide was filtered off and washed with diethyl ether. The combined filtrates were evaporated under reduced pressure, and the crude product was purified by silica column chromatograghy eluting with petroleum ether/dichloromethane (v: v=1: 2) to afford compound Ph2(PDPP)2 (0.24g, 26%) as a dark violet-black solid. FT-IR (KBr, cm-1): v=3084, 2923, 2850, 2193, 1660, 1555, 1513, 1447, 1405, 1372, 1339, 1225, 1097, 1065, 1019, 999, 855, 816, 731, 698; 1H NMR (400MHz, CDCl3, ppm): δ 8.90 (d, J=3.6Hz, 2H), 8.87 (d, J=3.6Hz, 2H), 7.59 (d, J=8.0Hz, 8H), 7.40 (d, J=3.6Hz, 2H), 7.36 (d, J=3.6Hz, 2H), 7.23 (t, J=4.0Hz, 2H), 4.02 (t, J=6.8Hz, 8H), 1.69 (m, 8H), 1.36 (m, 8H), 1.19-1.27 (m, 32H), 0.08-0.86 (m, 12H); 13C NMR (100MHz, CDCl3, ppm): δ 160.76, 160.71, 140.39, 139.97, 139.61, 138.17, 135.84, 134.97, 134.68, 133.53132.58, 131.55, 130.30, 129.27, 128.11, 126.46, 125.70, 121.29, 108.25, 107.52, 96.90, 82.94, 41.81, 31.24, 29.54, 29.42, 29.15, 28.64, 26.37, 22.08, 13.50; Elemental analysis calcd. for C76H86N4O4S4: C, 73.15%; H, 6.95%; N, 4.49%; S, 10.28%. Found: C, 72.77%; H, 7.77%; N, 4.05%; S, 8.09%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In diphenylether; at 260℃; for 8h;Inert atmosphere; | Compound A (2.21 g, 11 mmol), compound B (7.80 g, 22 mmol) and diphenyl ether (100 mL) were added to a 250-mL reaction flask.Nitrogen emptying 3 times, heating up to 260 , to maintain this temperature, the reaction 8 hours,TLC and HPLC detection of compound B complete reaction.During the reaction, the color change of the reaction liquid changed from black to yellow.Reaction after treatment: stop heating, cooling to 20 , adding methanol (100mL), stirring 2h precipitation of solid,The filter cake was washed with methanol and dried in vacuo to give the crude product.The crude product was added with ethyl acetate to give yellow compound 1 (4.32 g, 46% yield,HPLC purity 93.58%).Vacuum sublimation (360 C, 2 x 10-5 torr, 8 hours) to give a pale yellow solid powder,Purity 99.5%. see picture 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In toluene; at 110℃; for 24h;Inert atmosphere; | Following the Sonogashira coupling procedure, to a 150 mL three necked round-bottom flask were added <strong>[38215-38-2]4,4'-diethynyl-1,1'-biphenyl</strong> (0.30 g, 1.50 mmol), DPP-2 (1.80 g, 3.00 mmol), dry triethylamine (30 mL), dry toluene (30 mL), and the mixture was under nitrogen atmosphere for 30 min before Pd(PPh3)2Cl2 (0.06 g, 0.08 mmol) and CuI (0.30 g, 1.50 mmol) were added. Then the mixture was heated to 110 C for 24 h by stirring under nitrogen atmosphere. After cooled to room temperature, the resultant precipitate was filtered off and washed with diethyl ether (20 mL). Then the solvent was removed, and the crude product was purified by column chromatography on silica gel to give a dark violet-black solid DPP2Ph2 (0.42 g, 23%). 1H NMR (400 MHz, CDCl3, ppm): δ 8.87 (d, J = 3.2 Hz, 2H), 8.83 (d, J = 3.2 Hz, 2H), 7.58 (d, J = 4 Hz, 8H), 7.56 (d, J = 4 Hz, 2H), 7.35 (d, J = 3.6 Hz, 2H), 7.22 (t, J = 4 Hz, 2H), 3.97 (d, J = 5.6 Hz, 8H), 1.83 (m, 4H), 1.19-1.25 (m, 32H), 0.08-0.84 (t, J = 8 Hz, 24H); 13C NMR (100 MHz, CDCl3, ppm): δ 160.16, 160.10, 140.20, 140.00, 138.76, 135.01, 134.69, 132.55, 132.45, 131.66, 131.57, 130.23, 129.30, 127.96, 127.69, 126.50, 126.39, 121.29, 108.31, 107.62, 96.81, 82.97, 45.58, 45.48, 38.66, 38.60, 29.71, 29.17, 27.87, 23.10, 22.53, 13.45, 9.97; FT-IR (KBr, cm-1): v = 3082, 2922, 2852, 2192, 1663, 1554, 1515, 1449, 1406, 1370, 1337, 1228, 1095, 1062, 1022, 855, 815, 731, 699; HRMS (m/z+): 1247.3993, calculated 1247.5601 [M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26 mg | With C54H74Cl2N4O2Pd2; potassium hydroxide; In ethanol; at 22℃; for 48h; | Reaction flask (10 mL) equipped with stirring bar was charged with 4-(ethynyl)phenylboronic acid(100 mg, 0.68 mmol), ethanol (96%) (2 mL), [{Pd(μ-OH)Cl(IPr)}2] (7.5 10-3 g, 6.8 × 10-6 mol) andKOH (0.38 10-3 g, 6.8 × 10-6 mol). The mixture was stirred in air under at 22 C for 48 h. Aftercompletion of the reaction solvent was evaporated and the residue was purified by columnchromatography using n-hexane : ethyl acetate = 10 : 1 as an eluent. After evaporation of the solvent26 mg of 4,4'-diethynyl-1,1'-biphenyl was obtained as white solid. Yield = 38%. 1H NMR (403 MHz,CDCl3, ppm): 7.59 - 7.53 (m, 8H), 3.14 (s, 2H); 13C NMR (101 MHz, CDCl3, ppm) δ: 140.5, 132.6,126.9, 121.5, 83.4, 78.1. MS (EI) m/z (%): 202 (M+, 100). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With bis-triphenylphosphine-palladium(II) chloride; triethylamine; at 50℃; for 28h; | General procedure: General procedure: in a typical run, diethynylarene (1.0 mmol),thiophene acid chloride (2.5 mmol), PdCl2(PPh3)2 (2 mol%) and Et3N(20 mL) were mixed together in a 50 mL two-necked round bottom flask.The resulting mixture was left under stirring for 28 h at 50 C, then it wascooled to room temperature, hydrolyzed with saturated ammoniumchloride solution (20 mL) and extracted with CH2Cl2 (3x30 mL). Thecombined organic phases were washed with brine, dried over anhydrousNa2SO4 and the solvent was removed under vacuum. All the crudeproducts were purified through column chromatography on silica geland characterized with 1H NMR, 13C NMR, LC-MS and elemental analysistechniques. |
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